Find cheap flights from Chicago Midway Airport to Caribbean Islands from $56
This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight departing on 10/16. 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.Round-trip
1 adult
Economy
Sat 10/21
Sat 10/28
In the last 7 days travellers have searched 45,131,337 times on KAYAK, and here is why:
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Latest Caribbean Islands Flight Deals
Best round-trip prices found by our users on KAYAK in the last 72 hours
1 stop from $219
1 stop from $268
1 stop from $245
1 stop from $345
1 stop from $563
Good to know
Top tips for finding cheap flights to Caribbean Islands
- Looking for a cheap flight? 25% of our users found tickets from Chicago Midway Airport to the following destinations at these prices or less: San Juan $79 one-way - $128 round-trip
- High season is considered to be January, February and December. The cheapest month to fly from Chicago is January.
FAQs - booking Caribbean Islands flights
Which airlines have a flexible cancellation policy for flights from Chicago Midway to Caribbean Islands due to COVID-19?
Frontier has waived its change and cancellation fees on flights from Chicago Midway to Caribbean Islands. Confirm policy on booking site.
How does KAYAK find such low prices on flights from Chicago Midway Airport to Caribbean Islands?
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 Islands.
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 Islands?
KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Caribbean Islands 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 Islands?
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 Islands 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 Islands?
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 Islands from Chicago Midway Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.
Top 3 airlines serving from Midway to Caribbean Islands
8.3
Alaska AirlinesOverall score based on 29451 reviews
88crew
79food
85boarding
79entertainment
85overall
83comfort
Airline reviews
Pros: "Flight was safe"
Cons: "I was not given a seat until about 10 minutes before boarding despite having arrived hours early; the flight was delayed, I was not able to charge my phone despite there being a USB outlet on the seat back (it didn’t work somehow), and no snacks except a cookie"
Pros: "Flight was safe"
Cons: "I was not given a seat until about 10 minutes before boarding despite having arrived hours early; the flight was delayed, I was not able to charge my phone despite there being a USB outlet on the seat back (it didn’t work somehow), and no snacks except a cookie"
Pros: "Had a TV w/ lots of free movie options, seats were comfy, plane was nice and clean, staff was very kind"
Cons: "This is the best flight I’ve been on, would recommend anyone to Alaska Airlines"
Pros: "Premium economy seat was tolerable"
Cons: "Plane was too warm for comfort. Hell was getting from concourse N to C at SeaTac with the train OOC."
Cons: "Luggage space issue could have been handled prior to flight not on a volunteer basis."
Pros: "The flight was fine and comfortable"
Cons: "I just did not like that we were on flight for 6 hours and no food was given complimentary plus there was no vegetarian food at all to eat as we don’t eat meat at all"
Pros: "Friendly crew and quick easy boarding."
Cons: "Windows didn't have shades, coffee was cold initially. On the positive the attendant noticed and came back with a warm cup."
Pros: "Sarah provided excellent customer service. That was one of the faster flights back to Anchorage!"
Cons: "The pet relief area at Seatac airport was subpar at best. Zero ventilation in the pet area with made for a hazardous environment for both my pet and myself."
Cons: "Dog allowed to sit next to me. It should be ina crate or at least on the lap of the owner"
Cons: "The wait on the tarmac for plane to park in SEA"
Pros: "Very comfortable seating and humidity in the plane. The temperature was pleasant as well."
Cons: "We were only offered one small cup of a drink for a 4.5 hour flight. Additional drinks would have been better. Also, there were no headphones/earbuds available for the flight as they had run out earlier."
Pros: "Hospitality"
Cons: "Nos trataron con mucha seguridad de higiene y nos sentimos muy seguras de viajar con ustedes muchas gracias"
Pros: "Very controlled and safe Covid procedures. Outlets and screens at every seat."
Pros: "The crew was very courteous and friendly"
Cons: "Delays Why is it always a surprise for the crew that the plane needs to be de iced in the winter"
Pros: "Although the take off was delayed (having nothing to do with the crew or airplane or LAX), we arrived right on time. Good food. Great in flight entertainment. I appreciated the low lighting levels while we were trying to sleep/rest."
Cons: "The plane needs more bathrooms."
Cons: "More leg room and seat width. I don’t like having other passengers pressed against me."
Pros: "Crew and food"
Cons: "Spacing between seats and overhead luggage storage. They ran out of room before the entire plane had boarded"
Pros: "Having the whole center three seats to myself. The food and beverages were really good as well."
Cons: "Both flights were significantly late to depart. Also the WiFi on the transatlantic flight was out."
Cons: "On my opinion Delta is one of the best airlines. Staff are friendly and they made me feel service. They are really nice and they.take care of been on time and anything you ask them they are there to answer. Great airline"
Pros: "I liked the cookies and juice. The interactive screen to watch something. The cleanliness. The price. On time. The service. Thank you. The excitement of flying."
Cons: "Touch screen monitor was unable to register touch, so no entertainment available."
Flight was canceled both ways cost me a lot of time and money. Company takes advantage of people to make money, can’t call there is no phone number and in order to chat with an agent you have to know the secret way to get to a person rather than a robot. Never deal with them again.
Pros: "Finding a better price than the actual site of the air line"
Cons: "Nothin honestly."
Pros: "The plane was newer and decent quality. Pilot was fantastic!"
Cons: "Crew was curt. We could have boarded earlier, but instead waited for our 2 hour delay in the terminal."
Pros: "Crew was cool - seats were comfortable but"
Cons: "Not able to recline seats. Head rests did not have a cushion to pull around neck. AND - no charging stations for computers or phones - bad - looking elsewhere for my next flight. Come on, this is the charging age!"
Pros: "Yes, the crew was friendly & helpful. The pilot kept us updated throughout the flight."
Cons: "There was no explanation as to why our flight was delayed 2 hours. No plane was in sight for us to board for those 2 hours."
Pros: "The price"
Cons: "Packed in like sardines. Very uncomfortable seats for a three hour flight. Second time I’ve recently flown with them. Planes both times seemed old inside and I’ve ridden on their nice ones with screens to watch before."
Pros: "Saved me on price even when I called n checked on united website. Found a better deal with u for the situation I was in."
Cons: "I wish I didn't have to u use you do I had a flight but Internet did not work n 6 of us couldn't get on our orginal flights. So thanks for the plan B !!"
Pros: "My flights were on time. Boarding was fast and easy."
Cons: "I arrived 2 hours before my scheduled flight time but had to wait for at least 15 minutes before anyone came to the counter."
Pros: "Nothing"
Cons: "Frontier had 2 flights out of FLL all day. 1st scheduled to leave at 10am to Trenton. Our's to Cincy at 4. Trenton put passengers in and they sat on the tarmac back the APU was broke (essentially plane's starter). Then people finally were able to get off the plane. Meanwhile, our flight to Cincy couldn't leave because the airport wouldn't let us use a different gate! Apparently, Frontier wasn't paying what the City wanted so we sat there waiting for over 6 hours though our plane was at a different part of the airport waiting on is, we couldn't board and leave!!!"
Book cheap flights from Chicago to Caribbean Islands
Recent round-trip flight deals
10/21Sat
2 stopsFrontier
15h 52mMDW-SJU
10/25Wed
nonstopFrontier
5h 06mSJU-MDW
$134
10/27Fri
nonstopFrontier
4h 39mMDW-SJU
11/1Wed
nonstopFrontier
5h 06mSJU-MDW
$135
10/7Sat
1 stopFrontier
11h 25mMDW-SJU
10/14Sat
nonstopFrontier
5h 06mSJU-MDW
$136
10/23Mon
1 stopFrontier
13h 57mMDW-SJU
11/1Wed
nonstopFrontier
5h 06mSJU-MDW
$137
12/1Fri
1 stopFrontier
14h 20mMDW-SJU
12/5Tue
nonstopFrontier
5h 20mSJU-MDW
$138
10/21Sat
1 stopFrontier
11h 25mMDW-SJU
10/25Wed
nonstopFrontier
5h 06mSJU-MDW
$139
10/7Sat
2 stopsMultiple Airlines
14h 25mMDW-SJU
10/14Sat
nonstopMultiple Airlines
5h 06mSJU-MDW
$140
10/18Wed
1 stopMultiple Airlines
14h 12mMDW-SJU
10/24Tue
1 stopMultiple Airlines
15h 04mSJU-MDW
$141
10/25Wed
1 stopMultiple Airlines
8h 04mMDW-SJU
11/3Fri
nonstopMultiple Airlines
5h 06mSJU-MDW
$142
10/14Sat
nonstopFrontier
4h 39mMDW-SJU
10/16Mon
1 stopFrontier
13h 16mSJU-MDW
$143
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Recent one-way flight deals
10/16Mon
nonstopFrontier
4h 39mMDW-SJU
$56
10/28Sat
nonstopFrontier
4h 39mMDW-SJU
$57
10/11Wed
nonstopFrontier
4h 39mMDW-SJU
$58
9/27Wed
nonstopFrontier
4h 45mMDW-SJU
$59
10/14Sat
nonstopFrontier
4h 39mMDW-SJU
$60
10/17Tue
1 stopMultiple Airlines
13h 19mMDW-SJU
$72
10/1Sun
1 stopDelta
6h 22mMDW-PUJ
$202
10/10Tue
2 stopsDelta
17h 40mMDW-SDQ
$205
10/23Mon
2 stopsDelta
17h 33mMDW-MBJ
$210
10/3Tue
1 stopDelta
6h 22mMDW-PUJ
$212
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Last minute flights from Midway to Caribbean Islands
Last minute flight, train and bus deals
9/22Fri
nonstopFrontier
4h 45mMDW-SJU
9/29Fri
nonstopFrontier
4h 55mSJU-MDW
$153
9/25Mon
nonstopFrontier
4h 45mMDW-SJU
9/27Wed
nonstopFrontier
4h 55mSJU-MDW
$156
9/25Mon
nonstopFrontier
4h 45mMDW-SJU
9/29Fri
nonstopFrontier
4h 55mSJU-MDW
$162
9/22Fri
nonstopFrontier
4h 45mMDW-SJU
9/25Mon
nonstopFrontier
4h 55mSJU-MDW
$167
9/22Fri
nonstopFrontier
4h 45mMDW-SJU
9/27Wed
nonstopFrontier
4h 55mSJU-MDW
$169
9/26Tue
multi-stopMultiple Airlines
14h 21mMDW-SJU
9/30Sat
nonstopMultiple Airlines
4h 55mSJU-MDW
$210
9/25Mon
multi-stopDelta
8h 25mMDW-PUJ
10/2Mon
multi-stopDelta
18h 07mPUJ-MDW
$557
9/25Mon
multi-stopDelta
18h 18mMDW-PUJ
10/2Mon
multi-stopDelta
18h 07mPUJ-MDW
$562
9/22Fri
multi-stopDelta
8h 25mMDW-PUJ
9/27Wed
multi-stopDelta
18h 59mPUJ-MDW
$570
9/25Mon
multi-stopDelta
18h 18mMDW-PUJ
10/2Mon
multi-stopDelta
16h 49mPUJ-MDW
$625
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Chicago Midway Airport - Caribbean Islands Flights
Departure:
Chicago Midway Airport (MDW)United States
Return flight deals:
Caribbean Islands - Chicago Midway Airport
Cabin classes:
$593
$591
$398
$40
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Browse destinations:
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