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Cheap flights from Chicago to Saint Thomas Island from $128

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 11/14. 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
7:43 pm - 9:56 amORD-STT
13h 13m1 stop
Spirit Airlines Logo
11:01 am - 11:45 pmSTT-ORD
13h 44m1 stop
$226Spirit Airlines
Find Deal
Sat, Oct 18 - Sat, Oct 25
Spirit Airlines Logo
7:43 pm - 9:56 amORD-STT
13h 13m1 stop
Spirit Airlines Logo
11:01 am - 6:38 pmSTT-ORD
8h 37m1 stop
$236Spirit Airlines
Find Deal
Sat, Oct 18 - Sat, Oct 25
Spirit Airlines Logo
6:58 pm - 12:59 pmORD-STT
17h 01m1 stop
Spirit Airlines Logo
2:01 pm - 9:33 pmSTT-ORD
8h 32m1 stop
$239Spirit Airlines
Find Deal
Sat, Oct 18 - Sat, Oct 25
Spirit Airlines Logo
6:58 pm - 12:59 pmORD-STT
17h 01m1 stop
Spirit Airlines Logo
2:01 pm - 11:45 pmSTT-ORD
10h 44m2 stops
$256Spirit Airlines
Find Deal
Sat, Oct 18 - Sat, Oct 25
Logo
7:43 pm - 9:56 amORD-STT
13h 13m1 stop
Logo
2:40 pm - 7:10 amSTT-ORD
17h 30m1 stop
$302
Find Deal
Fri, Oct 24 - Sun, Oct 26
Logo
7:43 pm - 9:56 amORD-STT
13h 13m1 stop
Logo
2:40 pm - 7:10 amSTT-ORD
17h 30m1 stop
$317
Find Deal
Thu, Oct 23 - Sun, Oct 26
Delta Logo
6:00 am - 2:55 pmMDW-STT
6h 55m1 stop
Delta Logo
3:00 pm - 9:46 pmSTT-MDW
8h 46m1 stop
$509Delta
Find Deal
Tue, Jan 6 - Thu, Jan 15
Delta Logo
6:00 am - 3:54 pmMDW-STT
7h 54m1 stop
Delta Logo
4:00 pm - 9:46 pmSTT-MDW
7h 46m1 stop
$514Delta
Find Deal
Sun, Jan 18 - Sun, Jan 25
Southwest Logo
6:05 am - 2:55 pmMDW-STT
6h 50m1 stop
Southwest Logo
2:10 pm - 12:05 amSTT-MDW
11h 55m2 stops
$999Southwest
Find Deal
Thu, Feb 12 - Mon, Feb 16
Southwest Logo
5:00 am - 2:55 pmMDW-STT
7h 55m1 stop
Southwest Logo
3:55 pm - 9:00 pmSTT-MDW
7h 05m1 stop
$1,059Southwest
Find Deal
Wed, Feb 11 - Sun, Feb 15

Spirit Airlines flights from Chicago to Saint Thomas Island

Our best Spirit Airlines deals on Chicago to Saint Thomas Island flight tickets
Spirit Airlines
Oct 18
ORD7:43 pmChicago O'Hare Intl
13h 13m
1 stop
STT9:56 amSaint Thomas Island Cyril E King
Oct 25
STT11:01 amSaint Thomas Island Cyril E King
13h 44m
1 stop
ORD11:45 pmChicago O'Hare Intl
$226
Find similar
Spirit Airlines
Oct 18
ORD7:43 pmChicago O'Hare Intl
13h 13m
1 stop
STT9:56 amSaint Thomas Island Cyril E King
Oct 25
STT11:01 amSaint Thomas Island Cyril E King
8h 37m
1 stop
ORD6:38 pmChicago O'Hare Intl
$236
Find similar
Spirit Airlines
Oct 18
ORD6:58 pmChicago O'Hare Intl
17h 01m
1 stop
STT12:59 pmSaint Thomas Island Cyril E King
Oct 25
STT2:01 pmSaint Thomas Island Cyril E King
8h 32m
1 stop
ORD9:33 pmChicago O'Hare Intl
$239
Find similar

Delta flights from Chicago to Saint Thomas Island

Our best Delta deals on Chicago to Saint Thomas Island flight tickets
Delta
Jan 6
MDW6:00 amChicago Midway
6h 55m
1 stop
STT2:55 pmSaint Thomas Island Cyril E King
Jan 15
STT3:00 pmSaint Thomas Island Cyril E King
8h 46m
1 stop
MDW9:46 pmChicago Midway
$509
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
$514
Find similar
Delta
Mar 10
MDW6:00 amChicago Midway
6h 55m
1 stop
STT1:55 pmSaint Thomas Island Cyril E King
Mar 11
STT2:00 pmSaint Thomas Island Cyril E King
8h 46m
1 stop
MDW9:46 pmChicago Midway
$569
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 September 15, 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 10/18

7:43 pm-9:56 am

1 stop13h 13m

Saint Thomas Island Cyril E King

Sat 10/25

11:01 am-11:45 pm

1 stop13h 44m

$226

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Sat 10/18

7:43 pm-9:56 am

1 stop13h 13m

Saint Thomas Island Cyril E King

Sat 10/25

11:01 am-6:38 pm

1 stop8h 37m

$236

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Sat 10/18

6:58 pm-12:59 pm

1 stop17h 01m

Saint Thomas Island Cyril E King

Sat 10/25

2:01 pm-9:33 pm

1 stop8h 32m

$239

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Sat 10/18

6:58 pm-12:59 pm

1 stop17h 01m

Saint Thomas Island Cyril E King

Sat 10/25

2:01 pm-11:45 pm

2 stops10h 44m

$256

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Fri 10/24

7:43 pm-9:56 am

1 stop13h 13m

Saint Thomas Island Cyril E King

Sun 10/26

2:40 pm-7:10 am

1 stop17h 30m

$302

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Thu 10/23

7:43 pm-9:56 am

1 stop13h 13m

Saint Thomas Island Cyril E King

Sun 10/26

2:40 pm-7:10 am

1 stop17h 30m

$317

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Tue 1/6

6:00 am-2:55 pm

1 stop6h 55m

Saint Thomas Island Cyril E King

Thu 1/15

3:00 pm-9:46 pm

1 stop8h 46m

$509

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

$514

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Thu 2/12

6:05 am-2:55 pm

1 stop6h 50m

Saint Thomas Island Cyril E King

Mon 2/16

2:10 pm-12:05 am

2 stops11h 55m

$999

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Wed 2/11

5:00 am-2:55 pm

1 stop7h 55m

Saint Thomas Island Cyril E King

Sun 2/15

3:55 pm-9:00 pm

1 stop7h 05m

$1,059

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 cheapest month to fly to Saint Thomas Island?

The month of November is another great option to travel to Saint Thomas Island, with average flight prices from Chicago averaging around $545.

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 $637. 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 $1,222.

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 $771. 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 $639 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 $541 on momondo.

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

There are 2 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 49% on your flight if you consider stops on a Chicago to Saint Thomas Island flight.

How have Chicago to Saint Thomas Island flight prices changed over time?

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

$283

Fastest flight time

4h 35m

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 $283. The best round-trip flight deal from Chicago to Saint Thomas Island found on momondo in the last 72 hours is $595.
The fastest flight from Chicago to Saint Thomas Island takes 4h 35m
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 30m, 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
8,015 reviews
Search Spirit Airlines flights
DeltaPriceFrom $359Free CancellationRating
7.9
7,954 reviews
Search Delta flights
American AirlinesPriceFrom $478Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $479Free CancellationRating
7.4
8,929 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.

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Saint Croix Airport