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Tortola

$547+ Cheap flights from Chicago (CHI) to Tortola

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 12/19. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — EIS
Dez 8 — Dez 151
Mo 12/8
Mo 12/15
1 adult, Economy
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Find flight deals from Chicago to Tortola

Cheapest flights from Chicago to Tortola
Explore the most affordable flight options available from Chicago to Tortola. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 8, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Di 12/236:05 pmORD - EIS
2 stops44h 00mMultiple Airlines
Di 12/3012:10 pmEIS - ORD
1 stop13h 15mMultiple Airlines
Deal found 11/8$816
This American Airlines deal was found by Cheapflights users on 11/8. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Di 12/237:00 amORD - EIS
1 stop13h 14mAmerican Airlines
Di 12/3012:55 pmEIS - ORD
1 stop8h 49mAmerican Airlines
Deal found 11/8$869
This American Airlines deal was found by Cheapflights users on 11/7. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mo 12/224:41 pmORD - EIS
1 stop17h 34mAmerican Airlines
Do 1/18:00 amEIS - ORD
1 stop16h 59mAmerican Airlines
Deal found 11/7$944
This American Airlines deal was found by Cheapflights users on 11/8. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sa 12/67:00 amORD - EIS
1 stop8h 08mAmerican Airlines
Sa 12/135:48 pmEIS - ORD
1 stop17h 01mAmerican Airlines
Deal found 11/8$984
This American Airlines deal was found by Cheapflights users on 11/7. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fr 12/125:00 amORD - EIS
2 stops10h 08mAmerican Airlines
So 12/145:48 pmEIS - ORD
1 stop17h 01mAmerican Airlines
Deal found 11/7$994
This United Airlines deal was found by Cheapflights users on 11/7. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sa 11/298:55 amORD - EIS
1 stop25h 35mUnited Airlines
Mi 12/311:21 amEIS - ORD
2 stops29h 04mUnited Airlines
Deal found 11/7$1,015
This American Airlines deal was found by Cheapflights users on 11/7. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sa 11/295:00 amORD - EIS
1 stop7h 10mAmerican Airlines
Mi 12/34:45 pmEIS - ORD
1 stop8h 12mAmerican Airlines
Deal found 11/7$1,059

Cheap flight deals from Chicago to Tortola

Keep the following information in mind while searching for Chicago to Tortola flight deals. Data was last updated November 8, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$575
(Kiwi.com)

One-way from

$547
(American Airlines)
Provider with most accurate pricing for Chicago (CHI)-Road Town Beef Island flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Road Town Beef Island flights.
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From Chicago (CHI) to Tortola
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One-way flight from Chicago (CHI) to Tortola
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Tortola 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 November 8, 2025.
Use the filters below to find and compare flights from Chicago to Tortola that are best for you.

Fly from

Chicago

Fly to

Tortola

Route

Depart

Return

Price

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Fr 1/30

5:20 am-6:20 pm

2 stops11h 00m

Road Town Beef Island

Sa 2/21

8:55 am-4:37 pm

1 stop9h 42m

$575

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Di 2/3

12:22 pm-10:55 am

1 stop20h 33m

Road Town Beef Island

Sa 2/21

8:55 am-9:58 pm

2 stops39h 03m

$582

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Mo 2/2

12:22 pm-3:15 pm

1 stop24h 53m

Road Town Beef Island

Sa 2/21

8:55 am-4:37 pm

1 stop9h 42m

$620

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

So 2/1

12:22 pm-10:55 am

1 stop20h 33m

Road Town Beef Island

Sa 2/21

8:55 am-4:37 pm

1 stop9h 42m

$654

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Sa 2/28

8:42 pm-6:20 pm

3 stops19h 38m

Road Town Beef Island

So 3/8

4:00 pm-3:57 pm

2 stops24h 57m

$707

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Di 1/6

5:00 am-10:16 pm

1 stop15h 16m

Road Town Beef Island

Do 1/15

5:49 pm-9:05 am

1 stop17h 16m

$794

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

So 3/1

1:02 pm-4:15 pm

2 stops25h 13m

Road Town Beef Island

Sa 3/7

8:15 am-12:26 am

2 stops18h 11m

$837

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Fr 12/19

5:00 am-10:14 pm

1 stop15h 14m

$547

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Di 12/9

2:20 pm-2:32 pm

2 stops22h 12m

$2,962

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/8

Best time to book a flight from Chicago to Tortola

Have a flexible travel schedule? Discover the best time to fly to Tortola 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 Tortola
No data available for this route at this time. Please check back soon.

Reviews of airlines servicing Tortola

Get insights into the airlines that provide service to Tortola. 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 Tortola. Reviews last updated November 8, 2025.
Read through reviews of airlines operating flights from Chicago to Tortola, such as American Airlines. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
11,050 reviews

Boarding

7.5

Food

6.4

Entertainment

6.9

Crew

8.0

Comfort

7.2

Overall

7.2

Reviews

1 / 20
8.0
Excellent

Monica,Nov 2025

JAC - DFW

At least there was an option of entertainment on this flight.
American Airlines
7.2
Good
11,050 reviews
American Airlines
7.2
Good
11,050 reviews

Boarding

7.5

Food

6.4

Entertainment

6.9

Crew

8.0

Comfort

7.2

Overall

7.2

Reviews

1 / 20
8.0
Excellent

Monica,Nov 2025

JAC - DFW

At least there was an option of entertainment on this flight.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Tortola. 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 Tortola that include hotel bookings?

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

  • How can I find direct flights from Chicago to Tortola?

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

  • Can I find deals for business class flights from Chicago to Tortola?

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

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Alternative routes for Chicago to Tortola

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Road Town flights
St. Louis to Road Town flights

Top 2 airlines flying from Chicago to Tortola

Discover the top 2 airlines that operate flights from Chicago to Tortola. 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 November 8, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$693Average$878FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$747Average$921FlexibilityNo cancel feeOn-time69%

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