Find cheap flights from Chicago Midway Airport to Caribbean

Find cheap flights from Chicago Midway Airport to Caribbean

Round-trip
Economy
Chicago (MDW)
Caribbean
Wed 11/25
Wed 12/2
Any month
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Good to know

Low season

November Best time to beat the crowds with an average 6% drop in price.

High season

May Most popular time to fly with an average 19% increase in price.

Average price round-trip

$516 (avg. price over the last 2 weeks)

Good deal round-trip

$364 or less

Good deal one-way

$140 or less

Top tips for finding cheap flights to Caribbean

  • 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 is August.
  • Morning departure is around 5% more expensive 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 flights

Which airlines have a flexible cancellation policy for flights from Chicago Midway to Caribbean due to COVID-19?

Which airlines apply social distancing measures on flights from Chicago Midway to Caribbean due to COVID-19?

How long is the flight to Caribbean from Chicago Midway?

What is the cheapest flight to Caribbean from Chicago Midway?

Which airlines fly to Caribbean?

How does KAYAK find such low prices on flights to Caribbean?

How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago Midway Airport to Caribbean?

What is the Hacker Fare option on flights to Caribbean?

What is KAYAK's "flexible dates" feature and why should I care when looking for a flight to Caribbean?

Top airlines flying Chicago Midway to Caribbean

Scores according to KAYAK customer reviews

7.9
Delta
Overall score based on 28,787 reviews
8.1
Boarding
7.8
Comfort
8.5
Crew
7.8
Entertainment
7.5
Food
Airline reviews

Pros: "The crew was not overly friendly"

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: "Great crew. Seat was not too bad."

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."

Pros: "Nice suites though they feel a little cramped. Good for privacy"
Cons: "lounge in PEK was under renovation, temp lounge was not very nice"

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: "The crew was amazing had no problems!"
Cons: "Nothing had a great experience!"

Cons: "All was good"

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: "On Time. Nothing else to say,"

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: "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: "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: "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: "I have always kinda shied away from delta, but I have used them the last two times I flew. And I will be using them in the future! Friendly and professional!"

Cons: "I understand gate changes happen, but I got 4 texts switching the gates back and forth. Is that necessary?"

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: "Quick flight; helpful and friendly staff"

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: "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."

Cons: "I flew a dog in baggage on the JFK to SJU flight. It took almost a hour to receive her in San Juan and then the crate was cracked. I am wondering what happened to my dog if it was jarred so much to crack the plastic crate. Five days and still nothing from Delta on the clsim."

Pros: "Very efficient boarding and great crew!!"

Pros: "The crew was good."
Cons: "Seats where uncomfortable. They didn't have the adjustable padded headrest even though we did coming to Winnipeg. You can no longer change your seat selection 24 hrs before you're flight without a fee. There was also no entertainment coming from Winnipeg even though there was entertainment going to Winnipeg."

Pros: "The staff at WestJet was very accommodating to me."
Cons: "Better snack choices"

Pros: "The crew worked hard to ensure that we had a good flight with minimal interruptions"
Cons: "Delays always hurt, the flight was delayed yet there were no notifications and additionally the delay was closer to an hour long since boarding only started 20 minutes late."

Pros: "Excellent flight attendants. Comfortable seating. Nothing really was bad about the flight. Attendants at departure as well as arrival were helpful and attentive to our needs."
Cons: "Nothing I can think of."

Cons: "Minor point. They boarded the plane very early. We got to the gate 1/2 hour before departure, and were almost the last ones to board."

Pros: "Flights arrived early, boarding was very smooth"
Cons: "Kids on the flight were extremely disruptive despite flight attendants’ attempts to get them settled down"

Pros: "All the staff from airport baggage area, boarding to during flight and then leaving were efficient and personal. Even the pilot spoke as a caring person."
Cons: "Storm at Toronto arrival resulted in a long delay in being able to pick up luggage which had visibly been exposed to dirt and moisture."

Pros: "Super helpful gate agents and smooth entry process back into the country."
Cons: "Crew on plane weren’t great. The male attendant wasn’t very understanding when a little girl had to use bathroom before we even left the gate. One of the women attendants ended up letting her go while taxing. Clearly the guy doesn’t understand kids. We could have ended up with a plane smelling like"

Cons: "Always a ‘full flight’ and they run out of spacein the overhead storage"

Pros: "It was the last leg of my journey back home."
Cons: "Not much more could be done on such a short flight."

Pros: "Not much, other than it got us to our destination about 15 minutes ahead of schedule"
Cons: "The food on WestJet is atrocious when you purchase Plus seats. If you are on a flight less than 2.5 hrs you get cookies or pretzels and poor wine. If you are on a flight over 2.5 hrs you get some hot in a box. I had an egg and bacon fajita. The fajita was like warm cardboard."

Pros: "on time"

Pros: "Mate"
Cons: "Late"

Pros: "Flight was smooth no problems"
Cons: "Being 40 minutes late Cost to me $234.00"

Pros: "Great price"

Pros: "Smooth. On time"

Pros: "Crew and staff are pleasant."
Cons: "There was a typo in my reservation (either a WJ problem or a Kayak problem). As a result I couldn't do an online checkin and ended up getting a middle seat at the airport."

Pros: "Crew was funny."
Cons: "Flight delayed 3 times, ended up being a 4 hour delay after a delay on our first flight already. No help at terminals until just before flights. Employees seemed spread thin. Need more help."

Pros: "Wonderful family trip...comfortable seating, pleasant crew and enjoyable flight."
Cons: "Lots of walking in the airport"

Pros: "No hassle boarding and smooth flight. Courteous flight attendants."
Cons: "Wifi capability to watch movies was weak. I in fact paid for wifi on the way to Canada on June 28, but was not able to use the wifi at all. It could have been my laptops browser issue. All and all, great flight."

Pros: "Downloaded WestJet app in Toronto while waiting to board the next flight. Enjoyed the selection of free movies and TV shows. Flight was on time."
Cons: "The connecting flight to Halifax was a long haul at the end of B terminal. Same airline, just really far away! Maybe it has to be that way due to the international arrival, but it was stressful. Wear tennis shoes! Flight attendants were efficient but not as friendly as the Toronto folks. The advertised “power at every seat” did not work."

Pros: "Don’t upgrade to first class on this flight. One beverage. No food. Not worth it atall"
Cons: "Don’t upgrade to first class on this flight. One beverage. No food. Not worth it atall"

Cons: "Doing in flight entertainment via app is a fine idea. But your app requires way too many permissions so I won't use it. Otherwise, an excellent airline."

Pros: "Sweet and short flight."

Pros: "Arrived safely."
Cons: "The fact that planes still aren’t loaded back to front slows down any chance of efficiency. You’re slowing your own business down by not using common sense. Lots of turbulence on both flights."

Pros: "Flight crew very friendly."
Cons: "Entertainment app. is terrible, movies really old."

Pros: "Easy check in and nice crew!!!! No complaints at all!!! I would fly them again!!! I would definitely recommend them to others!"

Pros: "My flight got cancelled many times due to the weather condition. I’m happy that west Jet keep sending me the updated flight. And when I have to call and speak to someone, my calls got answered within 15 minutes. I’m happy with the service over all. Thank you."

Cons: "We sat on the tarmac in the plane for 4 hours when 20 minutes into the delay the flight attendants knew they weren't going to be able to fly with us, and instead of cancelling the flight 20 minutes into the delay we sat on the plane for 4 hours while the crew knew we were not going to take off. There were a handful of infants and children (my 10 month old nephew included) and for the crew to keep the passengers on the plane for 4 hours when they knew the flight was going to be cancelled is unacceptable."

Cons: "No movies available"

Pros: "No much.."
Cons: "To start.. due to your company combining two out going Toronto flights in Vancouver and then being late off the ground in Vancouver because if that we missed our connecting flight in Toronto to Ottawa. This in turn made us miss a very important appointment in Ottawa. I’m sure the company loves that they saved money by combining those flights however you flunked the test with me. All the corporate could care less about me missing my flight after they look at the bottom line but I will be taking my $1600 plus money elsewhere in the future because of the aggravation, frustration and I don’t care attitude that your company has provided me. I’ll I want to do is get back to Vancouver in my return flight hopefully put most likely on time with my two girls and forget that your company does exists. Thanks for the headaches and goodbye.."

Cons: "Our original flight was cancelled due to WestJet reasons (plane was not safe to fly) the following evening the flight was supposed to depart at 7pm we didn’t take off until 10:37 pm causing an arrival of 940AM into London instead of 7:23AM primarily because the crew they chose for this new flight was coming from Montreal so we had to wait for them to arrive."

Pros: "There is no entertainment so why ask.this question repeatedly and I understand on longer flights that is valid but on these flights it is not applicable"

Pros: "There was one nice, friendly flight attendant. Nice to have a variety of beverages and pretzels offered (I feel I don't expect this anymore from domestic flights-- usually just expecting the coffee or water option)."
Cons: "The seats were up there with the most uncomfortable I've ever experienced--mostly due to the lack of ability to recline. I feel a four hour flight is sufficiently long enough to provide people some space to relax. We were delayed for whatever reason, lack of communication from staff to the passengers that were boarded really quite early (perhaps too early). One of the staff, while nice enough, was being a bit snarky to people as they were trying to, what I thought was helpfully, give them their garbage."

Pros: "Great service all around."

Pros: "The wifi inflight service"
Cons: "No food, only snacks."

Cons: "No crew to load the baggage or guide us out of the terminal. After a day of cancellations and delays for my one flight, my baggage was lost. I felt like notifying us about delays and cancellations could have been handled more efficiently. Also, the staff was not helpful when my baggage was lost"

Pros: "I really enjoyed my Canadian Vacation. Everyone was nice and being from the islands it was really a Wonderful and Cold Experience. I never dreamed I would go skiing"
Cons: "Cleaning snow off my rental. Other than that it was Amazing"

Cons: "The reasons that I book with Westjet are that the attendants joke with each other, appear to really enjoy their jobs, and provide over the top customer service. On this flight no one was jovial or smiling, the garbage sat on our trays for the majority of the flight. The attendants spoke to each other more than the passengers. Very disappointing!"

Pros: "The pilot was awesome and the crew."

Pros: "The boarding process wasn't to bad"
Cons: "The crew did not ask if we wanted a snack. I had cranberry juice and thencupnwas barely full. Crew did not ask if I wanted a snack or even offer d a snack. . Yet the people behind me was asked if they wanted a snack. Rude ."

Pros: "Great efficient crew."
Cons: "I miss the free movies..."

Pros: "The professionalism of the crew and the spacious plane."

Pros: "Extra leg room"
Cons: "Entertainment system didn’t work. Food was non descriptive. Service was spotty and far from attentive"

Pros: "The crew was very nice."
Cons: "The plane was old so no entertainment, food was not good, could not sit in area waiting for flight, no chairs left and I was 5ere. Very early. Travelling is not great anymore, the crew try’s their best I know."

Pros: "Crew was very entertaining."
Cons: "Not enough space. On long flights (over 3 hours) a hot meal that you don't have to pay extra for would be nice. No tv's which is boring"

Pros: "Everything was streamlined and easy to understand. We made it on time and the staff were friendly, especially with our young son who is one Ana half."
Cons: "the Airline was pretty cramped but it was a short flight so it wasn’t too bad."

Pros: "The crew was very nice"
Cons: "The flight was 2 hours late and we missed our connection. NOT happy."

Pros: "Excellent customer service. On time flight."
Cons: "Bathroom was filthy but that's a reflection on the patrons not West jet."

Read more about Delta
COVID-19 information

Safety measures for airlines flying from Chicago Midway to Caribbean

Airlines flying from Chicago Midway to Caribbean 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

Mandatory masks

Masks required on board, masks provided

Social distancing seating

Middle seats unavailable to book

Pre-flight testing

Testing for antibodies, testing for symptoms

Book cheap flights from Chicago Midway Airport to Caribbean

Recent round-trip flight deals

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