$295 Find Cheap Flights from Chicago to the British Virgin Islands

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to the British Virgin Islands departing on 6/2. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Book Cheap Chicago to the British Virgin Islands Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to the British Virgin Islands that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to the British Virgin Islands

Sat, May 23 - Thu, May 28
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12:59 pm - 2:05 pm
ORD
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EIS
24h 06m
1 stop
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9:00 am - 10:46 pm
EIS
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ORD
14h 46m
1 stop
$528Multiple Airlines
Sat, May 23 - Thu, May 28
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1:18 pm - 2:05 pm
ORD
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EIS
47h 47m
2 stops
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4:00 pm - 10:46 pm
EIS
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ORD
7h 46m
1 stop
$576Multiple Airlines
Fri, May 22 - Thu, May 28
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4:44 pm - 6:10 pm
ORD
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EIS
24h 26m
1 stop
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4:00 pm - 10:46 pm
EIS
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ORD
7h 46m
1 stop
$589Multiple Airlines
Fri, May 22 - Thu, May 28
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7:52 pm - 2:05 pm
ORD
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EIS
41h 13m
2 stops
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9:00 am - 10:46 pm
EIS
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ORD
14h 46m
1 stop
$613Multiple Airlines
Thu, Jun 11 - Thu, Jun 18
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12:31 pm - 10:55 am
ORD
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EIS
21h 24m
2 stops
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11:35 am - 11:38 pm
EIS
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ORD
13h 03m
1 stop
$660Multiple Airlines
Fri, May 29 - Sat, Jun 6
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7:52 pm - 10:55 am
ORD
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EIS
14h 03m
2 stops
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9:00 am - 3:15 pm
EIS
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ORD
7h 15m
1 stop
$678Multiple Airlines
Thu, Jun 11 - Thu, Jun 18
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4:44 pm - 10:55 am
ORD
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EIS
17h 11m
1 stop
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11:35 am - 11:38 pm
EIS
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ORD
13h 03m
1 stop
$684Multiple Airlines
Mon, Jun 8 - Tue, Jun 16
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12:44 am - 6:10 pm
ORD
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EIS
16h 26m
1 stop
Multiple Airlines Logo
11:35 am - 12:43 pm
EIS
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ORD
26h 08m
2 stops
$687Multiple Airlines
Fri, Jun 5 - Wed, Jul 8
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7:52 pm - 10:55 am
ORD
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EIS
38h 03m
2 stops
Multiple Airlines Logo
4:00 pm - 11:27 pm
EIS
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ORD
8h 27m
1 stop
$706Multiple Airlines
Mon, Jun 8 - Tue, Jun 16
Multiple Airlines Logo
12:44 am - 6:10 pm
ORD
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EIS
16h 26m
1 stop
Multiple Airlines Logo
4:00 pm - 3:11 pm
EIS
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ORD
24h 11m
1 stop
$732Multiple Airlines
Booking Insights

KAYAK's insights & trends for Chicago to the British Virgin Islands flights

Get data-powered insights and trends into flights from Chicago to the British Virgin Islands to help you find the cheapest flights, the best time to fly and much more.

How long does a flight from Chicago to the British Virgin Islands take?

The duration of a flight to the British Virgin Islands depends on your arrival airport. The shortest route to the British Virgin Islands from Chicago is to Road Town, which takes 10h 05m.

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FAQs - booking British Virgin Islands flights

  • How does KAYAK find such low prices on flights from Chicago to the British Virgin Islands?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to the British Virgin Islands.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to the British Virgin Islands?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago to the British Virgin Islands is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to the British Virgin Islands?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Chicago to the British Virgin Islands with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to the British Virgin Islands?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Chicago to the British Virgin Islands up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airline flying from Chicago to the British Virgin Islands

 
Need help choosing which airline to fly with from Chicago to the British Virgin Islands? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.1
American AirlinesOverall score based on 11681 reviews
6.9Entertainment
7.5Boarding
7.2Comfort
6.4Food
7.9Crew
Airline reviews

The airplane was an old model, the overhead didn’t have enough room for people’s items and made boarding and boarding disappointing and stressful. Crew allowed passengers to bring more than the permitted baggage sizes.

2.0 MediocreStella, Apr 2026
ORD - DCA
Read more American Airlines reviews

The airplane was an old model, the overhead didn’t have enough room for people’s items and made boarding and boarding disappointing and stressful. Crew allowed passengers to bring more than the permitted baggage sizes.

Original flight was on time, then late, then changed gates...4 times. Once our newest plane came in, it was fine.

I almost missed my flight and they helped me out enormously

Delays experienced in boarding/take off due to incoming plane delayed. However, the boarding time/depart time in the app was significantly delayed in providing these updates. Usually not updated until an hour after we should have already boarded. Poorly managed.

Moved to earlier flight which unexpectedly had maintenance issues initially indicated as quick fix to ultimately plane changes. Moved back to original flight, also delayed. In all cases customer updates and communication very unclear, no updates on drivers for delays.

Typical AA - late by 90+ mn. Gate changed twice... Changed the departure time 6 times No explanation, no communication on reasons for delay I travel with AA twice a year... and it is consistently very poor.. I will continue to use AA only when i have to.

The gate got changed several times and the flight was delayed over an hour. Awful experience

American continues to decline in their customer service and its beyond disappointing.

It was an older plane. First Class was not especially roomy or comfortable. It was a short flight so there were no meal but they did offer mixed nuts which used to be normal but now is rare. Crew member was very polite and professional.

Flight to Tampa was delayed taking off due to plane arriving late but no other issues

Everything you need to know for your flight from Chicago to the British Virgin Islands

Cabin class types available on flights to the British Virgin Islands

Cabin classes available on flights to the British Virgin Islands. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.
First Class flights from Chicago to the British Virgin Islands
Business Class flights from Chicago to the British Virgin Islands
Premium Economy Class flights from Chicago to the British Virgin Islands
Economy Class flights from Chicago to the British Virgin Islands