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Cheap flights from Saint Thomas Island to Chicago from $243

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 9/1. 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

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Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
4:50 pm - 12:26 am
STT
-
ORD
8h 36m
1 stop
American Airlines Logo
6:47 pm - 11:03 am
ORD
-
STT
15h 16m
1 stop
$580American Airlines
Wed, Jul 22 - Sun, Jul 26
American Airlines Logo
4:50 pm - 9:08 am
STT
-
ORD
17h 18m
1 stop
American Airlines Logo
8:58 pm - 12:53 pm
ORD
-
STT
14h 55m
2 stops
$615American Airlines
Mon, Aug 3 - Tue, Aug 18
American Airlines Logo
2:41 pm - 12:01 am
STT
-
ORD
10h 20m
1 stop
American Airlines Logo
6:47 pm - 11:03 am
ORD
-
STT
15h 16m
1 stop
$665American Airlines
Wed, Jul 22 - Mon, Jul 27
JetBlue Logo
3:45 pm - 8:50 am
STT
-
ORD
18h 05m
2 stops
JetBlue Logo
8:20 pm - 3:32 pm
ORD
-
STT
18h 12m
2 stops
$702JetBlue
Mon, Aug 3 - Tue, Aug 18
American Airlines Logo
1:35 pm - 12:19 am
STT
-
ORD
11h 44m
1 stop
American Airlines Logo
4:30 pm - 10:59 am
ORD
-
STT
17h 29m
1 stop
$720American Airlines
Tue, Jun 30 - Wed, Jul 8
American Airlines Logo
1:50 pm - 11:21 pm
STT
-
ORD
10h 31m
2 stops
American Airlines Logo
7:05 pm - 12:40 pm
ORD
-
STT
16h 35m
1 stop
$750American Airlines
Thu, Oct 8 - Mon, Oct 12
American Airlines Logo
1:35 pm - 12:19 am
STT
-
ORD
11h 44m
1 stop
American Airlines Logo
5:07 am - 4:00 pm
ORD
-
STT
9h 53m
2 stops
$755American Airlines
Tue, Jun 30 - Wed, Jul 8
Multiple Airlines Logo
5:45 pm - 11:29 pm
STT
-
ORD
30h 44m
1 stop
Multiple Airlines Logo
12:44 am - 10:14 am
ORD
-
STT
8h 30m
1 stop
$761Multiple Airlines
Wed, Jul 1 - Tue, Jul 7
Multiple Airlines Logo
3:00 pm - 11:44 pm
STT
-
ORD
9h 44m
2 stops
Multiple Airlines Logo
9:40 am - 2:03 pm
ORD
-
STT
27h 23m
2 stops
$770Multiple Airlines
Wed, Jul 22 - Mon, Jul 27
American Airlines Logo
2:41 pm - 9:33 pm
STT
-
ORD
7h 52m
1 stop
American Airlines Logo
4:30 pm - 10:59 am
ORD
-
STT
17h 29m
1 stop
$775American Airlines
Tue, Jun 30 - Wed, Jul 8

American Airlines flights from Saint Thomas Island to Chicago O'Hare Intl Airport

Our best American Airlines deals on Saint Thomas Island to Chicago O'Hare Intl Airport flight tickets
American Airlines
Jul 22
STT4:50 pmSaint Thomas Island Cyril E King
8h 36m
1 stop
ORD12:26 amChicago O'Hare Intl
Jul 26
ORD6:47 pmChicago O'Hare Intl
15h 16m
1 stop
STT11:03 amSaint Thomas Island Cyril E King
$580
American Airlines
Aug 3
STT4:50 pmSaint Thomas Island Cyril E King
17h 18m
1 stop
ORD9:08 amChicago O'Hare Intl
Aug 18
ORD8:58 pmChicago O'Hare Intl
14h 55m
2 stops
STT12:53 pmSaint Thomas Island Cyril E King
$615
American Airlines
Jul 22
STT2:41 pmSaint Thomas Island Cyril E King
10h 20m
1 stop
ORD12:01 amChicago O'Hare Intl
Jul 27
ORD6:47 pmChicago O'Hare Intl
15h 16m
1 stop
STT11:03 amSaint Thomas Island Cyril E King
$665

JetBlue flights from Saint Thomas Island to Chicago O'Hare Intl Airport

Our best JetBlue deals on Saint Thomas Island to Chicago O'Hare Intl Airport flight tickets
JetBlue
Aug 3
STT3:45 pmSaint Thomas Island Cyril E King
18h 05m
2 stops
ORD8:50 amChicago O'Hare Intl
Aug 18
ORD8:20 pmChicago O'Hare Intl
18h 12m
2 stops
STT3:32 pmSaint Thomas Island Cyril E King
$702
JetBlue
Jul 4
STT5:45 pmSaint Thomas Island Cyril E King
16h 00m
2 stops
ORD8:45 amChicago O'Hare Intl
Jul 11
ORD7:00 amChicago O'Hare Intl
9h 20m
2 stops
STT5:20 pmSaint Thomas Island Cyril E King
$996

momondo Fare Finder

 
Customize your flight search to find flights from Saint Thomas Island to Chicago O'Hare Intl Airport 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 June 6, 2026.
Use the filters below to find and compare flights from Saint Thomas Island to Chicago O'Hare Intl Airport 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

Wed 7/22

4:50 pm-12:26 am

1 stop8h 36m

Chicago O'Hare Intl

Sun 7/26

6:47 pm-11:03 am

1 stop15h 16m

$580

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Mon 8/3

4:50 pm-9:08 am

1 stop17h 18m

Chicago O'Hare Intl

Tue 8/18

8:58 pm-12:53 pm

2 stops14h 55m

$615

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Wed 7/22

2:41 pm-12:01 am

1 stop10h 20m

Chicago O'Hare Intl

Mon 7/27

6:47 pm-11:03 am

1 stop15h 16m

$665

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Mon 8/3

3:45 pm-8:50 am

2 stops18h 05m

Chicago O'Hare Intl

Tue 8/18

8:20 pm-3:32 pm

2 stops18h 12m

$702

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Tue 6/30

1:35 pm-12:19 am

1 stop11h 44m

Chicago O'Hare Intl

Wed 7/8

4:30 pm-10:59 am

1 stop17h 29m

$720

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Thu 10/8

1:50 pm-11:21 pm

2 stops10h 31m

Chicago O'Hare Intl

Mon 10/12

7:05 pm-12:40 pm

1 stop16h 35m

$750
Quickest round-trip

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Tue 6/30

1:35 pm-12:19 am

1 stop11h 44m

Chicago O'Hare Intl

Wed 7/8

5:07 am-4:00 pm

2 stops9h 53m

$755

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Wed 7/1

5:45 pm-11:29 pm

1 stop30h 44m

Chicago O'Hare Intl

Tue 7/7

12:44 am-10:14 am

1 stop8h 30m

$761

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Wed 7/22

3:00 pm-11:44 pm

2 stops9h 44m

Chicago O'Hare Intl

Mon 7/27

9:40 am-2:03 pm

2 stops27h 23m

$770

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Tue 6/30

2:41 pm-9:33 pm

1 stop7h 52m

Chicago O'Hare Intl

Wed 7/8

4:30 pm-10:59 am

1 stop17h 29m

$775

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 O'Hare Intl Airport

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 typical price of a round-trip flight between Saint Thomas Island and Chicago O'Hare Intl Airport?

What is the cheapest month to fly to Chicago O'Hare Intl Airport?

The month of April is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Saint Thomas Island averaging around $0.

What is the cheapest day to depart on your flight to Chicago O'Hare Intl Airport?

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport 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. On the other hand, Friday is the most expensive day to depart from Saint Thomas Island because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $801.

What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?

Flying to Chicago O'Hare Intl Airport from Saint Thomas Island at noon is the least expensive time of day to depart. momondo users have found prices as low as $536 when looking at flights departing at noon. Try not to purchase tickets in the afternoon because they tend to be around $567. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Saint Thomas Island Cyril E King to Chicago O'Hare Intl 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 O'Hare Intl flight prices

What cabin class options are available on Saint Thomas Island to Chicago O'Hare Intl Airport flights?

There are 3 cabin classes available to choose from on Saint Thomas Island to Chicago O'Hare Intl Airport 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 O'Hare Intl Airport flights?

You could potentially save up to 28% on your flight if you consider stops on a Saint Thomas Island to Chicago O'Hare Intl Airport flight.

How have Saint Thomas Island to Chicago O'Hare Intl Airport flight prices changed over time?

As of June 2026, prices for Saint Thomas Island to Chicago O'Hare Intl Airport flights are approximately 19% more expensive when compared to flights at the same time last year.

When to book flights from Saint Thomas Island to Chicago O'Hare Intl Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Saint Thomas Island to Chicago O'Hare Intl Airport 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 O'Hare Intl Airport (STT to ORD) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Saint Thomas Island to Chicago O'Hare Intl Airport

Fastest flight time

5h 34m

Direct flights

Mon and Sun
The fastest flight from Saint Thomas Island to Chicago O'Hare Intl Airport takes 5h 34m
Direct flights go from Saint Thomas Island to Chicago O'Hare Intl Airport on Monday and Sunday. There are no airlines offering direct flights.
Search flight deals

Frequently asked questions about flying from Saint Thomas Island to Chicago O'Hare Intl Airport

  • How far is Saint Thomas Island Cyril E King to Chicago O'Hare Intl by plane?

    A flight from Saint Thomas Island Cyril E King to Chicago O'Hare Intl will travel around 2117.5 mi. In terms of flight time, this usually takes a little over 5h 34m.

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

    Prices for flights from Saint Thomas Island Cyril E King Airport to Chicago O'Hare Intl Airport were last updated today.

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

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

    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 O'Hare Intl Airport.

  • What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

    The necessary travel and health documents for your Chicago O'Hare Intl 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 plane model from Saint Thomas Island to Chicago O'Hare Intl Airport?

  • What is the most popular airline from Saint Thomas Island to Chicago O'Hare Intl Airport?

Best airlines flying from Saint Thomas Island to Chicago O'Hare Intl Airport

Compare and see reviews for airlines that fly from Saint Thomas Island to Chicago O'Hare Intl Airport with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $306Free CancellationRating
7.1
11,651 reviews
Search American Airlines flights

Traveling to a place near Chicago?

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Why use momondo?

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

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Saint Thomas Island.

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

Yes. All flights to Chicago from Saint Thomas Island on momondo can be compared and filtered by various policies on offer, including flexible booking.

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

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Saint Thomas Island.

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

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Saint Thomas Island and alert you when they change.

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