$94 Find Cheap Flights from Chicago Midway Airport to Caribbean Islands

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 4/13. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Caribbean Islands

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Caribbean Islands, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Caribbean Islands, as well as popular online travel agencies
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Flight Deals

Cheap Flights from Midway to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana2 stops$316
Santo Domingo
Santo Domingo1 stop$335
Montego Bay
Montego Bay1 stop$370
Oranjestad
Oranjestad1 stop$469
Nassau
Nassau1 stop$466
Kingston
Kingston1 stop$466
Simpson Bay
Simpson Bay1 stop$401
Providenciales
Providenciales1 stop$514
George Town
George Town2 stops$364
St. John's
St. John's1 stop$692
Aguadilla
Aguadilla1 stop$211
Punta Cana
Punta Cana2 stops$316
Santo Domingo
Santo Domingo1 stop$335
Montego Bay
Montego Bay1 stop$370
Oranjestad
Oranjestad1 stop$469
Nassau
Nassau1 stop$466
Kingston
Kingston1 stop$466
Simpson Bay
Simpson Bay1 stop$401
Providenciales
Providenciales1 stop$514
George Town
George Town2 stops$364
St. John's
St. John's1 stop$692
Aguadilla
Aguadilla1 stop$211

Book Cheap Midway to Caribbean Islands 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 Islands 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 Islands

Sun, Mar 1 - Wed, Mar 4
Multiple Airlines Logo
6:15 am - 2:09 am
MDW
-
SJU
17h 54m
1 stop
Multiple Airlines Logo
11:52 am - 1:56 pm
SJU
-
MDW
28h 04m
1 stop
$184Multiple Airlines
Mon, Feb 23 - Wed, Mar 4
Multiple Airlines Logo
2:19 pm - 3:31 pm
MDW
-
SJU
23h 12m
2 stops
Multiple Airlines Logo
11:52 am - 1:56 pm
SJU
-
MDW
28h 04m
1 stop
$185Multiple Airlines
Sun, Mar 1 - Wed, Mar 4
Multiple Airlines Logo
6:15 am - 2:09 am
MDW
-
SJU
17h 54m
1 stop
Multiple Airlines Logo
11:52 am - 1:56 pm
SJU
-
MDW
28h 04m
1 stop
$186Multiple Airlines
Sat, Feb 21 - Fri, Feb 27
Frontier Logo
8:00 am - 2:53 am
MDW
-
SJU
16h 53m
1 stop
Frontier Logo
3:53 am - 2:55 pm
SJU
-
MDW
13h 02m
1 stop
$188Frontier
Mon, Feb 23 - Thu, Feb 26
Multiple Airlines Logo
2:19 pm - 6:58 pm
MDW
-
SJU
26h 39m
2 stops
Multiple Airlines Logo
6:00 am - 1:56 pm
SJU
-
MDW
9h 56m
1 stop
$189Multiple Airlines
Mon, Feb 23 - Wed, Mar 4
Frontier Logo
9:22 pm - 9:54 am
MDW
-
SJU
10h 32m
1 stop
Frontier Logo
5:25 pm - 2:26 pm
SJU
-
MDW
23h 01m
1 stop
$194Frontier
Tue, Mar 3 - Tue, Mar 10
Southwest Logo
7:55 pm - 12:55 pm
MDW
-
GCM
16h 00m
2 stops
Southwest Logo
12:40 pm - 9:55 pm
GCM
-
MDW
9h 15m
2 stops
$364Southwest
Sun, Apr 12 - Thu, Apr 16
Southwest Logo
5:15 am - 2:20 pm
MDW
-
MBJ
9h 05m
1 stop
Southwest Logo
2:25 pm - 11:40 pm
MBJ
-
MDW
9h 15m
1 stop
$371Southwest
Tue, Mar 3 - Tue, Mar 10
Delta Logo
6:00 am - 3:19 pm
MDW
-
MBJ
8h 19m
1 stop
Delta Logo
11:15 am - 10:31 pm
MBJ
-
MDW
11h 16m
1 stop
$374Delta
Sun, Feb 22 - Wed, Feb 25
Delta Logo
6:40 pm - 11:10 am
MDW
-
MBJ
15h 30m
1 stop
Delta Logo
4:44 pm - 12:46 pm
MBJ
-
MDW
21h 02m
2 stops
$381Delta
Booking Insights

KAYAK's insights & trends for Midway to Caribbean Islands flights

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

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

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

The cheapest ticket to Caribbean Islands from Chicago Midway Airport found in the last 72 hours was to Montego Bay, at $476 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 $546.

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

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.

No, with an average price for the route of $376, prices are generally cheapest when you fly direct.

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

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 Islands, 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 Islands 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 Islands?

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

If your flying dates are flexible, you should consider flying to Caribbean Islands on a Tuesday, as we generally find the cheapest rates on that day for this route. On the other hand, Saturday is the most expensive day to fly from Chicago Midway Airport to Caribbean Islands. For your return ticket, we recommend flying on a Friday and avoiding Saturdays for the best deals.

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

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 Islands, 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 Islands, 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$94
Best time to beat the crowds but there is an average 3% increase in price.
Most popular time to fly and prices are also 17% 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 from Chicago Midway Airport to Caribbean Islands 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 from Chicago Midway Airport to Caribbean Islands 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 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 from Chicago Midway Airport to Caribbean Islands 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 Islands?

    The cheapest time of day to fly to Caribbean Islands is generally in the morning, when round-trip flights cost $526 on average. The most expensive time of day to fly to Caribbean Islands is generally in the morning, which is peak travel time and where the average cost of a ticket is $526.

Reviews of the top 3 airlines serving from Midway to Caribbean Islands

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Caribbean Islands. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
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
SouthwestOverall score based on 4280 reviews
8.6Crew
7.0Food
8.1Boarding
7.5Entertainment
8.0Comfort
Airline reviews

I appreciate the staff who allowed me to board though I arrived a little late! Regarding the assigned seating, I had booked my flight before this change and wasn't aware of the change at the time, and so I didn't select a seat at booking as I didn't realize it was relevant. Better communication about the change would have been helpful for preparing.

10.0 ExcellentMeghan, Feb 2026
MCO - DEN
Read more Southwest reviews

I appreciate the staff who allowed me to board though I arrived a little late! Regarding the assigned seating, I had booked my flight before this change and wasn't aware of the change at the time, and so I didn't select a seat at booking as I didn't realize it was relevant. Better communication about the change would have been helpful for preparing.

Flight attendants very hospitable and friendly. Pilot flew a smooth take off and landing.

Paid for premium extra leg room but the bin space for rows 1-3 had to go in rows 4-6 and 4-6 had to go to 7-9 because flight attendants have snacks and their luggage upfront. So we pay extra to have to fight thru traffic to get our bags. Only 2nd day of new seating so hope they fix this.

WIFI was great. My selection for seating is an aisle, but during my trip, I never had an aisle seat. If we can get that corrected, I will be thrilled. No snack or drink on this flight.

WIFI was great. My selection for seating is an aisle, but during my trip, I never had an aisle seat. If we can get that corrected, I will be thrilled.

The wifi on the plane is great. The only issue that I have is that I prefer an aisle seat and on my trips this week, I was either in the middle or window. If we can work to secure aisle seating, I will be thrilled. Nice trip.

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

Everything went smoothly and we even arrived a little bit early.

Great vacation. Can't wait till next year for another one.

Great flight but super high price. Glad it was a business trip and not personal

It was delayed but other than that it was great.

Got on the plane and sat there for an hour before departure.

Second flight in a row where the entertainment system is broken. 5 hour long flight with no entertainment and flight attendants did not seem interested in resolving the matter. Very shocked to be treated this poorly considering I paid for a first class experience and have Diamond Medallion status.

They double booked seats, the gate staff changed my ticket as I was boarding she went over to the computer and changed it without telling me. She messed up an entire three row section for me and others. Other travelers were outraged but the gate staff were so rude, so condescending saying it wasn't their problem to solve. I would rate this a zero if I could. Will not fly Delta again I'll stick with United and American.

It was nt delta. It was aeromexo. Service was awful. They served a very small drink and NO snack for a 3hr and 35min flight. Then for the first 30 min of the flight is was talk and talk over head interruption the movie/ show i picked to watch.

Comfort seating was on the tight side. Maybe it was a smaller plane(?)

I was given middle seat on this flight and prior Boston to Seoul flight That is a problem for long flights, Kayak system did not give me a change to select my seats and assigned me middle seats regardless of my elevated status in Delta. This needs immediate attention.

I didn't take this flight. I changed the flight. Why am I getting surveys and notifications on flights that I change. Seems like a defect with Kayak.

Delta One is extraordinary. I fly business when somebody hires me. I just wonder why there is such a chasm between business class and the insanely inhumane and nonsensical coach. The seats are not large enough to fit even my tiny wife. We fly 10% of what we did because we don’t want to pay 5-10 k but for $400 it’s unbearable. It seems like the accountants took over and made stupid decisions. Screw in 20 extra seats and make it so unbearable that people fly 90% less. Just put the damn price up and put some proper chairs in. But business, yay.

Timing, quality of service, promptness and courtesy of the staff

There was no food and no entertainment, so I'm not sure why these are even in the survey, as my understanding is frontier does not ever offer food without a few, not even a snack, and there are no screens so unless the flight safety talk is our entertainment why ask how we liked it?. One of the flight attendants say in the back of the plane as people filed in to their seats, yelling orders about where to put baggage and telling people to hurry up. It was the least professional experience I've ever had on a flight.

Very well recently! Frontier is improving and less harrassing customer on luggages! Positive!

Good for a budget airline! It was easy to get on, staff was really nice. Can’t say anything about the food or entertainment because it wasn’t available, which is fine.

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.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports