Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Chicago Midway Airport to Saint Thomas Island from $288

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Saint Thomas Island departing on 2/19. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Chicago Midway Airport to Saint Thomas Island (MDW-STT)

Cheap round-trip flights

Logo
5:28 pm - 12:59 pmMDW-STT
18h 31m1 stop
Logo
11:01 am - 1:38 pmSTT-MDW
27h 37m2 stops
$363
Find Deal
Fri, Oct 17 - Mon, Oct 20
Logo
6:21 am - 6:00 pmMDW-STT
10h 39m2 stops
Logo
4:02 pm - 9:51 amSTT-MDW
18h 49m1 stop
$505
Find Deal
Sun, Sep 28 - Fri, Oct 3
Delta Logo
6:00 am - 3:54 pmMDW-STT
7h 54m1 stop
Delta Logo
1:55 pm - 9:46 pmSTT-MDW
9h 51m1 stop
$519Delta
Find Deal
Mon, Jan 19 - Fri, Jan 23
Delta Logo
6:00 am - 3:54 pmMDW-STT
7h 54m1 stop
Delta Logo
3:00 pm - 9:46 pmSTT-MDW
8h 46m1 stop
$569Delta
Find Deal
Thu, Feb 19 - Tue, Feb 24
Delta Logo
6:00 am - 2:10 pmMDW-STT
7h 10m1 stop
Delta Logo
2:43 pm - 9:10 pmSTT-MDW
7h 27m1 stop
$619Delta
Find Deal
Wed, Sep 10 - Sat, Sep 20
Delta Logo
6:00 am - 2:40 pmMDW-STT
6h 40m1 stop
Delta Logo
3:50 pm - 11:32 pmSTT-MDW
9h 42m1 stop
$689Delta
Find Deal
Sun, Nov 16 - Wed, Nov 19
Delta Logo
6:00 am - 3:54 pmMDW-STT
7h 54m1 stop
Delta Logo
4:00 pm - 9:46 pmSTT-MDW
7h 46m1 stop
$704Delta
Find Deal
Wed, Feb 18 - Sun, Feb 22
Logo
2:15 pm - 12:28 pmMDW-STT
44h 13m2 stops
Logo
4:06 pm - 7:02 amSTT-MDW
16h 56m1 stop
$711
Find Deal
Mon, Dec 15 - Mon, Dec 22
Delta Logo
6:00 am - 1:39 pmMDW-STT
6h 39m1 stop
Delta Logo
2:49 pm - 10:14 pmSTT-MDW
8h 25m1 stop
$714Delta
Find Deal
Wed, Oct 22 - Wed, Oct 29
Southwest Logo
5:00 am - 2:55 pmMDW-STT
7h 55m1 stop
Southwest Logo
2:10 pm - 11:25 pmSTT-MDW
11h 15m1 stop
$1,132Southwest
Find Deal
Wed, Feb 11 - Sat, Feb 21

Delta flights from Chicago Midway Airport to Saint Thomas Island

Our best Delta deals on Chicago Midway Airport to Saint Thomas Island flight tickets
Delta
Jan 19
MDW6:00 amChicago Midway
7h 54m
1 stop
STT3:54 pmSaint Thomas Island Cyril E King
Jan 23
STT1:55 pmSaint Thomas Island Cyril E King
9h 51m
1 stop
MDW9:46 pmChicago Midway
$519
Find similar
Delta
Feb 19
MDW6:00 amChicago Midway
7h 54m
1 stop
STT3:54 pmSaint Thomas Island Cyril E King
Feb 24
STT3:00 pmSaint Thomas Island Cyril E King
8h 46m
1 stop
MDW9:46 pmChicago Midway
$569
Find similar
Delta
Sep 10
MDW6:00 amChicago Midway
7h 10m
1 stop
STT2:10 pmSaint Thomas Island Cyril E King
Sep 20
STT2:43 pmSaint Thomas Island Cyril E King
7h 27m
1 stop
MDW9:10 pmChicago Midway
$619
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to Saint Thomas Island that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated August 25, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Saint Thomas Island that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Fri 10/17

5:28 pm-12:59 pm

1 stop18h 31m

Saint Thomas Island Cyril E King

Mon 10/20

11:01 am-1:38 pm

2 stops27h 37m

$363

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Sun 9/28

6:21 am-6:00 pm

2 stops10h 39m

Saint Thomas Island Cyril E King

Fri 10/3

4:02 pm-9:51 am

1 stop18h 49m

$505

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Mon 1/19

6:00 am-3:54 pm

1 stop7h 54m

Saint Thomas Island Cyril E King

Fri 1/23

1:55 pm-9:46 pm

1 stop9h 51m

$519

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Thu 2/19

6:00 am-3:54 pm

1 stop7h 54m

Saint Thomas Island Cyril E King

Tue 2/24

3:00 pm-9:46 pm

1 stop8h 46m

$569

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Wed 9/10

6:00 am-2:10 pm

1 stop7h 10m

Saint Thomas Island Cyril E King

Sat 9/20

2:43 pm-9:10 pm

1 stop7h 27m

$619

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Sun 11/16

6:00 am-2:40 pm

1 stop6h 40m

Saint Thomas Island Cyril E King

Wed 11/19

3:50 pm-11:32 pm

1 stop9h 42m

$689

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Wed 2/18

6:00 am-3:54 pm

1 stop7h 54m

Saint Thomas Island Cyril E King

Sun 2/22

4:00 pm-9:46 pm

1 stop7h 46m

$704

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Mon 12/15

2:15 pm-12:28 pm

2 stops44h 13m

Saint Thomas Island Cyril E King

Mon 12/22

4:06 pm-7:02 am

1 stop16h 56m

$711

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Wed 10/22

6:00 am-1:39 pm

1 stop6h 39m

Saint Thomas Island Cyril E King

Wed 10/29

2:49 pm-10:14 pm

1 stop8h 25m

$714

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Wed 2/11

5:00 am-2:55 pm

1 stop7h 55m

Saint Thomas Island Cyril E King

Sat 2/21

2:10 pm-11:25 pm

1 stop11h 15m

$1,132

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 14 resultsSorted by cheapest first
1
2

See travel insights to Saint Thomas Island from

How to get the cheapest flight ticket from Chicago Midway Airport to Saint Thomas Island

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest day to depart on your flight to Saint Thomas Island?

On average, the least expensive day to fly to Saint Thomas Island from Chicago Midway Airport is on a Wednesday. momondo users have found tickets for Wednesday departures for as low as $639. However, this price may fluctuate depending on the airline, the season, and holidays. When flying out on a Friday, the most expensive travel day of the week, you can expect to see flight prices from Chicago Midway Airport to Saint Thomas Island for around $1,160.

What is the cheapest time of day to depart on your flight to Saint Thomas Island?

The cheapest time of day to fly to Saint Thomas Island is in the afternoon when flights can be purchased for as low as $397. Flights to Saint Thomas Island are more costly in the morning, with an average ticket price of $774. Departure times in the morning fall within the peak daily travel times, which is why tickets can be more expensive.

When to book flights from Chicago Midway Airport to Saint Thomas Island

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport to Saint Thomas Island according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago Midway Airport to Saint Thomas Island (MDW to STT) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Saint Thomas Island

Direct flights

None
There are no direct flights from Chicago Midway Airport to Saint Thomas Island. There are no popular flight routes from Chicago Midway Airport to Saint Thomas Island.
Search flight deals

  • How far is Chicago Midway to Saint Thomas Island Cyril E King by plane?

    A flight from Chicago Midway to Saint Thomas Island Cyril E King will travel around 2102.4 mi. A reasonable flight in good conditions will take 6h 22m.

  • When did momondo last update prices for flights from Chicago Midway Airport to Saint Thomas Island Cyril E King Airport?

    Prices for flights from Chicago Midway Airport to Saint Thomas Island Cyril E King Airport are updated daily.

  • How many operators does momondo search for flights from Chicago Midway Airport to Saint Thomas Island Cyril E King Airport?

  • How old do you have to be to fly from Chicago Midway Airport to Saint Thomas Island Cyril E King Airport?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago Midway Airport to Saint Thomas Island Cyril E King Airport.

  • What documentation or ID do you need to fly to Saint Thomas Island Cyril E King Airport?

    The necessary travel and health documents for your Saint Thomas Island Cyril E King Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular airline from Chicago Midway Airport to Saint Thomas Island?

Best airlines flying from Chicago Midway Airport to Saint Thomas Island

Compare and see reviews for airlines that fly from Chicago Midway Airport to Saint Thomas Island with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $487Free CancellationRating
7.9
7,981 reviews
Search Delta flights

Traveling to a place near Saint Thomas Island?

Book flights to Saint Thomas Island if you plan to visit one of these locations
St. John

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Saint Thomas Island?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Chicago to Saint Thomas Island. momondo saves you time and could save you money on your trip.

Can I find flights from Chicago to Saint Thomas Island with flexible booking policies on momondo?

All flight searches from Chicago to Saint Thomas Island on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Chicago to Saint Thomas Island?

momondo helps you find the best flight between Chicago and Saint Thomas Island by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Chicago to Saint Thomas Island right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Saint Thomas Island from Chicago. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

An easier way to manage your Saint Thomas Island trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Sat 8/30
Sat 9/6
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to the U.S. Virgin Islands

Airports servicing U.S. Virgin Islands

Saint Croix Airport