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Find cheap flights from Chicago Midway Airport to Saint Thomas Island from $518

This is the cheapest round-trip 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 8/20. 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
0 bags
Fri 5/24
Fri 5/31

Search 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
In the last 7 days travelers have searched 45,119,101 times on KAYAK, and here is why:

Save 22% or moreCompare multiple travel sites with one search.

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

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

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

Cheap flight deals 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 and deals for you by selecting your travel dates.
Choose your dates
6:00 am - 1:14 pmMDW-STT
6h 14m1 stop
2:24 pm - 9:47 pmSTT-MDW
8h 23m1 stop
$518Delta
Find Deal
Tue, Aug 20 - Tue, Aug 27
6:00 am - 1:14 pmMDW-STT
6h 14m1 stop
2:24 pm - 9:47 pmSTT-MDW
8h 23m1 stop
$543Delta
Find Deal
Mon, Aug 19 - Mon, Aug 26
6:00 am - 1:14 pmMDW-STT
6h 14m1 stop
2:24 pm - 9:47 pmSTT-MDW
8h 23m1 stop
$558Delta
Find Deal
Mon, Aug 19 - Tue, Aug 27
6:00 am - 2:35 pmMDW-STT
7h 35m1 stop
2:24 pm - 9:47 pmSTT-MDW
8h 23m1 stop
$573Delta
Find Deal
Sat, Aug 17 - Sat, Aug 24
6:00 am - 1:14 pmMDW-STT
6h 14m1 stop
2:24 pm - 9:47 pmSTT-MDW
8h 23m1 stop
$648Delta
Find Deal
Tue, Aug 20 - Wed, Aug 28
6:00 am - 1:30 pmMDW-STT
6h 30m1 stop
1:13 pm - 10:01 pmSTT-MDW
9h 48m1 stop
$658Delta
Find Deal
Wed, May 8 - Tue, May 14
6:00 am - 2:53 pmMDW-STT
7h 53m1 stop
2:43 pm - 10:01 pmSTT-MDW
8h 18m1 stop
$693Delta
Find Deal
Tue, May 21 - Tue, May 28
6:00 am - 2:53 pmMDW-STT
7h 53m1 stop
2:43 pm - 10:01 pmSTT-MDW
8h 18m1 stop
$698Delta
Find Deal
Fri, May 31 - Mon, Jun 3
6:00 am - 2:53 pmMDW-STT
7h 53m1 stop
2:43 pm - 10:01 pmSTT-MDW
8h 18m1 stop
$713Delta
Find Deal
Tue, May 21 - Tue, May 28
6:00 am - 2:53 pmMDW-STT
7h 53m1 stop
2:43 pm - 10:01 pmSTT-MDW
8h 18m1 stop
$723Delta
Find Deal
Tue, May 7 - Sat, May 11

Flights from Midway to Saint Thomas Island - Travel Insights & Trends

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.

What is the cheapest month to fly from Chicago Midway Airport to Saint Thomas Island?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from Chicago Midway Airport to Saint Thomas Island, 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 Saint Thomas Island is October, where tickets cost $458 on average. On the other hand, the most expensive months are April and March, where the average cost of tickets is $977 and $830 respectively.

How far in advance should I book a flight from Chicago Midway Airport to Saint Thomas Island?

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from Chicago Midway Airport to Saint Thomas Island, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
To get a below average price on the flight from Chicago Midway Airport to Saint Thomas Island, you should book around 1 day before departure. For the absolute cheapest price, our data suggests you should book 23 days before departure.

Good to know

Low season

August

High season

February

Cheapest flight

$518
Best time to beat the crowds with an average 36% drop in price.
Most popular time to fly and prices are also 22% lower on average.
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 $518 for a round-trip ticket.

  • 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.

See more FAQs

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.
8.0
DeltaOverall score based on 11004 reviews
8.6crew
7.9comfort
7.5food
8.0entertainment
8.2boarding
Airline reviews

Horrible. This was not first class. This was a connecting flight whi h was late. My original flight never came. I hated the fact that delta gave me a connecting flight from New York to Orlando Florida. No meals and the television screens were not working. There wasn't even any power to charge your phones. This is NOT FIRST CLASS DELTA!!! Do better next time!

4.0 OkayAndrew, Apr 2024RDU - MCO
Read more about Delta reviews

Horrible. This was not first class. This was a connecting flight whi h was late. My original flight never came. I hated the fact that delta gave me a connecting flight from New York to Orlando Florida. No meals and the television screens were not working. There wasn't even any power to charge your phones. This is NOT FIRST CLASS DELTA!!! Do better next time!

This flight was ridiculous. I had to have a connecting flight from New York to orlando Florida??? The flight left late and because it was a short flight there was no first class amenities. I had one alcohol drink. The flight crew was fine, but it sure did not feel like first class. Delta to me dropped the ball by giving me a connecting flight. By the time we got to Raleigh we would have missed the next flight. Lucky for me the flight never came so now I was stuck waiting for a later flight that came in late also.

Our flight was delayed in Atlanta. The staff could have gave us an explanation for the delay and how long it would be.

I liked the ease of checking in, luggage check in, wheel chair assistance, boarding and flight.

On my way home I had a layover. The flight from ATL to CLT was amended 5x while I was waiting. I could have driven home sooner. Overall from Dallas, Tx to Charlotte, NC I started my trip at 4:30pm, I didn’t get home until past midnight. I know things happen, but 5x to make me run back and forth in an airport from different terminals is excessive. I also upgraded to comfort + , I didn’t feel it was worth it. There was no benefit

On my way home I had a layover. The flight from ATL to CLT was amended 5x while I was waiting. I could have driven home sooner. Overall from Dallas, Tx to Charlotte, NC I started my trip at 4:30pm, I didn’t get home until past midnight. I know things happen, but 5x to make me run back and forth in an airport from different terminals is excessive.

They did a fine job. Can't wait to use Delta in the future.

There was a loud squeaky sound the whole time we were flying.

Had a broken tray in business class. Crew just shrugged it off.

Seat back monitors and outlets were dead and not working.

Last minute flights from Midway to Saint Thomas Island

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Chicago to Saint Thomas Island that are departing in the next 10 days.
4/25Thu
multi-stopDelta
6h 23mMDW-STT
4/29Mon
multi-stopDelta
9h 32mSTT-MDW
$888
4/26Fri
multi-stopDelta
7h 50mMDW-STT
4/29Mon
multi-stopDelta
7h 11mSTT-MDW
$898
4/25Thu
multi-stopDelta
6h 23mMDW-STT
4/27Sat
multi-stopDelta
9h 32mSTT-MDW
$1,038

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Chicago Midway Airport - Saint Thomas Island Flights

Departure:

Chicago Midway Airport (MDW)United States

Destination:

Saint Thomas Island (STT)U.S. Virgin Islands

Cabin classes:

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