Find cheap flights from Chicago to Saint Martin Island from $186

Round-trip
1 adult
Economy
0 bags
Sat 4/29
Sat 5/6

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Best round-trip prices found by our users on KAYAK in the last 72 hours

MOST POPULARSimpson Bay
1 stop from $447
1 stop from $186

Good to know

Low season

May

High season

February

Cheapest flight

$186

Average price round-trip

$798

Good deal round-trip

$686

Good deal one-way

$371
Best time to beat the crowds with an average 3% drop in price.
Most popular time to fly with an average 14% increase in price.
Flight from Chicago O'Hare Airport to Simpson Bay
(avg. price over the last 2 weeks)
or less
or less

Top tips for finding cheap flights to Saint Martin Island

  • High season is considered to be January, February and December. The cheapest month to fly from Chicago is January.

FAQs - booking Saint Martin Island flights

Top 4 airlines serving from Chicago to Saint Martin Island

Scores according to KAYAK customer reviews
7.9
DeltaOverall score based on 29333 reviews
8.1Boarding
7.8Comfort
8.5Crew
7.8Entertainment
7.5Food
Airline reviews

Very efficient and effective. Fight crew and captain did a good job given the weather delays and turbulence…

Read more about Delta

Very efficient and effective. Fight crew and captain did a good job given the weather delays and turbulence…

Flight delayed for people who “should’nt have gotten thru tsa” had to look for their bags took two hours With no explanation had never happened Poorly handled

Pros: "Crew was nasty. They acted like prison guards not like they supposed to act to customers."
Pros: "We've always enjoyed flying Delta and this trip had been just as nice as the previous ones we have taken through this airline."
Cons: "Our stewardess/stewards seem to be incredibly cranky on this trip and very unapproachable. They must have been having an "off" day I guess."
Pros: "Fast boarding and off boarding"
Cons: "Crew wasn’t as attentive. While my first flight (I had a layover) seemed extra attention and care was put into the cleanliness and order due to Covid, second flight seemed to be a little overcrowded."
Cons: "long delay in boarding"
Pros: "It was super"
Pros: "The flight attendant (age gentleman) with the quite sense of humor, and converse with a measure of ease. A role model for others, a nice aptitude than one can learn from."
Cons: "Just keep up the good work and always work towards self development. Treat others the way you would like to be treated, with respect."
Pros: "Departure dealyed more than 2h."
Cons: "Flight crew begging for good score/rating. They literally did nothing. No service. No nothing. Why would you get a 5 when you literally did nothing. Maybe a 3 at best. But pleading for a 5. Sorry. You get a 1"
Cons: "More leg room and seat width. I don’t like having other passengers pressed against me."
Pros: "Hands down one of the best flights ever. Great seats, great leg room, amazing crew; I even met some good people on the flight. All around pleasing experience."
Cons: "My only complaint is the food. Some of the other airlines feed us real food, I want to pay for something a bit better. Still a great airline!"
Pros: "Good crew. Nice seats."
Cons: "This A320 aircraft departed LGA with the first class toilet inoperative. Flight was entirely full. First class passengers had to fight their way to the rear two toilets, around serving carts, etc. Cabin Crew was very good natured about all of this; but flight crew never mentioned it."
Cons: "Crazy rough, fast landing but not boring!!!"
Pros: "Zero turbulence"
Cons: "Nothing"
Pros: "Very smooth and friendly TSA personnel at the security point. Very friendly and respectful of the military. My husband is a Vietnam veteran."
Pros: "I loved the flight attendants and the desk staff everyone was so friendly and made me want to travel delta again."
Cons: "Delta doesn’t offer military spouses free checked bags and I found this out at the airport. It was disheartening, but at least it’s Delta and not the airline that is supposed to represent America."
Cons: "At least one hour late"
Pros: "I liked the cookies and juice. The interactive screen to watch something. The cleanliness. The price. On time. The service. Thank you. The excitement of flying."
Pros: "Flight attendants were excellent, flight from Milan to JFK, while long was reasonably comfortable. Food was pretty good. Lots of free movie and TV choices. Leg room was OK."
Cons: "It would be nice if the seats leaned back just a little more for sleeping. Make certain you have used the restroom before you get to JFK and customs. Customs was a pain but I had lots of time between flights."
Cons: "Late boarding and take off with no explanation."
Pros: "Boarding and Arrival went smooth and quick. We were early to our destination. Short 3 hour flights are always easy."
Cons: "I was flying from CDG to LGD and my bag was lost, yet the baggage claim system showed it arrived...... Thankful I packed some essentials in my carry on. The bigger issue will be dealing with my medical insurance company to get medications replaced that were in the checked bag."
Pros: "The crew at the airport was very courteous and helpful."
Cons: "No food; not even offered water; I asked a Delta employee about our seats and she was very unprofessional (mind you I'm traveling with kids and my boarding pass said that seats were to be assigned at the gate)."
Pros: "Flight was fine. No real complaints other than a talkative neighbor when I wanted to sleep."
Cons: "Talkative neighbor when I wanted to sleep. Very narrow and cramped cabin."
Pros: "I can’t make it in mexico city on tuesday, wednesday’s performance had to be cancelled and we need to pay the cancellation fee 11500 mexican pesos, please reimburse on the credit card"
Cons: "I can’t make it in mexico city on tuesday, wednesday’s performance had to be cancelled and we need to pay the cancellation fee 11500 mexican pesos of the studio and musicians"
Pros: "The ticket agents and other airport personnel were tremendously understanding and helpful! As a matter of fact, a few said this happens more often than it should, which is sad and shocking! Had it not been for their help this would have been much worse!!!"
Cons: "Our original flight included a connection that overlapped and needed to be changed. I brought this to the attention of Kayak/Aeromexico and the flight appeared to changed for our entire party of six. When we arrived to depart from Akron-Canton there were MAJOR issues with Delta acknowledging the change on their end. We waited at check-in for an hour and half before this was resolved. This also happened when we left Cancun and almost missed our flight. Our daughter also had to put on stand-by in Atlanta due to this fiasco. We spent another two hours working with Delta customer service trying to get her a seat on our flight back to Akron-Canton. Had we not been to Cancun airport extra early AND had our flight delayed in Atlanta we would have missed both flights. This was without a doubt the worse experience we have ever had!! It should have been caught and resolved before I ever had to get involved. I am very disappointed and unhappy with the service offered for the tickets we purchased. This was extremely stressful for my wife and kids and tarnished our vacation. This was totally and completely avoidable!!! You can and should do better to service your customers!!"
Pros: "They offered some snacks"
Cons: "I didn’t like the fact that they had no backup pilots for the plane. We waited 12 hours!!!!!! For a flight"
Pros: "Excellent flight, great crew, smooth throughout!"
Cons: "Catering problem - no snacks!"
Pros: "The plane was on time, the crew was friendly, no delays, landing was fine. In fact we actually made it a little before the time that we were scheduled. Since the flight was so short, I did not have any food."
Cons: "The seats were a little small."
Pros: "Our original flight was delayed and Marika, at the Delta gate of another flight to the same city, was able to get us on the flight that was going to our city. We were so grateful to get home before the winter storm! We appreciate your staff and the help their quick, efficient manner to get us on a new flight!"
Cons: "Seeing as I’m still waiting for my flight, more than five hours later I am not inclined to rank it highly. This airport is an embarrassment and I will try my best to never fly Delta again. Weather is no excuse for this."
Pros: "Seating and boarding were fine. That process was relatively quick/straightforward"
Cons: "I have never had an on time Delta flight, and hopefully, it will happen one day"
Pros: "The entertainment unit allowed me to watch the Denver Broncos game live which helped lessen the delayed departure and uncomfortable seating."
Cons: "Uncomfortable seating....too crowded!! We had a delayed departure by 30-40 minutes because of a computer download issue. Too many folks carrying carry-ons delayed boarding. I wish folks were not encouraged to go that route but to check baggage. This time of year gets even tougher with folks carrying Christmas presents and over sized personal items. Ugh. Not fun to travel this time of year."
Cons: "Price to get a little more space"
Pros: "The flight attendant in Delta Comfort/Main Cabin was very nice and made for an excellent trip. Smooth ride and on time. I like that!"
Pros: "staff was good, flight was not so good"
Cons: "Hated the storm we flew through, luggage came out of overheads....ugh"
Pros: "nothing other than on time departure Ann's arrival"
Cons: "I specifically shopped carriers other than delta or united, tho my regret usa carriers have stopped offering comforts, service, quality food. Not sure how, but even though I bought virgin Australia ticket and flight, I ended up on delta. Terrible sitting, even though after I paid for tickets I was charged extra for more leg room and priority boarding, I got neither, they advertised free texts in flight, it didn't work either."
Pros: "Crew were good, flight on time, free drinks"
Cons: "Nothing"
Pros: "Movies"
Cons: "Not supplying headphones Crew not to helpful, one unpolite Refreshments ridiculous"
Cons: "11 hour overnight delay. Timed out crew. We were given a pillow and blanket to spend the night on the floor in the airport. We we given drinks and a snack box."
Pros: "Majority of the crew was pleasant"
Cons: "One flight attendant was EXTREMELY rude to me for no reason"
Pros: "When I finally was assigned a seat (after my "Runaround"), I got a slight upgrade: Row 12 was a roomier seat and I got a choice of fruit for a snack."
Cons: "Runaround by gate agent: The gate agent was located about 15 yards from the actual gate. I waited there 20 minutes before anyone showed up, to get a seat assignment. When she showed up, she said she would not give seat assignments for another 15 minutes, so come back then. When I came back she said she wasn't giving seat assignments; go see the person checking in boarding passengers at the gate. That agent said she couldn't give me a seat, but watch the monitor for my name for seat assignments, then come back. Why couldn't the first gate agent say that instead of giving me the runaround and wasting my time???"
Pros: "Flight attendant had nice attitude."
Cons: "I asked for an aisle seat to provide relief to my right leg. I was given an aisle on my left. This was compounded by sitting next to a man so large that part of my space was taken, and this was Delta Comfort. Had I been given the requested seat, I would not have the sore neck and back I now have from leaning for 2 hours."
Pros: "Left reasonably on time, arrived a bit early, able to find overhead storage for my roll-on, even boarding in Zone 3"
Cons: "Very tightly packed; minimal comfort for the flight."
Pros: "Flight attendant was very nice."
Cons: "My 6 pm flight left at 8:19. Debris wasn't cleaned from plane between flights. Want some French fries? Lady had two barking dogs in first class. I was in first class. It wasn't worth the extra money we paid to be in first class."
Pros: "The crew was nice"
Cons: "I didn't like the fact that I didn't get my luggage with me when I arrived to casablanca as I lived 4 hours away from the casablanca. I have to come back the next day to get my luggage. I was very mad about it.plus I noticed one of my luggage has been damaged so now I have to buy another one because I can t use it. It was disgusting."
Pros: "The flight crew was nice and polite. They served drinks and snacks in a timely manner while on the flight."
Cons: "Flight was scheduled to leave early, the plane arrived, but they couldn't turn the plane around fast enough. We left the gat late, then pilot said we would still be arriving half an hour early. We arrived about 45 minutes late, and that was a problem because our connecting flight was due to depart now in 15 minutes. Lightning forced the airport to shutdown, which was great, we had a chance to catch our flight, but we were stuck in the airplane, and we couldn't get to our gate until the all-clear. I know this is not Delta's fault, but they did arrive quite late on a flight that, according to them, would be early. They also never communicated to the other flight that there were several passengers catching that connection. So by the time we had ran to catch our connection they had closed the ramp. Lightning hit again, and they shutdown the airport once again, so the airplane was still at the gate for about an hour, and they did not allow the 20+ passengers to board that plane, which was right there. So frustrating. The only thing that saved it was that our new flight was the new airbus, and although it left an hour and a half later, the comfort level was phenomenal."
Cons: "The plane temperature was too hot from boarding to landing"
Pros: "Appreciate having movies available through wifi however didn't realize this until only an hour left in flight."
Pros: "The crew were excellent. Kept us updated throughout a long delay."
Cons: "We should have reached our destination at 7:40PM. We finally arrived about 9:50pm. We were held at the gate for about two hours while a mechanical issue was solved. The plane was not equipped with WiFi/internet and the entertainment was poor. Expected better from Delta."
Pros: "Nothing"
Cons: "Individual TVs, perhaps"
Cons: "Late and then mechanical issues."
Pros: "Crew was great"
Cons: "Seat was uncomfortable. Flight was much too crowded"
Pros: "Flight was cancelled after multiple delays & I changed to United."
Cons: "Stop delaying & canceling flights, especially last minute"
Pros: "Really easy boarding and flight. Great in flight entertainment options."
Pros: "All was good"
Cons: "Nothing to complain about."
Pros: "Seat assignment process was great and considerate of my preferences."
Cons: "If AA could fix its luggage handling process that would be great. BOTH (!) of my bags have been lost on this flight. Both have been eventually located, recovered and delivered to me, but experience was not pleasant this time."
Pros: "Flight attendants were friendly and thoughtful."
Cons: "Seating is too tight. Hard to believe that in 2019, major airlines still have seats without any electrical or UBS outlets for charging devices."
Pros: "Crew was great."
Cons: "Plane was about 1000 years old and I don’t think I’ve sat in a more uncomfortable seat."
Cons: "Unable to connect to the new AA so-fi"
Pros: "Comfortable seats and snack / drinks service"
Cons: "Delayed flight departure and bumpy landing"
Cons: "I was apparently "flagged" by British Airways for extra security checks. As I understood it in London, I was randomly selected for this security check. This then apparently meant that I was to be flagged for all subsequent flights. This meant that in Chicago, after going through two other security checks that day (Zurich and London) and completing customs, I had to engage in a full Homeland security check. This involved removing protective covers from my laptop and phone that were hard to get off (not meant to be taken off regularly) and a full body search that I did not have to do in London. After many hours of traveling, this was very a frustrating experience."
Cons: "I will never, ever book with Kayak again"
Pros: "Flight crew was great. The plane was half full, so the attendants allowed us to move."
Cons: "Terrible landing in Charlotte. The plane was rattling and had an annoying whistle."
Cons: "British Airways/American Airlines lost/delayed luggage again! Then send an email in the middle of night with a link to schedule home delivery of the luggage that was valid for 4 hours only. It is clearly an attempt to cheat out of their responsibility of home delivery of the luggage that was delayed the second time. Poor, poor service by American Airlines."
Cons: "It was not clear that I needed a different 6 letter code to checkin using the AA website. I finally got frustrated and called AA only to find out the code was different. The codes should have been the same or you should have referenced it on the website when I tried to check in"
Cons: "Flight was delayed for more than 4 hours with little communication from staff as to why, gate was changed to a gate across the airport."
Pros: "The boarding was quick and easy as well as the crew was friendly and accommodating. Great end to a fun weekend away."
Pros: "Our plane was late getting to the gate. They kept us informed and turned it around pretty quickly. There were storms between Chicago and Rochester so we were rerouted. As a result the hour flight was an hour and a half. The pilot kept us informed and it was a very smooth flight. So even though I was over an hour late arriving I so appreciated the communications and the safer route. AA seems to be communicating more than other airlines and I appreciate that. Flying is absolutely no fun anymore so you take what you can get for the positives."
Cons: "WiFi wasn’t working so I couldn’t communicate my late arrival to family picking me up."
Cons: "On my first flight from SLC to ORD I asked 3 different American Airlines employees if I needed to pay for my carryon before I got on the plane. They all said no. I got on the plane, put my carryon under the seat in front of me and everything was great. I landed in Chicago, got to my gate, went to board and this very rude employee stopped me after I scanned my ticket and told me I couldn’t board with my bag. The EXACT bag I had boarded with in SLC. After harshly grabbing my bag and putting it in the carryon basket to check for size, she wouldn’t let me pass by her into the boarding bridge and told me I was going to have to pay. I tried explaining that I had asked I’m SLC if I needed to check it and they had all said no and that it fit under my seat. She said, “I don’t care what they said in SL, this is what I’m saying here.” And directed me to the front desk where I had to pay $50!! $50 for a carryon backpack that fit under my seat comfortably 20 minutes before!! Without saying a word (cause I didn’t want to yell at the poor girl behind the desk) I paid the $50 and proceeded to enter the bridge but before I passed through, the rude woman said, “have a nice flight ma’am” and scoffed!! An audible scoff. So I’m short, I hate American Airlines and I will do my BEST to not have to fly with them in the future."
Pros: "The fact that they re-booked without me having to contact customer service."
Cons: "The connecting flight was cancelled while boarding was in progress at the start of the journey."
Cons: "Flight was delayed by untold circumstances causing us to miss our connecting flight to Venice."
Pros: "On time departure and early arrival"
Cons: "Nothing"
Pros: "Nice crew Spacious plane"
Pros: "The crew was amazing, flight was very smooth, arrived early, plane clean, service was great."
Cons: "For being in first class, my seat did not recline so I couldn't sleep and audio for my entertainment center was not working"
Pros: "Good time for flight"
Cons: "Tight, hot inside plane, no refreshments"
Cons: "They left the lights on the whole flight"
Pros: "They alerted me to problems with our flight and we switched to an earlier flight. No problems with new flight. Good service."
Cons: "Great trip"
Pros: "Not turbulence"
Pros: "Was on time."
Cons: "Not eventful."
Pros: "crew was great, plane seemed newer and clean. individual screens worked better than others I've used in flights."
Cons: "newer touch screens were great except viewing angle couldn't be adjusted. standard food was horrible, esp for an international flight; not sure if specialty diets have better meals. kid movies were dubbed into many language options but Chinese was not one for ANY kid films. bathrooms with the same crappy mini sinks that you can't really wash your hands in, esp if someone pukes in it. they should all learn from Japan's ANA airliners with the motion sensor sinks with faucets raised up high enough for you to wash your hands without touching the gross basin."
Pros: "On time, good service."
Cons: "Luggage did not make the transfer on time (Chicago-Charlotte after Tokyo), although they had about 45 minutes to load it. Do not buy an international ticket with less than 1.5 hours transfer time. (It took 45 minutes to get through customs/immigration and retrieve luggage for transfer."
Cons: "Missed it."
Pros: "Nothing"
Cons: "An S80? Really? This plane was older than me! Horrible plane! The crew looked like they had been up since 4 am. Looked exhausted and unfriendly. I do want to clarify that this was an American Airlines operated plane, not etihad."
Cons: "The cramped space"
Cons: "All was excellent! Only the internet was not working good , payed for all flight access but most of the time the internet was not working. Anyway I contacted support team and they refunded me"
Cons: "The flight was delayed more times than I can count, we got a different reason each time. Weather I can understand, but telling us we are waiting on a specific crew to arrive and then announcing that crew is not for our flight was just terrible communication. No one seemed apologetic. The only thing they did was bring a snack cart over for us, and that got raided by children so many people didn't get anything. We had arranged transport from Orlando to Tampa for that evening, and our rides had to cancel because instead of 7pm we were now arriving at 130am. Your airline's mistakes put everyone at an inconvenience and we weren't offered assistance to fix it. My husband went to ask for help in arranging new transport home, but he couldn't even get to the front of the line. The customer service was terrible. We really enjoyed our first leg of the flight home with American Airlines, but after the second leg and all of the problems we had... we will not fly with American Airlines in the future."
Pros: "on time"
Cons: "very cold"
Cons: "This made the check in process extremely frustrating and confusing. Traveling with my elderly dad who had to squeeze between two large men for 7 hours because people who actually booked the airline got priority seating. We had to pay an extra $500 to upgrade to comfortable seats. Not pleased w Kayak."
Pros: "The crew was great and getting 2 meals was very nice."
Cons: "My headphone jack kept malfunctioning (loud popping noises in my earbuds) while watching the movie and all the reading lights came on and stayed on the majority of the flight so sleeping was difficult."
Pros: "An agent found me a window seat for the Chicago-Barcelona leg of the trip with extra leg room. That was amazing. Also, the lost luggage assistant for American Airlines was super helpful and nice. Also, the 787 (I think that was the Chicago-Barcelona craft) was a very enjoyable airplane. It was super smooth. It had high tech windows that adjusted the amount or type of light that could filter through the windows depending on the settings."
Cons: "When I arrived in Barcelona my Bag went missing. It showed up an two hours after my flight landed."
Pros: "I enjoyed the entertainment because I don't watch movies in the theater often. The movies I saw in-flight were recent films I've been wanting to see and made time pass fairly quickly."
Cons: "I'm not a giant, but there definitely was not enough leg room in the main cabin. I could not sit comfortably, especially in the middle seat."
Pros: "Good flight. Arrived on time"
Cons: "Jet bridge was broken and needed repair. Delayed departure."
Pros: "The crew were exceptionally friendly and helpful. They made the negatives about the flight much more bearably be their excellence service whether during boarding, in flight, or after landing."
Cons: "I booked the flight originally through british airways and expected your standard, modern plane for cross atlantic travel. Boarding to find myself on a 767 designed (and likely built) in the 80s was rather disappointing."
Pros: "Seats were really neither notably comfortable nor notably uncomfortable. I think they were slightly on the comfortable side."
Cons: "Would be nice to have more modern aircraft amenities, like power outlets for device charging, and display screens with at least some complimentary entertainment, or at least flight path tracking. Boarding counter lady was obnoxiously strict about not letting our carry-on bags to be carry-on. She made us test them in the size device and said they were too big, even though they could easy be pushed into the space, and regardless of the fact that we just flew on an American Airlines flight with them as carry-on and were only on a layover with them! Regarding the previous AA agent who let them be carry-on, she said "shame on them." Complete opposite of the positive experience we had with her counterpart in Phoenix. ಠ_ಠ"
Cons: "They cancelled the flight and put me to fly the next day"
Pros: "Everybody was nice my ride was comfortable and they treat me with respect"
Cons: "I like everything"
Pros: "They were friendly. Seats are rarely comfortable..."
Cons: "I think all planes need better leg room...."
Cons: "Everything was good!"
Pros: "Flight attendants were absolutely amazing!!!!! They made the trip very enjoyable!"
Cons: "Food!"
Cons: "a 2nd snack for a 5 hr flight would have been nice. Also never heard that they were serving lunch meals to buy, heard the breakfast one!"
Pros: "Great crew"
Cons: "Very uncomfortable seats"
Pros: "Nothing"
Cons: "My economy plus seat wouldn’t recline!"
Pros: "getting bumped up to economy plus and being in an exit row."
Cons: "What I wrote above was meant to describe our experience from Chicago to Burlington- not Milwaukee to Chicago. Although, we had a delay in Milwaukee too. Overall, everything was only fair"
Pros: "Nothing at all!!! That should really tell you something!"
Cons: "The staff were rude, abrasive, ignored several passengers that were trying to get her attention before take off as 2 overhead bins were wide open and full to the brim. She of course was too busy playing on her cell phone in the back of the plane and ignored/silenced the passenger call button. They were so loud when people were sleeping, yelling ‘trash please’ every 5 minutes, we are not stupid, we can see what you are doing and if we have trash, we will give it to you - so please STOP disturbing my peace and let me bloody sleep!!!! I was never offered any food or drink during the entire flight, not even when I was awake - other airline attendants are more observant and come back and ask us when we are awake if we would like anything to eat or drink. So essentially that was 7 hours with nothing after having paid a little over $700 for what was seemingly the WORST transatlantic flight I’ve ever taken. I travel back and forth often, because I’m a dual national, but I will stick to BA or Virgin Atlantic - the planes and service are far superior to this pile of turd that goes by the name of United. There were no charging facilities (power outlet or USB port) and the TVs had such horrendous resolution that you would get a headache from having to squint at the screen."
Cons: "Great"
Pros: "Entertainment."
Cons: "Nothing."
Pros: "NOTHING"
Cons: "Every thing I will never fly with United"
Pros: "Quick"
Cons: "You better get rid of basic economy."
Cons: "Tight seats, seat belt uncomfortable"
Pros: "No delay, friendly crew"
Pros: "Associates were nice and knowledgeable. The airplanes were comfortable. Love the onetime performance of scheduling."
Cons: "Unite Airline performance wasn't the good. Also, there was nobody in Chicago to help us with the transferring process."
Pros: "Great captain and crew."
Cons: "I prefer the entertainment on your own device."
Pros: "Chicken wrap was very tasty. Very attentive flight crew."
Pros: "I had the exit window and that made a huge difference in my trip as I am a 6ft tall woman who is all legs."
Cons: "It was slightly turbulent and TSA at O'hare airport are the rudest and laziest humans on the planet."
Pros: "Snacks and drink"
Cons: "Average"
Pros: "Flight was on time."
Cons: "Seats are uncomfortable and cramped."
Pros: "Wasn't thrown off"
Cons: "Another delayed flight with United"
Cons: "They might as well have thrown us in a car trunk the crew was very unaccommodating they didn't really care about us and the room legroom is ridiculously smal. On the connecting flight, the last flight the plane was two thirds empty and the crew made us sit in our assigned seats, crammed together telling us that if we want to sit in a seat with more legroom we have to pay $180"
Cons: "Too many seats too close together. The entire trip was too hot and stuffy. The flight attendants showed minimal care about the uncomfortable hot and stuffy environment."
Pros: "On time, crew was friendly"
Pros: "Not much."
Cons: "Originally, there was an announcement that we would be delayed by 45 minutes because of "air traffic" issues in San Francisco, where we were landing. In spite of this, the captain decided to have passengers board the plane, and try to push our way up the line, so to speak. Well, once we were on the tarmac, the flight crew were told that the plane could not take off, and that we needed to wait there for 45 minutes, without moving, in our seats, with nothing to do. Even though it would still not have been ideal to wait 45 minutes at the gate, at least we could have walked around and could have entertained ourselves."
Pros: "Everything went smoothly"
Cons: "Good options are terrible"
Pros: "Excellent and content flight."
Cons: "No complaints"
Pros: "Crew was attentive."
Cons: "From Gregory at the check in being rude and anything but welcoming, to seats in first class needing replaced, this was anything BUT a first class trip. This was my second time giving United a chance as I normally fly Delta. I don't think I'll make that mistake again. I understand a late night flight doesn't have a meal service, but snacks of chips and bananas is not my idea of how you should serve Firat Class passengers. I would have a hard time recommending anyone choose United as their airline. Time for an upgrade of not just the seats, but overall customer service."
Cons: "Worst customer service of my life. I will NEVER fly United Airlines again."
Cons: "Turbulence was insane"
Pros: "We'll coordinated."
Pros: "The crew were very kind and attentive without being overbearing. They were helpful."
Cons: "I did not like how my boarding pass for a ticket I had paid for long in advance had a 'see us' note about my seating. The counter attendent waltzed in after boarding had already started and treated the issue like it was a joke. I ended up seated in between two hot messes of people which made the flight seriously uncomfortable, there were no other options supposedly for me. There weren't even options for me to pay the outrageous pick a seat option when I was doing my preflight check in 24 hours in advance."
Cons: "The seats were terribly uncomfortable (including her flight to Chicago). The cushion made me slide down the seat and could not get comfortable."
Cons: "I went on this trip as an veterinary humanitarian out reach. I was also guardian to one high school student so that she might have an experience of such to guild her future. Her flight was missed booked to leave after mine, I attempted to rebook my flight with Luthansia but they would not let me me even partial rebook. I attempted a number of times to rebook the flight but their solution was extreme financial gain for them when more reasonable alternative could have been arranged. They canceled my entire return flight and left me stranded. I had to piece together a return flight on a shoe string budget. Thankfully American Airlines was understanding for it appears Luthansia and United are not."
Pros: "Loved that it was an empty flight"
Pros: "."
Cons: "."
Cons: "2.5 hour delay. No working bathrooms. Couldn't hear the tv and headphones that they gave out were useless."
Cons: "The flight got cancelled"
Cons: "Flight was delayed due to severl technical issues. Crew at least offer free drinks or snacks for the five hour delay."
Pros: "Nice clean planes and seat, on time performance"
Cons: "The flight attendant was hard to understand"
Pros: "Flight itself was fine. Major delay resulted in arriving one day later than planned, additional transportation cost, unplanned, and unplanned parking fees. No travel voucher was offered and when I asked was told it was not possible to issue a travel voucher."
Cons: "It would have been helpful if hanging a garment bag were available, which was the case on my return flights to DC on American Airlines."
Pros: "The process was good"
Cons: "Wish there were more morning flights"
Pros: "Very good"
Cons: "Comfortable"
Pros: "I was comfortable and I didn't die."
Cons: "N/A"
Cons: "There should be some free tv"
Pros: "Flight was on time"
Cons: "It was full"
Pros: "Nothing"
Cons: "After getting to Chicago on another airline due to weather we come to find out that the flight from Chicago is cancelled due to "maintenance" . We talked to 7 different United representatives at 3 airports and none of them were any help to us. We were offered hotel accommodations in Miami to find out the hotel they booked us does not accept United vouchers leaving us to pay for it ourselves. Another expense added to the trip unexpected. Every phone call to United leads to 4+ hours of wait time followed by "go online and figure it out". I still need a refund for both flights and these bogus hotel vouchers ."
Pros: "No service issues. Our seats were arranged so the family was together for no charge. We were given a bottle of water to mix baby formula for no charge."
Cons: "Hard seats"
Pros: "the funny jokes by the flight attendant"
Cons: "there was a fee for EVERYTHING!"
Pros: "Utilization of Kiosk, check-in, boarding, crew, and pilots. The seats were clean, too. Thank you very much :) !! Flight was also on-time for departure and arrival at destination. * In the Review, put my name as Anonymous. Thank you."
Cons: "Prices for beverages, food, and/or snacks are extremely HIGH! $3 USD for a 12 oz. can of pop OR WATER (16-20 oz) ? ! ! $7 USD for a 5-6 oz bottle of wine ?! The prices are ridiculous!! You can't get water to cry with or if you were on fire. Upon viewing your menu, there is a "bundle" for three or more items. This IS NOT a bargain. You decrease the price by a dollar is nothing. It appears to be overly enrichment and a rip-off. I know that you're in business to make a profit. But dayumm!! REALLY??! You all are certainly taking advantage of your customers. There may be either a continued decrease of purchases or none at all. I noticed that there weren't many purchases in relation to the number of passengers on board at the time. BTW, the price paid for the single bottle of wine ($7 USD) is what it costs for the 4-pack, if not less. A person can purchase 750 ml or 1/5 gallon for the same amount or less (i.e., $5 USD + tax). This is wrong and obliges passenger to make a grudging purchase out of necessity. Have you ever been thirsty before? Can't have water to take medications without spending large amount of money. You can't even get tap water or courtesy cup of water / ice. What type of mess is this? $50+ bag check fee is horrendous!! Your competitors are much cheaper. Please add more cushion and room to your seats. Had this flight been more than 90 mins., I'd be making a trip to the hospital instead of home."
Pros: "Great for anyone simply looking to get from point A to point B - no fuss!"
Pros: "Left early. Comfortable seats"
Cons: "Na"
Pros: "Price"
Cons: "Seats too small. Didn’t recline"
Pros: "No way to contact wheelchair assistance when being dropped of to begin flight. Waited 30 minuted for a wheelchair. Had to ask Amer.Air agent for help. Other airlines are far more attentive. Seats need 2 more inches, felt squished. Very costly baggage policy, charge for carry- ons."
Cons: "Seats did not recline ( the whole plane - not just exit rows). All the extra charges for EVERYTHING were ridiculous, especially as you are not informed of any of them before booking. I'll not fly Spirit again."
Pros: "Friendly staff, fast flight, and no frills fares. They'll charge you for drinks, etc., But overall a good flight."
Cons: "Uncomfortable seats, no free water."
Pros: "Glad I tried spirit! Got me in early on both legs of my flight! Also glad I got the comfy seat-SO worth the money!"
Pros: "Change of gate wasn't fun but it was handled professional."
Pros: "Nothing"
Cons: "They didn't seat me and my husband next to each other. Take off and landing was rough. Everything cost extra. Bags snacks drinks. Only 1 bathroom. Crew was rude. Taxiing felt like whip lash."
Pros: "Of the 6 flights I took with Spirit on this trip, this was the only one where they boarded the flight in a timely and organized manner by using the zones printed on the boarding passes."
Cons: "Spirit airlines cancelled my flight the day of travel."
Pros: "Nothing. I was treated so poorly I walked away from their customer service and bought a ticket on another airline."
Cons: "I was 5 minutes late over their 45 minute required check in window. So they cancelled my ticket. For $100 they offered to reschedule me. And for another $50 they would check my bag. On a different airline I paid another $100 and got a complete round trip ticket, about 10 minutes later."
Pros: "The crew was nicer on this flight. They made more of an effort and the temp was much more comfortable."
Cons: "They don't give you water or snacks. You have to pay to pick your seat and CARRY ON your luggage. The hidden fees surpass the cheap flight"
Pros: "Nothing except the price"
Cons: "Delayed boarding"
Pros: "Low cost base ticket"
Cons: "Baggage fees added 80 to the flight cost and seat fees would have added another 40 if I paid them. If I knew that when I bought the ticket I would have gone with another airline. Oh, and no TSA pre-check option at O'hare"
Pros: "Everyone thing went smoothly and fast."
Cons: "All the added cost: seats, baggage, and snacks."
Cons: "No coomwnts on the airlines. It could br great if you provide atleast water yo the passengers"
Cons: "they were rude and uncooperative. They have no type of customer service. If you ask them a question they are short and direct. If you try to work out to find a solution...they just are plain rude and do not make an effort whatsoever to accommodate their customers. They abide by their ridiculous rules and plainly will not work with you. Besides that they started to charge for separate baggage fees. So you'll but a ticket for "cheap" but then they will charge you double for baggage both ways. My boyfriend purchased a ticket and wanted to make changes...they wanted to charge him $100 to change flight info. RIDICULOUS. He ended buying another ticket....Spirit took $200 in fees extra from us."
Pros: "Extremely friendly and funny staff. Very personable and professional."
Cons: "Small, uncomfortable seats."
Pros: "flight took off and landed on time."
Cons: "I was lucky his time and sat in the front of the plan on a better seat, but still not so comfortable. Very thin cushions. It was difficult to understand the crew n the PA system, spoke too fast and garbled. The purser was not clear."
Cons: "Delayed 2 hours because of a "late crew." Was also delayed on first flight to Chicago."
Pros: "Nothing"
Cons: "The airplane was dirty. And, a woman next to me asked for some water and the flight attendant says, "$3 for a bottle." This is very disrespectful and classist. Not everyone has $3, and I could tell that she didn't. Also, the plane made a terribly loud noise. I feared for my life! The flight was delayed but the crew did not give us updates.... We simply waited. And waited."
Pros: "Nothing"
Cons: "The flight was delayed with no reason given, the tray tables were too small, the seats were too narrow"
Pros: "We were off the plane and out of the door incredibly quick"
Cons: "Got bumped from flight because it was oversold. Personnel helped find flight on a different airline the next day. But that was not a direct flight and it was a major inconvenience to arrive a day later than planned."
Pros: "They try to get money in every way possible. They give you a good price on the flight ticket and then they get you on your luggage in a terrible way. 40 pounds instead of 50 like every one else. You have to pay for the carry on as well. They won't even give you water. First and last time with them. No thanks."
Cons: "I hate their crooked way to do business."
Pros: "we flew from oakland to ohare for the first time on Spirit airlines and we were very impressed. We left on time - or even a minute or two early - and landed safely. what more could we ask? The staff was friendly and the plane was clean. two thumbs up!"
Pros: "I like that there is more leg room than before"
Cons: "That i have to pay for even water. Chairs don't recline, no tv noting"
Cons: "I will never fly spirit airlines again."
Pros: "Crew and flight was very good"
Cons: "This was the second time I flew to MN with Spirit first time my return was cancelled and this time was delayed by an hours and delayed take off and delayed at Ohare"
Pros: "Nothing"
Cons: "Flight was delayed several hours. The staff did not inform us of the several delays. Only notification that was given was a gate change. We didn't have a pilot so we sat in the plane forever. Horrible service, but u get what u pay for with with spirit. Learned my lesson and will pay little extra to not fly spirit airlines."
Pros: "The guy who made the announcements was AWESOME."
Cons: "My seat. Pricing. Being forced to live out of a back pack. Tiny seats. No water. I won't deal w spirit again"
Pros: "The crew on the plane was great. Friendly, polite quick. Too bad they were like cops dealing with people that would not turn off their phones or stay in their seats."
Cons: "The Spirit counter had 2 people working and no customers. Would not give me a seat number. Gate agent had 40 people in line and was by herself. Seems odd to hold up people boarding while I got in line to get my seat number. Also the baggage fee really does suck. $50+ for a carry on was cheapest option. Passengers caused issues the whole time. Police called and met them on exit from the plane. Frontier is the better way to go out of the two sister airlines."
Pros: "The big seat that I upgraded to for $35 one way was nice - essentially a business class seat. The crew were helpful and pleasant, and the boarding process was well-organized."
Cons: "If I had known the philosophy of this airline ("bare fare" plus pay more than average prices for all other upgrades, including water on the flight), I never would have booked with this airline. Checked luggage is more expensive with Spirit than with other airlines, and fees are almost double at the airport if you don't pay ahead of time. Carry on bags are also an extra fee; only your personal item is free. If you have orthopedic challenges and a long flight, pick a different airline - only the extra cost seats ($35 each way) recline at all. This airline was more expensive to fly than the airlines I normally fly, once I added what I consider to be basic needs. It would have been nice to have this information (especially about the seats) available when I booked on Kayak."
Cons: "Never fly this airline"
Pros: "NOTHING"
Cons: "Canceled flight right before boarding. People at the gate were very rude. Made everyone leave and go out past security to the front gate to even know what was going on. Many Sprit employees knew that there were no more flights but wouldn't tell us. Made us all wait in line. They refused to help us find another flight. I will never again fly this airline."
Pros: "Not much"
Cons: "Not the best experience. Your airline is awful!"
Cons: "The price goes up so quickly. Also the website was down and when they were going to help me via the phone, they said I would be charged $100 as opposed to $35. It was awful."
Pros: "Everything"
Pros: "Other than the billing everything went very smooth"
Cons: "I was double charged for my bag leaving from Chicago. I disputed the charge on my credit card."
Cons: "Is always a surprise with extra charge on luggage, is never clear how is will be the size the shape the color etc etc!!!!"
Pros: "Flight was on time, boarded on time, and arrived at destination 20 minutes early"
Pros: "Only good thing was the staff aboard the plane."
Cons: "Delay, after delay, after delay. Got to ohare early, as you should. The second I arrived I got an email saying my flight may have been cancelled. Checked my bag anyway and found out it was only delayed. Aggravating but whatever. Got lunch, had a few drinks. Delayed even further. Approaching the time to board again...delayed another hour. Sat in three different terminals for 5 hours. Only to finally board and get delayed again. Flight was overbooked, people taking seats that weren't theirs. Absolute chaos. I get that it's cheap, but, it's at the cost of comfort and sanity. I'd consider a ricksha before I considered spirit airlines again."
Pros: "Never flying spirit again."
Pros: "Missed my flight due to your computer system failure at booking!!!!! No announcement made for the immediate flight while standing in security lines!!!!! Arrived at the gate at 11:12 and the plane door was already closed though the flight wouldn't departuntil 11:20!!! Ridiculous experience!"
Pros: "Everything was clean, staff was polite, boarding was fast."
Cons: "I paid the same amount for a one way Southwest flight as I did for a Spirit flight going the opposite direction - however, when you add all the extra costs Spirit piles on, it's stupid. They even charged for WATER. We only were able to get a free glass of ICE. Don't use "Only pay for what you use" as a positive advertisement. That's cheap & petty, and I'm never flying with Spirit again. Southwest all the way! The website was really hard to navigate, and when I tried to process a payment to have my bag paid for early, it didn't go through. They want you to pay the higher price at the airport."

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Recent round-trip flight deals

5/3Wed
1 stopSpirit Airlines
7h 50mORD-SXM
5/10Wed
1 stopSpirit Airlines
9h 15mSXM-ORD
$447
5/3Wed
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7h 50mORD-SXM
5/17Wed
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9h 33mSXM-ORD
$449
5/3Wed
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7h 50mORD-SXM
5/10Wed
2 stopsSpirit Airlines
18h 09mSXM-ORD
$474
5/3Wed
1 stopSpirit Airlines
7h 50mORD-SXM
5/17Wed
2 stopsSpirit Airlines
18h 09mSXM-ORD
$483
5/3Wed
1 stopSpirit Airlines
7h 50mORD-SXM
5/10Wed
2 stopsSpirit Airlines
26h 13mSXM-ORD
$484
4/19Wed
1 stopSpirit Airlines
7h 50mORD-SXM
4/26Wed
1 stopSpirit Airlines
7h 54mSXM-ORD
$497
8/23Wed
1 stopSpirit Airlines
7h 52mORD-SXM
8/30Wed
1 stopSpirit Airlines
9h 03mSXM-ORD
$498
4/11Tue
1 stopMultiple Airlines
16h 26mORD-SXM
4/18Tue
2 stopsMultiple Airlines
33h 33mSXM-ORD
$499
4/22Sat
2 stopsMultiple Airlines
15h 59mORD-SXM
4/26Wed
1 stopMultiple Airlines
9h 42mSXM-ORD
$521
4/11Tue
1 stopMultiple Airlines
25h 39mMDW-SXM
4/18Tue
2 stopsMultiple Airlines
23h 05mSXM-MDW
$523
5/13Sat
2 stopsMultiple Airlines
18h 35mORD-SXM
5/17Wed
1 stopMultiple Airlines
9h 15mSXM-ORD
$526
4/19Wed
1 stopMultiple Airlines
7h 50mORD-SXM
4/26Wed
2 stopsMultiple Airlines
16h 38mSXM-ORD
$528
4/22Sat
2 stopsMultiple Airlines
13h 25mORD-SXM
4/26Wed
2 stopsMultiple Airlines
18h 22mSXM-ORD
$537
4/22Sat
1 stopUnited Airlines
17h 45mORD-SXM
4/26Wed
1 stopUnited Airlines
10h 50mSXM-ORD
$586
8/24Thu
1 stopAmerican Airlines
6h 41mORD-SXM
8/29Tue
2 stopsAmerican Airlines
21h 14mSXM-ORD
$588
9/10Sun
1 stopDelta
6h 49mMDW-SXM
9/17Sun
2 stopsDelta
18h 54mSXM-MDW
$591
8/23Wed
2 stopsAmerican Airlines
21h 12mORD-SXM
8/30Wed
2 stopsAmerican Airlines
21h 29mSXM-ORD
$591
9/13Wed
2 stopsAmerican Airlines
22h 52mORD-SXM
9/18Mon
2 stopsAmerican Airlines
24h 44mSXM-ORD
$609
8/13Sun
1 stopDelta
6h 49mMDW-SXM
8/20Sun
1 stopDelta
19h 01mSXM-MDW
$631
8/13Sun
1 stopDelta
6h 49mMDW-SXM
8/20Sun
2 stopsDelta
18h 54mSXM-MDW
$681

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1 stopSpirit Airlines
16h 26mORD-SXM
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29h 15mORD-SXM
$193
4/25Tue
3 stopsSpirit Airlines
30h 05mORD-SXM
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43h 54mORD-SXM
$216
5/13Sat
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15h 34mMDW-SXM
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$246
4/28Fri
1 stopAmerican Airlines
8h 52mORD-SXM
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25h 48mORD-SXM
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4/24Mon
3 stopsMultiple Airlines
28h 30mORD-SXM
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4/28Fri
3 stopsMultiple Airlines
37h 18mORD-SXM
$270
4/27Thu
1 stopUnited Airlines
28h 25mORD-SXM
$271
5/13Sat
1 stopMultiple Airlines
26h 55mORD-SXM
$275
4/27Thu
2 stopsAmerican Airlines
23h 57mORD-SXM
$278
4/27Thu
3 stopsMultiple Airlines
44h 05mORD-SXM
$294
5/13Sat
1 stopUnited Airlines
14h 08mORD-SXM
$295
5/13Sat
2 stopsAmerican Airlines
19h 48mORD-SXM
$410
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17h 18mORD-SXM
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1 stopDelta
6h 50mMDW-SXM
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Flights to Saint Martin Island

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Saint Martin Island - Chicago

Cabin classes:

$242
$23
$14
$10