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$551+ Cheap flights from Chicago (CHI) to the British Virgin Islands

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/30. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — EIS
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
1 adult, Economy
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Cheap flight deals from Chicago to British Virgin Islands

Keep the following information in mind while searching for Chicago to British Virgin Islands flight deals. Data was last updated September 16, 2025.

Round-trip from

$551
(Kiwi.com)
From Chicago (CHI) to British Virgin Islands
Search Deals

Find flight deals from Chicago to British Virgin Islands

Cheapest flights from Chicago to British Virgin Islands
Explore the most affordable flight options available from Chicago to British Virgin Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 16, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/306:40 amORD - EIS
2 stops27h 15mMultiple Airlines
Thu 11/64:00 pmEIS - ORD
1 stop28h 00mMultiple Airlines
Deal found 9/15$551
This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/226:30 amORD - EIS
2 stops10h 50mMultiple Airlines
Fri 9/264:00 pmEIS - ORD
1 stop8h 56mMultiple Airlines
Deal found 9/14$566
This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/226:30 amORD - EIS
2 stops10h 50mMultiple Airlines
Thu 9/254:00 pmEIS - ORD
1 stop8h 56mMultiple Airlines
Deal found 9/14$569
This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/2112:55 pmORD - EIS
1 stop21h 00mMultiple Airlines
Fri 9/264:00 pmEIS - ORD
2 stops25h 12mMultiple Airlines
Deal found 9/14$570
This Kiwi.com deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/113:00 pmORD - EIS
1 stop18h 55mMultiple Airlines
Sat 10/1812:50 pmEIS - ORD
2 stops9h 43mMultiple Airlines
Deal found 9/16$574
This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/215:10 amORD - EIS
2 stops9h 55mMultiple Airlines
Thu 9/254:00 pmEIS - ORD
1 stop8h 56mMultiple Airlines
Deal found 9/14$600
This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/236:30 amORD - EIS
2 stops31h 45mMultiple Airlines
Fri 9/264:00 pmEIS - ORD
1 stop8h 56mMultiple Airlines
Deal found 9/14$604

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to British Virgin Islands 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, Cheapflights users made 2,558,603 searches. Data last updated September 16, 2025.
Use the filters below to find and compare flights from Chicago to the British Virgin Islands that are best for you.

Fly from

Chicago

Fly to

British Virgin Islands

Route

Depart

Return

Price

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Mon 1/5

1:35 pm-3:15 pm

2 stops23h 40m

Road Town Beef Island

Wed 1/14

12:10 pm-6:00 pm

1 stop7h 50m

$585

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Wed 1/7

6:55 am-6:20 pm

1 stop9h 25m

Road Town Beef Island

Wed 1/14

8:55 am-6:00 pm

1 stop11h 05m

$587

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Tue 1/6

4:35 pm-10:55 am

1 stop16h 20m

Road Town Beef Island

Wed 1/14

12:10 pm-9:59 pm

2 stops11h 49m

$601

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Tue 1/6

4:35 pm-10:55 am

1 stop16h 20m

Road Town Beef Island

Thu 1/15

12:10 pm-12:12 am

2 stops14h 02m

$601

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Mon 2/2

1:35 pm-3:15 pm

2 stops23h 40m

Road Town Beef Island

Thu 2/5

12:10 pm-6:00 pm

1 stop7h 50m

$618

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Mon 1/5

1:35 pm-3:15 pm

2 stops23h 40m

Road Town Beef Island

Thu 1/15

12:10 pm-6:00 pm

1 stop7h 50m

$619

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Sat 10/11

7:43 pm-4:05 pm

2 stops19h 22m

Road Town Beef Island

Sat 10/18

8:55 am-9:33 pm

2 stops13h 38m

$631

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Sat 2/7

10:18 am-10:55 am

2 stops22h 37m

Road Town Beef Island

Sun 2/15

8:55 am-6:00 pm

1 stop11h 05m

$661

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Mon 1/5

1:35 pm-3:15 pm

2 stops23h 40m

Road Town Beef Island

Fri 1/16

12:10 pm-6:00 pm

1 stop7h 50m

$663

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Tue 1/6

4:35 pm-10:55 am

1 stop16h 20m

Road Town Beef Island

Fri 1/16

12:10 pm-6:00 pm

1 stop7h 50m

$664

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 13 results
1
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Best time to book a flight from Chicago to British Virgin Islands

Have a flexible travel schedule? Discover the best time to fly to British Virgin Islands from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago to the British Virgin Islands
No data available for this route at this time. Please check back soon.

Reviews of airlines servicing British Virgin Islands

Get insights into the airlines that provide service to British Virgin Islands. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to British Virgin Islands. Reviews last updated September 16, 2025.
Peruse reviews from past customers who have flown with United Airlines and American Airlines from Chicago to the British Virgin Islands to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
8,924 reviews

Food

6.6

Comfort

7.3

Entertainment

7.1

Overall

7.4

Boarding

7.7

Crew

8.1

Reviews

1 / 20
4.0
Okay

Thomas,Mar 2025

SFO - TPE

When I asked for an extra snack, I got an unhappy look from the stewardess. Geez, does one extra snack really affect the bottom line??
United Airlines
7.4
Good
8,924 reviews
United Airlines
7.4
Good
8,924 reviews

Food

6.6

Comfort

7.3

Entertainment

7.1

Overall

7.4

Boarding

7.7

Crew

8.1

Reviews

1 / 20
4.0
Okay

Thomas,Mar 2025

SFO - TPE

When I asked for an extra snack, I got an unhappy look from the stewardess. Geez, does one extra snack really affect the bottom line??
American Airlines
7.2
Good
10,000 reviews
United Airlines
7.4
Good
8,924 reviews

Food

6.6

Comfort

7.3

Entertainment

7.1

Overall

7.4

Boarding

7.7

Crew

8.1

Reviews

1 / 20
4.0
Okay

Thomas,Mar 2025

SFO - TPE

When I asked for an extra snack, I got an unhappy look from the stewardess. Geez, does one extra snack really affect the bottom line??

Related info for your journey

Find useful and relevant information for your journey from Chicago to British Virgin Islands. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • Can I find deals for flights from Chicago to British Virgin Islands that include hotel bookings?

    Yes. In addition to deals on Chicago to British Virgin Islands flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to British Virgin Islands?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to British Virgin Islands.

  • Can I find deals for business class flights from Chicago to British Virgin Islands?

    Yes. Cheapflights offers flight deals from Chicago to British Virgin Islands by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to British Virgin Islands?

    Currently, August is the cheapest month in which you can book a flight from Chicago to British Virgin Islands (average of $702). Flying from Chicago to British Virgin Islands in March is currently the most expensive (average of $966). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Alternative routes for Chicago to British Virgin Islands

See prices for flight routes from nearby airports that may be better suited for you.
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Top 2 airlines flying from Chicago to British Virgin Islands

Discover the top 2 airlines that operate flights from Chicago to British Virgin Islands. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$672Average$862FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$747Average$921FlexibilityNo cancel feeOn-time69%

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