What is the cheapest airline that flies from Saint Thomas Island Cyril E King to Chicago?

United Airlines and Delta are the most popular carriers operating from Saint Thomas Island Cyril E King to Chicago

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?

As of August 2026, there is 1 operator available to choose from 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.

$178 Cheap Flights from Saint Thomas Island to Chicago in 2026

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Find the cheapest flights from Saint Thomas Island to Chicago

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5:40 pm - 1:20 pmSTT Saint Thomas Island Cyril E King-ORD Chicago O'Hare Intl

21h 40m2 stops San Juan Luis Munoz Marin Intl Boston Logan Intl

2:35 pm - 4:44 pmORD Chicago O'Hare Intl-STT Saint Thomas Island Cyril E King

24h 09m2 stops Fort Lauderdale San Juan Luis Munoz Marin Intl

$574JetBlue

Thu, Nov 5 - Mon, Nov 9

2:26 pm - 10:30 pmSTT Saint Thomas Island Cyril E King-ORD Chicago O'Hare Intl

10h 04m1 stop Philadelphia

5:05 am - 2:02 pmORD Chicago O'Hare Intl-STT Saint Thomas Island Cyril E King

6h 57m1 stop Miami

$580American Airlines

Fri, Feb 5 - Mon, Feb 8

2:54 pm - 11:36 pmSTT Saint Thomas Island Cyril E King-ORD Chicago O'Hare Intl

10h 42m2 stops Miami Washington, D.C. Reagan-National

6:00 am - 5:05 pmORD Chicago O'Hare Intl-STT Saint Thomas Island Cyril E King

9h 05m1 stop Miami

$580American Airlines

Fri, Feb 5 - Mon, Feb 8

2:54 pm - 11:14 pmSTT Saint Thomas Island Cyril E King-ORD Chicago O'Hare Intl

10h 20m2 stops Miami New York LaGuardia

5:00 am - 5:05 pmORD Chicago O'Hare Intl-STT Saint Thomas Island Cyril E King

10h 05m2 stops Dallas/Fort Worth Miami

$580American Airlines

Fri, Feb 5 - Mon, Feb 8

6:39 pm - 7:42 amSTT Saint Thomas Island Cyril E King-ORD Chicago O'Hare Intl

15h 03m1 stop Miami

8:05 am - 2:40 pmORD Chicago O'Hare Intl-STT Saint Thomas Island Cyril E King

4h 35mnonstop

$586American Airlines

Fri, Jan 8 - Sun, Jan 10

1:50 pm - 9:10 pmSTT Saint Thomas Island Cyril E King-ORD Chicago O'Hare Intl

9h 20m1 stop Atlanta Hartsfield-Jackson

7:10 am - 4:15 pmORD Chicago O'Hare Intl-STT Saint Thomas Island Cyril E King

7h 05m1 stop Atlanta Hartsfield-Jackson

$590Delta

Fri, Jan 8 - Sun, Jan 10

2:54 pm - 11:14 pmSTT Saint Thomas Island Cyril E King-ORD Chicago O'Hare Intl

10h 20m2 stops Miami New York LaGuardia

5:00 am - 5:05 pmORD Chicago O'Hare Intl-STT Saint Thomas Island Cyril E King

10h 05m2 stops Dallas/Fort Worth Miami

$590American Airlines

Fri, Feb 5 - Mon, Feb 8

1:48 pm - 12:08 amSTT Saint Thomas Island Cyril E King-ORD Chicago O'Hare Intl

11h 20m2 stops Miami Charlotte Douglas

7:29 pm - 12:58 pmORD Chicago O'Hare Intl-STT Saint Thomas Island Cyril E King

16h 29m1 stop Miami

$590American Airlines

Thu, Oct 8 - Mon, Oct 12

1:21 pm - 7:51 pmSTT Saint Thomas Island Cyril E King-ORD Chicago O'Hare Intl

7h 30m1 stop Charlotte Douglas

8:55 pm - 12:27 pmORD Chicago O'Hare Intl-STT Saint Thomas Island Cyril E King

14h 32m1 stop Charlotte Douglas

$590American Airlines

Thu, Oct 8 - Mon, Oct 12

1:48 pm - 12:08 amSTT Saint Thomas Island Cyril E King-ORD Chicago O'Hare Intl

11h 20m2 stops Miami Charlotte Douglas

8:55 pm - 12:27 pmORD Chicago O'Hare Intl-STT Saint Thomas Island Cyril E King

14h 32m1 stop Charlotte Douglas

$590American Airlines

Fri, Oct 9 - Mon, Oct 12

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American Airlines flights from Saint Thomas Island to Chicago

Our best American Airlines deals on Saint Thomas Island to Chicago flight tickets

American Airlines

Feb 5

STT2:26 pmSaint Thomas Island Cyril E King

10h 04m

1 stop

ORD10:30 pmChicago O'Hare Intl

Feb 8

ORD5:05 amChicago O'Hare Intl

6h 57m

1 stop

STT2:02 pmSaint Thomas Island Cyril E King

$580

American Airlines

Jan 8

STT6:39 pmSaint Thomas Island Cyril E King

15h 03m

1 stop

ORD7:42 amChicago O'Hare Intl

Jan 10

ORD8:05 amChicago O'Hare Intl

4h 35m

STT2:40 pmSaint Thomas Island Cyril E King

$586

American Airlines

Feb 5

STT2:26 pmSaint Thomas Island Cyril E King

10h 04m

1 stop

ORD10:30 pmChicago O'Hare Intl

Feb 8

ORD5:05 amChicago O'Hare Intl

6h 57m

1 stop

STT2:02 pmSaint Thomas Island Cyril E King

$590

United Airlines flights from Saint Thomas Island to Chicago

Our best United Airlines deals on Saint Thomas Island to Chicago flight tickets

United Airlines

Feb 5

STT1:02 pmSaint Thomas Island Cyril E King

7h 31m

1 stop

ORD6:33 pmChicago O'Hare Intl

Feb 8

ORD9:30 amChicago O'Hare Intl

4h 48m

STT4:18 pmSaint Thomas Island Cyril E King

$686

United Airlines

Feb 5

STT3:05 pmSaint Thomas Island Cyril E King

5h 40m

ORD6:45 pmChicago O'Hare Intl

Feb 8

ORD9:30 amChicago O'Hare Intl

4h 48m

STT4:18 pmSaint Thomas Island Cyril E King

$721

United Airlines

Feb 5

STT3:05 pmSaint Thomas Island Cyril E King

5h 40m

ORD6:45 pmChicago O'Hare Intl

Feb 8

ORD9:30 amChicago O'Hare Intl

4h 48m

STT4:18 pmSaint Thomas Island Cyril E King

$776

momondo Fare Finder

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

Cheapest round-trip

Saint Thomas IslandChicago

STT Saint Thomas Island Cyril E King - ORD Chicago O'Hare Intl

STTORD

Saint Thomas Island Cyril E King

Thu 11/5

5:40 pm-1:20 pm

2 stops21h 40m

Chicago O'Hare Intl

Mon 11/9

2:35 pm-4:44 pm

2 stops24h 09m

$574

Saint Thomas IslandChicago

STT Saint Thomas Island Cyril E King - ORD Chicago O'Hare Intl

STTORD

Saint Thomas Island Cyril E King

Fri 2/5

2:26 pm-10:30 pm

1 stop10h 04m

Chicago O'Hare Intl

Mon 2/8

5:05 am-2:02 pm

1 stop6h 57m

$580

Saint Thomas IslandChicago

STT Saint Thomas Island Cyril E King - ORD Chicago O'Hare Intl

STTORD

Saint Thomas Island Cyril E King

Fri 2/5

2:54 pm-11:36 pm

2 stops10h 42m

Chicago O'Hare Intl

Mon 2/8

6:00 am-5:05 pm

1 stop9h 05m

$580

Saint Thomas IslandChicago

STT Saint Thomas Island Cyril E King - ORD Chicago O'Hare Intl

STTORD

Saint Thomas Island Cyril E King

Fri 2/5

2:54 pm-11:14 pm

2 stops10h 20m

Chicago O'Hare Intl

Mon 2/8

5:00 am-5:05 pm

2 stops10h 05m

$580

Saint Thomas IslandChicago

STT Saint Thomas Island Cyril E King - ORD Chicago O'Hare Intl

STTORD

Saint Thomas Island Cyril E King

Fri 1/8

6:39 pm-7:42 am

1 stop15h 03m

Chicago O'Hare Intl

Sun 1/10

8:05 am-2:40 pm

Nonstop4h 35m

$586

Quickest round-trip

Saint Thomas IslandChicago

STT Saint Thomas Island Cyril E King - ORD Chicago O'Hare Intl

STTORD

Saint Thomas Island Cyril E King

Fri 1/8

1:50 pm-9:10 pm

1 stop9h 20m

Chicago O'Hare Intl

Sun 1/10

7:10 am-4:15 pm

1 stop7h 05m

$590

Saint Thomas IslandChicago

STT Saint Thomas Island Cyril E King - ORD Chicago O'Hare Intl

STTORD

Saint Thomas Island Cyril E King

Fri 2/5

2:54 pm-11:14 pm

2 stops10h 20m

Chicago O'Hare Intl

Mon 2/8

5:00 am-5:05 pm

2 stops10h 05m

$590

Saint Thomas IslandChicago

STT Saint Thomas Island Cyril E King - ORD Chicago O'Hare Intl

STTORD

Saint Thomas Island Cyril E King

Thu 10/8

1:48 pm-12:08 am

2 stops11h 20m

Chicago O'Hare Intl

Mon 10/12

7:29 pm-12:58 pm

1 stop16h 29m

$590

Saint Thomas IslandChicago

STT Saint Thomas Island Cyril E King - ORD Chicago O'Hare Intl

STTORD

Saint Thomas Island Cyril E King

Thu 10/8

1:21 pm-7:51 pm

1 stop7h 30m

Chicago O'Hare Intl

Mon 10/12

8:55 pm-12:27 pm

1 stop14h 32m

$590

Saint Thomas IslandChicago

STT Saint Thomas Island Cyril E King - ORD Chicago O'Hare Intl

STTORD

Saint Thomas Island Cyril E King

Fri 10/9

1:48 pm-12:08 am

2 stops11h 20m

Chicago O'Hare Intl

Mon 10/12

8:55 pm-12:27 pm

1 stop14h 32m

$590

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

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

Prices

Airlines

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 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. When flying out on a Saturday, the most expensive travel day of the week, you can expect to see flight prices from Saint Thomas Island to Chicago for around $684.

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 afternoon. Flights from Saint Thomas Island to Chicago during this time can be as low as $537. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $541.

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 to Chicago flights?

There are 2 cabin classes available to choose from on Saint Thomas Island 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 56% 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	$222
Fastest flight time	5h 40m
Direct flights	Every day
Airports in Chicago	3 airports

The best one-way flight to Chicago from Saint Thomas Island in the past 72 hours is $222. The best round-trip flight deal from Saint Thomas Island to Chicago found on momondo in the last 72 hours is $574.

The fastest flight from Saint Thomas Island to Chicago takes 5h 40m

Direct flights go from Saint Thomas Island to Chicago every day.

There are 3 airports in Chicago. From Saint Thomas Island there are direct flights to Chicago O'Hare Intl (ORD).

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Frequently asked questions about flying from Saint Thomas Island to Chicago

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 5h 40m 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?
As of August 2026, there is 1 operator available to choose from 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?
Based on momondo bookings for flights between Saint Thomas Island and Chicago, the leading plane model is Boeing 737 MAX 8, making up 33.33% of the total bookings. Other popular models include Airbus A319 with 33.33% and Boeing 737-800 with 33.33%.

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
American Airlines	PriceFrom $242	Free Cancellation	Rating 7.1 11,963 reviews		Search American Airlines flights

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Munster

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Monticello

Porter

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Griffith

Saint John

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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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Cheap flights from Saint Thomas Island to Chicago from $222

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 10/21. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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American Airlines flights from Saint Thomas Island to Chicago

Our best American Airlines deals on Saint Thomas Island to Chicago flight tickets

United Airlines flights from Saint Thomas Island to Chicago

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Use the filters below to find and compare flights from Saint Thomas Island to Chicago that are best for you.

See travel insights to Chicago from

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

What is the cheapest day to depart on your flight to Chicago?

What is the cheapest time of day to depart on your flight to Chicago?

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

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

Can stopping save me money on Saint Thomas Island to Chicago flights?

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

What is the cheapest airline that flies from Saint Thomas Island Cyril E King to Chicago?

When to book flights from Saint Thomas Island to Chicago

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

Best Price Found

Fastest flight time

Direct flights

Airports in Chicago

Frequently asked questions about flying 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

Traveling to a place near Chicago?

Why use momondo?

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

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

Fly your favorite airline to Chicago

Airlines are sorted and displayed according to clicks in the past 7 days on momondo

Cabin classes currently available on flights to Chicago

List of cabin classes available on flights landing in Chicago. Availability may vary depending on flight origin and airline.

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Popular flights according to clicks in the last 7 days on momondo

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