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British Virgin Islands

$243+ Cheap flights from Chicago (CHI) to the British Virgin Islands

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/28. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — EIS
Mar 5 — Mar 121
Thu 3/5
Thu 3/12
1 adult, Economy
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Cheap 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 February 3, 2026.

This Kiwi.com deal was found by Cheapflights users on 2/2. 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.
Wed 4/810:55 am
ORD
-
EIS
2 stops23h 00m
Multiple Airlines
Wed 4/159:00 am
EIS
-
ORD
1 stop8h 37m
Multiple Airlines
Deal found 2/2$509
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 4/710:55 am
ORD
-
EIS
2 stops23h 00m
Multiple Airlines
Mon 4/134:00 pm
EIS
-
ORD
1 stop14h 45m
Multiple Airlines
Deal found 2/1$510
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 4/114:51 pm
ORD
-
EIS
2 stops41h 04m
Multiple Airlines
Sat 4/189:00 am
EIS
-
ORD
1 stop8h 37m
Multiple Airlines
Deal found 2/1$513
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 4/68:56 pm
ORD
-
EIS
1 stop16h 09m
Multiple Airlines
Sun 4/124:00 pm
EIS
-
ORD
2 stops42h 50m
Multiple Airlines
Deal found 2/1$515
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 4/68:56 pm
ORD
-
EIS
1 stop16h 09m
Multiple Airlines
Tue 4/144:00 pm
EIS
-
ORD
2 stops27h 15m
Multiple Airlines
Deal found 2/1$522
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 4/1110:55 am
ORD
-
EIS
2 stops23h 00m
Multiple Airlines
Mon 4/134:00 pm
EIS
-
ORD
1 stop14h 45m
Multiple Airlines
Deal found 2/1$525
This Kiwi.com deal was found by Cheapflights users on 2/1. 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.
Wed 3/114:18 pm
ORD
-
EIS
2 stops17h 37m
Multiple Airlines
Sun 3/158:55 am
EIS
-
ORD
1 stop21h 50m
Multiple Airlines
Deal found 2/1$535
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 5/2312:22 pm
ORD
-
EIS
1 stop21h 33m
Multiple Airlines
Wed 5/274:00 pm
EIS
-
ORD
2 stops27h 15m
Multiple Airlines
Deal found 2/2$604

Find 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 February 3, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$509
(Kiwi.com)

One-way from

$243
(Kiwi.com)
Provider with most accurate pricing for Chicago (CHI)-Road Town Beef Island flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Road Town Beef Island flights.
Search Deals
From Chicago (CHI) to British Virgin Islands
Search Deals
One-way flight from Chicago (CHI) to British Virgin Islands
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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 February 3, 2026.
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

Tue 4/7

10:55 am-10:55 am

2 stops23h 00m

Road Town Beef Island

Sun 4/12

4:00 pm-5:45 am

1 stop14h 45m

$510

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Wed 4/8

10:55 am-10:55 am

2 stops23h 00m

Road Town Beef Island

Sun 4/12

4:00 pm-5:45 am

1 stop14h 45m

$510

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Mon 4/6

8:56 pm-2:05 pm

1 stop16h 09m

Road Town Beef Island

Mon 4/13

4:00 pm-6:31 pm

2 stops27h 31m

$510

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Mon 4/6

8:56 pm-2:05 pm

1 stop16h 09m

Road Town Beef Island

Sun 4/12

4:00 pm-9:50 am

2 stops42h 50m

$515

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Sat 4/11

10:55 am-10:55 am

2 stops23h 00m

Road Town Beef Island

Mon 4/13

4:00 pm-5:45 am

1 stop14h 45m

$525

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Tue 4/7

8:56 pm-10:55 am

1 stop12h 59m

Road Town Beef Island

Tue 4/14

4:00 pm-4:37 pm

1 stop25h 37m

$538

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Wed 4/8

8:56 pm-10:55 am

1 stop12h 59m

Road Town Beef Island

Tue 4/14

4:00 pm-4:37 pm

1 stop25h 37m

$538

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Tue 4/7

8:56 pm-10:55 am

1 stop12h 59m

Road Town Beef Island

Mon 4/13

4:00 pm-5:45 am

1 stop14h 45m

$538

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Thu 5/28

12:22 pm-10:55 am

1 stop21h 33m

$243

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Fri 6/19

12:22 pm-10:55 am

1 stop21h 33m

$448

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/2

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

How often are flights from Chicago to the British Virgin Islands delayed?

About 50% of weekly flights between Chicago and British Virgin Islands have experienced delays in the past year, with the average delay time being 41 minutes.

What is the most punctual flight time for Chicago to the British Virgin Islands flights?

Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the morning tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Thursday tends to have the lowest number of delays on this route, whereas Monday has historically faced a higher average of delays compared to other days of the week.

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 February 3, 2026.
Peruse reviews from past customers who have flown with 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.
American Airlines
7.2
Good
11,216 reviews

Boarding

7.5

Overall

7.2

Food

6.4

Comfort

7.2

Crew

8.0

Entertainment

6.9

Reviews

1 / 20
2.0
Mediocre

Susie,Jan 2026

CLT - TPA

This flight was delayed 3 or 4 times. We had boarded the plane, sat on plane for a good 30 minutes, then we had to board the aircraft, walk to a different gate, wait and then board another aircraft. We arrived in Tampa 4 hours later than the original booking. I feel there should have been some sort of compensation especially for the advantage members.
American Airlines
7.2
Good
11,216 reviews
American Airlines
7.2
Good
11,216 reviews

Boarding

7.5

Overall

7.2

Food

6.4

Comfort

7.2

Crew

8.0

Entertainment

6.9

Reviews

1 / 20
2.0
Mediocre

Susie,Jan 2026

CLT - TPA

This flight was delayed 3 or 4 times. We had boarded the plane, sat on plane for a good 30 minutes, then we had to board the aircraft, walk to a different gate, wait and then board another aircraft. We arrived in Tampa 4 hours later than the original booking. I feel there should have been some sort of compensation especially for the advantage members.

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.

Browse thousands of different options on Cheapflights for your next trip

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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 February 3, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$718Average$903FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$747Average$921FlexibilityNo cancel feeOn-time69%

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