$62 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 2/22. 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$258
Santo Domingo
Santo Domingo2 stops$338
Montego Bay
Montego Bay1 stop$330
Oranjestad
Oranjestad1 stop$584
Nassau
Nassau1 stop$386
Simpson Bay
Simpson Bay2 stops$602
Kingston
Kingston1 stop$735
Providenciales
Providenciales2 stops$535
George Town
George Town1 stop$526
St. John's
St. John's1 stop$987
Aguadilla
Aguadilla2 stops$338

Good to know

Low season

November

High season

March

Cheapest flight

$62
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly with an average 32% 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 March, April and May. The cheapest month to fly from Chicago is January.
  • On average*, there is no price difference when choosing to fly in the morning or the evening on this flight route.
*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 4821 reviews
7.7Entertainment
8.2Boarding
8.7Crew
8.1Comfort
7.2Food
Airline reviews

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.

10.0 ExcellentWilliam Drew, Dec 2024SJC - HNL
Read more Southwest reviews

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

Much better than the.last. flight on SW on Thanksgiving day

Fine, but how to board on SW versus othrr airlines, is just lame. Goood staff though and all was solid otherwise.

The movies using Southwest WiFi kept pausing and I had to restart multiple times.

It went well. Plane wasn't full. Will be great when assigned seating is in place

Everything was great except the food. The pretzels are really crappy.

For the first time in a long time we had a flawless experience with Southwest. Both flights were early and no mechanical errors at all. We were shocked and pleasantly surprised 😮.

It was fine. For some reason the flight was much longer than usual. It may have been explained, but I had noise cancelling earbuds on and missed a couple of announcements. The crew was fine, but there was a flight attendant who kept telling dumb jokes, occasionally one I found distasteful. This was my second time with him, but luckily it was a late flight so he didn't do as many. But I heard all of today's jokes twice, which was two times too many. Good takeout and landing.

One of the crew performed a hilarious skit to accompany the standard instructions. Passengers enjoyed it so much they applauded at the end!

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?

Typically I give delta excellent reviews. Our flight was delayed 2hrs, I was one of the fortunate ones who were able to get to my connecting flight. Also, annoying that on the connecting flight boarding personnel make me put away a small bag into my carryon. It small enough to put in back pocket seat, why hold me and the line up to just push it into my carryon.

Logan airport construction meant that boarding was chaotic crowded and delayed

Everything was great. Great service, excellent communication, and early arrival

We were forced to wait nearly 50 additional minutes before leaving the terminal.

Free Wi-Fi is good. That’s all - food mediocre, unfriendly crew, poor communication after trying to file a claim for my lost bag, which Delta didn’t even know was lost until I told them.

Delta flight attendants poorly managed the boarding process and overhead storage. My bag was checked last minute and no claim ticket was provided. My bag is now lost. Complete incompetence by all flight crew involved.

Inexpensive, got an exit row aisle aeat with no middle passenger, bought a great breakfast sandwich, flight comfortable & arrived ahead of schedule.

Customer service at the gate in the flight was exceptional. On time. Aircraft and seat was decent. Thanks Delta. 💗

I was comfortable because I upgraded. I would not have been comfortable in economy. It was a short flight so there was limited food service and no inflight entertainment.

I thought since I upgraded my seat I would get some perks. Free water, free snacks. Free carry on luggage.

Seats were surprisingly comfortable, and crew was polite. I did not like the baggage fee prices, the minimal amount of flight choices for my area and the difficulty of the self service bag drop.

Lost MacBook, had time to retrieve, but was told I had no time. Need Silver MacBook back

It’s ridiculous to pay for carry-on luggage. I also wasn’t given an option to specify I have carry on bag at time of ticket purchase. I also could not specify I have carry on luggage at time of online check-in.

I’ve now flown Spirit a few times and while the general perception of Spirit I feel is poor, I’ve had a great experience each time. They do charge extra for everything but you should know that going in

The people were wonderful, but I hated the way they over charged for luggage, especially for stops which were charged the same as starting point to final destination.

Horrible I paid for extra for better seats. At time of checking my seats were sold to someone else. I need a refund and more for my bad experience

First time flying Spirit and I was pleasantly surprised. Service was as advertised. Crew were very professional and friendly and excellent in dealing with a customer who felt ill on the flight.

Delayed fight LAS to LAX. OK, fog in LA, not your fault. But all your staff, onboard in in lounge, speak so fast, enunciate so poorly and often have a accent that it is impossible to understanding anything they are saying.

The takeoff was the smoothest I've ever experienced on any airline and this is the first time I've flown on frontier so this was an extremely pleasant surprise!

Delayed each time on a round trip with no significant weather interference. Updates to flight times came after the fact. 30 min behind in boarding and board and phone still show an on time departure. Some mysterious extra 300 miles that came so surprising they had to fuel while we were already on board?

A lady asked to stop the flight after the tunnel pulled away and we began to depart a flight that was already hours late. The attendance respectfully stopped the the plane and had the tunnel return. After the tunnel returned the passenger claimed to have changed her mind . The tunnel was then put in reverse and the passenger remained on the plane .. They should have sent the sick passenger off the plane like initially replaced. They existed a couple off the plane prior to that situation.. So.. all and all.. it was a long and flight.. .

terrible cascading delays and unhelpful customer service. uncomfortable plane. crew was great, however!

I ended up paying $70+ dollars to for a carryon because the website is confusing and misleading. I now realize I did not need to pay that. I request a refund. I will pay extra to other airlines and not fly Frontier again.

With frontier you get what you pay for. The flight was two hours late. It’s a tight fit for the number of people they bring but you get to where you’re going cheap. Sometimes that’s more important than a nifty drink and cool TV..

Charges unexpected. For seat that didnt recline. Please reverse extra seat and carryon charge. Bad business that is a bait and switch.

Although we received an email from Kayak AND the airline, turns out we were not on Frontier’s manifest for the flight. We had to purchase tickets at the gate. Not sure where this transaction fell apart, but it did. We are now disputing the charges for the SLC to PDX flight originally booked through Kayak.

We had an awful experience getting our bags checked in. Frontier’s check in on the app manipulated us into buying the business package because that was the only option available for a checked bag which included two checked bags per person which we did not need. Upon arriving to the airport, we stood in line for what seemed like forever at the baggage check in and there was no one available at the counter. We were first in line and we were afraid we were going to miss our flight due to the baggage attendant being late. After realizing there were a lot of other people waiting at the baggage check in and no one available. I reached out to Frontier and could not get any customer service so I had to call the airport to page the baggage attendant to send someone to the counter to check in our bags before we were able to go through security , I finally spoke to the attendant at the counter and explained to her that we had to pay for two checked bags person a total of six bags when we only had a total of three bags between three people she said to reach out to Frontier and they would issue a refund for the three bags that we paid for and did not need. I reached out to Frontier which I was not able to reach anybody by phone so I had to go through their automated chat feature, which sent me around in circles until I finally reached a representative to assist me. I explained to them what happened and they explained that they were not able to assist me. I continued to push the issue with them as this was very frustrating and they finally put in a customer service ticket where we were issued a flight credit and we were so disappointed because after this experience, we NEVER want to fly Frontier again, and we do not want a credit that we will not use. Frontier charged us almost $500 for us to check three bags which is absolutely absurd! The customer service agents were not able to offer anything else other than a flight credit and I do not feel like my frustrations were truly heard , we will never use Frontier Airlines again ! Truly Theft by Manipulation! They should be ashamed!

I couldn’t check in because the app didn’t work. It took 3 Frontier employees at the counter to get me checked in. Flight left 3 hours after departure time

Book cheap flights from Chicago to Caribbean

Recent round-trip flight deals

1/20Mon
1 stopFrontier
16h 14mMDW-SJU
1/23Thu
1 stopFrontier
23h 51mSJU-MDW
$136
1/13Mon
1 stopFrontier
15h 20mMDW-SJU
1/23Thu
1 stopFrontier
23h 51mSJU-MDW
$138
3/1Sat
2 stopsSouthwest
10h 35mMDW-SJU
3/4Tue
2 stopsSouthwest
12h 50mSJU-MDW
$304
1/31Fri
2 stopsSouthwest
12h 20mMDW-SJU
2/4Tue
2 stopsSouthwest
12h 50mSJU-MDW
$309
1/25Sat
1 stopDelta
6h 05mMDW-SJU
1/30Thu
1 stopDelta
10h 51mSJU-MDW
$324
1/20Mon
2 stops
23h 37mMDW-MBJ
1/23Thu
1 stop
7h 42mMBJ-MDW
$358
1/14Tue
1 stopDelta
6h 23mMDW-PUJ
1/23Thu
1 stopDelta
7h 30mPUJ-MDW
$363
1/31Fri
2 stops
22h 19mMDW-MBJ
2/8Sat
1 stop
10h 09mMBJ-MDW
$364
1/20Mon
2 stopsWestJet
24h 01mMDW-NAS
1/25Sat
2 stopsWestJet
19h 21mNAS-MDW
$686
1/17Fri
3 stopsWestJet
27h 38mMDW-NAS
1/20Mon
2 stopsWestJet
26h 57mNAS-MDW
$693

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Recent one-way flight deals

2/22Sat
1 stopFrontier
6h 40mMDW-SJU
$62
1/20Mon
1 stopFrontier
12h 46mMDW-SJU
$63
2/2Sun
2 stopsSouthwest
9h 30mMDW-SJU
$117
2/23Sun
1 stop
17h 41mMDW-NAS
$160
1/20Mon
3 stops
18h 29mMDW-MBJ
$161
2/24Mon
2 stopsSouthwest
10h 20mMDW-SJU
$162
2/25Tue
1 stopDelta
7h 25mMDW-PUJ
$170
1/23Thu
1 stopDelta
5h 57mMDW-SDQ
$186
2/15Sat
2 stopsWestJet
24h 40mMDW-SJU
$302
2/15Sat
2 stopsWestJet
24h 40mMDW-SJU
$303

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Last minute flights from Midway to Caribbean

Last minute flight, train and bus deals

12/23Mon
multi-stopFrontier
23h 09mMDW-SDQ
12/26Thu
multi-stopFrontier
13h 26mSDQ-MDW
$447
12/23Mon
multi-stopFrontier
25h 23mMDW-SJU
12/25Wed
multi-stopFrontier
11h 47mSJU-MDW
$469
12/24Tue
multi-stopSouthwest
10h 50mMDW-SJU
12/25Wed
multi-stopSouthwest
13h 00mSJU-MDW
$533
12/24Tue
multi-stopSouthwest
7h 20mMDW-SJU
12/25Wed
multi-stopSouthwest
11h 35mSJU-MDW
$542
12/24Tue
multi-stop
19h 27mMDW-NAS
12/31Tue
multi-stop
15h 51mNAS-MDW
$724
12/23Mon
multi-stop
11h 40mMDW-GCM
12/29Sun
multi-stop
26h 21mGCM-MDW
$732
12/25Wed
multi-stopDelta
8h 12mMDW-STT
12/28Sat
multi-stopDelta
10h 05mSTT-MDW
$813
12/23Mon
multi-stopDelta
8h 12mMDW-STT
12/27Fri
multi-stopDelta
10h 05mSTT-MDW
$833
12/25Wed
multi-stopWestJet
19h 59mMDW-GCM
12/29Sun
multi-stopWestJet
21h 18mGCM-MDW
$1,567
12/25Wed
multi-stopWestJet
25h 01mMDW-GCM
12/29Sun
multi-stopWestJet
27h 54mGCM-MDW
$1,584

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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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