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Find cheap flights from Caribbean to Chicago Midway Airport from $109

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 5/14. 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
ons. 6/5
ons. 6/12

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Good to know

Low season

March

High season

December

Cheapest flight

$109
Best time to beat the crowds but there is an average 53% increase in price.
Most popular time to fly and prices are also 11% lower on average.
Flight from San Juan to Chicago Midway Airport

FAQs for booking Caribbean to Chicago Midway Airport flights

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

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

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

Nonstop departures

Caribbean 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

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 3 airlines serving from Caribbean to Midway

 
Need help choosing which airline to fly with from Caribbean 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.
8.0
DeltaOverall score based on 10826 reviews
7.4Food
8.6Crew
7.9Comfort
8.0Entertainment
8.2Boarding
Airline reviews

Very frustrated with boarding gate crew. She announced the plane was small and they would be limiting us to one item to carry on. Not a problem for me as I understand the tiny planes have limited space!! Not the case here! It was a rather large plane and had plenty of room for bags! So because I don’t want to be one of “those people” who ignores the request to check a carry on I did so asking if I would be able to pick it up at the bottom of the ramp on arrival in Knoxville to which she responded “yes”! Then I watched as every other passenger held onto their 2 items and boarded!! Then when we arrived in Knoxville our 2 carry ons had been put with all the other luggage and we had to go to baggage pick up and wait for all the big checked bags to come off the carousel! So she lied!! Frustrating. Next time I won’t be so nice!

8.0 ExcellentCynthia, May 2024ATL - TYS
Read more about Delta reviews

Very frustrated with boarding gate crew. She announced the plane was small and they would be limiting us to one item to carry on. Not a problem for me as I understand the tiny planes have limited space!! Not the case here! It was a rather large plane and had plenty of room for bags! So because I don’t want to be one of “those people” who ignores the request to check a carry on I did so asking if I would be able to pick it up at the bottom of the ramp on arrival in Knoxville to which she responded “yes”! Then I watched as every other passenger held onto their 2 items and boarded!! Then when we arrived in Knoxville our 2 carry ons had been put with all the other luggage and we had to go to baggage pick up and wait for all the big checked bags to come off the carousel! So she lied!! Frustrating. Next time I won’t be so nice!

Everything was great. The big planes could still stand to have a bit more leg room. Crew was amazing!!

It was a good experience except when boarding a female flight attendant did not go out of her way to assist my teenage daughters in finding space for their carry-ons after their compartments were full.

The flight was excellent, I recommend people to fly with Delta

On time departure, smooth trip, flight attendant told through passengers the gate we would arrive at and the gate our outbound flight was departing from. Early arrival

The crew were very welcoming and helpful. I just wish economy had a bit more leg room. My knees were constantly hitting the chair in front of me.

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.

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 !

Crew was nice, explained emergency protocol very well. Flight took off and arrived on time. Pilot explained the small delay that occurred with docking and providing updates. I would definitely fly spirit again.

Terrible… missed our flight due to ridiculously long time to go thru baggage check-in!

The seat are terrible. Don’t even think of sleeping on a Spirit flight. The kids that run the plane aka flight attendants are pretty rude and straight forward. They get the job done but without class.

I had a death in my family and booked my flight on Spirit. My flight was cancelled the morning of my flight, no explanation, no help to rebook, nobody to talk to. The next available flight was 2days later !!!! Terrible airline, will NEVER fly with them again!

They took a horrible route with a lot of turbulence and I eneded up getting sick. Even if the flight takes longer. Don't put people life at risk just to get to the airport on time.

Every thing was fine ,low price,easy on time ,clean, good staff, really no issues

Had to board plan 2x due to lack of security check after 1st boarding

Miserable. The crew was rude, the flight was delayed 5 hours for mechanical reasons and then “weather” even though other planes were leaving.

They kept Changing the flight times. It was delayed several times and at one point it was supposed to depart at 3.40am! At which point we ended up staying overnight and booked long a separate United flight for early morning departure. The spirit flight then got moved up and left at 1.30 in the morning when it was supposed to leave at 9.40pm the night before.

Flight was delayed...not horribly late. Just before push back engine shut down for a quick replacement item that took about five minutes. After that, everything was smooth and the pilot was able to make up time in the air so that our arrival time was not too far off the original anticipated arrival time.

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

Didn't like anything!! Horrible flight. Small seating area and hard seats. Butt was sore after 2 hour flight to Seattle No entertainment or free refreshments No wifi or USB charging receptacles to charge phone entoute like other airliners Luggage rates were 3 times as much as competitors. Difficult to navigate online luggue process to pre pay before flight Overall bad experience WILL NEVER RIDE OR RECOMMEND FRONTIER TO FRIENDS OR FAMILY MEMBERS!!! THIS IS A SHAME!! MOST MESERIBLE FLIGHT OF MY LIFE!! AND I THOUGHT SPIRIT WAS 👎 YOU GOT THEM BEAD HANDS DOWN!!

Flight was a little late taking off. Seats are too upright, no ports to charge devices, no wifi, no entertainment

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.

Book cheap flights from Caribbean to Chicago

Recent round-trip flight deals

5/17fre.
1 stopFrontier
10h 03mSJU-MDW
5/20man.
1 stopFrontier
12h 21mMDW-SJU
$178
5/18lør.
1 stopFrontier
7h 31mSJU-MDW
5/21tir.
1 stopFrontier
12h 38mMDW-SJU
$180
5/17fre.
1 stopFrontier
10h 03mSJU-MDW
5/21tir.
1 stopFrontier
11h 49mMDW-SJU
$186
5/15ons.
1 stopFrontier
9h 53mSJU-MDW
5/19søn.
1 stopFrontier
12h 07mMDW-SJU
$188
5/16tor.
1 stopFrontier
12h 10mSJU-MDW
5/20man.
1 stopFrontier
12h 21mMDW-SJU
$222
5/22ons.
1 stop
8h 45mPUJ-MDW
6/9søn.
1 stop
15h 08mMDW-PUJ
$328
8/6tir.
1 stopDelta
8h 20mNAS-MDW
8/20tir.
1 stopDelta
5h 07mMDW-NAS
$414
8/7ons.
1 stopDelta
5h 38mNAS-MDW
8/20tir.
1 stopDelta
17h 28mMDW-NAS
$416
6/18tir.
2 stops
10h 20mMBJ-MDW
9/18ons.
1 stop
9h 13mMDW-MBJ
$472
10/22tir.
2 stopsLATAM Airlines
32h 47mPUJ-MDW
10/27søn.
2 stopsLATAM Airlines
19h 10mMDW-PUJ
$2,039

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Recent one-way flight deals

5/14tir.
1 stopFrontier
9h 49mSJU-MDW
$109
5/16tor.
1 stopFrontier
10h 31mBQN-MDW
$117
5/16tor.
1 stopFrontier
12h 10mSJU-MDW
$117
5/14tir.
1 stopFrontier
28h 46mSJU-MDW
$127
5/20man.
1 stopFrontier
10h 03mSJU-MDW
$129
9/24tir.
1 stopFrontier
8h 58mSJU-MDW
$134
5/29ons.
2 stops
13h 58mSDQ-MDW
$176
9/19tor.
2 stopsDelta
17h 22mPUJ-MDW
$248
5/26søn.
1 stopDelta
18h 25mSDQ-MDW
$305
9/19tor.
1 stopDelta
17h 54mPUJ-MDW
$307

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Last minute flights from Caribbean to Midway

Last minute flight, train and bus deals

5/8ons.
multi-stopFrontier
9h 44mSJU-MDW
5/14tir.
multi-stopFrontier
10h 16mMDW-SJU
$277
5/8ons.
multi-stopFrontier
10h 07mBQN-MDW
5/16tor.
multi-stopFrontier
8h 53mMDW-BQN
$278
5/8ons.
multi-stopFrontier
9h 53mSJU-MDW
5/12søn.
multi-stopFrontier
12h 21mMDW-SJU
$278
5/9tor.
multi-stopFrontier
28h 23mBQN-MDW
5/16tor.
multi-stopFrontier
17h 00mMDW-BQN
$280
5/8ons.
multi-stopFrontier
9h 53mSJU-MDW
5/15ons.
multi-stopFrontier
12h 31mMDW-SJU
$309
5/8ons.
multi-stopFrontier
9h 44mSJU-MDW
5/11lør.
multi-stopFrontier
13h 21mMDW-SJU
$336
5/8ons.
multi-stopDelta
25h 25mSDQ-MDW
5/11lør.
multi-stopDelta
20h 20mMDW-SDQ
$518
5/8ons.
multi-stopDelta
18h 25mSDQ-MDW
5/11lør.
multi-stopDelta
26h 33mMDW-SDQ
$528
5/8ons.
multi-stopDelta
14h 56mMBJ-MDW
5/11lør.
multi-stopDelta
28h 33mMDW-MBJ
$531
5/8ons.
multi-stop
25h 36mSJU-MDW
5/15ons.
multi-stop
21h 07mMDW-SJU
$1,151

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