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$88 Find Cheap Flights from Chicago Midway Airport to Caribbean

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 1/17. 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

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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$272
Montego Bay
Montego Bay1 stop$442
Santo Domingo
Santo Domingo2 stops$363
Oranjestad
Oranjestad1 stop$586
Nassau
Nassau1 stop$427
Simpson Bay
Simpson Bay2 stops$486
Kingston
Kingston1 stop$733
Providenciales
Providenciales2 stops$549
George Town
George Town1 stop$542
St. John's
St. John's1 stop$823
Aguadilla
Aguadilla1 stop$173

Good to know

Low season

July

High season

January

Cheapest flight

$88
Best time to beat the crowds but there is an average 21% increase in price.
Most popular time to fly and prices are also 32% 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 38% 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

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.
8.1
SouthwestOverall score based on 5045 reviews
8.1Comfort
8.3Boarding
8.7Crew
7.7Entertainment
7.2Food
Airline reviews

Easy to book and to get check in and get on and off.

10.0 ExcellentAnonymous, Nov 2024PNS - HOU
Read more Southwest reviews

Easy to book and to get check in and get on and off.

The last 30 min or so, they put the heat on full. We thought we were being basted.

Excellent experience. WiFi worked on this leg of My trip

Flight was great, but golf bag never made it until later in the day. Even though I had a nonstop flight it was placed on a different one. They made it right with flight credits and I was able to get it the same day.

It seems as though the provisions are even less. Although SWA used to be an economy Airline, that isn't really the case anymore. I paid over $700. for a round trip to Denver and I could have flown just about any airline for the price. The drinks are now in a 6-ounce cup and with ice I'm sure a can would fill more than 2 cups. However, I am very proud of SWA for using paper rather than continuing to contribute to the millions of plastic cups being used each day. I've thought of this fr many years and am so glad to see it come to fruition, if not by only SWA so far.

Exceptional crew! Friendly and professional. Pleasant attitude and treated everyone with respect.

Service was great, boarding and exiting went smoothly, and the flight was very pleasant.

Was as expected. Crowed planes. Too many carryons delaying takeoff. But the ride only took an hour and saved me a lot of time SFO is a not a great airport.

Was as expected. Crowed planes. Too many carryons delaying takeoff. But the ride only took an hour and saved me a lot of time SFO is a hell hole of an airport. It is the new LaGuardia. Everything Cobbled together. Security gates closed. Terri directional signage

Boarded the plane in Portland and sat on the tarmac for four hours before being given clearance to take off. Apparently a "scratch" was detected on the preflight inspection. This delay resulted in me missing my connection in Baltimore. I therefore had to stay overnight and then catch an early flight this morning, which resulted in my missing a mandatory class. I would like a refund / voucher to cover the cost of the missed flight. And additional voucher for the time spent on the plane in Portland would also be appreciated.

Crew was nice. Flight was timely. Seats could be better as well as the food considering it’s first class.

Left on time and arrived early this extending our 31 minute transfer. Bags made it also!

Good and consistent Printer in lounge did not work for me :(

Most of my discomfort was going through TSA. However, the Delta seats had inadequate leg room and I tried my very best to connect to the wi-fi and it was a cumbersome process that finally gave me the info that I needed to sign in AFTER I had completed the flight...Why make it so difficult to use? That said I really really appreciate the pilot taking a little extra time to avoid a bad storm area and both landings in Atlanta and Orlando were flawless to my delight!!!

Delayed in taking off because no flight crew. The in seat entertainment was working properly.

All fine save for the abominable catering. Really gone downhill. We found it all inedible.

I upgraded to first class only to find out that I still had no access to the sky lounge without a sky miles card or AmEx (something that should be emphasized outside of the fine print!) Also, no food or drink service provided during the flight, so I basically paid 4x more just for “free” checked baggage and a bigger seat. Not worth it.

I appreciated friendly service from check-in, to boarding, to in-flight amenities! Attendants were accommodating and helpful. Thank you! Elaine

Delta was really good about being transparent with why we were delayed it’s just that’s the plane was really old and outdated and a lot of the comfort and amenities we know Delta to have did not shine through

Bottom seat cushion is almost non existent. Very uncomfortable seat.

WiFi didn’t work despite paying for it. Crew was nice.

I upgraded my ticket at the ticket counter and was not informed of the huge bottleneck at TSA pre check. It took me over an hour to get through the line at this small airport and although I ran to the gate and reached it prior to scheduled departure, it had already pushed pack. I missed the flight. Spirit rebooked me on a flight to Orlando that evening, which would require me to then rent a car and drive to FLL. For scheduling reasons, I determined it be would better to rent a car in Pensacola and drive it to my destination in FLL. Spirit called me that evening and asked me if I was going to board the plane. I explained no, for scheduling reasons. The person apologized and said I would receive a refund, but I have not heard back. Certainly, I ought to be refunded the upgrade I paid for at the counter.

The staff from LAX to New Orleans were rude but the staff from New Orleans to LAX were nice!

Did what they needed to do. Brought us from point A to point B timely and without issue. Boarding through deplaning smooth.

Direct 2.5 hour flight good. Free snacks and coffee, water, or soft drinks not available...bad.

Atlanta airport gate area floor and nearly all seats disgusting. Spirit airlines crew fantastic!!

Over 2 hour delay due to “weather” but all other flights were taking off with no issues. We felt lied to the entire time as well.

Never been worse. Never again even if the ticket were free.

Everything was excellent and as expected. The boarding process was great but deboarding was a bit slow. No fault of the crew; it just seemed like the passengers didn’t want to leave! 😂

waited 5 hours to tell us it was cancelled even when they knew

Booked direct in July '24. Turned into a 14 hr layover (both ways) in Denver. My 5 day vaca turned into a 1 day . Not good, BUT,... Thank you for the people @ Frontier who were professionally friendly & approachable.

Stop changing gates at sfo. When you are elderly going back for it’s not fun.

We understand and comply with Frontier’s bag sizes. We’ve had some problems in past while having to await other passengers who do not understand the baggage restrictions or have not prepaid and that is usually our biggest concern (others delaying us) with flying Frontier. Flying OUT of ONT, however, has always been a great experience. I’ve also noted even on delayed Frontier flights very knowledgeable pilots who manage expectations well.

There was no easy way to check in. I don't want to install an app to checkin. I will use alaska from now on because they have a web check in method that is easy.

The crew was ghetto lol I felt like I was on an inner city field trip

Horrible! The short distance flight ended up taking 5 hrs! There was a 3 hr delay for the flight to take off and there was a 70 min wait on the tarmac for some bogus reason that the pilot said the gate he was supposed to board was taken up. After a 30 min wait he said the plane that was supposed to push out of the gate called a medical emergency and 40 min later he ended up boarding another gate. For the initial 3 hr delay there was no information/alert about the gate or delay in the app or the boards up until the boarding time and even beyond! Had to walk all the way to the end of the terminal to find the frontier staff to ask what was going on. Avoid this airline at all costs! If you have carryon bags or checked bags , their prices come equivalent to the prices of more reliable airlines. They are the worst in timeliness at 60% (reported as delayed) this year (check the data) by a high margin even compared to the second worst airline. If you are ok with having a miserable flight experience with the odds close to flip of a coin, feel free to try them. If you value your time , money and flying experience, stay away.

There was nothing to like, flight delayed had to move to different departure areas, disorganized to say the leasr

Delayed for two hours due to trivial issues. No reimbursment. Also on arrival further delay due to terminal malfunction.

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.

Allowed me to chose my seat without extra charge (I purchased full-price ticket) and boarding was in group1. Didn't even serve water.

Book cheap flights from Chicago to Caribbean

Recent round-trip flight deals

12/15Sun
1 stopFrontier
16h 32mMDW-SJU
12/20Fri
1 stopFrontier
9h 06mSJU-MDW
$174
12/16Mon
1 stopFrontier
16h 32mMDW-SJU
12/20Fri
1 stopFrontier
9h 06mSJU-MDW
$176
12/6Fri
1 stopFrontier
18h 04mMDW-SJU
12/9Mon
1 stopFrontier
7h 41mSJU-MDW
$177
1/15Wed
1 stopSouthwest
6h 20mMDW-SJU
1/23Thu
1 stopSouthwest
6h 50mSJU-MDW
$200
12/9Mon
1 stop
16h 32mMDW-SJU
12/13Fri
2 stops
30h 49mSJU-MDW
$201
12/9Mon
1 stop
16h 32mMDW-SJU
12/12Thu
2 stops
16h 17mSJU-MDW
$202
1/15Wed
1 stopSouthwest
9h 20mMDW-SJU
1/22Wed
2 stopsSouthwest
12h 50mSJU-MDW
$220
2/10Mon
1 stopDelta
6h 22mMDW-PUJ
2/13Thu
1 stopDelta
9h 14mPUJ-MDW
$343
1/11Sat
1 stopDelta
8h 42mMDW-PUJ
1/15Wed
1 stopDelta
8h 33mPUJ-MDW
$353
12/10Tue
1 stopKLM
6h 25mMDW-PUJ
12/13Fri
1 stopKLM
8h 16mPUJ-MDW
$473

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Recent one-way flight deals

1/17Fri
1 stopFrontier
17h 14mMDW-SJU
$88
12/12Thu
1 stopFrontier
11h 56mMDW-SJU
$89
1/22Wed
1 stopSouthwest
9h 50mMDW-SJU
$100
1/22Wed
1 stopSouthwest
9h 50mMDW-SJU
$110
12/14Sat
2 stops
28h 07mMDW-SJU
$130
12/14Sat
1 stop
14h 23mMDW-SJU
$133
1/6Mon
1 stopDelta
6h 22mMDW-PUJ
$160
1/4Sat
1 stopDelta
7h 34mMDW-PUJ
$170
11/25Mon
2 stopsWestJet
24h 05mMDW-UVF
$457
11/25Mon
2 stopsWestJet
24h 05mMDW-UVF
$490

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Last minute flights from Midway to Caribbean

Last minute flight, train and bus deals

11/18Mon
multi-stopFrontier
9h 35mMDW-SJU
11/25Mon
multi-stopFrontier
19h 09mSJU-MDW
$325
11/18Mon
multi-stopFrontier
12h 52mMDW-SJU
11/24Sun
multi-stopFrontier
29h 56mSJU-MDW
$375
11/17Sun
multi-stopDelta
6h 31mMDW-SJU
11/20Wed
multi-stopDelta
8h 34mSJU-MDW
$404
11/17Sun
multi-stopDelta
8h 40mMDW-PUJ
11/20Wed
multi-stopDelta
9h 43mPUJ-MDW
$408
11/16Sat
multi-stopSouthwest
10h 05mMDW-SJU
11/18Mon
multi-stopSouthwest
9h 40mSJU-MDW
$424
11/17Sun
multi-stopSouthwest
10h 10mMDW-SJU
11/19Tue
multi-stopSouthwest
10h 00mSJU-MDW
$444
11/18Mon
multi-stop
13h 29mMDW-NAS
11/20Wed
multi-stop
20h 55mNAS-MDW
$453
11/18Mon
multi-stop
15h 59mMDW-SDQ
11/25Mon
multi-stop
24h 53mSDQ-MDW
$456
11/17Sun
multi-stopWestJet
28h 08mMDW-AUA
11/19Tue
multi-stopWestJet
23h 05mAUA-MDW
$1,397
11/18Mon
multi-stopWestJet
23h 51mMDW-PUJ
11/20Wed
multi-stopWestJet
42h 32mPUJ-MDW
$3,236

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Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports