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Cheap flights from Chicago Midway Airport to Saint Thomas Island from $308

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 9/19. 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
1 adult, Economy, 0 bags

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.
Southwest Logo
5:00 am - 2:00 pmMDW  Chicago Midway-STT Saint Thomas Island Cyril E King
8h 00m1 stop Orlando
Southwest Logo
3:45 pm - 11:05 pmSTT  Saint Thomas Island Cyril E King-MDW Chicago Midway
9h 20m1 stop Baltimore/Washington
$533Southwest
Mon, Oct 26 - Mon, Nov 2
Southwest Logo
5:10 am - 3:00 pmMDW  Chicago Midway-STT Saint Thomas Island Cyril E King
7h 50m1 stop Orlando
Southwest Logo
3:15 pm - 5:40 amSTT  Saint Thomas Island Cyril E King-MDW Chicago Midway
16h 25m2 stops Orlando Las Vegas Harry Reid Intl
$542Southwest
Sun, Nov 1 - Wed, Nov 4
Southwest Logo
5:10 am - 3:00 pmMDW  Chicago Midway-STT Saint Thomas Island Cyril E King
7h 50m1 stop Orlando
Southwest Logo
3:15 pm - 9:15 pmSTT  Saint Thomas Island Cyril E King-MDW Chicago Midway
8h 00m1 stop Orlando
$542Southwest
Sun, Nov 1 - Wed, Nov 4
Southwest Logo
5:00 am - 1:50 pmMDW  Chicago Midway-STT Saint Thomas Island Cyril E King
7h 50m1 stop Orlando
Southwest Logo
2:50 pm - 12:20 amSTT  Saint Thomas Island Cyril E King-MDW Chicago Midway
10h 30m1 stop Orlando
$552Southwest
Fri, Sep 25 - Thu, Oct 1
Southwest Logo
8:25 pm - 3:00 pmMDW  Chicago Midway-STT Saint Thomas Island Cyril E King
16h 35m2 stops Baltimore/Washington Orlando
Southwest Logo
3:15 pm - 5:40 amSTT  Saint Thomas Island Cyril E King-MDW Chicago Midway
16h 25m2 stops Orlando Las Vegas Harry Reid Intl
$562Southwest
Sun, Nov 1 - Wed, Nov 4
Southwest Logo
8:15 pm - 1:20 pmMDW  Chicago Midway-STT Saint Thomas Island Cyril E King
16h 05m2 stops Denver Intl Orlando
Southwest Logo
2:50 pm - 9:40 pmSTT  Saint Thomas Island Cyril E King-MDW Chicago Midway
7h 50m1 stop Orlando
$566Southwest
Fri, Sep 25 - Thu, Oct 1
Southwest Logo
5:00 am - 2:00 pmMDW  Chicago Midway-STT Saint Thomas Island Cyril E King
8h 00m1 stop Orlando
Southwest Logo
3:15 pm - 5:40 amSTT  Saint Thomas Island Cyril E King-MDW Chicago Midway
16h 25m2 stops Orlando Las Vegas Harry Reid Intl
$574Southwest
Mon, Oct 26 - Wed, Nov 4
Southwest Logo
5:00 am - 2:00 pmMDW  Chicago Midway-STT Saint Thomas Island Cyril E King
8h 00m1 stop Orlando
Southwest Logo
3:45 pm - 11:05 pmSTT  Saint Thomas Island Cyril E King-MDW Chicago Midway
9h 20m1 stop Baltimore/Washington
$574Southwest
Mon, Oct 26 - Mon, Nov 2
Southwest Logo
5:00 am - 2:00 pmMDW  Chicago Midway-STT Saint Thomas Island Cyril E King
8h 00m1 stop Orlando
Southwest Logo
3:15 pm - 9:15 pmSTT  Saint Thomas Island Cyril E King-MDW Chicago Midway
8h 00m1 stop Orlando
$574Southwest
Mon, Oct 26 - Wed, Nov 4
Southwest Logo
9:20 pm - 2:05 pmMDW  Chicago Midway-STT Saint Thomas Island Cyril E King
15h 45m2 stops Denver Intl Orlando
Southwest Logo
2:50 pm - 9:40 pmSTT  Saint Thomas Island Cyril E King-MDW Chicago Midway
7h 50m1 stop Orlando
$586Southwest
Fri, Oct 2 - Mon, Oct 5

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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
Nov 2
MDW6:04 amChicago Midway
6h 33m
1 stop
STT2:37 pmSaint Thomas Island Cyril E King
Nov 4
STT3:47 pmSaint Thomas Island Cyril E King
8h 46m
1 stop
MDW10:33 pmChicago Midway
$650
Delta
Nov 15
MDW6:00 amChicago Midway
6h 40m
1 stop
STT2:40 pmSaint Thomas Island Cyril E King
Nov 21
STT3:50 pmSaint Thomas Island Cyril E King
9h 06m
1 stop
MDW10:56 pmChicago Midway
$670
Delta
Oct 31
MDW6:04 amChicago Midway
6h 33m
1 stop
STT1:37 pmSaint Thomas Island Cyril E King
Nov 5
STT3:47 pmSaint Thomas Island Cyril E King
8h 46m
1 stop
MDW10:33 pmChicago Midway
$685

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
Oct 26
MDW5:00 amChicago Midway
8h 00m
1 stop
STT2:00 pmSaint Thomas Island Cyril E King
Nov 2
STT3:45 pmSaint Thomas Island Cyril E King
9h 20m
1 stop
MDW11:05 pmChicago Midway
$533
Southwest
Nov 1
MDW5:10 amChicago Midway
7h 50m
1 stop
STT3:00 pmSaint Thomas Island Cyril E King
Nov 4
STT3:15 pmSaint Thomas Island Cyril E King
8h 00m
1 stop
MDW9:15 pmChicago Midway
$542
Southwest
Sep 25
MDW5:00 amChicago Midway
7h 50m
1 stop
STT1:50 pmSaint Thomas Island Cyril E King
Oct 1
STT2:50 pmSaint Thomas Island Cyril E King
10h 30m
1 stop
MDW12:20 amChicago Midway
$552

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 6, 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 Chicago Midway - STT Saint Thomas Island Cyril E King

MDWSTT

Chicago Midway

Mon 10/26

5:00 am-2:00 pm

1 stop8h 00m

Saint Thomas Island Cyril E King

Mon 11/2

3:45 pm-11:05 pm

1 stop9h 20m

$533

ChicagoSaint Thomas Island

MDW Chicago Midway - STT Saint Thomas Island Cyril E King

MDWSTT

Chicago Midway

Sun 11/1

5:10 am-3:00 pm

1 stop7h 50m

Saint Thomas Island Cyril E King

Wed 11/4

3:15 pm-5:40 am

2 stops16h 25m

$542
Quickest round-trip

ChicagoSaint Thomas Island

MDW Chicago Midway - STT Saint Thomas Island Cyril E King

MDWSTT

Chicago Midway

Sun 11/1

5:10 am-3:00 pm

1 stop7h 50m

Saint Thomas Island Cyril E King

Wed 11/4

3:15 pm-9:15 pm

1 stop8h 00m

$542

ChicagoSaint Thomas Island

MDW Chicago Midway - STT Saint Thomas Island Cyril E King

MDWSTT

Chicago Midway

Fri 9/25

5:00 am-1:50 pm

1 stop7h 50m

Saint Thomas Island Cyril E King

Thu 10/1

2:50 pm-12:20 am

1 stop10h 30m

$552

ChicagoSaint Thomas Island

MDW Chicago Midway - STT Saint Thomas Island Cyril E King

MDWSTT

Chicago Midway

Sun 11/1

8:25 pm-3:00 pm

2 stops16h 35m

Saint Thomas Island Cyril E King

Wed 11/4

3:15 pm-5:40 am

2 stops16h 25m

$562

ChicagoSaint Thomas Island

MDW Chicago Midway - STT Saint Thomas Island Cyril E King

MDWSTT

Chicago Midway

Fri 9/25

8:15 pm-1:20 pm

2 stops16h 05m

Saint Thomas Island Cyril E King

Thu 10/1

2:50 pm-9:40 pm

1 stop7h 50m

$566

ChicagoSaint Thomas Island

MDW Chicago Midway - STT Saint Thomas Island Cyril E King

MDWSTT

Chicago Midway

Mon 10/26

5:00 am-2:00 pm

1 stop8h 00m

Saint Thomas Island Cyril E King

Wed 11/4

3:15 pm-5:40 am

2 stops16h 25m

$574

ChicagoSaint Thomas Island

MDW Chicago Midway - STT Saint Thomas Island Cyril E King

MDWSTT

Chicago Midway

Mon 10/26

5:00 am-2:00 pm

1 stop8h 00m

Saint Thomas Island Cyril E King

Mon 11/2

3:45 pm-11:05 pm

1 stop9h 20m

$574

ChicagoSaint Thomas Island

MDW Chicago Midway - STT Saint Thomas Island Cyril E King

MDWSTT

Chicago Midway

Mon 10/26

5:00 am-2:00 pm

1 stop8h 00m

Saint Thomas Island Cyril E King

Wed 11/4

3:15 pm-9:15 pm

1 stop8h 00m

$574

ChicagoSaint Thomas Island

MDW Chicago Midway - STT Saint Thomas Island Cyril E King

MDWSTT

Chicago Midway

Fri 10/2

9:20 pm-2:05 pm

2 stops15h 45m

Saint Thomas Island Cyril E King

Mon 10/5

2:50 pm-9:40 pm

1 stop7h 50m

$586

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 $614. 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 $777.

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 29m

Direct flights

None
The fastest flight from Chicago Midway Airport to Saint Thomas Island takes 6h 29m
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 29m.

  • 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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