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Cheap flights from Chicago to Saint Thomas Island from $116

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Saint Thomas Island departing on 10/20. 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 Chicago to Saint Thomas Island

Cheap round-trip flights

Spirit Airlines Logo
11:36 am - 1:48 pmORD-STT
25h 12m2 stops
Spirit Airlines Logo
10:49 am - 5:39 pmSTT-ORD
7h 50m1 stop
$216Spirit Airlines
Find Deal
Sat, Aug 30 - Sat, Sep 6
Spirit Airlines Logo
8:12 pm - 1:48 pmORD-STT
16h 36m2 stops
Spirit Airlines Logo
2:43 pm - 10:22 pmSTT-ORD
8h 39m1 stop
$220Spirit Airlines
Find Deal
Tue, Aug 19 - Tue, Aug 26
Spirit Airlines Logo
6:05 am - 3:11 pmORD-STT
7h 06m1 stop
Spirit Airlines Logo
4:06 pm - 9:23 pmSTT-ORD
7h 17m1 stop
$223Spirit Airlines
Find Deal
Sat, Nov 8 - Wed, Nov 12
Spirit Airlines Logo
6:05 am - 3:11 pmORD-STT
7h 06m1 stop
Spirit Airlines Logo
4:06 pm - 9:23 pmSTT-ORD
7h 17m1 stop
$224Spirit Airlines
Find Deal
Wed, Nov 5 - Tue, Nov 11
Spirit Airlines Logo
8:12 pm - 11:13 amORD-STT
14h 01m1 stop
Spirit Airlines Logo
10:49 am - 5:39 pmSTT-ORD
7h 50m1 stop
$228Spirit Airlines
Find Deal
Sat, Aug 30 - Sat, Sep 6
Spirit Airlines Logo
11:48 am - 12:56 pmORD-STT
24h 08m2 stops
Spirit Airlines Logo
2:01 pm - 9:58 pmSTT-ORD
8h 57m1 stop
$231Spirit Airlines
Find Deal
Sat, Oct 25 - Sat, Nov 1
Delta Logo
6:00 am - 2:10 pmMDW-STT
7h 10m1 stop
Delta Logo
3:23 pm - 9:12 pmSTT-MDW
6h 49m1 stop
$559Delta
Find Deal
Sat, Aug 30 - Sat, Sep 6
Delta Logo
6:00 am - 3:54 pmMDW-STT
7h 54m1 stop
Delta Logo
4:00 pm - 9:46 pmSTT-MDW
7h 46m1 stop
$569Delta
Find Deal
Sun, Jan 18 - Sun, Jan 25
Delta Logo
6:00 am - 3:54 pmMDW-STT
7h 54m1 stop
Delta Logo
4:00 pm - 9:46 pmSTT-MDW
7h 46m1 stop
$584Delta
Find Deal
Sun, Jan 18 - Sun, Jan 25
Logo
4:56 pm - 9:44 amMDW-STT
15h 48m2 stops
Logo
10:49 am - 11:20 pmSTT-MDW
13h 31m2 stops
$586
Find Deal
Thu, Sep 18 - Sun, Sep 21

Spirit Airlines flights from Chicago to Saint Thomas Island

Our best Spirit Airlines deals on Chicago to Saint Thomas Island flight tickets
Spirit Airlines
Aug 30
ORD11:36 amChicago O'Hare Intl
25h 12m
2 stops
STT1:48 pmSaint Thomas Island Cyril E King
Sep 6
STT10:49 amSaint Thomas Island Cyril E King
7h 50m
1 stop
ORD5:39 pmChicago O'Hare Intl
$216
Find similar
Spirit Airlines
Aug 19
ORD8:12 pmChicago O'Hare Intl
16h 36m
2 stops
STT1:48 pmSaint Thomas Island Cyril E King
Aug 26
STT2:43 pmSaint Thomas Island Cyril E King
8h 39m
1 stop
ORD10:22 pmChicago O'Hare Intl
$220
Find similar
Spirit Airlines
Nov 8
ORD6:05 amChicago O'Hare Intl
7h 06m
1 stop
STT3:11 pmSaint Thomas Island Cyril E King
Nov 12
STT4:06 pmSaint Thomas Island Cyril E King
7h 17m
1 stop
ORD9:23 pmChicago O'Hare Intl
$223
Find similar

Delta flights from Chicago to Saint Thomas Island

Our best Delta deals on Chicago to Saint Thomas Island flight tickets
Delta
Aug 30
MDW6:00 amChicago Midway
7h 10m
1 stop
STT2:10 pmSaint Thomas Island Cyril E King
Sep 6
STT3:23 pmSaint Thomas Island Cyril E King
6h 49m
1 stop
MDW9:12 pmChicago Midway
$559
Find similar
Delta
Jan 18
MDW6:00 amChicago Midway
7h 54m
1 stop
STT3:54 pmSaint Thomas Island Cyril E King
Jan 25
STT4:00 pmSaint Thomas Island Cyril E King
7h 46m
1 stop
MDW9:46 pmChicago Midway
$569
Find similar
Delta
Jan 18
MDW6:00 amChicago Midway
7h 54m
1 stop
STT3:54 pmSaint Thomas Island Cyril E King
Jan 25
STT4:00 pmSaint Thomas Island Cyril E King
7h 46m
1 stop
MDW9:46 pmChicago Midway
$584
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago to Saint Thomas Island 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 July 31, 2025.
Use the filters below to find and compare flights from Chicago to Saint Thomas Island that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Sat 8/30

11:36 am-1:48 pm

2 stops25h 12m

Saint Thomas Island Cyril E King

Sat 9/6

10:49 am-5:39 pm

1 stop7h 50m

$216

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Tue 8/19

8:12 pm-1:48 pm

2 stops16h 36m

Saint Thomas Island Cyril E King

Tue 8/26

2:43 pm-10:22 pm

1 stop8h 39m

$220

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Sat 11/8

6:05 am-3:11 pm

1 stop7h 06m

Saint Thomas Island Cyril E King

Wed 11/12

4:06 pm-9:23 pm

1 stop7h 17m

$223

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Wed 11/5

6:05 am-3:11 pm

1 stop7h 06m

Saint Thomas Island Cyril E King

Tue 11/11

4:06 pm-9:23 pm

1 stop7h 17m

$224

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Sat 8/30

8:12 pm-11:13 am

1 stop14h 01m

Saint Thomas Island Cyril E King

Sat 9/6

10:49 am-5:39 pm

1 stop7h 50m

$228

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Sat 10/25

11:48 am-12:56 pm

2 stops24h 08m

Saint Thomas Island Cyril E King

Sat 11/1

2:01 pm-9:58 pm

1 stop8h 57m

$231

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Sat 8/30

6:00 am-2:10 pm

1 stop7h 10m

Saint Thomas Island Cyril E King

Sat 9/6

3:23 pm-9:12 pm

1 stop6h 49m

$559

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Sun 1/18

6:00 am-3:54 pm

1 stop7h 54m

Saint Thomas Island Cyril E King

Sun 1/25

4:00 pm-9:46 pm

1 stop7h 46m

$569

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Sun 1/18

6:00 am-3:54 pm

1 stop7h 54m

Saint Thomas Island Cyril E King

Sun 1/25

4:00 pm-9:46 pm

1 stop7h 46m

$584

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Thu 9/18

4:56 pm-9:44 am

2 stops15h 48m

Saint Thomas Island Cyril E King

Sun 9/21

10:49 am-11:20 pm

2 stops13h 31m

$586

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 Saint Thomas Island from

How to get the cheapest flight ticket from Chicago to Saint Thomas Island

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 Chicago and Saint Thomas Island?

What is the cheapest month to fly to Saint Thomas Island?

The month of August is another great option to travel to Saint Thomas Island, with average flight prices from Chicago averaging around $483.

What is the cheapest day to depart on your flight to Saint Thomas Island?

On average, the least expensive day to fly to Saint Thomas Island from Chicago is on a Wednesday. momondo users have found tickets for Wednesday departures for as low as $649. However, this price may fluctuate depending on the airline, the season, and holidays. When flying out on a Friday, the most expensive travel day of the week, you can expect to see flight prices from Chicago to Saint Thomas Island for around $1,350.

What is the cheapest time of day to depart on your flight to Saint Thomas Island?

The cheapest time of day to fly to Saint Thomas Island is in the afternoon when flights can be purchased for as low as $397. Flights to Saint Thomas Island are more costly in the morning, with an average ticket price of $783. Departure times in the morning fall within the peak daily travel times, which is why tickets can be more expensive.

What is the cheapest Chicago to Saint Thomas Island Cyril E King flight route?

Fly from Chicago O'Hare Intl to Saint Thomas Island Cyril E King for the best Chicago - Saint Thomas Island Cyril E King flight prices

How far in advance should I book a flight to Saint Thomas Island?

You are more likely to see cheaper flights to Saint Thomas Island from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Saint Thomas Island for around $638 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Saint Thomas Island from Chicago for as low as $515 on momondo.

What cabin class options are available on Chicago to Saint Thomas Island Cyril E King flights?

There are 3 cabin classes available to choose from on Chicago to Saint Thomas Island Cyril E King 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 Chicago to Saint Thomas Island flights?

You could potentially save up to 35% on your flight if you consider stops on a Chicago to Saint Thomas Island flight.

When to book flights from Chicago to Saint Thomas Island

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago to Saint Thomas Island according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago to Saint Thomas Island (CHI to STT) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Saint Thomas Island

Best Price Found

$116

Fastest flight time

6h 22m

Direct flights

Every day

Airports in Saint Thomas Island

1 airport
The best one-way flight to Saint Thomas Island from Chicago in the past 72 hours is $116. The best round-trip flight deal from Chicago to Saint Thomas Island found on momondo in the last 72 hours is $216.
The fastest flight from Chicago to Saint Thomas Island takes 6h 22m
Direct flights go from Chicago to Saint Thomas Island every day.
There is 1 airport near Saint Thomas Island: Saint Thomas Island Cyril E King (STT)
Search flight deals

  • How far is Chicago to Saint Thomas Island Cyril E King by plane?

    Chicago and Saint Thomas Island Cyril E King are 2102.2 mi apart from one another. Flights usually cover this in 6h 22m, depending on flying conditions and air traffic around both airports.

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

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

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

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

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago to Saint Thomas Island Cyril E King Airport.

  • What documentation or ID do you need to fly to Saint Thomas Island Cyril E King Airport?

    The travel and health documents required for your trip to Saint Thomas Island Cyril E King Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Saint Thomas Island Cyril E King Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular plane model from Chicago to Saint Thomas Island?

  • What is the most popular airline from Chicago to Saint Thomas Island?

Best airlines flying from Chicago to Saint Thomas Island

Compare and see reviews for airlines that fly from Chicago to Saint Thomas Island with momondo
Airline
Rating
Free Cancellation
Price
Spirit AirlinesPriceFrom $182Free CancellationRating
6.3
8,049 reviews
Search Spirit Airlines flights
DeltaPriceFrom $359Free CancellationRating
8.0
7,981 reviews
Search Delta flights
American AirlinesPriceFrom $467Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $479Free CancellationRating
7.4
8,900 reviews
Search United Airlines flights

Traveling to a place near Saint Thomas Island?

Book flights to Saint Thomas Island if you plan to visit one of these locations
St. John

Why use momondo?

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

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Chicago to Saint Thomas Island. Millions of users trust and use momondo every year so you are in good hands.

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

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

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

momondo helps you find the best flight between Chicago and Saint Thomas Island by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

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

Yes momondo offers price alerts on flights to Saint Thomas Island from Chicago. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

An easier way to manage your Saint Thomas Island trip

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Saint Croix Airport