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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 O'Hare Intl Airport

Our best Spirit Airlines deals on Saint Thomas Island to Chicago O'Hare Intl Airport flight tickets
Spirit Airlines
Mar 18
STT4:35 pmSaint Thomas Island Cyril E King
7h 42m
1 stop
ORD11:17 pmChicago O'Hare Intl
Mar 25
ORD6:10 pmChicago O'Hare Intl
20h 18m
1 stop
STT3:28 pmSaint Thomas Island Cyril E King
$234
Spirit Airlines
Mar 25
STT4:35 pmSaint Thomas Island Cyril E King
7h 42m
1 stop
ORD11:17 pmChicago O'Hare Intl
Mar 30
ORD8:58 pmChicago O'Hare Intl
17h 30m
2 stops
STT3:28 pmSaint Thomas Island Cyril E King
$239
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
$243

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
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
American Airlines
Feb 22
STT2:13 pmSaint Thomas Island Cyril E King
5h 46m
ORD5:59 pmChicago O'Hare Intl
Feb 26
ORD8:18 amChicago O'Hare Intl
4h 45m
STT3:03 pmSaint Thomas Island Cyril E King
$1,096

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 February 8, 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

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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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 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 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. On the other hand, Saturday 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 $813.

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 $540 when looking at flights departing at noon. Try not to purchase tickets in the afternoon because they tend to be around $606. 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 Cyril E King to Chicago O'Hare Intl flights?

There are 4 cabin classes available to choose from on Saint Thomas Island Cyril E King to Chicago O'Hare Intl 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 February 2026, prices for Saint Thomas Island to Chicago O'Hare Intl Airport flights are approximately 50% cheaper 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

Best Price Found

$402

Fastest flight time

5h 40m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Saint Thomas Island in the past 72 hours is $402. The best round-trip flight deal from Saint Thomas Island to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $346.
The fastest flight from Saint Thomas Island to Chicago O'Hare Intl Airport takes 5h 40m
Direct flights go from Saint Thomas Island to Chicago O'Hare Intl Airport every day.
Search flight deals

  • 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 40m.

  • 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
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 O'Hare Intl Airport

    American Airlines flight deals from Saint Thomas Island to Chicago O'Hare Intl Airport start from $306 round-trip. Over the 1 American Airlines flight for this route in a normal week, average airfare is usually $539 round-trip - but some users have found much cheaper deals with momondo.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lake Geneva
Schaumburg
South Haven
Rockford
Merrillville
Gurnee
Naperville
Rosemont
New Buffalo
Kenosha
Oak Brook
Joliet
Orland Park
Racine
Hammond
Janesville
Tinley Park
Elgin
Aurora
South Holland

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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