$113 Find Cheap Flights from Caribbean Islands to Chicago Midway Airport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Midway departing on 5/6. 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 Chicago Midway Airport

Travelers love KAYAK
41.299.237 searches in the past 7 days on KAYAK

Save 24% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Useful Info
Flight Deals

Cheap Flights from Caribbean Islands to Midway

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Caribbean Islands to Midway 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 Caribbean Islands to Midway

Fri, May 1 - Mon, May 4
Frontier Logo
3:23 pm - 10:26 pm
SJU
-
MDW
8h 03m
1 stop
Frontier Logo
6:00 am - 2:13 pm
MDW
-
SJU
7h 13m
1 stop
$186Frontier
Sat, May 2 - Sun, May 3
Frontier Logo
9:58 am - 4:13 pm
SJU
-
MDW
7h 15m
1 stop
Frontier Logo
8:39 am - 9:54 am
MDW
-
SJU
24h 15m
1 stop
$206Frontier
Fri, May 8 - Mon, May 11
Frontier Logo
8:59 am - 3:57 pm
SJU
-
MDW
7h 58m
1 stop
Frontier Logo
4:52 pm - 2:08 am
MDW
-
SJU
8h 16m
1 stop
$211Frontier
Thu, Apr 30 - Mon, May 4
Frontier Logo
3:03 pm - 10:19 pm
SJU
-
MDW
8h 16m
1 stop
Frontier Logo
6:00 am - 2:13 pm
MDW
-
SJU
7h 13m
1 stop
$216Frontier
Sat, May 2 - Wed, May 6
Delta Logo
7:30 am - 4:26 pm
SJU
-
MDW
9h 56m
1 stop
Delta Logo
6:00 am - 4:23 pm
MDW
-
SJU
9h 23m
1 stop
$236Delta
Sat, May 2 - Tue, May 5
Delta Logo
7:30 am - 4:26 pm
SJU
-
MDW
9h 56m
1 stop
Delta Logo
12:52 pm - 8:24 pm
MDW
-
SJU
6h 32m
1 stop
$256Delta
Thu, Jul 16 - Sun, Jul 19
Southwest Logo
1:50 pm - 5:50 pm
MBJ
-
MDW
4h 00mnonstop
Southwest Logo
7:50 am - 11:45 am
MDW
-
MBJ
3h 55mnonstop
$281Southwest
Thu, Jul 16 - Sun, Jul 19
Southwest Logo
1:50 pm - 5:50 pm
MBJ
-
MDW
4h 00mnonstop
Southwest Logo
5:05 am - 12:35 pm
MDW
-
MBJ
7h 30m
1 stop
$381Southwest
Fri, May 1 - Mon, May 4
Multiple Airlines Logo
2:38 am - 6:37 pm
BQN
-
MDW
16h 59m
2 stops
Multiple Airlines Logo
8:41 am - 1:43 am
MDW
-
BQN
16h 02m
1 stop
$399Multiple Airlines
Fri, Apr 24 - Wed, Apr 29
Multiple Airlines Logo
2:38 am - 4:13 pm
BQN
-
MDW
14h 35m
1 stop
Multiple Airlines Logo
6:10 am - 1:43 am
MDW
-
BQN
18h 33m
2 stops
$410Multiple Airlines
Useful Info

Good to know

Low seasonDecember
Cheapest flight$113
Best time to beat the crowds with an average 7% drop in price.
Most popular time to fly and prices are also 22% lower on average.
Flight from San Juan to Chicago Midway Airport

FAQs for booking Caribbean Islands to Chicago Midway Airport flights

  • How does KAYAK find such low prices on flights from Caribbean Islands to Chicago Midway Airport?

    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 Caribbean Islands to Chicago Midway Airport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Caribbean Islands to Chicago Midway Airport?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport from 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 Caribbean Islands to Chicago Midway Airport?

    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 to Chicago Midway Airport with an airline and back to Caribbean Islands with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Caribbean Islands to Chicago Midway Airport?

    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 to Chicago Midway Airport from Caribbean Islands up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airline flying from Caribbean Islands to Midway

 
Need help choosing which airline to fly with from Caribbean Islands to Midway? 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 4328 reviews
8.1Boarding
8.0Comfort
8.6Crew
7.0Food
7.5Entertainment
Airline reviews

The flight was okay. The pilots did an amazing job and kept us updated on the flight. The flight attendants were okay. They found time to be chatty with each other rather than focus on the guests. One of the attendants was a little less warm when asking about my bag I had on my lap that I was using during latter part of the mid- flight. Mind you, it was not the departure descent. I’m respectful to each and every attendant, it was the tone in her voice reminding me to place my carryon bag on the floor. I hope to have a better experience next time.

10.0 ExcellentMechelle, Apr 2026
MCI - PNS
Read more Southwest reviews

The flight was okay. The pilots did an amazing job and kept us updated on the flight. The flight attendants were okay. They found time to be chatty with each other rather than focus on the guests. One of the attendants was a little less warm when asking about my bag I had on my lap that I was using during latter part of the mid- flight. Mind you, it was not the departure descent. I’m respectful to each and every attendant, it was the tone in her voice reminding me to place my carryon bag on the floor. I hope to have a better experience next time.

The entire travel day was a disaster from beginning to end. Woke up at two in the morning to make it to San Juan airport in time for a 5:30 am flight to Milwaukee which connected in Baltimore. Massive delays lead to me missing original connection out of Baltimore. Sixteen hours of delays/rebooking/layover time later, arrived in Milwaukee to find that only one of two checked bags made it there (despite the fact that Southwest brought another 737 jet to San Juan to fly us out to our original Baltimore connection—-not squeezed into another booked flight). The flight from Baltimore to Milwaukee was barely half full, so there was no logical reason to ship my bags out of Baltimore on a different flight to Chicago to then ship to Milwaukee. Southwest decided that my bags should not have been on the same connecting flight I WAS ON to Milwaukee, and then proceeded to accidentally leave my larger bag with the important items in Chicago. Terrible logic and support all around. Extremely angered and disappointed with SW. What a clownish operation your company has become!

It was as expected and I was grateful for the wheel chair help and ease of use.

One of the best airlines for fast boarding, on time arrivals, and top notch service!

The new seat assignment thing is wierd. If you don’t pay for a seat they always assign you a middle seat regardless of how many people are on the flight. Idk… the new company that bought Southwest is trying to make it more profitable, but I’m just not seeing it. The flight attendants aren’t having as much fun anymore. It just feels like the airline is slowly dying. IMO. We shall see if Southwest is the next Toy’s R Us.

Terrible. Even though there’s assigned seating now, they are still the slowest boarding airline of anyone.

The Air hostess were very rude on my flight from Houston to Austin . Their regular communication itself felt a they are shouting at people.

Communication about the delayed flight was poor. We were told to move gates three times but that was bad information. We went from gate 128 to gate 126 and then to gate 123 and back to gate 126. Communication about the delay was bad. Ended up being 1 1/2 hour late getting home.

Plane was late. Zero service for 2+ hour flight and it was not that bumpy.

It was good from LAX to Phoenix, But the connection in Phoenix to Tulsa was not that great. The staff on both flights were great. The choice of free entertainment was ok nothing to brag about. The 45 min delay because of some electrical issue wasn't great from Phoenix to Tulsa. We sat there with hardly any air, The seat I had was between windows so the side of the plane pushed in on you. My being a bigger man it then made the seating area uncomfortable. The seats on the plane had no power to connect to recharge your phone or anything. I would recommend that they should look into a slot or clamp to hold your phone to enjoy while watching the entertainment choices hands-free. Also make it possible to raise the inner seat by the window be able to raise the arm rest up to make more room for larger people to set more comfortably. I would also say other then that stop price gouging the airfare or nickel and diming everything. Not fair for people having to fly for emergencies and be paying for higher prices due to the season or holidays. Your making your money either way and the cost of flying is still going to be the same regardless if there's 100 people or 200 people.

Traveling to a place near Midway?

Book flights to Midway if you plan to visit one of these locations
Merrillville
Saint Joseph
Hammond
Portage
Lansing
Valparaiso
Chesterton
Schererville
Munster
Porter
Monticello
Griffith
Saint John

Everything you need to know for your flight to Midway

Information on your arrival and departure airports