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$500+ 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 2/3. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — EIS
Jan 8 — Jan 151
Thu 1/8
Thu 1/15
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 December 9, 2025.

This Mytrip deal was found by Cheapflights users on 12/8. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/185:45 amORD - EIS
1 stop8h 20mMultiple Airlines
Sat 12/2712:50 pmEIS - ORD
1 stop12h 35mMultiple Airlines
Deal found 12/8$707
This Kiwi.com deal was found by Cheapflights users on 12/7. 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 12/115:40 amORD - EIS
1 stop8h 25mMultiple Airlines
Sat 12/138:55 amEIS - ORD
2 stops30h 36mMultiple Airlines
Deal found 12/7$709
This Kiwi.com deal was found by Cheapflights users on 12/7. 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 12/305:45 amORD - EIS
1 stop7h 30mMultiple Airlines
Mon 1/54:00 pmEIS - ORD
2 stops51h 00mMultiple Airlines
Deal found 12/7$820

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 December 9, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$500
(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
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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 December 9, 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

Tue 2/3

12:17 pm-10:55 am

1 stop20h 38m

Road Town Beef Island

Tue 2/10

12:10 pm-12:57 pm

2 stops50h 47m

$500

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Wed 1/21

12:17 pm-2:10 pm

1 stop23h 53m

Road Town Beef Island

Wed 1/28

4:00 pm-10:46 pm

2 stops32h 46m

$520

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Mon 2/16

12:22 pm-3:15 pm

1 stop24h 53m

Road Town Beef Island

Sun 2/22

4:00 pm-6:15 pm

2 stops28h 15m

$547

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Thu 1/22

12:44 pm-10:55 am

2 stops20h 11m

Road Town Beef Island

Thu 1/29

8:55 am-6:16 pm

2 stops11h 21m

$598

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Fri 12/19

9:50 am-10:14 pm

1 stop10h 24m

$682

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/7

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 December 9, 2025.
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
11,045 reviews

Entertainment

6.9

Boarding

7.5

Overall

7.2

Comfort

7.2

Crew

8.0

Food

6.5

Reviews

1 / 20
10.0
Excellent

Jeremy,Dec 2025

OKC - CLT

Was an okay flight. Had extra seat empty beside me so was able to stretch a bit
American Airlines
7.2
Good
11,045 reviews
American Airlines
7.2
Good
11,045 reviews

Entertainment

6.9

Boarding

7.5

Overall

7.2

Comfort

7.2

Crew

8.0

Food

6.5

Reviews

1 / 20
10.0
Excellent

Jeremy,Dec 2025

OKC - CLT

Was an okay flight. Had extra seat empty beside me so was able to stretch a bit

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 December 9, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$693Average$869FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$747Average$906FlexibilityNo cancel feeOn-time69%

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