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Cheap flights from Chicago Midway Airport to Saint Thomas Island from $228

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 8/3. 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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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.
Delta Logo
6:00 am - 3:20 pm
MDW
-
STT
8h 20m
1 stop
Delta Logo
3:33 pm - 10:15 pm
STT
-
MDW
7h 42m
1 stop
$580Delta
Wed, Jul 8 - Tue, Jul 14
Delta Logo
6:00 am - 4:37 pm
MDW
-
STT
9h 37m
1 stop
Delta Logo
1:21 pm - 10:15 pm
STT
-
MDW
9h 54m
1 stop
$585Delta
Sat, Jul 11 - Tue, Jul 21
Delta Logo
6:00 am - 3:20 pm
MDW
-
STT
8h 20m
1 stop
Delta Logo
3:33 pm - 10:36 pm
STT
-
MDW
8h 03m
1 stop
$590Delta
Sat, Aug 1 - Sat, Aug 8
Delta Logo
6:00 am - 3:20 pm
MDW
-
STT
8h 20m
1 stop
Delta Logo
1:21 pm - 10:15 pm
STT
-
MDW
9h 54m
1 stop
$620Delta
Mon, Jul 13 - Tue, Jul 21
Delta Logo
6:23 am - 1:51 pm
MDW
-
STT
6h 28m
1 stop
Delta Logo
1:20 pm - 10:17 pm
STT
-
MDW
9h 57m
1 stop
$625Delta
Wed, Jun 3 - Mon, Jun 8
Southwest Logo
5:10 am - 1:50 pm
MDW
-
STT
7h 40m
1 stop
Southwest Logo
2:35 pm - 10:40 pm
STT
-
MDW
9h 05m
1 stop
$650Southwest
Mon, Aug 3 - Mon, Aug 10
Delta Logo
6:00 am - 2:23 pm
MDW
-
STT
7h 23m
1 stop
Delta Logo
1:21 pm - 10:15 pm
STT
-
MDW
9h 54m
1 stop
$655Delta
Mon, Jul 13 - Wed, Jul 15
Delta Logo
6:00 am - 3:21 pm
MDW
-
STT
8h 21m
1 stop
Delta Logo
3:33 pm - 10:15 pm
STT
-
MDW
7h 42m
1 stop
$670Delta
Tue, Jun 30 - Fri, Jul 10
Delta Logo
6:00 am - 2:19 pm
MDW
-
STT
7h 19m
1 stop
Delta Logo
3:33 pm - 10:15 pm
STT
-
MDW
7h 42m
1 stop
$675Delta
Thu, Jul 2 - Fri, Jul 10
Delta Logo
6:00 am - 2:19 pm
MDW
-
STT
7h 19m
1 stop
Delta Logo
3:29 pm - 10:17 pm
STT
-
MDW
7h 48m
1 stop
$690Delta
Fri, Jul 3 - Mon, Jul 6

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
Aug 3
MDW5:10 amChicago Midway
7h 40m
1 stop
STT1:50 pmSaint Thomas Island Cyril E King
Aug 10
STT2:35 pmSaint Thomas Island Cyril E King
9h 05m
1 stop
MDW10:40 pmChicago Midway
$650
Southwest
Aug 3
MDW5:10 amChicago Midway
7h 40m
1 stop
STT1:50 pmSaint Thomas Island Cyril E King
Aug 6
STT2:35 pmSaint Thomas Island Cyril E King
9h 05m
1 stop
MDW10:40 pmChicago Midway
$720
Southwest
May 31
MDW5:15 amChicago Midway
8h 10m
1 stop
STT2:25 pmSaint Thomas Island Cyril E King
Jun 4
STT2:45 pmSaint Thomas Island Cyril E King
7h 40m
1 stop
MDW9:25 pmChicago Midway
$730

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
Jul 8
MDW6:00 amChicago Midway
8h 20m
1 stop
STT3:20 pmSaint Thomas Island Cyril E King
Jul 14
STT3:33 pmSaint Thomas Island Cyril E King
7h 42m
1 stop
MDW10:15 pmChicago Midway
$580
Delta
Jul 11
MDW6:00 amChicago Midway
9h 37m
1 stop
STT4:37 pmSaint Thomas Island Cyril E King
Jul 21
STT1:21 pmSaint Thomas Island Cyril E King
9h 54m
1 stop
MDW10:15 pmChicago Midway
$585
Delta
Aug 1
MDW6:00 amChicago Midway
8h 20m
1 stop
STT3:20 pmSaint Thomas Island Cyril E King
Aug 8
STT3:33 pmSaint Thomas Island Cyril E King
8h 03m
1 stop
MDW10:36 pmChicago Midway
$590

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 May 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

Wed 7/8

6:00 am-3:20 pm

1 stop8h 20m

Saint Thomas Island Cyril E King

Tue 7/14

3:33 pm-10:15 pm

1 stop7h 42m

$580

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Sat 7/11

6:00 am-4:37 pm

1 stop9h 37m

Saint Thomas Island Cyril E King

Tue 7/21

1:21 pm-10:15 pm

1 stop9h 54m

$585

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Sat 8/1

6:00 am-3:20 pm

1 stop8h 20m

Saint Thomas Island Cyril E King

Sat 8/8

3:33 pm-10:36 pm

1 stop8h 03m

$590

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Mon 7/13

6:00 am-3:20 pm

1 stop8h 20m

Saint Thomas Island Cyril E King

Tue 7/21

1:21 pm-10:15 pm

1 stop9h 54m

$620

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Wed 6/3

6:23 am-1:51 pm

1 stop6h 28m

Saint Thomas Island Cyril E King

Mon 6/8

1:20 pm-10:17 pm

1 stop9h 57m

$625

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Mon 8/3

5:10 am-1:50 pm

1 stop7h 40m

Saint Thomas Island Cyril E King

Mon 8/10

2:35 pm-10:40 pm

1 stop9h 05m

$650

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Mon 7/13

6:00 am-2:23 pm

1 stop7h 23m

Saint Thomas Island Cyril E King

Wed 7/15

1:21 pm-10:15 pm

1 stop9h 54m

$655

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Tue 6/30

6:00 am-3:21 pm

1 stop8h 21m

Saint Thomas Island Cyril E King

Fri 7/10

3:33 pm-10:15 pm

1 stop7h 42m

$670
Quickest round-trip

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Thu 7/2

6:00 am-2:19 pm

1 stop7h 19m

Saint Thomas Island Cyril E King

Fri 7/10

3:33 pm-10:15 pm

1 stop7h 42m

$675

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Fri 7/3

6:00 am-2:19 pm

1 stop7h 19m

Saint Thomas Island Cyril E King

Mon 7/6

3:29 pm-10:17 pm

1 stop7h 48m

$690

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 Thursday. momondo users have found tickets for Thursday 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 $772.

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 28m

Direct flights

None
The fastest flight from Chicago Midway Airport to Saint Thomas Island takes 6h 28m
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

Frequently asked questions about flying from Chicago Midway Airport to Saint Thomas Island

  • 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 28m.

  • 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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