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$80 Find cheap flights from Caribbean Islands 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 5/21. 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 6/15
Sat 6/22

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Good to know

Low season

March

High season

December

Cheapest flight

$80
Best time to beat the crowds but there is an average 65% increase in price.
Most popular time to fly and prices are also 4% lower on average.
Flight from San Juan to Chicago Midway Airport

FAQs for booking Caribbean Islands to Chicago Midway Airport flights

  • How does KAYAK find such low prices on flights from Caribbean Islands 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 Islands 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 Islands 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 Islands 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 Islands 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 Islands with another airline.

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

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

Nonstop departures

Caribbean Islands 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, +10 more

Aeromexico, Air France, +11 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, +10 more

Aeromexico, Air France, +11 more

See more direct flights

Nonstop returns

Chicago Midway to Caribbean Islands

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, +10 more

Aeromexico, Air France, +11 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, +10 more

Aeromexico, Air France, +11 more

See more direct flights
See more direct flights

Top airline flying from Caribbean Islands to Midway

 
Need help choosing which airline to fly with from Caribbean Islands 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.
6.2
FrontierOverall score based on 4060 reviews
4.9Entertainment
6.6Boarding
5.2Food
7.1Crew
5.8Comfort
Airline reviews

Check in online was easy. Seats aren’t very comfortable

6.0 GoodDaneika, May 2024ATL - LGA
Read more about Frontier reviews

Check in online was easy. Seats aren’t very comfortable

Fecal matter in seat back pocket. Presumably from a kids diaper.

Worst airline to travel with. They treat you like a prisoner in a jailhouse barking out orders and threats. Nickle and dime you to the same price or higher than a respectable airline like one of the big 3 . Might as well fly with standard airlines

Well I mean u get what u pay for so 🤷‍♂️

Over an hour delay in departure but I was notified beforehand. Another delay on tarmac upon arrival at LGA. We ended up departing the plane almost 2 hours later than expected

I fly Frontier because it’s affordable. I understand that the seats are tight and not the most comfortable…but that’s part of it. The problem with this flight was that there was a group of travelers directly behind me at the back of the plane who were ridiculously loud and obnoxious the entire flight. I’m pretty sure they were drunk and I could periodically smell an odd odor that I believe was one of them using a smokeless vape pen. The stewards had to remind them to keep quiet during the pre-flight instruction, but that was it. They never said another thing to them for the rest of the flight. It was a miserable.

I checked a bag because it was $5 less than carry on. They managed to lose my bag on a 2.5 hr direct flight! Frontier has no airport staff at baggage claim to help. As soon as I got home around 11 pm I tried to use their online system to file the claim for lost bag - system wouldn't take the # on my baggage claim ticket - said it was not the correct number. Also said that I had not checked a bag, which wasn't true - even my online boarding pass showed that I had checked a bag. Wasted about an hour on that process with no luck. Tried again in the morning - same thing. So tried online chat with Frontier bot - waited 35-40" twice to be connected to a baggage agent and it never happened. Eventually drove to PDX after work and waited 2 hrs for the Frontier ticket agents to arrive prior to the next Frontier flight out of PDX and FINALLY got some help from one of them, to take me to lost luggage area where I was able to retrive my bag. Probably took 4-5 hrs. of my time and endless frustration to get my bag. This was my first -- and LAST -- experience flying Frontier Airlines. Check-in was also extremely difficult and time consuming. The flight itself (and staff) were fine but everything else about the experience was a total disaster! The fact that Frontier literally has NO WAY to connect to a human voice for customer service (in this case for lost luggage) is the WORST!!!!!

Frontier is a crappy airline nothing about it is honest

I didn't get to do this flight l, hard to review

Not good 😐 Over priced baggage fees Small hard seats No wifi or entertainment options 😕

Book cheap flights from Caribbean Islands to Chicago

Recent round-trip flight deals

6/3Mon
1 stopFrontier
9h 53mSJU-MDW
6/10Mon
1 stopFrontier
17h 41mMDW-SJU
$213
5/29Wed
1 stopFrontier
10h 08mSJU-MDW
6/3Mon
1 stopFrontier
12h 21mMDW-SJU
$214
6/5Wed
1 stopFrontier
7h 23mSJU-MDW
6/10Mon
1 stopFrontier
17h 41mMDW-SJU
$217
10/22Tue
1 stopDelta
9h 50mSJU-MDW
10/26Sat
1 stopDelta
6h 58mMDW-SJU
$394
10/24Thu
1 stopDelta
9h 50mSJU-MDW
10/27Sun
1 stopDelta
9h 04mMDW-SJU
$395
7/31Wed
1 stop
9h 18mSDQ-MDW
8/26Mon
1 stop
13h 49mMDW-SDQ
$453
5/26Sun
2 stops
12h 00mMBJ-MDW
6/4Tue
1 stop
27h 12mMDW-MBJ
$507
10/22Tue
2 stopsLATAM Airlines
32h 47mPUJ-MDW
10/27Sun
2 stopsLATAM Airlines
28h 00mMDW-PUJ
$2,112
10/22Tue
2 stopsLATAM Airlines
32h 47mPUJ-MDW
10/27Sun
2 stopsLATAM Airlines
28h 00mMDW-PUJ
$2,121
7/18Thu
2 stopsWestJet
21h 54mAUA-MDW
7/31Wed
2 stopsWestJet
21h 05mMDW-AUA
$3,202

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Recent one-way flight deals

5/21Tue
1 stopFrontier
24h 44mSJU-MDW
$80
5/29Wed
1 stopFrontier
10h 08mSJU-MDW
$107
8/29Thu
1 stopFrontier
10h 36mBQN-MDW
$109
8/21Wed
1 stopFrontier
8h 58mSJU-MDW
$109
9/9Mon
2 stops
16h 04mSDQ-MDW
$171
9/22Sun
1 stopDelta
10h 44mSJU-MDW
$172
9/11Wed
2 stops
19h 45mSDQ-MDW
$173
10/18Fri
1 stopDelta
9h 50mSJU-MDW
$202
9/23Mon
3 stopsWestJet
29h 20mMBJ-MDW
$631
7/23Tue
2 stopsWestJet
22h 59mMBJ-MDW
$1,565

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Last minute flights from Caribbean Islands to Midway

Last minute flight, train and bus deals

5/21Tue
multi-stopFrontier
14h 10mSJU-MDW
5/27Mon
multi-stopFrontier
12h 21mMDW-SJU
$289
5/20Mon
multi-stopFrontier
10h 03mSJU-MDW
6/7Fri
multi-stopFrontier
17h 41mMDW-SJU
$293
5/21Tue
multi-stopFrontier
28h 54mSJU-MDW
5/26Sun
multi-stopFrontier
12h 07mMDW-SJU
$309
5/18Sat
multi-stopFrontier
7h 31mSJU-MDW
5/21Tue
multi-stopFrontier
11h 49mMDW-SJU
$318
5/19Sun
multi-stopFrontier
15h 00mSJU-MDW
6/7Fri
multi-stopFrontier
17h 41mMDW-SJU
$319
5/17Fri
multi-stopFrontier
15h 48mSJU-MDW
5/21Tue
multi-stopFrontier
11h 49mMDW-SJU
$328
5/17Fri
multi-stopFrontier
15h 48mSJU-MDW
5/20Mon
multi-stopFrontier
12h 21mMDW-SJU
$329
5/18Sat
multi-stopFrontier
9h 36mSJU-MDW
5/25Sat
multi-stopFrontier
8h 24mMDW-SJU
$363
5/17Fri
multi-stopDelta
23h 30mPUJ-MDW
5/21Tue
multi-stopDelta
8h 00mMDW-PUJ
$1,146
5/17Fri
multi-stopDelta
23h 30mPUJ-MDW
5/21Tue
multi-stopDelta
8h 00mMDW-PUJ
$1,158

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