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Cheap flights from Saint Thomas Island to Chicago from $250

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 11/3. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Saint Thomas Island to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
JetBlue Logo
2:58 pm - 10:06 am
STT
-
ORD
20h 08m
2 stops
JetBlue Logo
2:35 pm - 3:32 pm
ORD
-
STT
23h 57m
2 stops
$490JetBlue
Tue, Aug 4 - Tue, Aug 18
American Airlines Logo
4:50 pm - 11:30 pm
STT
-
ORD
7h 40m
1 stop
American Airlines Logo
5:07 am - 4:00 pm
ORD
-
STT
9h 53m
2 stops
$580American Airlines
Wed, Jul 22 - Mon, Jul 27
American Airlines Logo
11:43 am - 10:00 pm
STT
-
ORD
11h 17m
1 stop
American Airlines Logo
5:07 am - 4:00 pm
ORD
-
STT
9h 53m
2 stops
$615American Airlines
Thu, Jul 16 - Sun, Jul 19
American Airlines Logo
11:52 am - 9:37 pm
STT
-
ORD
10h 45m
1 stop
American Airlines Logo
6:47 pm - 11:03 am
ORD
-
STT
15h 16m
1 stop
$625American Airlines
Tue, Jun 2 - Tue, Jun 16
American Airlines Logo
2:41 pm - 9:37 pm
STT
-
ORD
7h 56m
1 stop
American Airlines Logo
5:10 am - 3:57 pm
ORD
-
STT
9h 47m
2 stops
$660American Airlines
Tue, Jun 2 - Tue, Jun 16
American Airlines Logo
1:35 pm - 12:19 am
STT
-
ORD
11h 44m
1 stop
American Airlines Logo
4:33 pm - 11:12 am
ORD
-
STT
17h 39m
1 stop
$665American Airlines
Wed, Jun 17 - Mon, Jun 22
Multiple Airlines Logo
5:45 pm - 8:48 am
STT
-
ORD
16h 03m
2 stops
Multiple Airlines Logo
2:35 pm - 3:32 pm
ORD
-
STT
23h 57m
2 stops
$694Multiple Airlines
Mon, Aug 3 - Tue, Aug 18
American Airlines Logo
4:42 pm - 7:25 am
STT
-
ORD
15h 43m
1 stop
American Airlines Logo
9:10 pm - 11:03 am
ORD
-
STT
12h 53m
2 stops
$701American Airlines
Mon, Jun 1 - Mon, Jun 8
American Airlines Logo
4:42 pm - 9:02 am
STT
-
ORD
17h 20m
1 stop
American Airlines Logo
8:52 pm - 11:03 am
ORD
-
STT
13h 11m
1 stop
$715American Airlines
Mon, Jun 1 - Mon, Jun 8
American Airlines Logo
1:35 pm - 11:58 pm
STT
-
ORD
11h 23m
2 stops
American Airlines Logo
4:33 pm - 11:12 am
ORD
-
STT
17h 39m
1 stop
$720American Airlines
Wed, Jun 17 - Mon, Jun 22

American Airlines flights from Saint Thomas Island to Chicago

Our best American Airlines deals on Saint Thomas Island to Chicago flight tickets
American Airlines
Jul 22
STT4:50 pmSaint Thomas Island Cyril E King
7h 40m
1 stop
ORD11:30 pmChicago O'Hare Intl
Jul 27
ORD5:07 amChicago O'Hare Intl
9h 53m
2 stops
STT4:00 pmSaint Thomas Island Cyril E King
$580
American Airlines
Jul 16
STT11:43 amSaint Thomas Island Cyril E King
11h 17m
1 stop
ORD10:00 pmChicago O'Hare Intl
Jul 19
ORD5:07 amChicago O'Hare Intl
9h 53m
2 stops
STT4:00 pmSaint Thomas Island Cyril E King
$615
American Airlines
Jun 2
STT11:52 amSaint Thomas Island Cyril E King
10h 45m
1 stop
ORD9:37 pmChicago O'Hare Intl
Jun 16
ORD6:47 pmChicago O'Hare Intl
15h 16m
1 stop
STT11:03 amSaint Thomas Island Cyril E King
$625

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 May 15, 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

Cheapest round-trip

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Tue 8/4

2:58 pm-10:06 am

2 stops20h 08m

Chicago O'Hare Intl

Tue 8/18

2:35 pm-3:32 pm

2 stops23h 57m

$490
Quickest round-trip

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Wed 7/22

4:50 pm-11:30 pm

1 stop7h 40m

Chicago O'Hare Intl

Mon 7/27

5:07 am-4:00 pm

2 stops9h 53m

$580

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Thu 7/16

11:43 am-10:00 pm

1 stop11h 17m

Chicago O'Hare Intl

Sun 7/19

5:07 am-4:00 pm

2 stops9h 53m

$615

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Tue 6/2

11:52 am-9:37 pm

1 stop10h 45m

Chicago O'Hare Intl

Tue 6/16

6:47 pm-11:03 am

1 stop15h 16m

$625

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Tue 6/2

2:41 pm-9:37 pm

1 stop7h 56m

Chicago O'Hare Intl

Tue 6/16

5:10 am-3:57 pm

2 stops9h 47m

$660

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Wed 6/17

1:35 pm-12:19 am

1 stop11h 44m

Chicago O'Hare Intl

Mon 6/22

4:33 pm-11:12 am

1 stop17h 39m

$665

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Mon 8/3

5:45 pm-8:48 am

2 stops16h 03m

Chicago O'Hare Intl

Tue 8/18

2:35 pm-3:32 pm

2 stops23h 57m

$694

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Mon 6/1

4:42 pm-7:25 am

1 stop15h 43m

Chicago O'Hare Intl

Mon 6/8

9:10 pm-11:03 am

2 stops12h 53m

$701

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Mon 6/1

4:42 pm-9:02 am

1 stop17h 20m

Chicago O'Hare Intl

Mon 6/8

8:52 pm-11:03 am

1 stop13h 11m

$715

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Wed 6/17

1:35 pm-11:58 pm

2 stops11h 23m

Chicago O'Hare Intl

Mon 6/22

4:33 pm-11:12 am

1 stop17h 39m

$720

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 month to fly to Chicago?

The month of May is, on average, the cheapest month to fly to Chicago from Saint Thomas Island, with most prices found around $0. If you’re not able to fly to Chicago in May, then April is your next best option. Flight prices from Saint Thomas Island to Chicago during April average around $0.

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 Sunday when prices can be found for as low as $505. This is often the case because there is less demand to fly during this day of the week. When flying out on a Friday, the most expensive travel day of the week, you can expect to see flight prices from Saint Thomas Island to Chicago for around $801.

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 $536. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $567.

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

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

Fastest flight time

7h 41m

Direct flights

Mon and Sun

Airports in Chicago

3 airports
The fastest flight from Saint Thomas Island to Chicago takes 7h 41m
Direct flights go from Saint Thomas Island to Chicago on Monday and Sunday. There are no airlines offering direct flights.
There are 3 airports in Chicago. From Saint Thomas Island there are direct flights to Chicago O'Hare Intl (ORD).
Search flight deals

Frequently asked questions about flying from Saint Thomas Island to Chicago

  • 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 7h 41m 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
American AirlinesPriceFrom $306Free CancellationRating
7.1
11,665 reviews
Search American Airlines flights

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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