Find cheap flights from Chicago Midway Airport to Caribbean Islands

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MDW — Caribbean Islands
Feb 21 — Feb 281
Round-trip
1 adult
Economy
0 bags
From?
To?
Mon 2/21
Mon 2/28

Good to know

Low season

November

High season

December

Cheapest flight

$94

Average price round-trip

$671

Good deal round-trip

$266

Good deal one-way

$153
Best time to beat the crowds with an average 6% drop in price.
Most popular time to fly with an average 19% increase in price.
Flight from Chicago Midway to San Juan Luis Munoz Marin Intl
(avg. price over the last 2 weeks)
or less
or less

Top tips for finding cheap flights to Caribbean Islands

  • Book at least 2 weeks before departure in order to get a below-average price.
  • High season is considered to be November and December. The cheapest month to fly to Caribbean Islands is August.
  • Morning departure is around 16% cheaper than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

FAQs - booking Caribbean Islands flights

Top 3 airlines serving Chicago Midway to Caribbean Islands

Scores according to KAYAK customer reviews
7.9
DeltaOverall score based on 30296 reviews
8.1Boarding
7.8Comfort
8.5Crew
7.8Entertainment
7.5Food
Airline reviews

O liked the entertainment. I didn’t like being so close to other passengers, especially when they wore their masks wrong or took them down.

Read more about Delta

O liked the entertainment. I didn’t like being so close to other passengers, especially when they wore their masks wrong or took them down.

The best was the timeliness from JFK to SJU, and the comfortless of the Business Class seats. The worse is their poor choices of meals and beverages (Plate of Quinoa or a plate of Charcuterie). The should put more attention to those details, maybe even give something more generic that most people will love.

very good

Felt safe. No bathroom lines since many toilets are located throughout the plane. Passengers did great at following the rules.

Pros: "Excellent crew."
Cons: "Gate agents were a little snippy."
Pros: "The crew was amazing. But there were to many people on the flight for what’s going on. There were middle seats sold and people were upset."
Pros: "Mal servicio; compre un tickets que no permitía escoger los asientos y nos seleccionó la última fila en cada vuelo. La diferencia entre ser priority y regula es bien marcada"
Cons: "Mejor trato a todo pasajero; se reconoce las ventajas de estar en primera clase pero el servicio debe ser excelente"
Pros: "The crew was not overly friendly"
Pros: "Comfortable seats, nice staff, clean facilities"
Cons: "Nothing"
Pros: "Movies"
Cons: "Comfort. Jetblue offers betwee seats ne apacing betqeen rows"
Pros: "Great crew"
Cons: "More leg room and seat width. I don’t like having other passengers pressed against me."
Pros: "Nice service"
Pros: "Love it"
Cons: "In the last months I have travel 3 times , this is the first with Delta. I can say it has been the best experience I had. Good entertainment, the access to texting and the variety of snacks make superior this airline."
Pros: "Crew was awesome. Very friendly."
Cons: "I’m 6 foot tall and I found my seat space feeling crowded. I found myself wishing for just 2 more inches of legroom. It feels that airplanes are being built for quantity of passengers, not quality of flight."
Pros: "Crew was very fast but not enough during boarding and people had brought oversized carry on luggage to the gate requiring stowing. We had checked a carry-on at check in and paid $30 while several people got theirs stowed for free which seemed unfair."
Cons: "The charging for checked luggage has created a situation that was unfair for all travellers and ultimately made the plane’s departure late. This policy drives people to bring too much luggage into the cabin, putting at risk the safety of others and delays."
Pros: "The friendliness of the passengers and most of the crew."
Cons: "One of the younger female flight attendants was rude . She was collecting trash and took my neighbor’s (aisle seat) trash but wouldn’t take mine. I tapped her elbow to show that I had trash, she looked at me but didn’t take it. She returned and still refused until I exclaimed. She rolled her eyes."
Cons: "Cabin was cold enough to store meat. Entertainment system was poor at best. And, of course, the seats were too small and uncomfortable. Time to start looking at other airlines."
Pros: "Friendly crew"
Cons: "No food was served"
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."
Cons: "I was flying standby. I checked the list on line and my name was number 5. I get to the gate and there’s just a handful of customers. The agent said there was enough seats for the standbys I wait and wait for my name to be called but no luck. My name wasn’t cleared yet. Finally I was the next to last one to get a seat. The gate agent who didn’t ask for my name tells me I was all the down at the bottom of the list. While I am glad that I got on I wish I knew what method is use to get your name on the stand by list?"
Cons: "Cabin was too hot since the very beginning. Even in first class."
Pros: "The counter assistant change my seats and my wife and me seat together"
Cons: "Hot cabin"
Pros: "Although our flight was fully booked. The crewmembers on this flight was professional, friendly and efficient. We boarded quickly and took off on time. We even arrived ahead of schedule. Each passenger was given free headphones and complimentary beverages and snacks. I love Delta they are a cut above the rest. They are constantly striving to put the customers needs and wants top priority"
Cons: "Tight seats need more legroom"
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: "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: "Arrived early. Got a beverage & snack which is becoming rarer with American carriers. Video selection was very good. Staff was nice and attentive. Overall a good flight at a reasonable price."
Cons: "Narrow corridor to seats"
Pros: "Everything escept the seat that was too small. I also had problems with the entertainment when trying to see movies."
Cons: "Seats too small ant could not watch Movies beacause the screen was defective."
Cons: "Flight was delayed over 1hr."
Pros: "Buen entretenimiento."
Cons: "La incomodidad de los asientos además que la escala fue de más de 6 horas y fuimos los últimos en abordar. Para colmo los asientos fueron los últimos de la fila y ni siquiera eran reclinables. Creo que deben tomar en consideración a las personas que estamos tantas horas en la escala y permitirles abordar primero además de darles asientos más cómodos más aún si hemos comprado los boletos con tanto tiempo de anticipación."
Pros: "Giid free sandwixh. Very good entertainment system. Good seats."
Pros: "Well, the seats and the lavatories are smaller than ever. And I am quite petite."
Pros: "Excelente"
Pros: "Entertainment is very good"
Cons: "Send my carry on bag, outside."
Pros: "Late delay notification"
Cons: "Called the airline directly to verify the status of flight within 24hrs and everything was on schedule according to them. Even tho the airport at San Juan have not night arrivals due to the effects of Hurricane Maria, and on previous days the same flight had been moved to a morning schedule for that reason. I was notified of the delay within hours of departure of the connecting flight."
Cons: "Small plane"
Pros: "The flight left on time and we got in 15 minutes before the scheduled time. Awesome service from gate to gate."
Cons: "I didn't like that I had to pay for my bags and still purchase food on plane. The price for ticket is already overpriced to begin with. Fuel is cheaper, the planes burn less fuel due to updated design and still the tickets are three times the cost of five years ago. No one should have to pay for bags period. Show that you really care."
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: "Movie selection"
Pros: "Comfortable seating and clean interior. Flight attendants are helpful and courteous."
Cons: "Flight takeoff delayed one hour. Boarding has zoning, but with no structural boarding process, resulted some later zoning customers blocking earlier zoning customers in a single line. Suggest using multiple labeled queue lines, like southwest."
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: "Food was OK. Crew was very friendly"
Cons: "No Entertainment for a 4 hour flight. Plane was very old."
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."
Pros: "Although I am a vegetarian, It was nice Delta was serving sandwiches."
Pros: "newer aircraft; good entertainment options; large overhead storage compartments"
Cons: "cramped passenger space"
Pros: "Excellent choices for entertainment in the 737-900ER. 110V AC and USB ports at each seat, lots of choices for movies and games on seatback screen. Free sandwiches handed out on board."
Cons: "Intercom didn't work super well. JFK is a terrible airport for connections."
Pros: "The plane,plane, plane! Very new and clean , good entertainment. Love it"
Cons: "People taking their time to put their luggage in the bin... Very annoying."
Pros: "Westjet crew are always amazing"
Cons: "Nothing."
Cons: "Everything was great. Westjet is so much better than Air Canada!"
Pros: "Everyone was friendly and efficient."
Cons: "Need to use your own device for entertainment, no screens in flight."
Pros: "Left early and arrived early"
Cons: "Cabin was way too warm. Also not as much space on 737-700 as 737-800"
Cons: "The flight was delayed for over 2 hours without explanation or apology. The entertainment system did not work on my computer. Either the system was not working properly and/or the troubleshooting instructions were incorrect. This was a five hour flight with no entertainment, in a cramped seat."
Pros: "The crew was efficient, but not like some WestJet flight attendants where they crack jokes, & make everyone feel glad they were on that flight."
Cons: "The pilot was going too fast on taxiing to the runway (trying to catch up from a ground delay), & nearly overshot the runway. Had to stop very suddenly and make a sharp turn. Not a great way to begin a flight"
Pros: "Good seat exit row"
Cons: "Flight did not leave on time and no updates"
Cons: "Sat in Plus. Horrible service. No hot towels. Had to ask for 2nd drink and was refused a coffee and Baileys with at least an hour left in flight. No snacks offered or served. The attendant spent most of her flight hiding in her seat and reading a novel. Brutal!"
Pros: "The crew was ok and the service acceptable"
Cons: "The got us a terminal in Toronto (for connection flight to Montreal) which took us 1 hr and 10 mins to switch. It is Air Canada which is sabotaging this good airlline. Is it unacceptable and Air Canada Rouge service is worst. Never fly ever again with Air Canada. I will give another chance to WestJ"
Cons: "Food options are terrible especially when you pay for them. Better quality needed"
Cons: "No beverage service at all and only pretzels offered when I asked if I could have nuts or cookies."
Pros: "The crew filled up my reusable cup instead of using a single use one for my drink. They were very friendly and great."
Cons: "A lot of single use plastics are used on the flight for food and such. It is very wasteful. It would be great is WestJet could find a way to lessen their plastic foot print"
Pros: "Great flight! Great service and way more room than air canada! And ACTUALLY on time!"
Pros: "Staff is friendly."
Cons: "We didn’t appreciate the walk from Gate 4 to Gate 41 TWICE when the departure gate was changed. We are in our 80’s and it was quite a trek!"
Pros: "The flight was on time."
Cons: "That I had to pay $30 for one checked bag, would have thought the first one was free!"
Cons: "Coffe was soooo bad!"
Pros: "Flight attendants, movie on board, price"
Cons: "Plane was delayed and the baggage handlers in Denver were Atrocious!! I actually took video I was so shocked!"
Pros: "One thing that was thoroughly entertaining and unique was magic mory our flight attendant. She was brilliant and fun making jokes or comments when she made announcements. I have never heard anyone like that before and loved it. It was no like the nonchalant speaking that no one wants to listen to because they’ve heard it so many times before. When Magic Mory spoke, she made sure she was entertaining us, cared cause she knows we listened to it who knows how many times. Thanks for the authentic experience on west jet Magic Mory! I personally love how she also made a little song dedication and sung over the intercom. Thanks for a memory experience!!"
Pros: "On time both sides"
Pros: "The check in staff are very helpful and kind especially Rachel! The service was excellent very happy and helpful staff during our flight. The pilots made such a smooth landing and we are so thankful to be home safely!"
Cons: "Still cramped in the seats!"
Pros: "Loved WestJet! They are the best airline, always super friendly"
Pros: "In the flight there was a crew member she was not polite ...As I want to use washroom urgently & I was not very much familiar where is washroom I asked her three times she did not reply back...Just walk away...if she does not understand me, she cam say pardon me...but she just left"
Cons: "Everything else was good...great help from Abbotsford staff...I really appreciate that"
Cons: "The wifi is paid.. no TVs"
Cons: "Did not purchase food on the plane"
Pros: "Agreed to check bag at gate, early boarding in return. Great gift!"
Cons: "LaGuardia is terrible. They shrank departure lanes and we got stuck on the plane for an hour. I hate this airport. Something always goes wrong."
Cons: "We didn’t like having to take the red eye to meet our Costa Rica connection. We"
Cons: "The flight from Toronto to Phoenix was even worse than Air Canada. No food available to purchase. Cramped seating. Entertainment system was difficult to navigate...the buttons didn't work half the time, the movies were already playing and all the "bad" words were edited out which changed the entire movie. Waste of time. Would not fly WestJet again based on this experience. And what's the point of checking in online when you're called to verify id again at the check in counter."
Cons: "Flight crew arrived late delaying take off"
Pros: "Arrived early"
Cons: "Seating in the back"
Pros: "Always friendly"
Cons: "No complimentary drink all of a sudden"
Pros: "Staff are always fun and efficient, but the drinks came very late. In Asia, even if the flight is only 1 hour, they have the time to serve a lunch and clean up....."
Cons: "Meal"
Pros: "Nice flight crew."
Cons: "Ground crew couldn’t get luggage on plane fast enough because of lack of staff so we sat on tarmac for 2 hours."
Pros: "Boarding was quick and the staff as very friendly. The pilot was hilarious."
Pros: "It was a smaller aircraft and the staff were friendly"
Cons: "was right at the back of the plane and could not hear the announcements clearly."
Pros: "The crew was friendly and attentive. Boarding was seamless and smooth. Departing from New York, they proactively asked the passenger to volunteer checking their carry-ons ahead of boarding so they didn't have to waste time when boarding the flight."
Cons: "There was no entertainment. The snack could have been something more substantial. The overhead cabin space both for departing Toronto and departing New York was was insufficient."
Pros: "Ease to board, on time boarding"
Cons: "Return to gate prior to take off"
Pros: "Great experience...."
Cons: "There were wait times...too long"
Pros: "We arrived early."
Cons: "Checked bag fees. Agents at check-in tried to get me to check my carry-on claiming my carry-on was too big. My carry-on is a pilot crew bag by TravelPro, which I pointed out to them. Had to get a supervisor. No free food during the flight. Luckily, someone told me. I ended up purchasing food from a restaurant in the terminal to bring on the flight."
Pros: "Very cheerful and friendly crew. Made the journey very enjoyable."
Cons: "Nothing"
Pros: "The staff were very good jumped in by running with me in a wheelchair till we met up with a cart then next team met up and took me again in a wheelchair down elevator made it just on time"
Cons: "Not having my rides there’s that I set up and almost late"
Cons: "Flight was delayed and they never let us onboard even when I was able to make it to the gate before it was closed. After missing the flight the hotel vouchers was provided but we were asked to report in 2 hours (i.e 4AM) so think abou whole night was literally wasted. Finally next flight was 11AM in the morning which I ended up boarding and finally reach Toronto after 8 hours of delay."
Cons: "Il serait bien d'avertir plus à l'avance les passagers au sujet de l'application nécessaire pour l'entertainement ou permettre de l télécharger via le wifi de westjet"
Pros: "A bit more seat room. I'm a tall guy and was a bit cramp"
Pros: "Westjet flight crews are always really nice and helpful. When we travelled out to kelowna on the 14th it was a day after our daughters 1st birthday and they announced it over the intercom which was sweet"
Cons: "The flight back was an hour late to begin with, flight itself was good landing was probably the worst landing I've ever felt in my 20-25 flights, was an extremely tough landing. Smoke alarms went off in he airport so we had to wait for a bridge and luggage"
Pros: "westjet connect to watch a tv show or the news or something"
Pros: "Great crew, West jet connect worked fabulously"
Cons: "Cramped space and airplane food"
Cons: "No entertain system"
Pros: "My daughter ordered the tickets for us but she didn't pick seats. We forget to pre checked in, either. Our flight was very full so We are so lucky got the first class seats! This is the first time in our life with first class experiences! It was on the July 4th and saw a lots of fireworks in the airplane! We are so exciting! Thank you for West Jet Airline!"
Pros: "Friendly staff"
Pros: "The young man who finally boarded passengers after multiple delays stayed very calm and profession and communicated clearly to expedite our boarding process."
Cons: "Everything. We had three gate changes and an hour delay. Frontier communicated these changes terribly. The seats were painfully uncomfortable. No beverages available on the flight unless you paid. The entire A concourse of DIA seemed full of angry Frontier passengers. The customer service was packed"
Pros: "I got back on time and smooth flight!"
Cons: "Recliner sitting"
Pros: "Was fine overall for a no frills airline"
Cons: "We were not notified prior to the flight that we could not of been a plane so of course the only snack I had with me for a four hour flight was a bag of peanuts. We were told we were not allowed to take any peanut products out on the plane and this was told to us from at takeoff."
Pros: "Seat is too tight and small . Dart has no decline lean back . It’s very uncomfortable ."
Cons: "Fix the issue above."
Cons: "We arrived at the airport to find out Frontier had failed to notify us our flight had been delayed. There was no call or email notification. Because of this delay, we would be missing our connecting flight from Denver to Miami, and because of that, missing our check in time to board our Cruise in Miami. We could not find any reasonable one way plane ticket from SLC to Miami to arrive in time that was less than $700 per person. We ended up having to make the choice to miss our cruise, our vacation, and all our flights. Over $1000 down the drain. Absolutely Unbelievable. I am shocked and disappointed by this, I cannot believe what a huge let down this is. The one thing I can say is that Frontier did attempt to make amends by offering a small $100 flight voucher (although frankly after this experience, why on earth should I fly with them?) but the attempts to fix it, like offering to rebook us (for a fee I should add) to fly to Orlando, but that WE’D have to pay to find a way to Miami (which is at least a 3 hour drive!) were absolute nonsense. I’m out $1000, I missed an amazing opportunity, I lost my vacation, and I now have had to waste limited time off days at work. Absolutely horrific experience"
Pros: "6 hour delayed 3 dollars for a can use?.. really"
Cons: "Everything"
Pros: "Pretty much smooth flight"
Cons: "Have to pay $2.99 for can of soda"
Cons: "Flight was not on time, no communication the aircraft cabin temperature was uncomfortable. Charged for all beverages no blankets available."
Pros: "Same as TPA to DEN"
Cons: "Same as TPA to DEN"
Pros: "Price good"
Cons: "Ticket counter people terrible. Rude and brusque. No help with bags. Seats on plane close and hard. Uncomfortable to point of back pain. Will only fly Frontier in nothing else available. Price is only thing they have going for them."
Pros: "There is only so much you can do on airplane mode. I asked for hand sanitizer and the steward gave me some of his personal stuff. How awesome!"
Cons: "Lady next to me applying vice vapor rub every 20 mins"
Pros: "Plane was new. Very surprised"
Cons: "My personal information was wrong from kayak so I couldn't get my boarding pass or prepay for my carry on bag so had to pay $45"
Pros: "I would say the price, but with all the add ons of paying for your carry on, I would have rather paid more for a comfortable flight."
Cons: "The seat first and foremost. I felt like I was sitting on a cement chair. No refreshments. No entertainment. Far too crowded."
Pros: "Leave on time, Arrive on time- wonderful!"
Cons: "Charged $45.00 for the check in luggage."
Cons: "I hated every aspect of that flight."
Cons: "Charged for the food. The prices were not reasonable"
Pros: "On time departures and early arrivals followed by early access to gate. Other airlines often arrive early and sit on the tarmac until departing flight vacates gate."
Pros: "Watching the plane arrive to pick us up. Once in place the pilot had to stick his head out of front window to see why they couldn't fit for the arm of disembarkment platform!"
Cons: "I was never notified of delay"
Cons: "LITERALLY EVERYTHING WENT WRONG. From "paying" for a seat, paying for a CARRY-ON bag, and if you check, to having to check a bag 1 hr prior (no one tells you any of this beforehand). They delayed the flight 2 hours, and I was waiting outside gate because there were more things to do. I kept checking my phone to make sure the flight wasn't delayed longer. All of a sudden, the flight was BOARDING! An HOUR early! It was 3:00 and the flight was leaving 3:15. I raced through security, hopped on the shuttle, ran the wrong direction (even their departure gate had changed) and finally made it at 3:14. The doors were closed, but the attendant let me on, which was the ONLY decent part of this experience. Someone was sitting in the seat I paid for, but I let it go. Adding insult to injury, I had to pay for WATER ON THE PLANE. NEVER EVER FLY FRONTIER-you aren't saving money and the experience was shoddy and unreliable. #findanewfrontier"
Pros: "The markup on a can of soda is near 200% when selling it for 2.99. Lower that price and your sales will actually increase which will then rolli into more credit card sales."
Cons: "Every other airline offers you peanuts and a drink. Frontier nick and dimes the passenger for everything."
Cons: "Nothing about this flight was comfortable. Seats do not recline, bathroom ran out of water to wash your hands, and flight was incredibly delayed and not well communicated to passengers."
Pros: "No info on delay, extra bag fees, bad seating...good thing is that we made it safely."
Pros: "40 dollars for checked luggage + 45 dollars for a carry on bag is more than shocking. I will choose Frontier again because of all the rediculous and surprise fees."
Cons: "Rediculous baggage fees"
Pros: "----------"
Cons: "Main thing was gate, ticket said one gate, got on at another. Was never posted at gate sign, had to ask someone which plane they were getting on. Seemed very mis-happened arrangement. Seats suck on their planes also. Probably won't fly with them again because of that reason mostly."
Cons: "Everything it sucked. Heard they had 20 pilots walk off the job today. Flights cancelled people really upset. What the F... is management doing and at Christmas time too. So many disappointments!!"
Pros: "I enjoyed that I had an aisle seat when I chose a random seat instead of paying for one. The crew seemed nice, a little overwhelmed but I had limited interactions with them. Boarding was fine and I was relatively comfortable on the plane."
Cons: "I did not like that Frontier allowed for multiple people on the plane to yell and scream about the flight being delayed and how terrible their service was using lewd, degrading language that I felt unconfortable listening to after spending 6+ hours traveling before I even got on the plane! As a holiday traveler I am aware that there are delays and things are congested, maybe I'm the only one. I did not enjoy that I had to be subjected to that while sitting on an airplane that landed 45 minutes before even reaching gate. This continued on to the baggage claim section for another 45 minutes until finally I told the guys to shut up! The 2 men should have had security called on them or taken to another room to air their grievances instead of subjecting the rest of us to their tirade. I was extremely uncomfortable and disappointed in the way Frontier airlines at O'Hare handles disgruntled passengers and will most likely not fly Frontier again despite having a relatively enjoyable flight."
Pros: "Direct flight"
Cons: "Frontier charges you for EVERYTHING. Drinks, carry on bags. And there's no comfort at all. The seats are thin and don't recline. There is zero entertainment. Don't fly them if you think you're saving money because by the time you are done, you've paid extra for everything so it's the same price as other airlines, and definitely less comfortable. Will never fly them again."
Pros: "Smooth flight. Kind efficient staff"
Cons: "Extra "fees""
Cons: "nice price, but i didnt know id be charged for a carry on or to check in and seat assign - also on midnight return - you woke me up 6 times blabbing loudly with announcements dont have 6 am departures and 7 pm returns? shut up while i am sleeping - tell me up front of your extra charges"
Pros: "The plane was clean, comfortable, and the crew was great."
Cons: "Everything has a price tag. Pay more for specific seats, pay more to select a seat at booking, pay more for carry on bags. No beverages, no snacks, unless you pay more. Last time I rode Frontier they had warm cookies. Now it is the most low budget, no frills airline still flying. Inevitably there will be credit card slots on the lavatories. Credit card slots to allow the seat belts to extend, and the O2 masks only drop if you swipe your card, yet again."
Pros: "Friendly crew and professional flight"
Pros: "The price was great"
Cons: "Crying babies on flights not enjoyable. That felt like the longest flight ever."
Cons: "My flight was changed to a red eye and didn't receive any help changing my flight or discount back. I ended up having to go into a different airport since I could not afford to fly in at 5am the next day. Horrible customer service and will never be Flying frontier again or recommend anyone else to fly with you."
Pros: "The flight was at the right time (overnight and arrived on time) and the price of the ticket was competitive."
Cons: "The seats and spacing between the rows was incredible. The quality of the seats were extremely poor and uncomfortable. The pull down tray was not large enough to set my IPAD."
Cons: "For starters what is the point of paying a $400 ticket if I have to pay for a seat again?? This makes no sense. When i board i noticed the tray sizes where cut to 3/4s of the original size, and the seats where plastic and VERY uncomfortable. I am 5 feet tall and even my knees were cramped. TERRIBLE airlines. NEVER will fly Frontier again."
Cons: "At least apologize to passengers and let them know estimated time of arrival if you are delayed. Pilot acted like we were on time"
Pros: "when I got to the counter in Miami the person was awful and how is it that you have to pay so much money for a carry on ,"
Cons: "the comfort of the plain is awful won't get on again"
Pros: "The crew was great. Thats where it ends."
Cons: "New hard plastic seats laughable table trays Obscenely high baggage fees, even for carry-ons! A diabetes inducing snack menu that is some how MOM certified This is the cheapest airline I have ever seen and while you get low ticket rates, you end up paying more than you normally would if you want to travel and take your clothes with you. Never again."
Cons: "Carry on bag charge is WAY too costly . space is there, no more work for Frontier employees. I paid $35 going and $40 returning for my bag. Also, purchasing your seat, maybe it should be first come first serve."
Pros: "Crew and pilot were helpful."
Cons: ". When I made my connecting Th seats were equally uncomfortable. I am an average fit person. This was a terribly uncomfortable flight as a result."
Pros: "It was sorta cheap, not frills. After the delay we did make up some time, but.... nothing too amazing overall."
Cons: "Paying for Cary-on bag was super expensive ($40 bought with the ticket, it's even more expensive at the airport) and sort of offset the benefit of a cheap flight. There was no food or entertainment, and the flight was delayed by an hour because we had to wait for another Frontier flight ---- so that says something. Seats were super uncomfortable and the tray tables are stupidly small, maybe could hold a sandwich and nothing else. No other amenities at all. I'd rather pay $40 more for the flight, get some snacks and comfy seat and a free carry-on. Won't fly Frontier again unless I have to."
Pros: "The whole crew was so nice and very understanding"
Cons: "The seat where so uncomfortable it was terrible I just almost wanted to lay down on the floor"
Pros: "On time. Courteous crew."
Cons: "All the extra fees for booking a seat in advance."
Pros: "Not a thing"
Cons: "Trays were the size of my plane ticket had to sit laptop in lap, had to pay $6 for a diet coke when I thought it was free and couldn't return it because attendant opened it. By far the worst airline ever"
Cons: "Flight delay, no reason given."
Cons: "They don't ever provide water! But, then, the fold-down tray was so small a cup wouldn't balance on it."
Pros: "the price was right and the flights were on time."
Cons: "they nickel and dime you right up to a nicer carrier! It's horrible! You have to pay for a carry on bag and the seats are SOOOOOOO uncomfortable. I will attempt to avoid frontier in the future."
Pros: "The crew"
Cons: "At no time was I made aware during my booking that I would be charged for a carry on either. The crew was great. Did not like not being offered even water."
Pros: "Crew was great flight was good"
Cons: "When I booked the ticket it was 317. When I went to check in on the website it told me I could only bring a carry on if it fit under seat and had to pay for overhead storage which was MORE expensive than checking in belly of plane which is what I had to do because I had a Small what used to be a carry on bag...THEN I went to pick a seat and I could ONLY pick a seat I HAD to pay for!....so my "economy" fare cost me an extra 77.00 ONE WAY!....I will not be flying your airline again. Had I know about the MANYextra expenses You really should be more upfront and transparent with the ACTUAL fees to fly Frontier"
COVID-19 information

Safety measures for airlines flying from Chicago Midway Airport to Caribbean Islands

Airlines flying from Chicago Midway Airport to Caribbean Islands have enacted additional safety measures and adjusted policies to better accommodate travelers. Policies vary by airline.

Heightened sanitation

Daily cleaning, installation of cabin HEPA filters on flights from Chicago Midway Airport to Caribbean Islands

Mandatory masks

Masks required on board, masks provided on flights from Chicago Midway Airport to Caribbean Islands

Social distancing seating

Middle seats unavailable to book on flights from Chicago Midway Airport to Caribbean Islands

Pre-flight testing

Testing for antibodies, testing for symptoms for flights from Chicago Midway Airport to Caribbean Islands

Book cheap flights from Chicago Midway Airport to Caribbean Islands

Recent round-trip flight deals

3/2Wed
1 stopDelta
6h 10mMDW-SJU
3/8Tue
1 stopDelta
6h 32mSJU-MDW
$187
3/8Tue
1 stopDelta
9h 10mMDW-SJU
3/16Wed
1 stopDelta
6h 32mSJU-MDW
$197
3/21Mon
1 stopDelta
8h 48mMDW-STT
3/23Wed
1 stopDelta
10h 17mSTT-MDW
$203
2/5Sat
1 stopDelta
9h 10mMDW-SJU
2/9Wed
1 stopDelta
8h 40mSJU-MDW
$207
2/1Tue
1 stopDelta
6h 10mMDW-SJU
2/8Tue
1 stopDelta
8h 40mSJU-MDW
$238
2/15Tue
1 stopDelta
9h 34mMDW-SJU
2/17Thu
1 stopDelta
8h 35mSJU-MDW
$239
2/8Tue
1 stopMultiple Airlines
16h 14mMDW-SJU
2/10Thu
1 stopMultiple Airlines
11h 22mSJU-MDW
$244
2/7Mon
1 stopDelta
9h 10mMDW-SJU
2/17Thu
1 stopDelta
8h 35mSJU-MDW
$248
4/6Wed
2 stopsMultiple Airlines
22h 11mMDW-SJU
4/12Tue
2 stopsMultiple Airlines
19h 25mSJU-MDW
$253
2/9Wed
1 stopDelta
8h 47mMDW-STT
2/16Wed
1 stopDelta
9h 24mSTT-MDW
$253
2/1Tue
1 stopDelta
6h 10mMDW-SJU
2/10Thu
1 stopDelta
8h 40mSJU-MDW
$254
2/8Tue
1 stopMultiple Airlines
10h 58mMDW-SJU
2/15Tue
1 stopMultiple Airlines
23h 06mSJU-MDW
$255
5/1Sun
2 stopsMultiple Airlines
27h 05mMDW-SJU
5/10Tue
2 stopsMultiple Airlines
15h 36mSJU-MDW
$256
2/5Sat
1 stopDelta
9h 34mMDW-SJU
2/10Thu
1 stopDelta
11h 32mSJU-MDW
$257
2/12Sat
2 stopsMultiple Airlines
21h 16mMDW-SJU
2/19Sat
2 stopsMultiple Airlines
14h 05mSJU-MDW
$258
2/9Wed
3 stopsMultiple Airlines
19h 45mMDW-SJU
2/15Tue
2 stopsMultiple Airlines
22h 20mSJU-MDW
$259
3/2Wed
2 stopsMultiple Airlines
21h 16mMDW-SJU
3/8Tue
2 stopsMultiple Airlines
17h 26mSJU-MDW
$260
3/1Tue
2 stopsMultiple Airlines
37h 47mMDW-SJU
3/9Wed
2 stopsMultiple Airlines
17h 30mSJU-MDW
$261
2/9Wed
3 stopsMultiple Airlines
19h 45mMDW-SJU
2/15Tue
2 stopsMultiple Airlines
22h 20mSJU-MDW
$264
3/30Wed
1 stopFrontier
14h 50mMDW-PUJ
4/10Sun
1 stopFrontier
11h 30mPUJ-MDW
$517

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Recent one-way flight deals

3/8Tue
1 stopDelta
9h 10mMDW-SJU
$94
2/6Sun
1 stopDelta
9h 10mMDW-SJU
$104
3/29Tue
1 stopDelta
6h 10mMDW-SJU
$120
2/4Fri
1 stopDelta
9h 10mMDW-SJU
$129
1/30Sun
1 stopDelta
6h 10mMDW-SJU
$135
2/26Sat
1 stopDelta
6h 40mMDW-STX
$135
3/4Fri
2 stopsMultiple Airlines
42h 22mMDW-STT
$151
2/6Sun
3 stopsMultiple Airlines
45h 38mMDW-SJU
$159
3/4Fri
3 stopsMultiple Airlines
41h 05mMDW-STT
$169
3/29Tue
1 stopDelta
7h 29mMDW-MBJ
$186
3/21Mon
2 stopsMultiple Airlines
21h 38mMDW-NAS
$192
5/20Fri
2 stopsMultiple Airlines
24h 38mMDW-SJU
$193
2/28Mon
1 stopDelta
6h 21mMDW-PUJ
$194
5/20Fri
2 stopsMultiple Airlines
35h 18mMDW-SJU
$199
3/21Mon
3 stopsMultiple Airlines
38h 08mMDW-PUJ
$207
2/13Sun
1 stopFrontier
9h 30mMDW-SJU
$209
3/26Sat
1 stopFrontier
9h 40mMDW-SJU
$215
3/26Sat
1 stopFrontier
9h 40mMDW-SJU
$274
2/21Mon
1 stopFrontier
8h 45mMDW-SJU
$285
3/2Wed
2 stopsWestJet
26h 04mMDW-PUJ
$346

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Chicago Midway Airport - Caribbean Islands Flights