MDW - STT

$149 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 11/27. 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 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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 23% 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.

Everything you should know

Cheapest round-trip
$251
Delta
Thu 1/22Mon 1/26
MDW - STT • 1 stop
Cheapest one-way
$149
Multiple Airlines
Thu 11/27
MDW - STT • 1 stop
Top airlines
Delta
Cheapest • from $251 (round-trip)
Delta
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Saint Thomas Island!
Flight Deals
Booking Insights
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

Thu, Jan 22 - Mon, Jan 26
Delta Logo
6:00 am - 3:04 pmMDW-STT
7h 04m1 stop
Delta Logo
4:15 pm - 10:26 pmSTT-MDW
8h 11m1 stop
$251Delta
Find Deal
Tue, Jan 6 - Fri, Jan 16
Delta Logo
6:45 am - 3:04 pmMDW-STT
6h 19m1 stop
Delta Logo
4:15 pm - 10:09 pmSTT-MDW
7h 54m1 stop
$345Delta
Find Deal
Fri, Jan 2 - Thu, Jan 8
Multiple Airlines Logo
3:10 pm - 2:28 pmMDW-STT
21h 18m1 stop
Multiple Airlines Logo
1:33 pm - 11:25 pmSTT-MDW
11h 52m2 stops
$353Multiple Airlines
Find Deal
Fri, Dec 12 - Fri, Dec 19
Multiple Airlines Logo
8:42 pm - 11:56 amMDW-STT
13h 14m2 stops
Multiple Airlines Logo
3:23 pm - 9:58 pmSTT-MDW
8h 35m1 stop
$370Multiple Airlines
Find Deal
Fri, Nov 28 - Fri, Dec 5
Multiple Airlines Logo
4:46 pm - 12:55 pmMDW-STT
18h 09m2 stops
Multiple Airlines Logo
3:54 pm - 10:39 pmSTT-MDW
8h 45m1 stop
$372Multiple Airlines
Find Deal
Fri, Jan 9 - Fri, Jan 16
Delta Logo
6:45 am - 4:10 pmMDW-STT
7h 25m1 stop
Delta Logo
4:15 pm - 10:09 pmSTT-MDW
7h 54m1 stop
$410Delta
Find Deal
Tue, Jan 6 - Fri, Jan 16
Delta Logo
6:45 am - 3:04 pmMDW-STT
6h 19m1 stop
Delta Logo
3:10 pm - 10:09 pmSTT-MDW
8h 59m1 stop
$439Delta
Find Deal
Wed, Feb 11 - Thu, Feb 12
Southwest Logo
5:00 am - 2:55 pmMDW-STT
7h 55m1 stop
Southwest Logo
3:45 pm - 10:45 pmSTT-MDW
9h 00m1 stop
$769Southwest
Find Deal
Wed, Mar 18 - Wed, Mar 25
Southwest Logo
6:00 am - 2:20 pmMDW-STT
7h 20m1 stop
Southwest Logo
1:50 pm - 9:55 pmSTT-MDW
9h 05m2 stops
$789Southwest
Find Deal
Wed, Mar 4 - Wed, Mar 18
Southwest Logo
7:55 pm - 3:20 pmMDW-STT
17h 25m2 stops
Southwest Logo
1:50 pm - 7:50 amSTT-MDW
19h 00m2 stops
$799Southwest
Find Deal
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 ($251) and Southwest ($769).

Which airlines fly non-stop between Chicago Midway Airport and Saint Thomas Island?

Airline and price data is aggregated from results in KAYAK’s search results from the last 2 weeks for round-trip flights from Chicago Midway Airport to Saint Thomas Island.

There is just one airline that flies from Chicago Midway Airport to Saint Thomas Island direct and that is Delta. The best round-trip deal found from Delta for the route is $469.

Good to know

Cheapest flight$149
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 $149 for a one-way ticket and $251 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 7992 reviews
7.9Comfort
7.9Entertainment
7.3Food
8.5Crew
8.2Boarding
Airline reviews

Staff were friendly and happy. Delta could make sure passengers that don't have the app know of changes. Without Kayak I would not have known about the change of gate or the delay. Kayak was faster to notify me.

8.0 ExcellentJulie, Oct 2025LAX - SFO
Read more Delta reviews

Staff were friendly and happy. Delta could make sure passengers that don't have the app know of changes. Without Kayak I would not have known about the change of gate or the delay. Kayak was faster to notify me.

They ended up paying for the bag twice, but the counter wouldn't take my baggage receipt. Left it to me to resolve. Not sure how to resolve the issue.

The customer service before board was very rude and when I expressed my concerns about making the connecting flight she laughed and told me I bought the wrong ticket. I explained once it showed the flight was delayed it no longer let me change seats or anything. I was trying to upgrade to make sure I would get to the next gate on time.

Non stop on long haul is the way to go. Great experience

The aircraft interior is old and tired on this aircraft. The entertainment system never worked despite the crews attempt to reset the system.

The flight used a B767 with a very old interior from before 2014. The entertainment system did not work at all during the flight despite attempts to reset the system. It was like they flew this route just to be competitive.

Old plane and old configuration/seats but still comfortable for a morning flight

They changed planes and the new plane couldn’t carry enough fuel to fly across the country so we had to stop in Kansas City to refuel. Flight was delayed .

Flight was too crowded and seats are too small, especially since passengrs are getting larger. Having a middle seat is ALWAYS tough! Woman on my left was large & kept creeping in to my space. Flight personnel were great! Have more savory rather than sweet snacks please.

Flight was crowded and the woman sitting on my left was large & kept crouching in to my space. You need bigger seats or smaller passengers to fit into the seats you DO have! Snack were OK. Would appreciate if airlines had more savory rather than sweet snacks, thank you!

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

Information on your arrival and departure airports

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.