$97 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 2/19. 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
1 adult, Economy, 0 bags

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Cheap Flights from Midway to Caribbean

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$336
Santo Domingo
Santo Domingo1 stop$341
Montego Bay
Montego Bay1 stop$401
Oranjestad
Oranjestad1 stop$341
Nassau
Nassau1 stop$428
Kingston
Kingston1 stop$466
Simpson Bay
Simpson Bay1 stop$529
Providenciales
Providenciales1 stop$456
George Town
George Town1 stop$444
St. John's
St. John's1 stop$692
Aguadilla
Aguadilla1 stop$203
Punta Cana
Punta Cana1 stop$336
Santo Domingo
Santo Domingo1 stop$341
Montego Bay
Montego Bay1 stop$401
Oranjestad
Oranjestad1 stop$341
Nassau
Nassau1 stop$428
Kingston
Kingston1 stop$466
Simpson Bay
Simpson Bay1 stop$529
Providenciales
Providenciales1 stop$456
George Town
George Town1 stop$444
St. John's
St. John's1 stop$692
Aguadilla
Aguadilla1 stop$203

Book Cheap Midway to Caribbean Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to Caribbean that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Midway to Caribbean

Tue, Feb 24 - Thu, Mar 5
Frontier Logo
6:10 am - 3:06 pm
MDW
-
SJU
6h 56m
1 stop
Frontier Logo
4:11 pm - 10:29 pm
SJU
-
MDW
8h 18m
1 stop
$197Frontier
Tue, Feb 24 - Wed, Mar 11
Frontier Logo
6:10 am - 3:06 pm
MDW
-
SJU
6h 56m
1 stop
Frontier Logo
6:30 am - 6:13 pm
SJU
-
MDW
12h 43m
1 stop
$198Frontier
Sat, Feb 28 - Wed, Mar 4
Frontier Logo
8:00 am - 2:53 am
MDW
-
SJU
16h 53m
1 stop
Frontier Logo
5:25 pm - 2:26 pm
SJU
-
MDW
23h 01m
1 stop
$199Frontier
Sat, Feb 28 - Wed, Mar 4
Frontier Logo
8:00 am - 12:43 am
MDW
-
SJU
14h 43m
1 stop
Frontier Logo
5:25 pm - 2:26 pm
SJU
-
MDW
23h 01m
1 stop
$200Frontier
Fri, Feb 6 - Fri, Feb 13
Multiple Airlines Logo
5:01 pm - 3:01 pm
MDW
-
PUJ
20h 00m
1 stop
Multiple Airlines Logo
1:10 pm - 2:55 pm
PUJ
-
MDW
27h 45m
1 stop
$336Multiple Airlines
Wed, Feb 18 - Wed, Feb 25
Multiple Airlines Logo
7:00 am - 11:02 am
MDW
-
PUJ
26h 02m
2 stops
Multiple Airlines Logo
1:01 pm - 1:56 pm
PUJ
-
MDW
26h 55m
1 stop
$337Multiple Airlines
Tue, Feb 3 - Wed, Feb 11
Delta Logo
6:00 am - 3:20 pm
MDW
-
MBJ
8h 20m
1 stop
Delta Logo
4:45 pm - 10:22 pm
MBJ
-
MDW
6h 37m
1 stop
$404Delta
Thu, Apr 16 - Tue, Apr 21
Delta Logo
6:30 am - 3:29 pm
MDW
-
MBJ
8h 59m
1 stop
Delta Logo
2:40 pm - 10:29 pm
MBJ
-
MDW
7h 49m
1 stop
$409Delta
Mon, Feb 23 - Fri, Feb 27
Southwest Logo
5:30 am - 1:00 pm
MDW
-
MBJ
6h 30m
1 stop
Southwest Logo
1:30 pm - 12:55 am
MBJ
-
MDW
12h 25m
2 stops
$432Southwest
Wed, Feb 25 - Wed, Mar 4
Southwest Logo
5:00 am - 1:45 pm
MDW
-
PLS
7h 45m
1 stop
Southwest Logo
2:40 pm - 7:50 am
PLS
-
MDW
18h 10m
2 stops
$456Southwest
Booking Insights

KAYAK's insights & trends for Midway to Caribbean flights

Get data-powered insights and trends into flights from Midway to Caribbean to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Chicago Midway Airport to Caribbean flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Caribbean from Chicago Midway Airport found in the last 72 hours was to Punta Cana, at $475 round-trip. The most popular route is from Chicago Midway Airport (MDW) to Punta Cana (PUJ), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $475.

Can I save money by flying with a layover from Chicago Midway Airport to Caribbean?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $564 on average.

What is the cheapest month to fly from Chicago Midway Airport to Caribbean?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago Midway Airport to Caribbean, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago Midway Airport to Caribbean is May, when tickets cost $330 (return) on average. On the other hand, the most expensive months are June and July, when the average cost of round-trip tickets is $479 and $476 respectively.

What’s the cheapest day of the week to fly from Chicago Midway Airport to Caribbean?

The average price of all round-trip flights from Chicago Midway Airport to Caribbean clicked on KAYAK for each day over the last 12 months.

Your flight ticket price will generally be cheaper if you fly to Caribbean on a Tuesday and more expensive on a Saturday. On your return trip to Chicago Midway Airport, you should consider flying back on a Friday, and avoid Saturdays for better deals.

How far in advance should I book a flight from Chicago Midway Airport to Caribbean?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago Midway Airport to Caribbean, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Chicago Midway Airport to Caribbean, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 8 weeks before departure.

Good to know

Low seasonAugust
Cheapest flight$97
Best time to beat the crowds but there is an average 1% increase in price.
Most popular time to fly and prices are also 18% lower on average.
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.

  • What is the cheapest time of day to fly to Caribbean?

    The cheapest time of day to fly to Caribbean is generally in the morning, when round-trip flights cost $530 on average. The most expensive time of day to fly to Caribbean is generally in the morning, which is peak travel time and where the average cost of a ticket is $530.

Reviews of the top 3 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.
8.0
SouthwestOverall score based on 4261 reviews
8.6Crew
7.5Entertainment
8.0Comfort
8.1Boarding
7.0Food
Airline reviews

The seats were comfortable, and the boarding process was pretty smooth.

10.0 ExcellentJohn, Jan 2026
BWI - MDW
Read more Southwest reviews

The seats were comfortable, and the boarding process was pretty smooth.

3 hour delay. Had to change plans and was still delayed.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

The crew canceled the complementary snack and drink in anticipation of turbulence that never materialized. I was counting on the drink (water) to take the the doses of medication - prescribed for my heart condition - that were due during the flight. Since no snack or meal was served on this flight, I cannot rate the food quality. Otherwise, this flight was excellent.

Departure was delayed more than 1/2 hour while we waited for luggage (only) transfer from another flight/plane. Once approved for takeoff, the flight was excellent.

We got exit row seats both flights. Everything was running on time

The flight crew was extremely rude and especially not helpful when our flight was delayed.

Pretty seamless, just a tad bit late in taking off and landing.

Flight was fine other than there was a gate change that I was not notified of. By chance I happened to check my phone and saw the change, otherwise, we would have missed our connecting flight.

Haven’t flown on SW in years. Flight was on time departing and arriving. Served vegan butter onion flavored pretzels which were bad. Coke served was in a tiny paper cup. Crew was not engaging. Felt like they were going through the motions. Old plane, tight seats and no leg room.

Probably not the fault of Delta but there was delay after delay after delay and I ended up getting home 4 hours later then I should have at 1:30 in the morning

Easiest airport experience ever in my life at MSP with Delta check-in and flight attendant gave us a bottle of champagne in celebration of our 10-year wedding anniversary, so overall amazing!

No in flight service, no explanation - FC got service, C+ did not, unsure about Economy. No turbulence to speak of, so I guess another way to cut cost, or promote health and well being of Delta employees? Also, boarding in MEM combined zones, and with overhead space already full on both flights after Zone 2/ Diamond, presents a huge challenge to find a space for a bag. Delta, other than point A to B, is no longer reasonable to fly - very poor experiences, not even taking into account the chastising at the gate and rude crews, across the board.

It would have been better if the flight wasn't delayed by 2.5 hours

Delta’s staff is unmatched. From the gate agents, to the pilots, to the flight attendants… all top of the industry.

Delta flight Delay for ,more that two hours i.e original flight was 6.30 PM and it starts at 8.45 PM, When we connect Delta team for meal vouchers as it is late arrival in designation,But we did not get it as per delta policy , which is not good for mid night arrival,

Inexperienced boarding crew allowed too many bags on to a full flight and delayed takeoff causing a missed connection and unplanned overnight stay. There was a hotel at the airport but Delta would not pay for it offering only to shuttle me to an area hotel. Never even offerred so much as an apology by anyone working for Delta.

Staff was great! Kind and cordial! Middle seat row 28 seat B has a hump in it. Trays were getting stuck when putting down and up. Good flight

Departure was delayed resulting in me missing my connection. Delta did not autimatically find me another flight.

The seats weren’t reclining even though it wasn’t as exit seat

I am writing to express my disappointment with my recent Frontier Airlines flight. I was charged $99 at the gate because my bag was said to be too large, yet once onboard there was no available overhead bin space, and I was required to place the bag under the seat in front of me anyway. This made the charge feel unnecessary and unfair. Additionally, before the flight even took off, I was asked to move from the seat I paid for into a middle seat so another passenger and her cat could have my seat to themselves. I was not offered compensation or an explanation for being moved from a paid seat. Between the unexpected bag fee and being forced to give up my seat, this experience fell well below acceptable customer service standards. I would appreciate a review of this situation and appropriate compensation.

It was costly and difficult to check in. $85 to take a small suitcase with me, carry on or checked and $75 on the return trip, Plus $25 if I didn't check my self in check in $25, because I couldn't do it on the kiosk. Small very uncomfortable seats, waited on the runway for near an hour each way. It was my worst flight to date.

It was ok. It was expensive to check 2 bags ($75.00 per bag), and then it took a long time to wait for shuttle to take us from one terminal to the terminal where the plane was taking off at LAX. And all of this for a flight where we had to pay for any food or drink that was not water.

It didn’t happen. I booked it and then was told it wasn’t available and then forced to pay far higher prices for a worse option

A 630departure flight Delayed 6hours! They changed my gate, I moved to the new gate. Had our flight on the screen for 12noon departure. I go get above to eat, check screen again and the flight was gone, no notice no announcement, nothing!! They sent my bag on the flight I wasn’t on, got it back to me 3days later. Thank goodness they did refund my money but I will NEVER fly them again.

Due to weather, my flight was delayed, further delayed, then canceled. I eventually got through to a support person who helped me find a different route out of MSP, but to get to DIA, they didn't want to, but eventually did help with the connection ticket purchase. But even this replacement flight was delayed time and time again, and I would have missed my connecting flights and I didn't want to get stuck in a layover city, so after 12 hours at the airport with two young boys who were very tired, we just cancelled our plans and spent the week at home, instead of Nana's.

Plane and crew on board were fine. Everything else was terrible.

The third party booking with cheapflightsfares was awful. Kayak should NOT partner with them. They sold me a bundle including seat selection and carry-on, but did not book the carry-ons with Frontier, so I’m out of pocket for $414 more while I await resolution.

This company socks. It's fraud. They canceled our flight yesterday, and today we were late because of a really long line at the check in bag. At the rebook station, there was ton of people. The workers were all rude. I am gonna make a report to FTC.

One of the worst travel experiences I've had. Had a flight scheduled with CVG to RSW on VLSWQX this morning departing at 5:30. Two individuals at the gate and one was in training. Not her fault but she didn't have the ability to check people in resulting in at least 15 families that didn't make it on the plane because they weren't checked into the system in time. When arriving at the airport to drop off our prepaid checked bags, the bag drop off agent asked if we could check our bags at the gate because of the long line. We said no problem so arrived at the gate by 5:00. They told those people that had previously paid for checked bags to stand off to the side while they let others that either didn't have a checked bag or their bag was already on the plan through. Realizing the gate workers had an issue, they either called for help or this lady showed up late for work as she didn't arrive until 5:15. The worker who had been there training the other individual and working diligently to make sure all passengers got on board. He even said that at one point all people that are currently in line are fine but asked the person in training to stand outside the ticketing area around 5:15 to notify any late travels that the flight was in boarding process and they arrrived too late. At that point, we're sill standing off to the side with our pre-paid checked bags patiently waiting. When the new lady arrived she couldn't have been more rude. It was an awful seen. Essentially they had asked for those without an assigned seat to board last, those with pre-paid checked bag stand off to the site and any traveling with a larger items that needed to be checked at the gate (such as a stroller), wait on the side. They realized that the flight needed to leave on time so the gate attendant shut the gate. So anyone without a seat assignment, those that had pre-checked bags, and the worst one I saw was a mother with two infant children was in line with use because she was asked to stand to the side because her stroller. When they shut the door to the plan they told her she could no longer get on. Her checked bags were already on the plane with her car keys in them, and the lady told her we couldn't accept anyone else on because the door was shut. She didn't even have a way to get home from the airport. Truely evil behavior. I've flown Frontier enough to know customer service is not a top priority in the company's mission, but this was an all-time low. I'm sending this after an 18 hour drive that our family just completed to Bonita Springs . I felt really bad for the lady being trained and the other individual trying to help, but when the new lady came to the gate she was truly one of the rudest individuals I've ever met. One lady had been there since 4am but because she didn't have an assigned seat they wouldn't let her on the plan.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports