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$98 Find cheap flights from Caribbean to Chicago Midway Airport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Midway departing on 6/5. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
Sat 6/29
Sat 7/6

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Good to know

Low season

March

High season

December

Cheapest flight

$98
Best time to beat the crowds but there is an average 62% increase in price.
Most popular time to fly and prices are also 6% lower on average.
Flight from San Juan to Chicago Midway Airport

FAQs for booking Caribbean to Chicago Midway Airport flights

  • How does KAYAK find such low prices on flights from Caribbean to Chicago Midway Airport?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Caribbean to Chicago Midway Airport.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport from Caribbean is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Caribbean to Chicago Midway Airport?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago Midway Airport with an airline and back to Caribbean with another airline.

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

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago Midway Airport from Caribbean up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Prefer to fly non-stop from Caribbean to Chicago Midway Airport?

Find which airlines fly direct from Caribbean to Midway, which days they fly and book direct flights.

Nonstop departures

Caribbean to Chicago Midway

Monday

Aeromexico, Air France, Allegiant Air, +11 more

Aeromexico, Air France, +12 more

Tuesday

Aeromexico, Air France, Delta, +9 more

Aeromexico, Air France, +10 more

Wednesday

Aeromexico, Air France, Delta, +9 more

Aeromexico, Air France, +10 more

Thursday

Aeromexico, Air France, Allegiant Air, +11 more

Aeromexico, Air France, +12 more

Friday

Aeromexico, Air France, Allegiant Air, +11 more

Aeromexico, Air France, +12 more

Saturday

Aeromexico, Air France, Delta, +9 more

Aeromexico, Air France, +10 more

Sunday

Aeromexico, Air France, Allegiant Air, +11 more

Aeromexico, Air France, +12 more

See more direct flights

Nonstop returns

Chicago Midway to Caribbean

Monday

Aeromexico, Air France, Allegiant Air, +11 more

Aeromexico, Air France, +12 more

Tuesday

Aeromexico, Air France, Delta, +9 more

Aeromexico, Air France, +10 more

Wednesday

Aeromexico, Air France, Delta, +9 more

Aeromexico, Air France, +10 more

Thursday

Aeromexico, Air France, Allegiant Air, +11 more

Aeromexico, Air France, +12 more

Friday

Aeromexico, Air France, Allegiant Air, +11 more

Aeromexico, Air France, +12 more

Saturday

Aeromexico, Air France, Delta, +9 more

Aeromexico, Air France, +10 more

Sunday

Aeromexico, Air France, Allegiant Air, +11 more

Aeromexico, Air France, +12 more

See more direct flights
See more direct flights

Top 3 airlines serving from Caribbean to Midway

 
Need help choosing which airline to fly with from Caribbean to Midway? 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
DeltaOverall score based on 10457 reviews
8.6Crew
8.2Boarding
8.0Entertainment
7.9Comfort
7.4Food
Airline reviews

Flew first class so everything was great. But maybe because the flights were red eye, no meals were served, just chips. I flew Alaska Air 1st class at 9PM (2 hour flight) and they served beef short rib sliders!

10.0 ExcellentMichael, May 2024SJC - ATL
Read more about Delta reviews

Flew first class so everything was great. But maybe because the flights were red eye, no meals were served, just chips. I flew Alaska Air 1st class at 9PM (2 hour flight) and they served beef short rib sliders!

Had to change aircraft due to a faulty door. Surprisingly it only caused about an hour and a half of delay. Delta handled this situation as well as can be expected.

Awful. Flight was continuously getting delayed and gates kept changing without any reason. Flight was delayed for more then 3 hours

Paid premium for Delta only to be on safe but tired old 767 with ancient cabin in mediocre condition. Poor wifi and horrible inflight entertainment. Hardly a premium experience. Should have flown SW and had fun flight crew and no pretense

Our flight to Zurich was delayed by almost 3 hours, so we missed our next flight. There was no indication it would be delayed this much. We were told the gate had changed and then it apparently took over 2 hours to load the "catering" on the plane. We were not compensated in any way for the trouble.

The comfort is typical of what I would expect from main cabin. I've been on flights with other airlines where the seats needed to be changed, the cushions were non-existent. So happy this was not the case. I enjoyed the movie selection. Happy pillow and blanket was provided since I forgot my own. The food was also ok. Great that we arrived early and my luggage arrived undamaged. Again in the past (not with Delta), luggage was lost or broken.

Crew went over and above to be helpful. Plane had mechanical problems that caused us to depart late.

The 676 plane is much more comfortable in business class than the A330 and he food was a little better. I didn’t use the entertainment.

Rated entertainment as Mediocre as there were major problems with the Infotainment system that took probably a half hour for them to fix.

Your crew could maybe answer the call bell at least one of the times I pressed it. I pressed it first time with 2.5 hours left in our flight bc my partner was hungry and wanted a sandwich. We finally got the sandwich with 40 mins left in the flight.

Crew was nice, explained emergency protocol very well. Flight took off and arrived on time. Pilot explained the small delay that occurred with docking and providing updates. I would definitely fly spirit again.

The seat are terrible. Don’t even think of sleeping on a Spirit flight. The kids that run the plane aka flight attendants are pretty rude and straight forward. They get the job done but without class.

I had a death in my family and booked my flight on Spirit. My flight was cancelled the morning of my flight, no explanation, no help to rebook, nobody to talk to. The next available flight was 2days later !!!! Terrible airline, will NEVER fly with them again!

They took a horrible route with a lot of turbulence and I eneded up getting sick. Even if the flight takes longer. Don't put people life at risk just to get to the airport on time.

Every thing was fine ,low price,easy on time ,clean, good staff, really no issues

Had to board plan 2x due to lack of security check after 1st boarding

Miserable. The crew was rude, the flight was delayed 5 hours for mechanical reasons and then “weather” even though other planes were leaving.

They kept Changing the flight times. It was delayed several times and at one point it was supposed to depart at 3.40am! At which point we ended up staying overnight and booked long a separate United flight for early morning departure. The spirit flight then got moved up and left at 1.30 in the morning when it was supposed to leave at 9.40pm the night before.

Flight was delayed...not horribly late. Just before push back engine shut down for a quick replacement item that took about five minutes. After that, everything was smooth and the pilot was able to make up time in the air so that our arrival time was not too far off the original anticipated arrival time.

Only inflight purchases for food and water. Nothing comes with ticket price. Have to purchase bags, food...

9hrs delay and didn’t provided anything until after flight landed $75 voucher for fiuture travel no meals or anything.

It was ridiculously hard to check in for the flight, and Frontier charged us a LOT of money to have a carry on suitcase, and then told everyone we could not carry on bags and had to check them through at the gate, and didn't refund the extra money we paid to have the suitcase as carry on.

I had a terrible experience with Frontier. I arrived before the 60 minute cut off and was told that Frontier has a two hour window for bags. I was then told the next available flight wasn’t until the end of the day (I had booked a 6am flight). I took a look around and saw other people being told that they could not board their flights or that they had to pay additional fees. I opted to rebook on American Airlines. There’s absolutely no straightforward way to contact Frontier, so this ticket was a complete waste of money. Oh - and the kicker is that the lady lied about the two hour cut off.

Frontier won’t help you at the airport without paying $25. Carry on was $75. Then you get on the plain and every beverage or snack is also a charge. Seats are hard and real packed in. I would never fly them again.

Worst experience I have seen. The flight was cancelled without any reason.

My experience with frontier staff at the Denver airport was absolutely horrible. The manager on duty was even worst if was the worst experience I have ever had, I have never been treated so poorly as a customer in my life! The staff was extremely rude, eye rolls and attitude and then refusal to help me at all. I wish I could never fly frontier again that’s how horrible it was!

The Frontier app wasn’t working. So I could not pay for a carry on the week prior to flying. They charged me 99$ at the gate to carry on a duffle bag.

Good for the price. My only complaint is that the pilot should keep the air flowing while passengers are waiting to getting out of airplane.

Plane could have been more on time. More leg room .

I arrived 1 hour prior to boarding, and they said I was too late for a domestic flight. First time I heard that :-(

Book cheap flights from Caribbean to Chicago

Recent round-trip flight deals

7/9Tue
1 stopFrontier
23h 01mPUJ-MDW
7/15Mon
1 stopFrontier
15h 14mMDW-PUJ
$219
7/26Fri
1 stopFrontier
29h 20mSDQ-MDW
8/15Thu
1 stopFrontier
18h 31mMDW-SDQ
$249
7/9Tue
1 stopFrontier
23h 01mPUJ-MDW
7/16Tue
1 stopFrontier
11h 17mMDW-PUJ
$252
7/4Thu
1 stop
12h 23mPUJ-MDW
7/12Fri
1 stop
19h 32mMDW-PUJ
$337
7/4Thu
1 stop
12h 23mPUJ-MDW
7/16Tue
1 stop
11h 35mMDW-PUJ
$362
9/21Sat
1 stopDelta
7h 48mSDQ-MDW
9/30Mon
1 stopDelta
17h 33mMDW-SDQ
$422
10/10Thu
1 stopDelta
7h 41mSJU-MDW
10/15Tue
1 stopDelta
9h 04mMDW-SJU
$428
7/8Mon
3 stopsWestJet
28h 54mPUJ-MDW
7/11Thu
3 stopsWestJet
27h 30mMDW-PUJ
$1,092
10/22Tue
2 stopsLATAM Airlines
32h 47mPUJ-MDW
10/27Sun
2 stopsLATAM Airlines
27h 00mMDW-PUJ
$2,240
7/14Sun
2 stopsLATAM Airlines
17h 06mPUJ-MDW
7/17Wed
2 stopsLATAM Airlines
19h 05mMDW-PUJ
$3,187

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Recent one-way flight deals

6/5Wed
1 stopFrontier
9h 24mSJU-MDW
$98
6/13Thu
1 stop
11h 16mSJU-MDW
$99
6/4Tue
1 stopFrontier
13h 28mSJU-MDW
$103
9/19Thu
1 stopFrontier
13h 08mSJU-MDW
$129
6/12Wed
2 stopsFrontier
24h 51mSJU-MDW
$134
8/21Wed
1 stopFrontier
8h 58mSJU-MDW
$135
8/28Wed
1 stopDelta
9h 50mSJU-MDW
$172
9/14Sat
2 stops
14h 32mSDQ-MDW
$191
7/22Mon
1 stopDelta
11h 35mSJU-MDW
$201
7/6Sat
1 stopDelta
9h 54mSJU-MDW
$222

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Last minute flights from Caribbean to Midway

Last minute flight, train and bus deals

6/3Mon
multi-stopFrontier
9h 53mSJU-MDW
6/6Thu
multi-stopFrontier
11h 32mMDW-SJU
$217
6/2Sun
multi-stopFrontier
23h 09mSJU-MDW
6/6Thu
multi-stopFrontier
11h 32mMDW-SJU
$223
6/1Sat
multi-stopFrontier
19h 46mSJU-MDW
6/6Thu
multi-stopFrontier
16h 33mMDW-SJU
$288
6/3Mon
multi-stopFrontier
9h 53mSJU-MDW
6/5Wed
multi-stopFrontier
17h 41mMDW-SJU
$295
5/31Fri
multi-stopFrontier
7h 05mSJU-MDW
6/12Wed
multi-stopFrontier
9h 19mMDW-SJU
$298
6/2Sun
multi-stopFrontier
17h 46mSJU-MDW
6/6Thu
multi-stopFrontier
11h 32mMDW-SJU
$301
6/2Sun
multi-stop
17h 28mSJU-MDW
6/7Fri
multi-stop
10h 07mMDW-SJU
$553
6/4Tue
multi-stopDelta
12h 32mSDQ-MDW
6/8Sat
multi-stopDelta
17h 55mMDW-SDQ
$770
5/31Fri
multi-stopDelta
8h 30mSJU-MDW
6/6Thu
multi-stopDelta
6h 37mMDW-SJU
$1,314
6/4Tue
multi-stopDelta
16h 07mMBJ-MDW
6/11Tue
multi-stopDelta
17h 14mMDW-MBJ
$1,920

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