$65 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 3/1. 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$285
Santo Domingo
Santo Domingo2 stops$292
Montego Bay
Montego Bay2 stops$357
Oranjestad
Oranjestad2 stops$590
Nassau
Nassau1 stop$395
Simpson Bay
Simpson Bay2 stops$507
Kingston
Kingston2 stops$436
Providenciales
Providenciales1 stop$546
George Town
George Town1 stop$464
St. John's
St. John's1 stop$792
Aguadilla
Aguadilla1 stop$319

Good to know

Low season

November

High season

March

Cheapest flight

$65
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly with an average 35% 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 September, October and November. The cheapest month to fly from Chicago is June.
  • Morning departure is around 5% more expensive 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 4662 reviews
8.2Boarding
7.2Food
8.1Comfort
8.7Crew
7.7Entertainment
Airline reviews

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.

10.0 ExcellentRachel, Jan 2025TPA - MDW
Read more Southwest reviews

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.

Crew was great flight was great baggage claim was a failure. It took over 1 hour for bags to arrive. Poor communication poor effort when I spoke to the supervisor about the delay

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

Flight left early and arrived early. the whole trip was excellent.

Seats were really tight and the seat belts did not give enough slack.

I like in St George and prefer to fly out of CDC than SGU. Hopefully, they will continue the flights out of Cedar

Broken jer bridge. Poor communication about it. Lost 2 of 4 luggage pieces

Overall, it was okay. Seat was a little cramped. Would’ve liked more substantial snacks or opportunity to buy some.

Newer plane, relatively easy boarding, not a full flight and was told that we could not be moved up because of weight and balance issues. Otherwise, a very good experience.

Other then mechanical/ computer problem and 3.5 hours flight delay the flight was great. I guess that what happened when you fly an old airplane now a day.

I was with one of the last zones to board. It was kind of annoying to finally get called to board and my whole section was already on the plane. Clearly they boarded with previous zones. So by the time I got on board, there were no spaces for my luggage above my head. I had to put my luggage 4+ rows behind me, which meant that I had to wait even longer to get off the plane, since I had to wait for those rows to clear the aisle before I could retrieve my luggage and exit the plane. This also held up the plane cleaners, as they couldn't service my row until I cleared it, so they were all standing there waiting for me, while I'm standing there waiting for the other passengers to clear the aisle. Anyways, I wasn't in a rush this time, so I just waited, but I could see that being a problem in the future. Now, I could have checked my luggage, of course, but coincidentally, a friend of mine on the same flight got their luggage damaged (wheel completely knocked off) and was told by the Baggage Attendant in the airport that Delta doesn't "cover wheel damage" on luggage. This was disappointing to hear. I'm glad I didn't check mine through. If it were my luggage, I'd be highly frustrated to hear that. It makes me not want to check my luggage in the future.

The dear was very limited in space. I could put my water bottle in seat basket. Also, there was no inflight entertainment in the delta app?

Boarding was smooth and on time. Flight itself was smooth (aside from some turbulence) and no glitches. On the downside, Spirit's no-frills service was as expected (no food or drink, cramped seating, extra cost for carry-ons, etc.), the announcements were nearly incomprehensible, and the constant niggling offers of upgrades and other services for sale (wifi, sandwiches, etc.) is annoying. Overall, a pleasant and uneventful experience - definitely worth the price.

Lower cost is the reason to fly Spirit. Should give free baggage with credit card.

From gate to flight crew... All Spirit employees were great! Everyone was kind and helpful. Ride was almost smooth... A few bumps... But no problems. Seats were tight and uncomfortable. Our biggest issue was no free drinks. I can understand paying for adult beverages and can understand no snacks on a 3 hour flight... But no drinks???? I had to pay $4 for an apple juice for my son. That's not right. You should probably reconsider that.

Loved staff help @ kiosk, staff on airplane. Commitment to punctuality. I sat in a "blocked" row, where the middle seat had no passenger & loved it! I appreciate not having to pay for water, which I've experienced even on international flights. Only negative was how dirty the bathroom was for a 4.5 hrs flight. But I don't think flight attendants monitor this.

- flight attendants not very friendly. - Paid for WiFi and plane didn’t have it working , never got a refund.

Great! First time flying with Spirit and I definitely loved it!

Not efficient. Missed my connecting flight over improper operation of spirit crew.

Very difficult. Flew out on Dec 24th and it was a mess. They know it is going to be the busiest time of the year and they had no organization. Finally they called for people going on certiam flights so they could get them thru thw line then we had to rush to our gate to get in li e to board.We missed our flight do to being stuck at the border of Mexico. They would not work with us to make an affordable price so we had to wait a day with no where to go and pay 280 more for our flights. I would think that a complimentary drink would be nice. But we had to pay 4.49 for a coke. Not an overall good experience

Better service, stop treating people like cattle, have REAL FOOD for the price of the ticket. YOU ARE IN BANKRUPTCY, WAKE UP!!! ... DO BETTER, PLAN BETTER, GIVE COMFORT AND CARE TO PASSENGERS ... EARN RESPECT AND ADMIRATION, YOU'LL BE REWARDED BY THE PUBLIC.

It was good. All snacks/ drinks must be paid during flight. Bring cash with you.

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.

The plane was clean, the crew was friendly and helpful. It’s a low cost airline so there was no food, drinks or in flight entertainment but we didn’t expect any of these things. In the room for improvement department, they should install USB ports in seats to charge mobile devices.

The seats were extremely hard and uncomfortable, even for a budget airline.

The seats were extremely hard and uncomfortable. It was disappointing even for a budget airline.

Charging $74 for one checked bag is outrageous. I will never fly Frontier again.

Boarding was very well executed. Got my bag right away.

Book cheap flights from Chicago to Caribbean

Recent round-trip flight deals

2/3Mon
1 stopFrontier
16h 14mMDW-SJU
2/8Sat
1 stopFrontier
14h 47mSJU-MDW
$133
3/1Sat
1 stopFrontier
13h 36mMDW-SJU
3/10Mon
1 stopFrontier
18h 25mSJU-MDW
$134
2/2Sun
2 stopsSouthwest
9h 30mMDW-SJU
2/7Fri
1 stopSouthwest
10h 15mSJU-MDW
$235
3/2Sun
2 stopsSouthwest
8h 30mMDW-SJU
3/10Mon
1 stopSouthwest
13h 20mSJU-MDW
$310
3/1Sat
1 stopDelta
10h 45mMDW-SJU
3/4Tue
1 stopDelta
10h 50mSJU-MDW
$325
2/25Tue
1 stopDelta
7h 25mMDW-PUJ
2/28Fri
1 stopDelta
10h 20mPUJ-MDW
$355
3/1Sat
2 stops
26h 17mMDW-MBJ
3/8Sat
1 stop
9h 05mMBJ-MDW
$357
3/2Sun
2 stops
20h 35mMDW-MBJ
3/8Sat
1 stop
9h 05mMBJ-MDW
$385
2/25Tue
3 stopsWestJet
27h 35mMDW-NAS
3/2Sun
2 stopsWestJet
26h 53mNAS-MDW
$843
3/11Tue
2 stopsWestJet
27h 10mMDW-AUA
3/18Tue
3 stopsWestJet
23h 50mAUA-MDW
$906

Search by stops

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Recent one-way flight deals

3/1Sat
1 stopFrontier
6h 40mMDW-SJU
$65
2/3Mon
1 stopFrontier
12h 46mMDW-SJU
$66
3/2Sun
2 stopsSouthwest
8h 30mMDW-SJU
$118
4/15Tue
1 stop
28h 00mMDW-NAS
$144
2/25Tue
2 stops
27h 56mMDW-MBJ
$150
3/11Tue
nonstopSouthwest
4h 25mMDW-PUJ
$161
1/28Tue
1 stopDelta
9h 14mMDW-SJU
$163
2/25Tue
1 stopDelta
7h 25mMDW-PUJ
$166
3/15Sat
3 stopsWestJet
23h 10mMDW-MBJ
$418
6/27Fri
2 stopsWestJet
22h 55mMDW-AUA
$603

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Last minute flights from Midway to Caribbean

Last minute flight, train and bus deals

1/26Sun
multi-stopFrontier
13h 21mMDW-SJU
1/27Mon
multi-stopFrontier
11h 02mSJU-MDW
$321
1/24Fri
multi-stopFrontier
8h 42mMDW-SJU
1/27Mon
multi-stopFrontier
11h 02mSJU-MDW
$326
1/26Sun
multi-stopFrontier
13h 21mMDW-SJU
1/30Thu
multi-stopFrontier
25h 51mSJU-MDW
$328
1/24Fri
multi-stopDelta
7h 25mMDW-PUJ
1/31Fri
multi-stopDelta
7h 30mPUJ-MDW
$420
1/25Sat
multi-stopDelta
6h 23mMDW-PUJ
2/1Sat
multi-stopDelta
8h 32mPUJ-MDW
$435
1/24Fri
multi-stopSouthwest
12h 20mMDW-SJU
2/4Tue
multi-stopSouthwest
12h 50mSJU-MDW
$445
1/25Sat
nonstopSouthwest
4h 35mMDW-SJU
1/28Tue
multi-stopSouthwest
7h 45mSJU-MDW
$491
1/24Fri
multi-stop
28h 00mMDW-PUJ
1/31Fri
multi-stop
34h 57mPUJ-MDW
$593
1/26Sun
multi-stop
6h 25mMDW-GCM
2/2Sun
multi-stop
28h 32mGCM-MDW
$622
1/25Sat
multi-stopAir Transat
21h 25mMDW-PUJ
2/1Sat
multi-stopAir Transat
16h 55mPUJ-MDW
$1,000

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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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