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Find cheap flights from Chicago Midway Airport to Caribbean Islands from $74

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 Islands 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
Fri 6/7
Fri 6/14

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Best Caribbean Islands Flight Deals

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Punta Cana
Punta Cana1 stop$214
Montego Bay
Montego Bay1 stop$362
Santo Domingo
Santo Domingo1 stop$220
Oranjestad
Oranjestad2 stops$586
Nassau
Nassau1 stop$367
Kingston
Kingston1 stop$480
Simpson Bay
Simpson Bay2 stops$299
Providenciales
Providenciales1 stop$462
George Town
George Town1 stop$474
Aguadilla
Aguadilla1 stop$261
St. John's
St. John's2 stops$3,053

Good to know

Low season

April

High season

December

Cheapest flight

$74
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly and prices are also 4% lower on average.
Flight from Chicago Midway Airport to San Juan

FAQs - booking Caribbean Islands flights

  • 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.

See more FAQs

Top 3 airlines serving from Midway to Caribbean Islands

 
Need help choosing which airline to fly with from Midway to Caribbean Islands? 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 9141 reviews
8.6Crew
7.3Food
7.3Entertainment
8.2Boarding
7.9Comfort
Airline reviews

The flight was decent again if there was a place that you could put crying children that would be great. Or maybe make a rule against allowing infants on the plane.

6.0 GoodAnonymous, May 2024SEA - HNL
Read more about Alaska Airlines reviews

The flight was decent again if there was a place that you could put crying children that would be great. Or maybe make a rule against allowing infants on the plane.

The flight was great. The pilot was great. It was really annoying that the staff had facemasks on. Hard to hear what they’re saying when a mask is covering their mouth. I enjoyed the flight, but there was a crying baby in front of me. You guys should offer flights baby free. I would be very into that me and the person next to me discussed how they should make free flights for all of us that don’t have kids. I wouldn’t mind paying extra to not have to deal with the smell of a dirty diaper or screaming of a child. Also, if they had a separate room, the babies could be sent to the back with a curtain or something muddle the horrible sounds.

Smooth. Courteous. Fun. One problem: the wheels on my checked roller back were broken when I picked up baggage at destination. Must have happened during flight baggage handling but I don’t know where.

Staff very helpful and friendly, in flight entertainment poor. Flight left late and thus arrived 20 minutes late to final destination.

Ground crew was great in Austin, flight crew left a lot to be desired. Not particularly friendly, helpful or nice.

Everything was fine -- on time, clear, clean. I don't want to pay extra for in-flight wi-fi

First time flying with Alaska and the staff were All professional from checkin to departure! I do plan to book more flights with Alaska. Thanks

The flight was delayed because the pilots had not arrived on their previous flight yet. The flight was 100% full so it was pretty crowded. I miss having the screens on the back of the seats. It would be great if the Alaska planes had the clip so you can put your phone or tablet on the back of the seat in front of you to not strain your neck. Everything else was very smooth.

Boarded the plain and had to wait 1 hour for crew Captain to arrive from another flight

It was fine since it ensure we went to our destination in time.

West Jet has a horrible boarding process and the seats have no cushion.

Everything went smoothly. I didn’t like that when I booked in the main cabin my wife and I weren’t seated together. One would think when booking on an option that allows picking your seat. They would put you and your travel partner together. Had to call to get it sorted. They did fix.

The gate area was incredibly short staffed, with one representative manning 4-5 flights, which caused a 3 hr delay in boarding even though the plane was all ready to leave. Other flights also were delayed because of this. The flight crew was awesome and I feel bad for the only gate worker on call, but Delta needs to hire more employees.

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!

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.

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

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!

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 😕

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.

Book cheap flights from Chicago to Caribbean Islands

Recent round-trip flight deals

5/18Sat
1 stopFrontier
14h 45mMDW-SJU
5/22Wed
1 stopFrontier
16h 05mSJU-MDW
$188
5/22Wed
1 stopFrontier
12h 21mMDW-SJU
6/6Thu
1 stopFrontier
15h 35mSJU-MDW
$212
5/21Tue
1 stopFrontier
11h 49mMDW-SJU
6/1Sat
1 stopFrontier
11h 36mSJU-MDW
$213
5/19Sun
1 stopFrontier
13h 04mMDW-PUJ
5/30Thu
1 stopFrontier
14h 48mPUJ-MDW
$214
5/20Mon
2 stops
16h 27mMDW-PUJ
5/29Wed
1 stop
8h 45mPUJ-MDW
$336
7/16Tue
1 stop
23h 32mMDW-NAS
7/23Tue
1 stop
8h 03mNAS-MDW
$367
7/7Sun
1 stopDelta
6h 55mMDW-NAS
7/24Wed
2 stopsDelta
16h 05mNAS-MDW
$428
9/14Sat
1 stopDelta
18h 08mMDW-SDQ
9/21Sat
1 stopDelta
7h 48mSDQ-MDW
$433
7/3Wed
2 stopsWestJet
18h 54mMDW-NAS
7/7Sun
2 stopsWestJet
23h 04mNAS-MDW
$2,706
6/13Thu
2 stopsWestJet
20h 35mMDW-NAS
6/17Mon
2 stopsWestJet
23h 05mNAS-MDW
$2,943

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Recent one-way flight deals

5/21Tue
1 stopFrontier
12h 38mMDW-SJU
$74
5/18Sat
1 stopFrontier
10h 15mMDW-SJU
$84
5/14Tue
1 stopFrontier
11h 04mMDW-MBJ
$99
5/17Fri
1 stopFrontier
11h 45mMDW-SJU
$109
6/25Tue
2 stops
31h 14mMDW-SDQ
$150
5/20Mon
2 stops
16h 10mMDW-MBJ
$156
9/25Wed
1 stopDelta
6h 23mMDW-SDQ
$190
10/15Tue
1 stopDelta
17h 33mMDW-SDQ
$200
5/30Thu
2 stopsWestJet
23h 49mMDW-PLS
$1,204
5/22Wed
2 stopsWestJet
23h 05mMDW-MBJ
$1,517

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Last minute flights from Midway to Caribbean Islands

Last minute flight, train and bus deals

5/13Mon
multi-stopFrontier
9h 12mMDW-SJU
5/22Wed
multi-stopFrontier
16h 05mSJU-MDW
$248
5/10Fri
multi-stopFrontier
9h 35mMDW-SJU
5/15Wed
multi-stopFrontier
11h 43mSJU-MDW
$278
5/10Fri
multi-stopFrontier
18h 04mMDW-SJU
5/14Tue
multi-stopFrontier
28h 46mSJU-MDW
$284
5/13Mon
multi-stopFrontier
12h 17mMDW-SJU
5/14Tue
multi-stopFrontier
28h 46mSJU-MDW
$287
5/9Thu
multi-stop
18h 04mMDW-MBJ
5/14Tue
multi-stop
10h 43mMBJ-MDW
$511
5/9Thu
multi-stop
23h 18mMDW-MBJ
5/14Tue
multi-stop
10h 43mMBJ-MDW
$522
5/10Fri
multi-stopDelta
17h 37mMDW-PUJ
5/14Tue
multi-stopDelta
17h 42mPUJ-MDW
$604
5/13Mon
multi-stopDelta
4h 52mMDW-NAS
5/14Tue
multi-stopDelta
9h 44mNAS-MDW
$683
5/13Mon
multi-stopWestJet
20h 08mMDW-NAS
5/17Fri
multi-stopWestJet
24h 16mNAS-MDW
$3,047
5/11Sat
multi-stopWestJet
42h 53mMDW-NAS
5/14Tue
multi-stopWestJet
23h 02mNAS-MDW
$3,199

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