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Find cheap flights from Chicago Midway Airport to Saint Thomas Island from $437

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 7/20. 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
Sat 6/8
Sat 6/15

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 43,895,468 times on KAYAK, and here is why:

Save 21% or moreCompare multiple travel sites with one search.

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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 - 9:44 pmSTT-MDW
8h 20m1 stop
$573Delta
Find Deal
Sat, Sep 14 - Sat, Sep 21
6:00 am - 1:14 pmMDW-STT
6h 14m1 stop
2:24 pm - 9:44 pmSTT-MDW
8h 20m1 stop
$588Delta
Find Deal
Fri, Sep 20 - Tue, Sep 24
6:00 am - 2:52 pmMDW-STT
7h 52m1 stop
1:40 pm - 9:41 pmSTT-MDW
9h 01m1 stop
$678Delta
Find Deal
Thu, Jul 4 - Thu, Jul 11
6:00 am - 2:52 pmMDW-STT
7h 52m1 stop
3:00 pm - 9:46 pmSTT-MDW
7h 46m1 stop
$698Delta
Find Deal
Tue, Jul 2 - Sat, Jul 6
6:00 am - 2:35 pmMDW-STT
7h 35m1 stop
3:40 pm - 9:41 pmSTT-MDW
7h 01m1 stop
$713Delta
Find Deal
Wed, Jul 10 - Wed, Jul 17
6:00 am - 1:14 pmMDW-STT
6h 14m1 stop
3:40 pm - 9:41 pmSTT-MDW
7h 01m1 stop
$738Delta
Find Deal
Fri, Jul 12 - Fri, Jul 19
6:00 am - 2:52 pmMDW-STT
7h 52m1 stop
3:00 pm - 9:46 pmSTT-MDW
7h 46m1 stop
$763Delta
Find Deal
Wed, Jun 5 - Tue, Jun 11
6:00 am - 2:52 pmMDW-STT
7h 52m1 stop
3:00 pm - 9:46 pmSTT-MDW
7h 46m1 stop
$768Delta
Find Deal
Wed, Jun 5 - Tue, Jun 11
6:00 am - 2:52 pmMDW-STT
7h 52m1 stop
1:13 pm - 10:01 pmSTT-MDW
9h 48m1 stop
$793Delta
Find Deal
Sat, Jun 1 - Thu, Jun 6
8:00 am - 4:44 pmMDW-STT
31h 44m3 stops
5:34 pm - 4:17 pmSTT-MDW
23h 43m3 stops
Sat, Jun 8 - Sat, Jun 15

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 $411 on average. On the other hand, the most expensive months are November and December, where the average cost of tickets is $754 and $746 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 week before departure. For the absolute cheapest price, our data suggests you should book 21 days before departure.

Good to know

Low season

September

High season

October

Cheapest flight

$437
Best time to beat the crowds with an average 39% drop in price.
Most popular time to fly with an average 38% increase in price.
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 $437 for a one-way ticket and $573 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.

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 10778 reviews
7.4Food
8.2Boarding
7.9Comfort
8.0Entertainment
8.6Crew
Airline reviews

West Jet has a horrible boarding process and the seats have no cushion.

4.0 OkayDouglas, May 2024MSP - YEG
Read more about Delta reviews

West Jet has a horrible boarding process and the seats have no cushion.

Everything went smoothly. I didn’t like that when I booked in the main cabin my wife and I weren’t seated together. One would think when booking on an option that allows picking your seat. They would put you and your travel partner together. Had to call to get it sorted. They did fix.

The gate area was incredibly short staffed, with one representative manning 4-5 flights, which caused a 3 hr delay in boarding even though the plane was all ready to leave. Other flights also were delayed because of this. The flight crew was awesome and I feel bad for the only gate worker on call, but Delta needs to hire more employees.

Very frustrated with boarding gate crew. She announced the plane was small and they would be limiting us to one item to carry on. Not a problem for me as I understand the tiny planes have limited space!! Not the case here! It was a rather large plane and had plenty of room for bags! So because I don’t want to be one of “those people” who ignores the request to check a carry on I did so asking if I would be able to pick it up at the bottom of the ramp on arrival in Knoxville to which she responded “yes”! Then I watched as every other passenger held onto their 2 items and boarded!! Then when we arrived in Knoxville our 2 carry ons had been put with all the other luggage and we had to go to baggage pick up and wait for all the big checked bags to come off the carousel! So she lied!! Frustrating. Next time I won’t be so nice!

It was a good experience except when boarding a female flight attendant did not go out of her way to assist my teenage daughters in finding space for their carry-ons after their compartments were full.

On time departure, smooth trip, flight attendant told through passengers the gate we would arrive at and the gate our outbound flight was departing from. Early arrival

Checking in at the airport the agent only booked the first keg of my trip and had my checked luggage going to the airport with a layover! Never was issued a boarding pass for the second leg or received sticker fir my checked bag. All was well in the end! Delta agents helped to resolve the situation!!!

Delayed due to an ill passenger after loading. Not preventable on Delta's part. Was in first class. The seats are becoming worn and detaching from their velcro attachments. Only got snacks on flight. The attendant was not the friendliest.

I would fly again the whole experience was great. The only feed back I can give that they don't do that American Airlines does is the crew there is more humorous with boarding and thank their passengers. It makes it more fun to fly with them. I would however fly Delta again.

Big plane, long flight, absolutely no leg room and basically non existent air! I am 5”4’ and always travel Main Cabin, I was miserable on this plane and could barely move when we arrived in Cabo due to the cramped leg area!

Book cheap flights from Chicago to Saint Thomas Island

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Chicago to Saint Thomas Island found on KAYAK in the last 72 hours.
7/20Sat
1 stopDelta
9h 05mMDW-STT
$437

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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.
5/13Mon
multi-stopDelta
7h 53mMDW-STT
5/18Sat
multi-stopDelta
8h 18mSTT-MDW
$913
5/13Mon
multi-stopDelta
7h 53mMDW-STT
5/17Fri
multi-stopDelta
9h 48mSTT-MDW
$1,166

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Chicago Midway Airport - Saint Thomas Island Flights

Departure:

Chicago Midway Airport (undefined)United States

Destination:

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

Cabin classes: