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Cheap flights from Chicago Midway Airport to Saint Thomas Island from $149

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 11/27. 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

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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
9:27 am - 1:00 pmMDW-STT
25h 33m2 stops
Multiple Airlines Logo
3:25 pm - 4:30 pmSTT-MDW
27h 05m1 stop
$340Multiple Airlines
Find Deal
lun., nov. 17 - sáb., nov. 22
Delta Logo
6:45 am - 3:04 pmMDW-STT
6h 19m1 stop
Delta Logo
4:15 pm - 10:09 pmSTT-MDW
7h 54m1 stop
$345Delta
Find Deal
mar., ene. 6 - mar., ene. 13
Multiple Airlines Logo
3:10 pm - 2:28 pmMDW-STT
21h 18m1 stop
Multiple Airlines Logo
1:33 pm - 11:25 pmSTT-MDW
11h 52m2 stops
$368Multiple Airlines
Find Deal
vie., ene. 2 - jue., ene. 8
Delta Logo
6:00 am - 4:10 pmMDW-STT
8h 10m1 stop
Delta Logo
4:15 pm - 10:26 pmSTT-MDW
8h 11m1 stop
$410Delta
Find Deal
dom., ene. 25 - vie., ene. 30
Delta Logo
6:45 am - 3:04 pmMDW-STT
6h 19m1 stop
Delta Logo
4:15 pm - 10:09 pmSTT-MDW
7h 54m1 stop
$439Delta
Find Deal
mar., ene. 6 - vie., ene. 16
Multiple Airlines Logo
9:43 pm - 3:11 pmMDW-STT
15h 28m1 stop
Multiple Airlines Logo
1:33 pm - 11:25 pmSTT-MDW
11h 52m2 stops
$477Multiple Airlines
Find Deal
dom., ene. 18 - sáb., ene. 24
Multiple Airlines Logo
6:12 am - 11:41 amMDW-STT
51h 29m2 stops
Multiple Airlines Logo
3:23 pm - 9:58 pmSTT-MDW
8h 35m1 stop
$542Multiple Airlines
Find Deal
lun., dic. 22 - mar., dic. 30
Delta Logo
6:00 am - 2:40 pmMDW-STT
6h 40m1 stop
Delta Logo
2:27 pm - 11:40 pmSTT-MDW
11h 13m1 stop
$549Delta
Find Deal
lun., nov. 17 - sáb., nov. 22
Multiple Airlines Logo
8:15 am - 11:41 amMDW-STT
25h 26m2 stops
Multiple Airlines Logo
3:23 pm - 9:58 pmSTT-MDW
8h 35m1 stop
$551Multiple Airlines
Find Deal
sáb., dic. 27 - mié., dic. 31
Multiple Airlines Logo
3:52 pm - 2:49 pmMDW-STT
20h 57m1 stop
Multiple Airlines Logo
11:45 am - 9:53 pmSTT-MDW
36h 08m2 stops
$559Multiple Airlines
Find Deal
vie., dic. 5 - mié., dic. 10

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 6
MDW6:45 amChicago Midway
6h 19m
1 stop
STT3:04 pmSaint Thomas Island Cyril E King
Jan 13
STT4:15 pmSaint Thomas Island Cyril E King
7h 54m
1 stop
MDW10:09 pmChicago Midway
$345
Find similar
Delta
Jan 25
MDW6:00 amChicago Midway
8h 10m
1 stop
STT4:10 pmSaint Thomas Island Cyril E King
Jan 30
STT4:15 pmSaint Thomas Island Cyril E King
8h 11m
1 stop
MDW10:26 pmChicago Midway
$410
Find similar
Delta
Jan 6
MDW6:45 amChicago Midway
6h 19m
1 stop
STT3:04 pmSaint Thomas Island Cyril E King
Jan 16
STT4:15 pmSaint Thomas Island Cyril E King
7h 54m
1 stop
MDW10:09 pmChicago Midway
$439
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 octubre 28, 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

lun. 11/17

9:27 am-1:00 pm

2 stops25h 33m

Saint Thomas Island Cyril E King

sáb. 11/22

3:25 pm-4:30 pm

1 stop27h 05m

$340

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

mar. 1/6

6:45 am-3:04 pm

1 stop6h 19m

Saint Thomas Island Cyril E King

mar. 1/13

4:15 pm-10:09 pm

1 stop7h 54m

$345

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

vie. 1/2

3:10 pm-2:28 pm

1 stop21h 18m

Saint Thomas Island Cyril E King

jue. 1/8

1:33 pm-11:25 pm

2 stops11h 52m

$368

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

dom. 1/25

6:00 am-4:10 pm

1 stop8h 10m

Saint Thomas Island Cyril E King

vie. 1/30

4:15 pm-10:26 pm

1 stop8h 11m

$410

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

mar. 1/6

6:45 am-3:04 pm

1 stop6h 19m

Saint Thomas Island Cyril E King

vie. 1/16

4:15 pm-10:09 pm

1 stop7h 54m

$439

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

dom. 1/18

9:43 pm-3:11 pm

1 stop15h 28m

Saint Thomas Island Cyril E King

sáb. 1/24

1:33 pm-11:25 pm

2 stops11h 52m

$477

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

lun. 12/22

6:12 am-11:41 am

2 stops51h 29m

Saint Thomas Island Cyril E King

mar. 12/30

3:23 pm-9:58 pm

1 stop8h 35m

$542

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

lun. 11/17

6:00 am-2:40 pm

1 stop6h 40m

Saint Thomas Island Cyril E King

sáb. 11/22

2:27 pm-11:40 pm

1 stop11h 13m

$549

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

sáb. 12/27

8:15 am-11:41 am

2 stops25h 26m

Saint Thomas Island Cyril E King

mié. 12/31

3:23 pm-9:58 pm

1 stop8h 35m

$551

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

vie. 12/5

3:52 pm-2:49 pm

1 stop20h 57m

Saint Thomas Island Cyril E King

mié. 12/10

11:45 am-9:53 pm

2 stops36h 08m

$559

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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 $653. 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 $1,075.

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 $772. 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 19m.

  • 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 $469Free CancellationRating
7.9
7,994 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.

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