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Cheap flights from Saint Thomas Island to Chicago from $135

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Saint Thomas Island to Chicago departing on 2/18. 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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Cheap round-trip flights

Enter your travel dates to find the best prices.
Spirit Airlines Logo
5:42 pm - 11:46 pm
STT
-
ORD
8h 04m1 stop
Spirit Airlines Logo
3:22 pm - 2:52 pm
ORD
-
STT
21h 30m2 stops
$317Spirit Airlines
do, jan. 15 - do, jan. 22
Spirit Airlines Logo
5:42 pm - 11:46 pm
STT
-
ORD
8h 04m1 stop
Spirit Airlines Logo
8:43 pm - 2:52 pm
ORD
-
STT
16h 09m2 stops
$321Spirit Airlines
ma, jan. 26 - ma, feb. 9
Spirit Airlines Logo
5:42 pm - 11:46 pm
STT
-
ORD
8h 04m1 stop
Spirit Airlines Logo
7:20 am - 4:37 pm
ORD
-
STT
7h 17m1 stop
$323Spirit Airlines
do, jan. 15 - do, jan. 22
Spirit Airlines Logo
5:42 pm - 11:46 pm
STT
-
ORD
8h 04m1 stop
Spirit Airlines Logo
7:20 am - 4:37 pm
ORD
-
STT
7h 17m1 stop
$325Spirit Airlines
ma, jan. 26 - ma, feb. 9
American Airlines Logo
1:13 pm - 6:04 pm
STT
-
ORD
5h 51mnonstop
American Airlines Logo
8:13 am - 2:01 pm
ORD
-
STT
4h 48mnonstop
$414American Airlines
wo, mrt. 25 - ma, mrt. 30
American Airlines Logo
3:16 pm - 6:50 pm
STT
-
ORD
5h 34mnonstop
American Airlines Logo
7:00 am - 5:05 pm
ORD
-
STT
8h 05m1 stop
$419American Airlines
do, jan. 15 - do, jan. 22
American Airlines Logo
2:43 pm - 11:37 pm
STT
-
ORD
9h 54m1 stop
American Airlines Logo
6:46 pm - 12:05 pm
ORD
-
STT
16h 19m1 stop
$423American Airlines
wo, mrt. 25 - ma, mrt. 30
American Airlines Logo
3:16 pm - 6:50 pm
STT
-
ORD
5h 34mnonstop
American Airlines Logo
8:50 am - 3:30 pm
ORD
-
STT
4h 40mnonstop
$487American Airlines
do, jan. 15 - do, jan. 22
American Airlines Logo
2:43 pm - 9:45 am
STT
-
ORD
20h 02m1 stop
American Airlines Logo
8:13 am - 2:01 pm
ORD
-
STT
4h 48mnonstop
$492American Airlines
ma, mrt. 16 - do, mrt. 19
American Airlines Logo
1:52 pm - 11:17 pm
STT
-
ORD
10h 25m1 stop
American Airlines Logo
6:10 am - 4:02 pm
ORD
-
STT
8h 52m1 stop
$496American Airlines
ma, mrt. 16 - do, mrt. 19

Spirit Airlines flights from Saint Thomas Island to Chicago

Our best Spirit Airlines deals on Saint Thomas Island to Chicago flight tickets
Spirit Airlines
Jan 15
STT5:42 pmSaint Thomas Island Cyril E King
8h 04m
1 stop
ORD11:46 pmChicago O'Hare Intl
Jan 22
ORD3:22 pmChicago O'Hare Intl
21h 30m
2 stops
STT2:52 pmSaint Thomas Island Cyril E King
$317
Find similar
Spirit Airlines
Jan 26
STT5:42 pmSaint Thomas Island Cyril E King
8h 04m
1 stop
ORD11:46 pmChicago O'Hare Intl
Feb 9
ORD8:43 pmChicago O'Hare Intl
16h 09m
2 stops
STT2:52 pmSaint Thomas Island Cyril E King
$321
Find similar
Spirit Airlines
Jan 15
STT5:42 pmSaint Thomas Island Cyril E King
8h 04m
1 stop
ORD11:46 pmChicago O'Hare Intl
Jan 22
ORD7:20 amChicago O'Hare Intl
7h 17m
1 stop
STT4:37 pmSaint Thomas Island Cyril E King
$323
Find similar

American Airlines flights from Saint Thomas Island to Chicago

Our best American Airlines deals on Saint Thomas Island to Chicago flight tickets
American Airlines
Mar 25
STT1:13 pmSaint Thomas Island Cyril E King
5h 51m
ORD6:04 pmChicago O'Hare Intl
Mar 30
ORD8:13 amChicago O'Hare Intl
4h 48m
STT2:01 pmSaint Thomas Island Cyril E King
$414
Find similar
American Airlines
Jan 15
STT3:16 pmSaint Thomas Island Cyril E King
5h 34m
ORD6:50 pmChicago O'Hare Intl
Jan 22
ORD7:00 amChicago O'Hare Intl
8h 05m
1 stop
STT5:05 pmSaint Thomas Island Cyril E King
$419
Find similar
American Airlines
Mar 25
STT2:43 pmSaint Thomas Island Cyril E King
9h 54m
1 stop
ORD11:37 pmChicago O'Hare Intl
Mar 30
ORD6:46 pmChicago O'Hare Intl
16h 19m
1 stop
STT12:05 pmSaint Thomas Island Cyril E King
$423
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Saint Thomas Island to Chicago 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 december 21, 2025.
Use the filters below to find and compare flights from Saint Thomas Island to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

do 1/15

5:42 pm-11:46 pm

1 stop8h 04m

Chicago O'Hare Intl

do 1/22

3:22 pm-2:52 pm

2 stops21h 30m

$317

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

ma 1/26

5:42 pm-11:46 pm

1 stop8h 04m

Chicago O'Hare Intl

ma 2/9

8:43 pm-2:52 pm

2 stops16h 09m

$321

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

do 1/15

5:42 pm-11:46 pm

1 stop8h 04m

Chicago O'Hare Intl

do 1/22

7:20 am-4:37 pm

1 stop7h 17m

$323

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

ma 1/26

5:42 pm-11:46 pm

1 stop8h 04m

Chicago O'Hare Intl

ma 2/9

7:20 am-4:37 pm

1 stop7h 17m

$325

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

wo 3/25

1:13 pm-6:04 pm

Nonstop5h 51m

Chicago O'Hare Intl

ma 3/30

8:13 am-2:01 pm

Nonstop4h 48m

$414

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

do 1/15

3:16 pm-6:50 pm

Nonstop5h 34m

Chicago O'Hare Intl

do 1/22

7:00 am-5:05 pm

1 stop8h 05m

$419

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

wo 3/25

2:43 pm-11:37 pm

1 stop9h 54m

Chicago O'Hare Intl

ma 3/30

6:46 pm-12:05 pm

1 stop16h 19m

$423

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

do 1/15

3:16 pm-6:50 pm

Nonstop5h 34m

Chicago O'Hare Intl

do 1/22

8:50 am-3:30 pm

Nonstop4h 40m

$487

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

ma 3/16

2:43 pm-9:45 am

1 stop20h 02m

Chicago O'Hare Intl

do 3/19

8:13 am-2:01 pm

Nonstop4h 48m

$492

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

ma 3/16

1:52 pm-11:17 pm

1 stop10h 25m

Chicago O'Hare Intl

do 3/19

6:10 am-4:02 pm

1 stop8h 52m

$496

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 Chicago from

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

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 Chicago?

The cheapest day to depart on your flight to Chicago is on a Thursday when prices can be found for as low as $479. This is often the case because there is less demand to fly during this day of the week. When flying out on a Saturday, the most expensive travel day of the week, you can expect to see flight prices from Saint Thomas Island to Chicago for around $813.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the morning. Flights from Saint Thomas Island to Chicago during this time can be as low as $383. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $606.

What is the cheapest Saint Thomas Island Cyril E King to Chicago flight route?

Fly from Saint Thomas Island Cyril E King to Chicago O'Hare Intl for the best Saint Thomas Island Cyril E King - Chicago flight prices

What cabin class options are available on Saint Thomas Island Cyril E King to Chicago flights?

There are 4 cabin classes available to choose from on Saint Thomas Island Cyril E King to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Saint Thomas Island to Chicago flights?

You could potentially save up to 21% on your flight if you consider stops on a Saint Thomas Island to Chicago flight.

How have Saint Thomas Island to Chicago flight prices changed over time?

As of December 2025, prices for Saint Thomas Island to Chicago flights are approximately 54% cheaper when compared to flights at the same time last year.

When to book flights from Saint Thomas Island to Chicago

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

Cheap Saint Thomas Island to Chicago (STT to CHI) flight deals and tips

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

Fastest flight time

5h 40m

Direct flights

Every day

Airports in Chicago

3 airports
The fastest flight from Saint Thomas Island to Chicago takes 5h 40m
Direct flights go from Saint Thomas Island to Chicago every day.
There are 3 airports in Chicago. From Saint Thomas Island there are direct flights to Chicago O'Hare Intl (ORD).
Search flight deals

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

    There are 2102.2 mi between Saint Thomas Island Cyril E King and Chicago. Typically, this will take 5h 40m by plane in normal conditions.

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

    Prices for flights from Saint Thomas Island Cyril E King Airport to Chicago are refreshed on a daily basis.

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

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

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Saint Thomas Island Cyril E King Airport to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The required travel and health documents for your Chicago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

  • What is the most popular plane model from Saint Thomas Island to Chicago?

Best airlines flying from Saint Thomas Island to Chicago

Compare and see reviews for airlines that fly from Saint Thomas Island to Chicago with momondo
Airline
Rating
Free Cancellation
Price
Spirit AirlinesPriceFrom $227Free CancellationRating
6.3
8,190 reviews
Search Spirit Airlines flights
American AirlinesPriceFrom $306Free CancellationRating
7.2
11,050 reviews
Search American Airlines flights

  • American Airlines Flights From Saint Thomas Island to Chicago

    Across 7 American Airlines flights from Saint Thomas Island to Chicago this week, the average price was $559, with the best American Airlines deals starting from $306 round-trip. 11,052 users have rated American Airlines on momondo, with an average score of 7.2/10.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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Saint John

Why use momondo?

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

It is quick and easy to find Saint Thomas Island to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

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

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

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

momondo provides multiple filters to help you find the best flight to Chicago from Saint Thomas Island. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

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

Price alerts on flights to Chicago from Saint Thomas Island are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport