MDW - STT

$148 Find Cheap Flights from Chicago Midway Airport to Saint Thomas Island

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 Saint Thomas Island departing on 11/1. 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.
1 adult
1 adult, Economy

KAYAK searches hundreds of travel sites at once for deals on flights to Saint Thomas Island

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

Cheap Flights from Midway to Saint Thomas Island (MDW-STT)

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

Sat, Nov 1 - Sat, Nov 8
Multiple Airlines Logo
11:36 am - 2:30 pmMDW-STT
25h 54m1 stop
Multiple Airlines Logo
4:06 pm - 9:12 amSTT-MDW
19h 06m1 stop
$351Multiple Airlines
Find Deal
Sun, Dec 7 - Fri, Dec 12
Multiple Airlines Logo
2:15 pm - 3:11 pmMDW-STT
22h 56m1 stop
Multiple Airlines Logo
9:49 am - 8:38 pmSTT-MDW
12h 49m2 stops
$500Multiple Airlines
Find Deal
Tue, Jan 6 - Fri, Jan 16
Delta Logo
6:00 am - 2:55 pmMDW-STT
6h 55m1 stop
Delta Logo
4:00 pm - 9:46 pmSTT-MDW
7h 46m1 stop
$509Delta
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Sun, Jan 18 - Sun, Jan 25
Delta Logo
6:00 am - 3:54 pmMDW-STT
7h 54m1 stop
Delta Logo
4:00 pm - 9:46 pmSTT-MDW
7h 46m1 stop
$514Delta
Find Deal
Sun, Dec 7 - Fri, Dec 12
Multiple Airlines Logo
2:15 pm - 3:11 pmMDW-STT
22h 56m1 stop
Multiple Airlines Logo
9:49 am - 8:38 pmSTT-MDW
12h 49m2 stops
$515Multiple Airlines
Find Deal
Tue, Mar 10 - Wed, Mar 11
Delta Logo
6:00 am - 1:55 pmMDW-STT
6h 55m1 stop
Delta Logo
2:00 pm - 9:46 pmSTT-MDW
8h 46m1 stop
$569Delta
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Tue, Jan 6 - Sat, Jan 17
Delta Logo
6:00 am - 2:55 pmMDW-STT
6h 55m1 stop
Delta Logo
4:00 pm - 9:46 pmSTT-MDW
7h 46m1 stop
$584Delta
Find Deal
Tue, Feb 10 - Wed, Feb 11
Southwest Logo
5:00 am - 2:55 pmMDW-STT
7h 55m1 stop
Southwest Logo
3:55 pm - 8:45 amSTT-MDW
18h 50m2 stops
$699Southwest
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Tue, Feb 10 - Sun, Feb 15
Southwest Logo
7:55 pm - 2:55 pmMDW-STT
17h 00m2 stops
Southwest Logo
3:55 pm - 10:50 amSTT-MDW
20h 55m2 stops
$769Southwest
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Sat, Feb 21 - Sat, Feb 28
Southwest Logo
8:45 pm - 2:55 pmMDW-STT
16h 10m2 stops
Southwest Logo
3:45 pm - 9:50 pmSTT-MDW
8h 05m1 stop
$789Southwest
Find Deal

Everything you should know

Top airlines
Delta
Cheapest • from $509 (round-trip)
Delta
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Cheapest round-trip
$351
Multiple Airlines
Sat 11/1Sat 11/8
MDW - STT • 1 stop
Cheapest one-way
$148
Multiple Airlines
Sat 11/1
MDW - STT • 1 stop
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Booking Insights

KAYAK's insights & trends for Midway to Saint Thomas Island flights

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

Which airlines provide the cheapest flights from Chicago Midway Airport to Saint Thomas Island?

The cheapest round-trip price for the route for each airline clicked by KAYAK users in the last 72 hours.

In the past 3 days, the cheapest round-trip tickets from Chicago Midway Airport to Saint Thomas Island were found on Delta ($509) and Southwest ($699).

Find deals

Good to know

Cheapest flight$148
Flight from Chicago Midway Airport to Saint Thomas Island

When to book flights from Midway to Saint Thomas Island

Are your dates flexible? Find out the best times to travel from Midway to Saint Thomas Island based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Chicago Midway Airport to Saint Thomas Island flights

  • What is the cheapest flight from Chicago Midway Airport to Saint Thomas Island?

    In the last 3 days, the lowest price for a flight from Chicago Midway Airport to Saint Thomas Island was $148 for a one-way ticket and $351 for a round-trip.

  • Do I need a passport to fly between Chicago Midway Airport and Saint Thomas Island?

    Yes, you'll most likely have to show a valid passport before boarding the plane in Chicago Midway Airport and on arrival in Saint Thomas Island.

  • Which aircraft models fly most regularly from Chicago Midway Airport to Saint Thomas Island?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Chicago Midway Airport to Saint Thomas Island?

    SkyTeam is the only airline alliance operating flights between Chicago Midway Airport and Saint Thomas Island.

  • How does KAYAK find such low prices on flights from Chicago Midway Airport to Saint Thomas Island?

    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 Saint Thomas Island.

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

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

    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 Saint Thomas Island with an airline and back to Chicago Midway Airport with another airline. Booking your flights between Chicago Midway Airport and STT can sometimes prove cheaper using this method.

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

    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 Saint Thomas Island from Chicago Midway Airport 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 Midway to Saint Thomas Island

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Saint Thomas Island. 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 Saint Thomas Island? 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.
7.9
DeltaOverall score based on 7957 reviews
7.9Comfort
7.9Entertainment
7.3Food
8.5Crew
8.2Boarding
Airline reviews

The staff and the boarding procedure were all amazing . The one flight was not equipped with WIFI which now adays seems odd. All in all the experience was good

8.0 ExcellentAnonymous, Sep 2025GFK - MSP
Read more Delta reviews

The staff and the boarding procedure were all amazing . The one flight was not equipped with WIFI which now adays seems odd. All in all the experience was good

Passengers need to check in big baggage instead of bringing on the plane. That cause inconvenience for everyone. Otherwise flight was good.

Perfect flight both ways. On time, courteous staff, plane comfortable and cool. Best domestic flights I’ve had in awhile.

The food was terrible especially for a 15 hour international flight. The crew was unpleasant as well.

Really low quality food especially for an international flight. The crew also was surprisingly unpleasant except couple of ladies. I know we were not in first class but that’s no reason to treat customers as less.

Flight delayed for two and half hours and then canceled altogether due to mechanical issues. No mechanic onsite to fix so had to send one from LAX.

Quick check in. Everything went smooth. I don't know what can be done about airline food.

Crew was good. The reservation got mixed up and they didn't have my TSA number. I am also a Silver Medallion and wasn't able to use Sky Priority.

Delta made it easy, comfortable and timely. The crew was fantastic.

This route with Delta always has delays or is cancelled. Aircrafts seem smaller and older. I fly Delta quite a bit - haven’t had issues with the international flights. But this route has always been the troublesome one

Everything you need to know for your flight from Midway to Saint Thomas Island

Information on your arrival and departure airports

Chicago Midway Airport (MDW)
Saint Thomas Island (STT)

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