$58 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 3/25. 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.
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Best Caribbean Flight Deals from Midway

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

Punta Cana
Punta Cana1 stop$239
Santo Domingo
Santo Domingo2 stops$289
Montego Bay
Montego Bay1 stop$349
Oranjestad
Oranjestad1 stop$585
Nassau
Nassau1 stop$425
Kingston
Kingston1 stop$379
Simpson Bay
Simpson Bay1 stop$474
Providenciales
Providenciales2 stops$532
George Town
George Town1 stop$522
St. John's
St. John's1 stop$978
Aguadilla
Aguadilla1 stop$353

Good to know

Low season

November

High season

March

Cheapest flight

$58
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly with an average 40% increase in price.
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 from Chicago Midway Airport to 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 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 from Chicago Midway Airport to Caribbean with an airline and back 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 from Chicago Midway Airport to Caribbean 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

  • Book at least 1 week before departure in order to get a below-average price.
  • High season is considered to be February, March and April. The cheapest month to fly from Chicago is June.
  • Morning departure is around 4% cheaper 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 4411 reviews
8.7Crew
8.2Boarding
7.6Entertainment
7.1Food
8.1Comfort
Airline reviews

Gate agents were informative and friendly… flight attendants were as well. Had a fun time chatting about their legacy AirTran experiences as a former fan of the airline that Southwest acquired.

10.0 ExcellentAnonymous, Jan 2025ATL - LGA
Read more Southwest reviews

Gate agents were informative and friendly… flight attendants were as well. Had a fun time chatting about their legacy AirTran experiences as a former fan of the airline that Southwest acquired.

Flight was awfully bumpy and landing was a bit jolting. I was in the restroom when snacks and drinks were served and was not asked if i wanted any. I had to ask for water finally.

Wi Fi was horrible kept cutting out the whole time and too expensive

I really like open seating. I hate that I've heard this is going away. This is one of the unique things that makes Southwest my goto choice.

Boarding was a little late, but made up for it. It was quick to taxi to the runway, since it's a smallish airport.

Excellent! Only question is how we check in at exactly 24 hours in advance and end up at the end of the B boarding group

Multiple delays and gate changes. Arrived at final destination 6 hours late. All rental cars had been taken.

Employees were kind and funny, as always! Flight was late but no announcements were made for people with tight connections to help them transition quickly. No service due to turbulence.

It was 2 hours 45 minutes late, for no apparently clear reason.

I recently flew Southwest from San Jose to Honolulu. I was very impressed with the flight crew, especially the flight attendant in charge of the front of the plane. She came through the aisle at least five times for drinks and water, and two times for snacks. I have not seen such service since I flew first class. Also, for the first time, they gave us the correct baggage claim number, and the luggage came out quickly. I can't wait for Southwest to have assigned seating! I absolutely hate the Cattle Call boarding procedure and the mad dash to get seats and overhead bins. However, the boarding was efficient.

Boarding is, as it always is… horrible. Gate lice. Slow moving zones. Too many people with carry ons

I loved having a most black flight crew during Black History Month; rather by design or accident I appreciated the representation. ❤️

This was the second flight this week with flight attendant Marcus I’m not sure if his last name is Lane or Lang but this guy is awesome. He funny, attentive and his service is 5 stars. Marcus makes business travel more enjoyable !

Although the flight left late, we arrived early. It was one of the quickest boarding and off boarding experiences I’ve had. It was kind of annoying the only drinks they had were water, coffee, and tea. The flight was very smooth, temperature was just right, and flight attendants were friendly.

Rode in a smaller plane and short trip meant no snacks, no free wifi or tv. It was only 30min flight so honestly wasn’t a big deal to lack these items.

Lower number on this flight so spaced out passengers. Able to enjoy more room to relax during flight. It was lovely.

Kind staff. Snacks are small but that’s the new normal.

Overall, terrible. Flight from SFO was delayed due to “air traffic control issues”, and we were all mislead about connecting flights. Told “you have 20 minutes to catch your connection”. Reality was 5. We got to watch the plane sit at the bridge. Won’t fly Delta with a connection again.

The young man who was our flight attendant in first class was lazy and did not do his job well at all. Never offered drinks upon boarding - actually I take that back... said "are you okay with water" as if I do not want to get you anything else, only passed the snacks around once, got my drink order wrong and then never offered a second round of drinks. He was the worst I have ever seen on Delta and we fly a lot.

Great service. Great staff. Boarding was a little slow, but I think there was a service dog slowing things down.

Flight was on time It was a good flight overall

Check in at dtw was understaffed and chaotic. Flight itself was smooth. Airplane seats seemed newly upholstered and comfortable, flight attendants attentive.

Amazing flying experience, even in not the best of weather. The staff made us comfortable and the flight was actually pretty smooth.

The plane flew smoothly and the crew was polite and kind. We loved our flight!

Your crew is a representation of your Standards and Values. The crew from Seattle to LAX, was very disappointing. The crew was more interested in hanging out at the lobby area. Talking, laughing loudly and eating all the snacks. They did not do regular rounds to see if customers needed anything. This was a huge disappointment. I will no longer be flying with your airlines moving forward.

The senior flight attendant was engaging, funny and made everyone feel at ease. She is an asset to your team.

Terrible-extreme delay with very little communication, plane was overfull, luggage was returned on baggage claim in filthy condition.

Needs legroom for tall people. Needs to offer a glass of water.

Seats are very uncomfortable pls make your seats comfortable pls pls pls

They changed our departure time 6 times before I even reached the airport. Delayed, Ontime, Delayed Back on time, Then Delayed. We finally boarded the plane and then we had to sit on the runway for over an hour only to be told they were taking us back to the gate for an additional 2 hour delay. Lack of communication and a complete waste of time! Never again!

The check in process was a mess for no reason. I spent an hour waiting in line trying to get them to print my boarding pass and as a result I missed my flight.

The airline used deceptive tactics to charge us more for our trip. Search Frontier Class Action Lawsuit to find out more or read the hundreds of reviews that have nearly identical stories.. don't fly this airline.. you've been warned.

Check in at Philadelphia international was absolutely terrible! I fly 2 to 3 times a month and avoid frontier at all cost and will never fly Frontier again! The night before travel, I tried checking in however, the app was giving me an error, so I went to the desktop, which instructed you that you need to use the app. The next day I presented at the check-in gate after trying at least a half dozen times prior to getting into the airport and continuing to getting the error in the app. I actually had rebooted my phone numerous times and reinstall the app just in case. My phone is only one generation older than the current model. It has no problems completing a frontier flight purchase or any other app issues. There was only three frontier employees working at check-in and a huge line while I was in line I continued to try and check in via the app. As I approach the desk, I was dreading dealing with the agent. He was extremely unprofessional, anti-semantic & very ignorant, and mean to the people in front of me, as well as the people who ended up being behind me. He literally told people “Man I don’t care bout y’all” in his native dialect! Maintaining my composure I approached and explained the situation. To which he replied, you’re gonna have to pay then! I don’t understand. It’s an issue with their app not allowing me to check in! Not my issue! He told me if I pay cash it would be $15, $25 if I pay credit card. I don’t understand a $10 difference for paying with a credit card? I am completely cashless so I continued to try using the app to avoid the $25 fee, Which I still don’t believe that I should be responsible for since it was Frontier’s technical issue!!! I continued to check in via the app a couple more times after he verified I was doing everything right he proceeded to continue to belittle the people behind me. Yelling at them saying I don’t care about you people! I cannot believe that this is the way that businesses would treat its customers! Unfortunately, the black mail with dreadlocks did not have a name tag all he had was a frontier sweater on! For the $25 fee that I ended up getting charged on my credit card. I should’ve just booked originally with Spirit or any other carrier! I have no problem paying fees that I should be responsible for, but when it’s due to a technical failure of a company, the customer should not be responsible for it! I cannot believe that it’s not frontier going out of business!

they delayed my flight which ended up, causing my layover flight to leave without me, resulting in me missing a flight and having to stay overnight in Houston international. I got no compensation other than a flight to my original location only a day later. i’ve never experienced such a unprofessional situation

The flight left over two hours late. They charged me $180 to bring a carry on. There was an error with the spelling of my name and Frontair agent lied that I would need to pay $200 for her to fix the spelling, and pressured me that if I don't do it quick I would lose the flight. I called back and another agent said it costs $75 to fix. All in all, this company is a complete scam.

Very easy with the app to board and staff skills

I took my first and last flight with FRONTIER. The seats are not able to be reclined so it’s not a very comfortable experience when you take a flight of 3 hours or longer. You must pay for your luggage either carry on or check in, so taking all this in consideration at the end what you think you’re saving your paying in services that should be included. Not a beverage in sight. . You’re seriously better off getting on a proper airline such as Delta, AA, United, etc.

After waiting several minutes to be acknowledged by 3 employees on their phones, was told we had missed our flight because the doors were closed at that literal moment. Had they given any actual service or help while we were standing there we would have been on with time to spare. More than 10 people were turned away in this fashion claiming there was no way they could let us on the plane, even though it was still sitting connected to the terminal. After the desk agents let us know they didn't care about the situation we were forced to pay more than twice the price of our original tickets as no credits were given for the price of the "missed" flight. And the icing on the cake was after being treated poorly, fleeced for another few hundred dollars for new tickets? We waited on the next plane for 25 minutes passed the "doors closed" time, letting almost an extra dozen passengers on board. You're company has lazy, disinterested employees and your lack of any real help will ensure this was the first and last time we fly Frontier. Awful.

My experience with the phoenix airport was terrible, the personnel lay the ticket counter charged me for a carry on that fit in the carry on size box, and the two women I spoke with were terribly rude and not willing to help.,,, there was one lady “candy” on the flight crew that was amazing and is the only reason I stayed on the flight at all, because the other stewards helping people to get seated on the plane were terrible

I loked walking out on the tarmac to board and no first class. I didn't like that they have no snacks or onboard wifi to bide your time.

Book cheap flights from Chicago to Caribbean

Recent round-trip flight deals

3/26Wed
1 stopFrontier
8h 21mMDW-SJU
4/3Thu
1 stopFrontier
12h 31mSJU-MDW
$130
3/10Mon
1 stopFrontier
18h 46mMDW-SJU
3/16Sun
1 stopFrontier
17h 51mSJU-MDW
$132
4/15Tue
1 stop
18h 04mMDW-PUJ
5/15Thu
1 stop
9h 32mPUJ-MDW
$285
3/25Tue
2 stops
21h 41mMDW-SDQ
4/1Tue
1 stop
9h 30mSDQ-MDW
$289
3/5Wed
1 stopDelta
10h 49mMDW-SJU
3/8Sat
1 stopDelta
10h 20mSJU-MDW
$296
3/11Tue
1 stopDelta
9h 16mMDW-SJU
3/18Tue
1 stopDelta
10h 59mSJU-MDW
$328
3/12Wed
1 stopSouthwest
5h 50mMDW-MBJ
3/18Tue
nonstopSouthwest
4h 15mMBJ-MDW
$439
3/12Wed
1 stopSouthwest
5h 50mMDW-MBJ
3/19Wed
1 stopSouthwest
7h 15mMBJ-MDW
$449
3/6Thu
2 stopsKLM
16h 56mMDW-SDQ
3/9Sun
2 stopsKLM
23h 35mSDQ-MDW
$782
3/6Thu
1 stopKLM
5h 57mMDW-SDQ
3/9Sun
2 stopsKLM
23h 35mSDQ-MDW
$785

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Recent one-way flight deals

3/25Tue
1 stopFrontier
17h 51mMDW-SJU
$58
4/8Tue
1 stopFrontier
8h 10mMDW-SJU
$65
5/1Thu
1 stopFrontier
25h 47mMDW-SJU
$72
4/1Tue
1 stop
18h 37mMDW-PUJ
$118
4/1Tue
2 stops
18h 22mMDW-MBJ
$120
5/3Sat
1 stopDelta
8h 57mMDW-SJU
$136
3/4Tue
2 stopsSouthwest
8h 55mMDW-SJU
$161
4/20Sun
1 stopDelta
7h 26mMDW-PUJ
$161
2/26Wed
2 stopsSouthwest
9h 10mMDW-SJU
$192
7/24Thu
1 stopAvelo Airlines
25h 11mMDW-SJU
$252

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Last minute flights from Midway to Caribbean

Last minute flight, train and bus deals

2/22Sat
multi-stopFrontier
6h 40mMDW-SJU
3/7Fri
multi-stopFrontier
7h 09mSJU-MDW
$259
2/24Mon
multi-stopFrontier
10h 25mMDW-SJU
3/3Mon
multi-stopFrontier
13h 23mSJU-MDW
$261
2/25Tue
multi-stop
26h 12mMDW-PUJ
3/3Mon
multi-stop
20h 20mPUJ-MDW
$321
2/25Tue
multi-stop
26h 12mMDW-PUJ
3/3Mon
multi-stop
27h 33mPUJ-MDW
$400
2/22Sat
multi-stopDelta
7h 25mMDW-PUJ
2/26Wed
multi-stopDelta
8h 32mPUJ-MDW
$410
2/25Tue
multi-stopSouthwest
12h 20mMDW-SJU
3/4Tue
multi-stopSouthwest
11h 10mSJU-MDW
$434
2/25Tue
multi-stopSouthwest
9h 20mMDW-SJU
3/4Tue
multi-stopSouthwest
7h 45mSJU-MDW
$454
2/22Sat
multi-stopDelta
9h 07mMDW-SJU
2/26Wed
multi-stopDelta
10h 20mSJU-MDW
$462
2/24Mon
multi-stopLATAM Airlines
19h 55mMDW-PUJ
2/25Tue
multi-stopLATAM Airlines
21h 35mPUJ-MDW
$2,534
2/24Mon
multi-stopLATAM Airlines
19h 55mMDW-PUJ
2/25Tue
multi-stopLATAM Airlines
21h 35mPUJ-MDW
$2,549

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Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports

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