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Find cheap flights from Chicago Midway Airport to Caribbean from $99

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 5/19. 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
Sun 6/2
Sun 6/9

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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$210
Montego Bay
Montego Bay1 stop$257
Santo Domingo
Santo Domingo1 stop$216
Oranjestad
Oranjestad2 stops$561
Nassau
Nassau1 stop$427
Kingston
Kingston1 stop$480
Simpson Bay
Simpson Bay1 stop$229
Providenciales
Providenciales1 stop$462
George Town
George Town1 stop$525
Aguadilla
Aguadilla1 stop$255
St. John's
St. John's2 stops$3,013

Good to know

Low season

April

High season

May

Cheapest flight

$99
Best time to beat the crowds with an average 4% drop in price.
Most popular time to fly with an average 8% increase in price.
Flight from Chicago Midway Airport to Punta Cana

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 20% 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 9128 reviews
8.2Boarding
7.3Food
7.3Entertainment
7.9Comfort
8.6Crew
Airline reviews

No entertainment, food was cookies & juice,water, soda or coffee.

10.0 ExcellentAnonymous, May 2024SEA - RDM
Read more about Alaska Airlines reviews

No entertainment, food was cookies & juice,water, soda or coffee.

My baggage was in another flight, anit was delayed for one hour.

The maintenance delay was seemingly handled very poorly... Little to no information was provided to the passengers sitting on board for an extended period of time. On a brighter note, at least the cabin crew (flight attendants) did the best they could. They seemingly were provided very little information with regards to the delay. Unless absolutely beyond my control, I can’t imagine buying a ticket on Alaska airlines again, based on this and a previous experience my wife recently had, along with complaints overheard from other passengers.

They oversold my flight by 9 seats so when I went to check in I was not assigned a seat and the only one available if I didn’t want to chance it were 100 dollars more

The seats were incredibly small and the attendants were grumpy the whole time.

Honestly, there was not much they could do. Due to wind, the flight was delayed for several hours because we had to be diverted to San Jose where we needed to refuel before departing to Hawaii. Wish they had offered some snacks during the delays/diversion because we had to wait such a long time to finally get our food served during the flight after leaving California.

The only issue was in the wheelchair waiting area before we got on the plane. They seemed very disorganized. Everyone we encountered after that was great! We loved Cassandra at check-in. She was awesome. The flight attendants were wonderful too! The lady helping with the waiting wheelchair when we got off the plane was awesome too!

They canceled the flight 30 minutes prior to departure without any heads up.

Like South West(2 check in baggage free) if Alaskan Airlines could give at least one check in baggage free then it would be great.

Expect to get miles for us having to miss our first planned flight due to them waiting on passengers that decided to be late to the airport.

Checking in at the airport the agent only booked the first keg of my trip and had my checked luggage going to the airport with a layover! Never was issued a boarding pass for the second leg or received sticker fir my checked bag. All was well in the end! Delta agents helped to resolve the situation!!!

Delayed due to an ill passenger after loading. Not preventable on Delta's part. Was in first class. The seats are becoming worn and detaching from their velcro attachments. Only got snacks on flight. The attendant was not the friendliest.

I would fly again the whole experience was great. The only feed back I can give that they don't do that American Airlines does is the crew there is more humorous with boarding and thank their passengers. It makes it more fun to fly with them. I would however fly Delta again.

Big plane, long flight, absolutely no leg room and basically non existent air! I am 5”4’ and always travel Main Cabin, I was miserable on this plane and could barely move when we arrived in Cabo due to the cramped leg area!

From Atlanta to Cabo I would have hoped on a plane that size I would have been able to breathe and wiggle my feet a little! The leg room in that plane is non existent and I am only 5”4’. And the air vent either wasn’t working very well or just could not blow air from the ceiling to the seat area as I was suffocating through the entire flight! And please don’t say I would have been more comfortable in first class because I cannot afford those rates and have always travelled Main Cabin without issues !

The pilots were good. Disappointing when planes don't have electrical ports

I liked the piloting of the aircraft. Very disappointed about lack of electrical ports. Also, although a short flight. there was enough time to hand out snacks to comfort + seats as was done for first class.

I had a wonderful experience flying with delta. The gentleman taking care of us on our flight was so nice, accommodating, and attentive. He always was smiling and giving pins to the kids which made me smile. The flight was quick too and without turbulence. Thank you for the great flying experience.

Delta is one of the best airlines I have flown

Made the Atlanta to Pittsburgh trip many times, with Delta no issues

The crew was not great or professional. It seemed like they didn't really want to be there. A true lack of effort for accommodating customers.

Everything was really good but the seats are not very comfortable.

I paid for WiFi, but it (WiFi) was very very slow, will never take again! Impossible open Utube 😤😤😤

I had no legroom, although I paid for extra legroom. I could barely put my bag in front of my feet and under the seat. The Wi-Fi was horrible. In fact the flight attendant said that they had to reboot it and see if it was going to work and never did.

The guy with severe body odor sat next to me. For the whole duration of the flight it was a torture. The airline should have better policy on limiting people with bad body odor to board the flight. Passengers should not be the ones to endure bad odor for the whole duration of the flight. The airline should be e the one to ensure decent air quality for ever passenger.

Overall it was a miserable experience... I will never fly spirit for more than a 3 hour flight or overnight.

The boarding attendant was slightly rude when I asked about checking our stroller. Made me feel like I was bothering her.

My wife and I are both handicapped and at boarding they upgraded us to a seat closer to the front rather than all the way towards the back. Much appreciated.

Not much seat room, but that was unexpected. But the seat headrest was very uncomfortable.

First the good, everyone was friendly and efficient. Flight was smooth and plane was very clean and new. Now the bad, seats have almost no padding on your behind. I was in exit row so I had tons of leg room for a 6' 2" bean pole with long legs. Everything was extra - water, soda, snacks everything besides oxygen. Ya get what you pay for, and my flight was cheap as you could ever want it, so no worries.

Six hour delay. Poor customer service. No voucher. Bad communication. Missed important appointments.

Our flight was delayed an hour, then when we got to board our flight finally, we were waiting in our seats for take off for 45 minutes before it was communicated that there was a maintenance issue therefore we waited on the plane for over an hour while that was resolved. We did not get to Phoenix until almost 3 hours after we were originally supposed to. This was the first and last time I will be flying Frontier.

Flight was canceled with little warning. Flight was rebooked through Ontario, California and connecting flight was delayed by over three hours. Frontier is living up to their Greyhound of the skies reputation for sure.

I purchased a carry on bag online…was supposed to cost $72 but after a whole slew of bs charges, the total was over $175.00. Because of these hidden charges, I will not even consider flying Frontier ever again. It’s just not worth the hassle. I’m scratching this company off my list forever.

Flight was OK. Seats were good no cell phone charges on the plane no TVs or entertainment.

There were 3 leg for the trip and each leg was delayed by 90 minutes or more. The boarding process takes forever with people waiting on the jetway even though most folks do not have carry-on. The whole process is poorly managed.

Flight cancelled and was told by a rude gate agent that they don’t accommodate on other airlines. Had to wait 5 hours for a connecting flight that had a 7 hour layover. Would not allow bags to be checked early so we couldn’t go through security .Had to rent a car for the afternoon to store bags and get a meal. Also incurred a hotel fee. No apology or reason given for the cancellation- just rudeness.

They cancelled the flight then did nothing to help us rebook. It was awful - I won’t fly with them again

The process of buying the ticket and navigating all the hidden charges that Frontier throws at you was a terrible experience. The actual airport experience and flying was fine.

The truck that was refueling the plane drove away with the hose still connected to the plane and ripped part of the plane off with it

Book cheap flights from Chicago to Caribbean

Recent round-trip flight deals

5/29Wed
1 stopFrontier
20h 33mMDW-PUJ
6/4Tue
1 stopFrontier
21h 34mPUJ-MDW
$210
5/29Wed
1 stopFrontier
20h 33mMDW-PUJ
6/2Sun
1 stopFrontier
25h 11mPUJ-MDW
$211
6/9Sun
1 stop
7h 15mMDW-MBJ
6/15Sat
2 stops
17h 14mMBJ-MDW
$400
5/19Sun
1 stop
28h 11mMDW-MBJ
5/23Thu
1 stop
9h 10mMBJ-MDW
$401
7/1Mon
1 stopDelta
10h 02mMDW-NAS
7/31Wed
1 stopDelta
5h 38mNAS-MDW
$433
7/16Tue
1 stopDelta
6h 18mMDW-NAS
7/30Tue
2 stopsDelta
16h 05mNAS-MDW
$438
6/6Thu
2 stopsKLM
18h 33mMDW-PLS
6/11Tue
1 stopKLM
7h 44mPLS-MDW
$862
6/6Thu
2 stopsKLM
18h 33mMDW-PLS
6/11Tue
1 stopKLM
7h 44mPLS-MDW
$870
5/20Mon
2 stopsWestJet
26h 07mMDW-NAS
5/25Sat
2 stopsWestJet
26h 20mNAS-MDW
$893
5/25Sat
3 stopsWestJet
19h 10mMDW-SXM
5/30Thu
2 stopsWestJet
24h 25mSXM-MDW
$933

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Recent one-way flight deals

5/19Sun
1 stopFrontier
13h 04mMDW-PUJ
$99
5/14Tue
1 stopFrontier
7h 53mMDW-MBJ
$99
5/11Sat
1 stopFrontier
13h 21mMDW-SJU
$109
6/11Tue
1 stopFrontier
11h 38mMDW-PUJ
$111
6/10Mon
2 stops
25h 34mMDW-AUA
$140
6/1Sat
1 stop
21h 52mMDW-PUJ
$150
9/25Wed
1 stopDelta
6h 23mMDW-SDQ
$190
9/25Wed
1 stopDelta
6h 23mMDW-SDQ
$195
5/30Thu
2 stopsWestJet
20h 46mMDW-PLS
$1,218
6/15Sat
2 stopsWestJet
17h 33mMDW-NAS
$1,297

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Last minute flights from Midway to Caribbean

Last minute flight, train and bus deals

5/8Wed
multi-stopFrontier
12h 31mMDW-SJU
5/15Wed
multi-stopFrontier
9h 53mSJU-MDW
$218
5/8Wed
multi-stopFrontier
9h 38mMDW-SJU
5/17Fri
multi-stopFrontier
10h 03mSJU-MDW
$226
5/7Tue
multi-stopFrontier
11h 39mMDW-SJU
5/8Wed
multi-stopFrontier
9h 53mSJU-MDW
$273
5/8Wed
multi-stopFrontier
9h 38mMDW-SJU
5/14Tue
multi-stopFrontier
9h 49mSJU-MDW
$278
5/7Tue
multi-stopDelta
8h 00mMDW-PUJ
5/8Wed
multi-stopDelta
16h 30mPUJ-MDW
$435
5/6Mon
multi-stopDelta
6h 36mMDW-PUJ
5/10Fri
multi-stopDelta
19h 01mPUJ-MDW
$440
5/4Sat
multi-stop
15h 28mMDW-MBJ
5/12Sun
multi-stop
23h 30mMBJ-MDW
$599
5/4Sat
multi-stop
17h 41mMDW-NAS
5/7Tue
multi-stop
13h 16mNAS-MDW
$714
5/4Sat
multi-stopWestJet
22h 05mMDW-NAS
5/7Tue
multi-stopWestJet
27h 00mNAS-MDW
$3,222
5/8Wed
multi-stopWestJet
49h 45mMDW-MBJ
5/11Sat
multi-stopWestJet
21h 05mMBJ-MDW
$3,927

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