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Cheap flights from the U.S. Virgin Islands to Chicago from $246

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from the U.S. Virgin Islands to Chicago departing on 10/28. 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
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from the U.S. Virgin Islands to Chicago

Recent round-trip flight deals from the U.S. Virgin Islands to Chicago

Enter your travel dates to find the best prices.
American Airlines Logo
6:39 pm - 7:32 amSTT  Saint Thomas Island Cyril E King-ORD Chicago O'Hare Intl
14h 53m2 stops Miami Raleigh-Durham
American Airlines Logo
9:12 pm - 5:30 pmORD  Chicago O'Hare Intl-STT Saint Thomas Island Cyril E King
18h 18m2 stops Baltimore/Washington Miami
$488American Airlines
Wed, Feb 10 - Wed, Feb 17
American Airlines Logo
4:46 pm - 7:32 amSTT  Saint Thomas Island Cyril E King-ORD Chicago O'Hare Intl
16h 46m2 stops Miami Raleigh-Durham
American Airlines Logo
9:12 pm - 5:30 pmORD  Chicago O'Hare Intl-STT Saint Thomas Island Cyril E King
18h 18m2 stops Baltimore/Washington Miami
$488American Airlines
Fri, Feb 5 - Wed, Feb 17
American Airlines Logo
6:39 pm - 7:32 amSTT  Saint Thomas Island Cyril E King-ORD Chicago O'Hare Intl
14h 53m2 stops Miami Raleigh-Durham
American Airlines Logo
9:12 pm - 5:30 pmORD  Chicago O'Hare Intl-STT Saint Thomas Island Cyril E King
18h 18m2 stops Baltimore/Washington Miami
$488American Airlines
Mon, Feb 8 - Wed, Feb 17
American Airlines Logo
6:39 pm - 9:34 amSTT  Saint Thomas Island Cyril E King-ORD Chicago O'Hare Intl
16h 55m2 stops Miami Orlando
American Airlines Logo
9:12 pm - 5:30 pmORD  Chicago O'Hare Intl-STT Saint Thomas Island Cyril E King
18h 18m2 stops Baltimore/Washington Miami
$499American Airlines
Tue, Feb 9 - Wed, Feb 17
American Airlines Logo
6:39 pm - 9:00 amSTT  Saint Thomas Island Cyril E King-ORD Chicago O'Hare Intl
16h 21m2 stops Miami Nashville Intl
American Airlines Logo
9:12 pm - 5:30 pmORD  Chicago O'Hare Intl-STT Saint Thomas Island Cyril E King
18h 18m2 stops Baltimore/Washington Miami
$513American Airlines
Sun, Feb 7 - Wed, Feb 17
American Airlines Logo
6:39 pm - 7:32 amSTT  Saint Thomas Island Cyril E King-ORD Chicago O'Hare Intl
14h 53m2 stops Miami Raleigh-Durham
American Airlines Logo
9:12 pm - 5:30 pmORD  Chicago O'Hare Intl-STT Saint Thomas Island Cyril E King
18h 18m2 stops Baltimore/Washington Miami
$516American Airlines
Thu, Feb 4 - Wed, Feb 17
American Airlines Logo
4:46 pm - 7:32 amSTT  Saint Thomas Island Cyril E King-ORD Chicago O'Hare Intl
16h 46m2 stops Miami Raleigh-Durham
American Airlines Logo
10:35 pm - 5:30 pmORD  Chicago O'Hare Intl-STT Saint Thomas Island Cyril E King
16h 55m2 stops Nashville Intl Miami
$522American Airlines
Wed, Feb 10 - Sat, Feb 13
American Airlines Logo
6:39 pm - 7:32 amSTT  Saint Thomas Island Cyril E King-ORD Chicago O'Hare Intl
14h 53m2 stops Miami Raleigh-Durham
American Airlines Logo
10:35 pm - 5:30 pmORD  Chicago O'Hare Intl-STT Saint Thomas Island Cyril E King
16h 55m2 stops Nashville Intl Miami
$522American Airlines
Fri, Feb 5 - Sat, Feb 13
JetBlue Logo
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
JetBlue Logo
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
JetBlue Logo
3:00 pm - 8:48 amSTT  Saint Thomas Island Cyril E King-ORD Chicago O'Hare Intl
18h 48m2 stops San Juan Luis Munoz Marin Intl Boston Logan Intl
JetBlue Logo
6:00 am - 2:01 pmORD  Chicago O'Hare Intl-STT Saint Thomas Island Cyril E King
31h 01m2 stops Fort Lauderdale San Juan Luis Munoz Marin Intl
$588JetBlue
Fri, Sep 25 - Tue, Sep 29

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American Airlines flights from U.S. Virgin Islands to Chicago

Our best American Airlines deals on U.S. Virgin Islands to Chicago flight tickets
American Airlines
Feb 5
STT4:46 pmSaint Thomas Island Cyril E King
16h 46m
2 stops
ORD7:32 amChicago O'Hare Intl
Feb 17
ORD9:12 pmChicago O'Hare Intl
18h 18m
2 stops
STT5:30 pmSaint Thomas Island Cyril E King
$488
American Airlines
Feb 9
STT6:39 pmSaint Thomas Island Cyril E King
16h 55m
2 stops
ORD9:34 amChicago O'Hare Intl
Feb 17
ORD9:12 pmChicago O'Hare Intl
18h 18m
2 stops
STT5:30 pmSaint Thomas Island Cyril E King
$499
American Airlines
Feb 7
STT6:39 pmSaint Thomas Island Cyril E King
16h 21m
2 stops
ORD9:00 amChicago O'Hare Intl
Feb 17
ORD9:12 pmChicago O'Hare Intl
18h 18m
2 stops
STT5:30 pmSaint Thomas Island Cyril E King
$513

JetBlue flights from U.S. Virgin Islands to Chicago

Our best JetBlue deals on U.S. Virgin Islands to Chicago flight tickets
JetBlue
Nov 5
STT5:40 pmSaint Thomas Island Cyril E King
21h 40m
2 stops
ORD1:20 pmChicago O'Hare Intl
Nov 9
ORD2:35 pmChicago O'Hare Intl
24h 09m
2 stops
STT4:44 pmSaint Thomas Island Cyril E King
$574
JetBlue
Sep 25
STT3:00 pmSaint Thomas Island Cyril E King
18h 48m
2 stops
ORD8:48 amChicago O'Hare Intl
Sep 29
ORD6:00 amChicago O'Hare Intl
31h 01m
2 stops
STT2:01 pmSaint Thomas Island Cyril E King
$588
JetBlue
Sep 1
STT1:53 pmSaint Thomas Island Cyril E King
21h 18m
2 stops
ORD10:11 amChicago O'Hare Intl
Sep 10
ORD9:38 amChicago O'Hare Intl
27h 23m
2 stops
STT2:01 pmSaint Thomas Island Cyril E King
$628

momondo Fare Finder

 
Customize your flight search to find flights from U.S. Virgin Islands 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 17, 2026.
Use the filters below to find and compare flights from the U.S. Virgin Islands 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

Wed 2/10

6:39 pm-7:32 am

2 stops14h 53m

Chicago O'Hare Intl

Wed 2/17

9:12 pm-5:30 pm

2 stops18h 18m

$488

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

4:46 pm-7:32 am

2 stops16h 46m

Chicago O'Hare Intl

Wed 2/17

9:12 pm-5:30 pm

2 stops18h 18m

$488

Saint Thomas IslandChicago

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

STTORD

Saint Thomas Island Cyril E King

Mon 2/8

6:39 pm-7:32 am

2 stops14h 53m

Chicago O'Hare Intl

Wed 2/17

9:12 pm-5:30 pm

2 stops18h 18m

$488

Saint Thomas IslandChicago

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

STTORD

Saint Thomas Island Cyril E King

Tue 2/9

6:39 pm-9:34 am

2 stops16h 55m

Chicago O'Hare Intl

Wed 2/17

9:12 pm-5:30 pm

2 stops18h 18m

$499

Saint Thomas IslandChicago

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

STTORD

Saint Thomas Island Cyril E King

Sun 2/7

6:39 pm-9:00 am

2 stops16h 21m

Chicago O'Hare Intl

Wed 2/17

9:12 pm-5:30 pm

2 stops18h 18m

$513

Saint Thomas IslandChicago

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

STTORD

Saint Thomas Island Cyril E King

Thu 2/4

6:39 pm-7:32 am

2 stops14h 53m

Chicago O'Hare Intl

Wed 2/17

9:12 pm-5:30 pm

2 stops18h 18m

$516

Saint Thomas IslandChicago

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

STTORD

Saint Thomas Island Cyril E King

Wed 2/10

4:46 pm-7:32 am

2 stops16h 46m

Chicago O'Hare Intl

Sat 2/13

10:35 pm-5:30 pm

2 stops16h 55m

$522
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 2/5

6:39 pm-7:32 am

2 stops14h 53m

Chicago O'Hare Intl

Sat 2/13

10:35 pm-5:30 pm

2 stops16h 55m

$522

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 9/25

3:00 pm-8:48 am

2 stops18h 48m

Chicago O'Hare Intl

Tue 9/29

6:00 am-2:01 pm

2 stops31h 01m

$588

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 U.S. Virgin Islands 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 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 U.S. Virgin Islands 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 U.S. Virgin Islands 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 U.S. Virgin Islands to Chicago flight route?

Fly from Christiansted Henry Rohlsen to Chicago O'Hare Intl for the best U.S. Virgin Islands - Chicago flight prices

What cabin class options are available on U.S. Virgin Islands to Chicago flights?

There are 2 cabin classes available to choose from on U.S. Virgin Islands to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Cheap U.S. Virgin Islands to Chicago flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from U.S. Virgin Islands to Chicago

Fastest flight time

5h 40m

Direct flights

Every day

Airports in Chicago

3 airports
The fastest flight from U.S. Virgin Islands to Chicago takes 5h 40m
Direct flights go from U.S. Virgin Islands to Chicago every day.
There are 3 airports in Chicago. From U.S. Virgin Islands there are direct flights to Chicago O'Hare Intl (ORD).
Search flight deals

Frequently asked questions about flying from the U.S. Virgin Islands to Chicago

  • When did momondo last update prices for flights from U.S. Virgin Islands to Chicago?

    Prices for flights from U.S. Virgin Islands to Chicago are refreshed on a daily basis.

  • How many operators does momondo search for flights from U.S. Virgin Islands to Chicago?

  • How old do you have to be to fly from U.S. Virgin Islands 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 U.S. Virgin Islands to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The travel and health documents required for your trip to Chicago 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 Chicago. 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 U.S. Virgin Islands to Chicago?

Best airlines flying from U.S. Virgin Islands to Chicago

Compare and see reviews for airlines that fly from U.S. Virgin Islands to Chicago with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $242Free CancellationRating
7.1
11,947 reviews
Search American Airlines flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Portage
Benton Harbor
Lansing
Saint Joseph
Valparaiso
Schererville
Munster
Chesterton
Monticello
Porter
Crown Point
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from U.S. Virgin Islands to Chicago?

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

Can I find flights from U.S. Virgin Islands to Chicago with flexible booking policies on momondo?

momondo does allow users to show only those flights to Chicago from U.S. Virgin Islands which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from U.S. Virgin Islands 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 U.S. Virgin Islands.

I’m not ready to book a flight from U.S. Virgin Islands to Chicago right now. Can momondo alert me if prices change?

Yes. momondo can track prices for U.S. Virgin Islands to Chicago flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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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