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Cheap flights from Saint Thomas Island to Chicago from $82

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 3/4. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Cheap round-trip flights

Enter your travel dates to find the best prices.
Spirit Airlines Logo
4:35 pm - 11:17 pm
STT
-
ORD
7h 42m
1 stop
Spirit Airlines Logo
6:10 pm - 3:28 pm
ORD
-
STT
20h 18m
1 stop
$234Spirit Airlines
Wed, Mar 18 - Wed, Mar 25
Spirit Airlines Logo
4:35 pm - 11:17 pm
STT
-
ORD
7h 42m
1 stop
Spirit Airlines Logo
8:58 pm - 3:28 pm
ORD
-
STT
17h 30m
2 stops
$239Spirit Airlines
Wed, Mar 25 - Mon, Mar 30
Spirit Airlines Logo
4:35 pm - 11:17 pm
STT
-
ORD
7h 42m
1 stop
Spirit Airlines Logo
6:10 pm - 3:28 pm
ORD
-
STT
20h 18m
1 stop
$243Spirit Airlines
Wed, Mar 25 - Mon, Mar 30
Spirit Airlines Logo
3:36 pm - 11:47 pm
STT
-
ORD
10h 11m
2 stops
Spirit Airlines Logo
8:16 pm - 2:31 pm
ORD
-
STT
16h 15m
2 stops
$255Spirit Airlines
Thu, Feb 19 - Mon, Feb 23
Spirit Airlines Logo
2:36 pm - 11:17 am
STT
-
ORD
21h 41m
2 stops
Spirit Airlines Logo
7:17 am - 3:28 pm
ORD
-
STT
7h 11m
1 stop
$259Spirit Airlines
Wed, Mar 18 - Wed, Mar 25
Spirit Airlines Logo
4:35 pm - 11:17 pm
STT
-
ORD
7h 42m
1 stop
Spirit Airlines Logo
6:10 pm - 3:28 pm
ORD
-
STT
20h 18m
1 stop
$263Spirit Airlines
Wed, Mar 25 - Mon, Mar 30
Spirit Airlines Logo
5:40 pm - 11:47 pm
STT
-
ORD
8h 07m
1 stop
Spirit Airlines Logo
4:43 pm - 4:34 pm
ORD
-
STT
21h 51m
1 stop
$265Spirit Airlines
Thu, Feb 19 - Mon, Feb 23
Spirit Airlines Logo
5:40 pm - 11:47 pm
STT
-
ORD
8h 07m
1 stop
Spirit Airlines Logo
4:43 pm - 2:31 pm
ORD
-
STT
19h 48m
2 stops
$268Spirit Airlines
Wed, Feb 25 - Fri, Feb 27
Spirit Airlines Logo
4:35 pm - 11:17 pm
STT
-
ORD
7h 42m
1 stop
Spirit Airlines Logo
6:10 pm - 3:28 pm
ORD
-
STT
20h 18m
1 stop
$271Spirit Airlines
Thu, Mar 19 - Wed, Mar 25
Spirit Airlines Logo
5:40 pm - 11:47 pm
STT
-
ORD
8h 07m
1 stop
Spirit Airlines Logo
8:16 pm - 2:31 pm
ORD
-
STT
16h 15m
2 stops
$274Spirit Airlines
Thu, Feb 19 - Mon, Feb 23

Spirit Airlines flights from Saint Thomas Island to Chicago

Our best Spirit Airlines deals on Saint Thomas Island to Chicago flight tickets
Spirit Airlines
Mar 25
STT4:35 pmSaint Thomas Island Cyril E King
7h 42m
1 stop
ORD11:17 pmChicago O'Hare Intl
Mar 30
ORD6:10 pmChicago O'Hare Intl
20h 18m
1 stop
STT3:28 pmSaint Thomas Island Cyril E King
$263
Spirit Airlines
Feb 25
STT5:40 pmSaint Thomas Island Cyril E King
8h 07m
1 stop
ORD11:47 pmChicago O'Hare Intl
Feb 27
ORD4:43 pmChicago O'Hare Intl
21h 51m
1 stop
STT4:34 pmSaint Thomas Island Cyril E King
$265
Spirit Airlines
Feb 25
STT5:40 pmSaint Thomas Island Cyril E King
8h 07m
1 stop
ORD11:47 pmChicago O'Hare Intl
Feb 27
ORD4:43 pmChicago O'Hare Intl
19h 48m
2 stops
STT2:31 pmSaint Thomas Island Cyril E King
$268

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 46m
ORD5:59 pmChicago O'Hare Intl
Mar 30
ORD8:18 amChicago O'Hare Intl
4h 45m
STT2:03 pmSaint Thomas Island Cyril E King
$521
American Airlines
Mar 25
STT1:13 pmSaint Thomas Island Cyril E King
5h 46m
ORD5:59 pmChicago O'Hare Intl
Mar 30
ORD6:00 amChicago O'Hare Intl
9h 29m
1 stop
STT4:29 pmSaint Thomas Island Cyril E King
$526
American Airlines
Feb 22
STT1:02 pmSaint Thomas Island Cyril E King
12h 32m
1 stop
ORD11:34 pmChicago O'Hare Intl
Feb 26
ORD8:18 amChicago O'Hare Intl
4h 45m
STT3:03 pmSaint Thomas Island Cyril E King
$676

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 February 8, 2026.
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

Wed 3/18

4:35 pm-11:17 pm

1 stop7h 42m

Chicago O'Hare Intl

Wed 3/25

6:10 pm-3:28 pm

1 stop20h 18m

$234

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Wed 3/25

4:35 pm-11:17 pm

1 stop7h 42m

Chicago O'Hare Intl

Mon 3/30

8:58 pm-3:28 pm

2 stops17h 30m

$239

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Wed 3/25

4:35 pm-11:17 pm

1 stop7h 42m

Chicago O'Hare Intl

Mon 3/30

6:10 pm-3:28 pm

1 stop20h 18m

$243

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Thu 2/19

3:36 pm-11:47 pm

2 stops10h 11m

Chicago O'Hare Intl

Mon 2/23

8:16 pm-2:31 pm

2 stops16h 15m

$255

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Wed 3/18

2:36 pm-11:17 am

2 stops21h 41m

Chicago O'Hare Intl

Wed 3/25

7:17 am-3:28 pm

1 stop7h 11m

$259

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Wed 3/25

4:35 pm-11:17 pm

1 stop7h 42m

Chicago O'Hare Intl

Mon 3/30

6:10 pm-3:28 pm

1 stop20h 18m

$263

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Thu 2/19

5:40 pm-11:47 pm

1 stop8h 07m

Chicago O'Hare Intl

Mon 2/23

4:43 pm-4:34 pm

1 stop21h 51m

$265

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Wed 2/25

5:40 pm-11:47 pm

1 stop8h 07m

Chicago O'Hare Intl

Fri 2/27

4:43 pm-2:31 pm

2 stops19h 48m

$268

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Thu 3/19

4:35 pm-11:17 pm

1 stop7h 42m

Chicago O'Hare Intl

Wed 3/25

6:10 pm-3:28 pm

1 stop20h 18m

$271

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Thu 2/19

5:40 pm-11:47 pm

1 stop8h 07m

Chicago O'Hare Intl

Mon 2/23

8:16 pm-2:31 pm

2 stops16h 15m

$274

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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2

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 Tuesday when prices can be found for as low as $536. 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 at noon. Flights from Saint Thomas Island to Chicago during this time can be as low as $540. 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 28% 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?

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

Best Price Found

$402

Fastest flight time

5h 40m

Direct flights

Every day

Airports in Chicago

3 airports
The best one-way flight to Chicago from Saint Thomas Island in the past 72 hours is $402. The best round-trip flight deal from Saint Thomas Island to Chicago found on momondo in the last 72 hours is $346.
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 $204Free CancellationRating
6.3
8,430 reviews
Search Spirit Airlines flights
American AirlinesPriceFrom $306Free CancellationRating
7.2
11,249 reviews
Search American Airlines flights

  • American Airlines Flights From Saint Thomas Island to Chicago

    Across 1 American Airlines flight from Saint Thomas Island to Chicago this week, the average price was $539, with the best American Airlines deals starting from $306 round-trip. 11,249 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