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Cheap Flights from Midway to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Punta Cana
Punta Cana1 stop$420
Santo Domingo
Santo Domingo1 stop$520
Montego Bay
Montego Bay1 stop$486
Oranjestad
Oranjestad1 stop$614
Nassau
Nassau1 stop$550
Kingston
Kingston1 stop$873
Simpson Bay
Simpson Bay1 stop$605
Providenciales
Providenciales1 stop$544
George Town
George Town1 stop$540
Aguadilla
Aguadilla1 stop$284
St. John's
St. John's1 stop$771
Punta Cana
Punta Cana1 stop$420
Santo Domingo
Santo Domingo1 stop$520
Montego Bay
Montego Bay1 stop$486
Oranjestad
Oranjestad1 stop$614
Nassau
Nassau1 stop$550
Kingston
Kingston1 stop$873
Simpson Bay
Simpson Bay1 stop$605
Providenciales
Providenciales1 stop$544
George Town
George Town1 stop$540
Aguadilla
Aguadilla1 stop$284
St. John's
St. John's1 stop$771
Booking Insights

Price, demand and travel trends for Chicago Midway Airport to Caribbean Islands flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

Are flights from Chicago Midway Airport to Caribbean Islands cheaper or more expensive than last year?

Fares from Chicago Midway Airport to Caribbean Islands are about the same as they were in November last year, averaging $691 round-trip.

What's the cheapest month to fly from Chicago Midway Airport to Caribbean Islands?

May is typically the cheapest month to fly from Chicago Midway Airport to Caribbean Islands, with round-trip fares averaging $545. November and October are usually the most expensive, averaging $743 and $703, respectively.

How do fares from Chicago Midway Airport to Caribbean Islands vary by day of the week?

On average, Tuesday is the cheapest day to fly from Chicago Midway Airport to Caribbean Islands and Thursday is the most expensive. Looking at the past 12 months of KAYAK data, it's 22% more expensive to fly on a Thursday compared to Tuesday.

What's the best time of day to fly from Chicago Midway Airport to Caribbean Islands?

It's cheapest to fly to Caribbean Islands in the evening with average prices of $491. The morning is the most expensive time to fly, with average prices of $671.

What's the best time to book a flight from Chicago Midway Airport to Caribbean Islands?

Book your flights 15 weeks before your trip. KAYAK data collected over the past 12 months shows that booking in this window can save you around 20% compared to booking at the last minute (within 2 weeks of departure).

Key details for Chicago Midway Airport to Caribbean Islands flights

Low season

December
Beat the crowds with an average 45% drop in travelers.
The most popular month to fly with an average 47% increase in travelers.

Your Chicago Midway Airport to Caribbean Islands flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • How much should I budget for a flight from Chicago Midway Airport to Caribbean Islands?

    Over the past 12 months, round-trip fares from Chicago Midway Airport to Caribbean Islands have typically cost between $512 and $857.

  • Which airlines fly nonstop from Chicago Midway Airport to Caribbean Islands?

    Based on the flight schedule for the next 3 months, just one airline regularly flies nonstop from Chicago Midway Airport to Caribbean Islands: Southwest.

  • Is it cheaper to fly with a layover from Chicago Midway Airport to Caribbean Islands?

    Yes, nonstop flights from Chicago Midway Airport to Caribbean Islands average $682 over the past 12 months. Flights with a layover can cost less, cheapest when connecting through Baltimore/Washington (BWI), with average fares of $608.

  • How long is a flight from Chicago Midway Airport to Caribbean Islands?

    Nonstop flights from Chicago Midway Airport to Caribbean Islands take 4h 08m on average.

  • Which cabin classes are available from Chicago Midway Airport to Caribbean Islands?

    On flights from Chicago Midway Airport to Caribbean Islands you can book Economy Class or First Class.

  • What are some popular landmarks around Caribbean Islands?

    Caribbean Islands is home to many popular sights. KAYAK travelers' favorites include:

    • Viejo San Juan
    • Palm Beach
    • Eagle Beach
    • Puerto Rico Convention Center

  • What are the earliest and latest flights from Chicago Midway Airport to Caribbean Islands?

    The earliest nonstop flight from Chicago Midway Airport to Caribbean Islands departs at 7:45 am and the latest leaves at 8:40 am. Nonstop flights take about 4h 08m.

Your guide to booking Chicago Midway Airport to Caribbean Islands flights

Get tips on when to book, when to fly and what to know before your trip.
  • If you can plan ahead, the sweet spot for booking your flight is 15 weeks before your trip. KAYAK data shows fares in this window are around 20% lower than last-minute bookings (made within 2 weeks of departure). Not ready to commit? Set a Price Alert and we'll let you know when prices change.
  • Flexible with your dates? Fly in May to save some money. It's typically the cheapest month on this route, while flights in November will cost you the most.
  • Fly out on a Tuesday to get the cheapest fares. Avoid Thursday flights, which are about 22% more expensive.
  • Start your trip in Punta Cana, the most popular destination in Caribbean Islands. From there, it's easy to continue on to other popular spots such as San Juan, Oranjestad and Nassau.

Reviews of the top 3 airlines serving from Midway to Caribbean Islands

 
Need help choosing which airline to fly with from Midway to Caribbean Islands? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4220 reviews
7.5Entertainment
7.0Food
8.1Boarding
8.6Crew
8.0Comfort
Airline reviews

Multiple delays due to weather in Chicago, but the crew did their best to get flights rescheduled and on to their destination. I felt like the crews handled a frustrating situation very well, kudos to them! I was very glad to not have a cancelled flight.

8.0 ExcellentEmmalee, Oct 2026
Read more Southwest reviews

Multiple delays due to weather in Chicago, but the crew did their best to get flights rescheduled and on to their destination. I felt like the crews handled a frustrating situation very well, kudos to them! I was very glad to not have a cancelled flight.

Southwest’s point to point system caused a 2 hour delay due to the crew being late from their inbound flight. Also, the WiFi and entertainment didn’t work on the plane.

A) Checked my luggage at the gate but never got to pre board B) if we are helping with checking our carryon and waiting 40 minutes for it we should have some privileges c) luggage took 40-45 minutes to come.. d) I asked for another snack and was told the plane is full.. seriously a small snack

I like the staff members they were super nice and helpful very sweet people :)

Boarding process of asking for volunteers to check bags goes against the system you had before with 2 bags checked free. This process is more of a guilt trip than a caring attitude toward the customer. In addition bag-size scrutiny has increased which also slows down the process of boarding. My wife said she will not fly on your airline again unless there is no other option.

Overall good, just screaming kids in the area the whole flight.

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

No beverage/snack service without any explanation or reason. Late boarding and delayed flight.

The cabin and bathroom experience was poor as the cabin and bathroom were dirty and showed signs of an older plane that had not been updated for Customer’s, comfort and health. There was gum on my seat when I arrived and dirt spots around the fan and light controls. The flight was almost entirely full, so there was no way I could be moved from my seat. Th bathroom had the peeling paint.

I'm 6' 2" and even in economy plenty of leg room

Horrible experience. Delta delayed the flight to 11pm which happens. Apparently the pilots were there but we were waiting for flight attendants to arrive from Detroit and they were delayed. They could have made arrangements but that’s fine. What was truly horrible was that at 10:50pm the pilot comes out and says the flight will be cancelled but hasn’t been cancelled yet in the system. It’s being cancelled because the pilots have timed out. As soon as that plane got delayed past 10:50pm delta knew it couldn’t fly. Yet they made us wait around for hours. When the flight finally got cancelled all the area hotels were booked and flights for the next day were unavailable until midday. All I wanted was to spend one day with my family before needing to fly abroad on another delta flight. That will be my last flight with them. I’ll take my 800k miles flown and annual spend to an airline that isn’t so thoughtless.

THI IS THE 3RD CONSECUTIVE FLIGHT FROM ORD TO MSP THAT HAS BEEN DELAYED 2+ HOURS. CRAZY

The plane was a rather tired 737-800, with old style small luggage bins. Poor air flow. USB charger in the infotainment system was not functioning. The flight was 2 hours late due to crew rest requirements (not their fault). On arrival in Seattle, waited on the tarmac for 30 minutes with very few updates from the crew.

The crew was very inconsiderate and rude. My flight was scheduled to depart at 6:00am. I received a call from the crew at 5:40am, asking if I was going to make the flight because I was the only one that hasn't boarded yet and boarding ends at 5:50am. I let them know that I will be at the gate in a few minutes, before the 5:50am cutoff. When I arrived at the gate at 5:45am the gate was closed. Departing early on last minute notice without having all passengers on board is inconsiderate and unprofessional.

Very easy to use and convenient, you can perform any action within the same portal

Okay considering we had weather delays which the Pilot notified us of immediately!

The boarding was organized and informative but the plane was tight meaning that you were sitting on one another and extremely uncomfortable. It’s disappointing that can’t have common seating comfort on the plane.

During the flight I suddenly felt very sick, and no one from the crew even tried to help me or check on my condition. They seemed completely indifferent and showed no concern for my well-being. I was very disappointed by the lack of care and compassion. I hope the airline improves its customer service and trains its crew to respond better when passengers need assistance.

Flight was canceled. Most upsetting was message from Kayak, stating that the flight was canceled and click with Kayak for details regarding rebook, refund details. THERE'S NO INFORMATION PROVIDED BY KAYAK EXCEPT THAT FLIGHT IS CANCELED. AND NOW THIS SURVEY TO FIND OUT HOW WAS THE FLIGHT !!!!!!!

Better than expected. Staff were friendly and nice on both flights.

Just know that everything, and I mean everything is “ala cart”. 60$ just to put something in the overhead bin. I will never fly Frontier again nor do I recommend them to anyone else.

Great for the price. No wifi or entertainment, but gate agents and crew were fantastic and we boarded quickly and left on time.

Our flight was canceled for no known reason. We weren’t told until we were checking in at 5:00 am. This was after our last flight with Frontier where we sat on the plane for three hours (not an exaggeration) before we took off because of a mechanical issue. We won’t be flying Frontier again.

I didn’t have enough time to catch my connecting flight and had to use a different Airline. I will be requesting a refund.

I brought a ticket and car rental through Travelocity. There was no where to add a KTN. So I thought i’d add it by looking up ticket on frontier website. I tried 3 times with the frontier chat bot to add my KTN it never updated my boarding pass. So then I tried showing up early to do it in person at the airport. The first employee update my ktn in the system and gave me a new boarding pass. I was sent back by tsa to join regular line. Then I was told to add my Ktn. It would cost me $25 extra. Given the length of the cue I did pay. Congratulations! BUT I will NEVER fly frontier again. Plus the plane was very old. It had actual ashtrays and old looking tray backs. Worst travel experience ever. Im warning my friends and family not to use frontier ever.

Was just ok with over selling I guess. A lot of people in a short space and when we finally arrive i20 minutes, waiting to get out from the plain because we were waiting authorization for out boarding? Something like that.

They changed my flight and did not want to accommodate me or try to help me in any way. They do not care about their customers.

More options for your flight to Caribbean Islands

Complete your trip to Caribbean Islands with a hotel stay or car rental