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Cheap flights from Chicago Midway Airport to Saint Thomas Island from $152

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 5/4. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Chicago Midway Airport to Saint Thomas Island

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
6:00 am - 9:54 am
MDW
-
STT
26h 54m
2 stops
Multiple Airlines Logo
10:49 am - 8:04 am
STT
-
MDW
22h 15m
1 stop
$263Multiple Airlines
Sat, May 9 - Wed, May 13
Multiple Airlines Logo
9:14 am - 9:54 am
MDW
-
STT
23h 40m
1 stop
Multiple Airlines Logo
10:49 am - 10:19 pm
STT
-
MDW
12h 30m
2 stops
$277Multiple Airlines
Sat, May 9 - Wed, May 13
Multiple Airlines Logo
2:15 pm - 9:54 am
MDW
-
STT
18h 39m
2 stops
Multiple Airlines Logo
10:49 am - 7:26 am
STT
-
MDW
21h 37m
1 stop
$282Multiple Airlines
Wed, Apr 15 - Wed, Apr 22
Multiple Airlines Logo
6:00 am - 4:15 pm
MDW
-
STT
9h 15m
2 stops
Multiple Airlines Logo
10:49 am - 8:04 am
STT
-
MDW
22h 15m
1 stop
$297Multiple Airlines
Sat, May 9 - Wed, May 13
Multiple Airlines Logo
6:00 am - 4:15 pm
MDW
-
STT
9h 15m
2 stops
Multiple Airlines Logo
10:49 am - 8:04 am
STT
-
MDW
22h 15m
1 stop
$303Multiple Airlines
Thu, May 7 - Wed, May 13
Multiple Airlines Logo
9:51 pm - 1:26 pm
MDW
-
STT
14h 35m
1 stop
Multiple Airlines Logo
2:36 pm - 7:47 pm
STT
-
MDW
30h 11m
2 stops
$316Multiple Airlines
Mon, Mar 16 - Thu, Mar 19
Multiple Airlines Logo
9:51 pm - 1:26 pm
MDW
-
STT
14h 35m
1 stop
Multiple Airlines Logo
2:36 pm - 10:19 pm
STT
-
MDW
32h 43m
2 stops
$318Multiple Airlines
Mon, Mar 23 - Tue, Mar 31
Multiple Airlines Logo
9:51 pm - 1:26 pm
MDW
-
STT
14h 35m
1 stop
Multiple Airlines Logo
2:36 pm - 8:54 pm
STT
-
MDW
31h 18m
2 stops
$322Multiple Airlines
Mon, Mar 23 - Mon, Mar 30
Multiple Airlines Logo
4:33 pm - 1:26 pm
MDW
-
STT
19h 53m
1 stop
Multiple Airlines Logo
2:36 pm - 10:19 pm
STT
-
MDW
32h 43m
2 stops
$331Multiple Airlines
Tue, Mar 24 - Tue, Mar 31
Multiple Airlines Logo
4:33 pm - 1:26 pm
MDW
-
STT
19h 53m
1 stop
Multiple Airlines Logo
2:36 pm - 8:54 pm
STT
-
MDW
31h 18m
2 stops
$335Multiple Airlines
Tue, Mar 24 - Mon, Mar 30

Southwest flights from Chicago Midway Airport to Saint Thomas Island

Our best Southwest deals on Chicago Midway Airport to Saint Thomas Island flight tickets
Southwest
Apr 26
MDW8:55 pmChicago Midway
15h 40m
2 stops
STT1:35 pmSaint Thomas Island Cyril E King
Apr 30
STT2:30 pmSaint Thomas Island Cyril E King
7h 10m
1 stop
MDW8:40 pmChicago Midway
$484
Southwest
Mar 24
MDW6:00 amChicago Midway
7h 20m
1 stop
STT2:20 pmSaint Thomas Island Cyril E King
Mar 31
STT1:50 pmSaint Thomas Island Cyril E King
10h 00m
2 stops
MDW10:50 pmChicago Midway
$504
Southwest
Mar 17
MDW6:00 amChicago Midway
7h 20m
1 stop
STT2:20 pmSaint Thomas Island Cyril E King
Mar 31
STT1:50 pmSaint Thomas Island Cyril E King
8h 00m
1 stop
MDW8:50 pmChicago Midway
$600

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
Mar 19
MDW6:00 amChicago Midway
7h 45m
1 stop
STT2:45 pmSaint Thomas Island Cyril E King
Mar 23
STT3:00 pmSaint Thomas Island Cyril E King
8h 31m
1 stop
MDW10:31 pmChicago Midway
$730
Delta
Mar 16
MDW6:00 amChicago Midway
6h 47m
1 stop
STT1:47 pmSaint Thomas Island Cyril E King
Mar 19
STT3:00 pmSaint Thomas Island Cyril E King
8h 31m
1 stop
MDW10:31 pmChicago Midway
$780
Delta
Mar 9
MDW6:00 amChicago Midway
7h 45m
1 stop
STT2:45 pmSaint Thomas Island Cyril E King
Mar 15
STT3:00 pmSaint Thomas Island Cyril E King
8h 31m
1 stop
MDW10:31 pmChicago Midway
$828

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 March 7, 2026.
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

Cheapest round-trip

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Sat 5/9

6:00 am-9:54 am

2 stops26h 54m

Saint Thomas Island Cyril E King

Wed 5/13

10:49 am-8:04 am

1 stop22h 15m

$263

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Sat 5/9

9:14 am-9:54 am

1 stop23h 40m

Saint Thomas Island Cyril E King

Wed 5/13

10:49 am-10:19 pm

2 stops12h 30m

$277

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Wed 4/15

2:15 pm-9:54 am

2 stops18h 39m

Saint Thomas Island Cyril E King

Wed 4/22

10:49 am-7:26 am

1 stop21h 37m

$282
Quickest round-trip

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Sat 5/9

6:00 am-4:15 pm

2 stops9h 15m

Saint Thomas Island Cyril E King

Wed 5/13

10:49 am-8:04 am

1 stop22h 15m

$297

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Thu 5/7

6:00 am-4:15 pm

2 stops9h 15m

Saint Thomas Island Cyril E King

Wed 5/13

10:49 am-8:04 am

1 stop22h 15m

$303

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Mon 3/16

9:51 pm-1:26 pm

1 stop14h 35m

Saint Thomas Island Cyril E King

Thu 3/19

2:36 pm-7:47 pm

2 stops30h 11m

$316

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Mon 3/23

9:51 pm-1:26 pm

1 stop14h 35m

Saint Thomas Island Cyril E King

Tue 3/31

2:36 pm-10:19 pm

2 stops32h 43m

$318

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Mon 3/23

9:51 pm-1:26 pm

1 stop14h 35m

Saint Thomas Island Cyril E King

Mon 3/30

2:36 pm-8:54 pm

2 stops31h 18m

$322

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Tue 3/24

4:33 pm-1:26 pm

1 stop19h 53m

Saint Thomas Island Cyril E King

Tue 3/31

2:36 pm-10:19 pm

2 stops32h 43m

$331

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Tue 3/24

4:33 pm-1:26 pm

1 stop19h 53m

Saint Thomas Island Cyril E King

Mon 3/30

2:36 pm-8:54 pm

2 stops31h 18m

$335

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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 $610. However, this price may fluctuate depending on the airline, the season, and holidays. When flying out on a Saturday, 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 $812.

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

Fastest flight time

6h 47m

Direct flights

None
The fastest flight from Chicago Midway Airport to Saint Thomas Island takes 6h 47m
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 47m.

  • 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 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.

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.

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