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Cheap flights from Saint Thomas Island to Chicago from $115

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 9/6. 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

Spirit Airlines Logo
2:43 pm - 11:59 pmSTT-ORD
10h 16m2 stops
Spirit Airlines Logo
8:47 pm - 1:48 pmORD-STT
16h 01m2 stops
$243Spirit Airlines
Find Deal
Mon, Aug 25 - Wed, Aug 27
Spirit Airlines Logo
12:18 pm - 7:07 pmSTT-ORD
7h 49m1 stop
Spirit Airlines Logo
8:47 pm - 1:48 pmORD-STT
16h 01m2 stops
$254Spirit Airlines
Find Deal
Mon, Aug 25 - Wed, Aug 27
Spirit Airlines Logo
12:18 pm - 7:07 pmSTT-ORD
7h 49m1 stop
Spirit Airlines Logo
8:12 pm - 11:13 amORD-STT
14h 01m1 stop
$264Spirit Airlines
Find Deal
Mon, Aug 25 - Wed, Aug 27
Spirit Airlines Logo
10:49 am - 10:48 pmSTT-ORD
12h 59m1 stop
Spirit Airlines Logo
6:30 am - 2:57 pmORD-STT
7h 27m1 stop
$271Spirit Airlines
Find Deal
Thu, Sep 18 - Mon, Sep 22
Spirit Airlines Logo
4:02 pm - 4:12 pmSTT-ORD
25h 10m1 stop
Spirit Airlines Logo
6:30 am - 2:57 pmORD-STT
7h 27m1 stop
$277Spirit Airlines
Find Deal
Fri, Sep 5 - Fri, Sep 12
Spirit Airlines Logo
2:01 pm - 11:45 pmSTT-ORD
10h 44m2 stops
Spirit Airlines Logo
7:11 pm - 9:49 amORD-STT
13h 38m1 stop
$281Spirit Airlines
Find Deal
Sat, Oct 11 - Sat, Oct 18
Spirit Airlines Logo
10:49 am - 5:39 pmSTT-ORD
7h 50m1 stop
Spirit Airlines Logo
6:30 am - 2:57 pmORD-STT
7h 27m1 stop
$283Spirit Airlines
Find Deal
Tue, Sep 23 - Mon, Sep 29
Spirit Airlines Logo
2:43 pm - 11:59 pmSTT-ORD
10h 16m2 stops
Spirit Airlines Logo
8:12 pm - 3:19 pmORD-STT
18h 07m2 stops
$286Spirit Airlines
Find Deal
Mon, Aug 25 - Thu, Aug 28
Logo
7:49 am - 9:58 pmSTT-ORD
15h 09m2 stops
Logo
6:30 am - 2:57 pmORD-STT
7h 27m1 stop
$491
Find Deal
Wed, Sep 17 - Mon, Sep 22
Logo
7:49 am - 10:52 amSTT-ORD
28h 03m3 stops
Logo
6:30 am - 2:57 pmORD-STT
7h 27m1 stop
$509
Find Deal
Wed, Sep 17 - Mon, Sep 22

Spirit Airlines flights from Saint Thomas Island to Chicago

Our best Spirit Airlines deals on Saint Thomas Island to Chicago flight tickets
Spirit Airlines
Aug 25
STT2:43 pmSaint Thomas Island Cyril E King
10h 16m
2 stops
ORD11:59 pmChicago O'Hare Intl
Aug 27
ORD8:47 pmChicago O'Hare Intl
16h 01m
2 stops
STT1:48 pmSaint Thomas Island Cyril E King
$243
Find similar
Spirit Airlines
Aug 25
STT12:18 pmSaint Thomas Island Cyril E King
7h 49m
1 stop
ORD7:07 pmChicago O'Hare Intl
Aug 27
ORD8:47 pmChicago O'Hare Intl
16h 01m
2 stops
STT1:48 pmSaint Thomas Island Cyril E King
$254
Find similar
Spirit Airlines
Aug 25
STT12:18 pmSaint Thomas Island Cyril E King
7h 49m
1 stop
ORD7:07 pmChicago O'Hare Intl
Aug 27
ORD8:12 pmChicago O'Hare Intl
14h 01m
1 stop
STT11:13 amSaint Thomas Island Cyril E King
$264
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 August 7, 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

Mon 8/25

2:43 pm-11:59 pm

2 stops10h 16m

Chicago O'Hare Intl

Wed 8/27

8:47 pm-1:48 pm

2 stops16h 01m

$243

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Mon 8/25

12:18 pm-7:07 pm

1 stop7h 49m

Chicago O'Hare Intl

Wed 8/27

8:47 pm-1:48 pm

2 stops16h 01m

$254

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Mon 8/25

12:18 pm-7:07 pm

1 stop7h 49m

Chicago O'Hare Intl

Wed 8/27

8:12 pm-11:13 am

1 stop14h 01m

$264

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Thu 9/18

10:49 am-10:48 pm

1 stop12h 59m

Chicago O'Hare Intl

Mon 9/22

6:30 am-2:57 pm

1 stop7h 27m

$271

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Fri 9/5

4:02 pm-4:12 pm

1 stop25h 10m

Chicago O'Hare Intl

Fri 9/12

6:30 am-2:57 pm

1 stop7h 27m

$277

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Sat 10/11

2:01 pm-11:45 pm

2 stops10h 44m

Chicago O'Hare Intl

Sat 10/18

7:11 pm-9:49 am

1 stop13h 38m

$281

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Tue 9/23

10:49 am-5:39 pm

1 stop7h 50m

Chicago O'Hare Intl

Mon 9/29

6:30 am-2:57 pm

1 stop7h 27m

$283

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Mon 8/25

2:43 pm-11:59 pm

2 stops10h 16m

Chicago O'Hare Intl

Thu 8/28

8:12 pm-3:19 pm

2 stops18h 07m

$286

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Wed 9/17

7:49 am-9:58 pm

2 stops15h 09m

Chicago O'Hare Intl

Mon 9/22

6:30 am-2:57 pm

1 stop7h 27m

$491

Saint Thomas IslandChicago

STT - ORD

STTORD

Saint Thomas Island Cyril E King

Wed 9/17

7:49 am-10:52 am

3 stops28h 03m

Chicago O'Hare Intl

Mon 9/22

6:30 am-2:57 pm

1 stop7h 27m

$509

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 Wednesday when prices can be found for as low as $557. 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 $1,141.

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 $615.

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

$115

Fastest flight time

7h 17m

Direct flights

Mon, Tue, Wed, Thu, Sat and Sun

Airports in Chicago

1 airport
The best one-way flight to Chicago from Saint Thomas Island in the past 72 hours is $115. The best round-trip flight deal from Saint Thomas Island to Chicago found on momondo in the last 72 hours is $243.
The fastest flight from Saint Thomas Island to Chicago takes 7h 17m
Direct flights go from Saint Thomas Island to Chicago on Monday, Tuesday, Wednesday, Thursday, Saturday and Sunday. Airlines offering direct flights are: United Airlines and American Airlines.
There is 1 airport near Chicago: 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 7h 49m 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
8,055 reviews
Search Spirit Airlines flights
United AirlinesPriceFrom $509Free CancellationRating
7.4
8,917 reviews
Search United Airlines flights
American AirlinesPriceFrom $509Free CancellationRating
7.2
10,000 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