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Find cheap flights from Chicago Midway Airport to Caribbean from $98

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to Caribbean departing on 6/4. 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
sáb 6/29
sáb 7/6

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Best Caribbean Flight Deals

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

Punta Cana
Punta Cana1 stop$213
Montego Bay
Montego Bay1 stop$365
Santo Domingo
Santo Domingo1 stop$261
Oranjestad
Oranjestad1 stop$556
Nassau
Nassau1 stop$369
Kingston
Kingston1 stop$480
Simpson Bay
Simpson Bay2 stops$396
Providenciales
Providenciales1 stop$462
George Town
George Town1 stop$418
Aguadilla
Aguadilla1 stop$290
St. John's
St. John's2 stops$3,034

Good to know

Low season

April

High season

December

Cheapest flight

$98
Best time to beat the crowds with an average 6% drop in price.
Most popular time to fly and prices are also 4% lower on average.
Flight from Chicago Midway Airport to San Juan

FAQs - booking Caribbean flights

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

    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 Chicago Midway Airport 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?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Caribbean from Chicago Midway Airport 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 Chicago Midway Airport to Caribbean?

    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 Caribbean with an airline and back to Chicago Midway Airport with another airline.

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

    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 Caribbean from Chicago Midway Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top tips for finding cheap flights to Caribbean

  • Morning departure is around 26% 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

Top 4 airlines serving from Midway to Caribbean

 
Need help choosing which airline to fly with from Midway to Caribbean? 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
Alaska AirlinesOverall score based on 9192 reviews
7.3Entertainment
8.2Boarding
8.6Crew
7.3Food
7.9Comfort
Airline reviews

I didn’t know that food needed to be ordered ahead. Please include this in the reservation information. Overall, very good experience.

8.0 ExcellentNorma, May 2024SNA - SEA
Read more about Alaska Airlines reviews

I didn’t know that food needed to be ordered ahead. Please include this in the reservation information. Overall, very good experience.

Plane hit turbulence diverted to Houston. We'll probably get in after 3am

Cabin crew very friendly and pleasant. Flight left late but we didn't know why. Alaska Airlines app was not user friendly -- app wouldn't let us upgrade our seats, but no indication if flight was full. We wound up having to call the airline to request an upgrade and we were told none was available. Waste of time. Baggage retrieval was easy.

Full flight where I had another passenger sitting in middle seat who said that he had lost 250 lbs from 500. The stewardess on exiting the flight advise me that I was going to receive a refund. I thought she was talking about another passenger. The stewardess saw that to make him comfortable I had lifted the armrest and flew for 5 hours to Seattle from Reagan DCA with a portion of his body on my seat. I survived. I flight to remember!!!!

the flight was delayed almost 3 hours and not one time was we told that it was delayed or why. I had asked one of the crew members why it was delayed, 20 minutes after the flight was supposed to take off, and was told that they had no idea what was going on and that they had not been told anything. this is FRIGHTENING!!!! No excuse!!

Given incorrect gate upon check-in, corrected by the gate attendant, D6 rather than D5, minor inconvenience. As with the previous flight, passengers were admonished to voluntarily gate-check carry-on luggage with the statement that those in the last boarding group would have no choice but to do so. If the Boeing 737 MAX8/MAX9 doesn't have room for carry-ons it's an interior design flaw on the part of Boeing. Posting an advance warning would be helpful, such as "Boeing 737 MAX planes feature limited carry-on space. Please be aware." SFO's amenities and TSA much better than MCO's. Crew was amazing! Brought my own food because Alaska's onboard selection has soy in everything. Beverage service was excellent. This was the first and last trip with Alaska after the previous flight's issues. It's no reflection on the crew of this flight. They were great.

Flights were on time. Check in was fine. Crew members were pleasant.

The boarding gate is literally just an aisle to the concourse. There is no seating and it's shared with several other airlines. It's crowded, hot, and standing-room only. It's difficult to hear gate announcements over the PA system with too many other carriers crammed into a small space. I've enjoyed flying AA in the past on the west coast, but the BNA single gate experience is horrendous! Never again from BNA to SEA with AA.

I would have liked it to have been easier to order food for the flight. My son was not happy with the snack pack I bought him and it was a very long flight for a little boy to go without food.

It was a partial full flight. But even with a spare seat it was hard to get comfortable More on me being a wide body probably

I've flown many many times on Northwest and then Delta. The crew on this flight were absolutely the best I've had the pleasure of being looked after by.

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.

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.

Half the bathrooms assigned to economy were out of action

Delta crushed it. Flight attendant in first was attentive and just never stopped. Honestly one of the best domestic flights I’ve been on.

This was the smoothest flight I have had in awhile. I was also offered an exit row seat for a great upgrade cost and was able to sleep almost thr whole flight due to comfort and a smooth flight. We left on time and arrived on time.

No food not even water offered unless you buy it and no usb in the seat but other than that everything was good

Because our flight from marsh Harbor to Fort Lauderdale was over three hours delayed it caused us to miss our flight in Fort Lauderdale. Because we missed that flight, it cost us nearly $100 apiece for four different travelers which totaled nearly $400. We are seeking a reimbursement for the flight that we missed in Fort Lauderdale Florida.

Flight expected to leave at 6:40 pm ended leaving at 8:00 am the following day. I slept in a cold airport. Never again Spirit for me…

Flight was cancelled just 6 days before. No more flights that day, and the following date was sold out. Had to obtain a refund and buy more expensive flights on another airline.

The flight was on time and nice as always for me with spirit but the cabin crew were not good. They left the lights on on a red eye for the entire flight.

This was the return leg of my journey with Spirit Airlines. Despite its reputation, I found no issues as it got me from point A to B safely and without delay, especially with no mechanical delays, which is fantastic in my book! The staff, from ground crew to cabin crew, were all pleasant and hassle-free. The flight was smooth from takeoff to landing. I have absolutely no complaints about this no-frills airline!

I got a one-way, last-minute nonstop flight from PDX to BWI for only $125. Yes, I got nicked $79 more for a checked suitcase and $89 more for the BIG SEAT option, but it was worth it, even with $4.50 for coffee and $10 for a snack (the latter no different than any other airline). The grand total was still less flying on any other airline.

It was the worst ever, i will be filing a lawsuit to get a refund. Our flight was delayed 4 hours so we would miss our connecting flight, we were not rebooked to our destination the same day, we were not offered any options to get home on the same day despite being clear that we absolutely cannot get stranded at night due to family, we were forced to book our own flights on a different airline to get home, and spririt is refusing a refund because our flight wasn't cancelled, only delayed. oh yeah, and they lost our luggage on the first part of the trip and you cannot get a hold of customer service when anything goes wrong, on hold for 30+ minutes. and their app breaks so you can't use that either.

This recognisable no-frills airline gets me from point-A to point-B. I was able to get to Chicago without stress. The checked baggage collection and reclaim could be improved.

It was delayed 9 hours for operational reasons, despite the plane arriving to the airport on time.

I am very disappointed with Frontier Airlines. They cancelled our flight because they couldn't find a crew member, and then didn't get us to our connecting flight. We had to cancel our whole vacation. We were promised flight and hotel vouchers, but they never sent them.

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.

Book cheap flights from Chicago to Caribbean

Recent round-trip flight deals

6/8sáb
1 stopFrontier
16h 37mMDW-SJU
6/12qua
1 stopFrontier
9h 24mSJU-MDW
$195
6/13qui
1 stopFrontier
17h 40mMDW-PUJ
6/20qui
1 stopFrontier
14h 21mPUJ-MDW
$213
7/8seg
1 stopFrontier
22h 49mMDW-PUJ
7/11qui
1 stopFrontier
12h 56mPUJ-MDW
$215
6/24seg
1 stopFrontier
15h 14mMDW-PUJ
6/27qui
1 stopFrontier
14h 28mPUJ-MDW
$216
6/13qui
1 stop
11h 32mMDW-SJU
6/20qui
1 stop
20h 01mSJU-MDW
$233
7/4qui
2 stops
17h 16mMDW-PUJ
7/9ter
1 stop
23h 01mPUJ-MDW
$368
8/8qui
1 stopDelta
9h 44mMDW-SJU
8/14qua
1 stopDelta
8h 16mSJU-MDW
$369
8/6ter
1 stopDelta
10h 39mMDW-SJU
8/14qua
1 stopDelta
9h 50mSJU-MDW
$373
6/24seg
2 stopsWestJet
27h 38mMDW-AUA
6/29sáb
3 stopsWestJet
28h 40mAUA-MDW
$910
6/14sex
2 stopsWestJet
18h 54mMDW-NAS
6/16dom
2 stopsWestJet
27h 34mNAS-MDW
$1,156

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Recent one-way flight deals

6/4ter
1 stopFrontier
12h 38mMDW-SJU
$98
6/13qui
1 stopFrontier
17h 40mMDW-PUJ
$104
7/24qua
1 stopFrontier
22h 58mMDW-SDQ
$107
6/28sex
1 stopFrontier
24h 59mMDW-SXM
$108
7/23ter
1 stop
24h 08mMDW-NAS
$127
6/12qua
1 stop
9h 38mMDW-SJU
$134
9/25qua
2 stopsDelta
15h 40mMDW-SDQ
$190
9/9seg
2 stopsDelta
17h 37mMDW-PUJ
$206
7/4qui
2 stopsWestJet
25h 59mMDW-PLS
$357
11/16sáb
2 stopsWestJet
19h 35mMDW-GCM
$1,459

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Last minute flights from Midway to Caribbean

Last minute flight, train and bus deals

5/31sex
multi-stopFrontier
7h 10mMDW-SJU
6/1sáb
multi-stopFrontier
9h 31mSJU-MDW
$195
5/31sex
multi-stopFrontier
7h 10mMDW-SJU
5/31sex
multi-stopFrontier
28h 46mSJU-MDW
$201
6/1sáb
multi-stopFrontier
18h 49mMDW-SJU
6/9dom
multi-stopFrontier
26h 40mSJU-MDW
$267
6/4ter
multi-stopFrontier
12h 38mMDW-SJU
6/5qua
multi-stopFrontier
8h 32mSJU-MDW
$293
6/1sáb
multi-stopDelta
18h 11mMDW-PUJ
6/4ter
multi-stopDelta
17h 41mPUJ-MDW
$490
6/4ter
multi-stop
27h 12mMDW-MBJ
6/11ter
multi-stop
19h 13mMBJ-MDW
$534
6/1sáb
multi-stopDelta
11h 56mMDW-SDQ
6/3seg
multi-stopDelta
18h 25mSDQ-MDW
$560
6/2dom
multi-stop
28h 11mMDW-MBJ
6/5qua
multi-stop
14h 45mMBJ-MDW
$588
6/4ter
multi-stopWestJet
38h 10mMDW-NAS
6/8sáb
multi-stopWestJet
25h 55mNAS-MDW
$3,068
6/1sáb
multi-stopWestJet
42h 53mMDW-NAS
6/8sáb
multi-stopWestJet
25h 55mNAS-MDW
$3,072

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