HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Tortola

$472+ Cheap flights from Chicago (CHI) to Tortola

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 1/19. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — EIS
févr. 7 — févr. 141
sam. 2/7
sam. 2/14
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to Tortola with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 janvier 8, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$497
(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 Tortola
Search Deals

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 janvier 8, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/5. 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.
lun. 1/1912:17 pmORD - EIS
1 stop24h 58mMultiple Airlines
jeu. 1/228:55 amEIS - ORD
1 stop9h 42mMultiple Airlines
Deal found 1/5$472
This Kiwi.com deal was found by Cheapflights users on 1/5. 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.
mer. 2/412:17 pmORD - EIS
1 stop23h 53mMultiple Airlines
dim. 2/84:00 pmEIS - ORD
2 stops42h 18mMultiple Airlines
Deal found 1/5$484
This Kiwi.com deal was found by Cheapflights users on 1/8. 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.
lun. 2/912:17 pmORD - EIS
1 stop24h 58mMultiple Airlines
lun. 2/164:00 pmEIS - ORD
2 stops49h 52mMultiple Airlines
Deal found 1/8$497
This Kiwi.com deal was found by Cheapflights users on 1/7. 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.
sam. 1/1712:17 pmORD - EIS
1 stop24h 58mMultiple Airlines
mar. 1/2012:10 pmEIS - ORD
1 stop30h 27mMultiple Airlines
Deal found 1/7$522
This Kiwi.com deal was found by Cheapflights users on 1/7. 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.
mer. 1/2812:17 pmORD - EIS
1 stop20h 38mMultiple Airlines
lun. 2/24:00 pmEIS - ORD
2 stops31h 44mMultiple Airlines
Deal found 1/7$525
This Kiwi.com deal was found by Cheapflights users on 1/7. 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.
mer. 3/114:18 pmORD - EIS
2 stops17h 37mMultiple Airlines
lun. 3/164:00 pmEIS - ORD
1 stop14h 45mMultiple Airlines
Deal found 1/7$534
This Kiwi.com deal was found by Cheapflights users on 1/7. 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.
sam. 2/218:15 amORD - EIS
2 stops29h 00mMultiple Airlines
sam. 2/288:55 amEIS - ORD
1 stop8h 53mMultiple Airlines
Deal found 1/7$537
This Kiwi.com deal was found by Cheapflights users on 1/6. 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.
mer. 3/117:25 pmORD - EIS
2 stops41h 45mMultiple Airlines
mar. 3/1712:10 pmEIS - ORD
1 stop18h 35mMultiple Airlines
Deal found 1/6$552
This Trip.com deal was found by Cheapflights users on 1/8. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dim. 3/296:00 amMDW - EIS
2 stops35h 10mMultiple Airlines
dim. 4/54:00 pmEIS - MDW
2 stops32h 42mMultiple Airlines
Deal found 1/8$817

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 janvier 8, 2026.
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

lun. 1/19

12:17 pm-3:15 pm

1 stop24h 58m

Road Town Beef Island

jeu. 1/22

8:55 am-4:37 pm

1 stop9h 42m

$472

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

mer. 1/28

12:17 pm-10:55 am

1 stop20h 38m

Road Town Beef Island

lun. 2/2

4:00 pm-9:44 pm

2 stops31h 44m

$525

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

mer. 3/11

4:18 pm-10:55 am

2 stops17h 37m

Road Town Beef Island

mar. 3/17

12:10 pm-5:45 am

1 stop18h 35m

$534

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

ven. 2/6

4:44 pm-3:15 pm

2 stops20h 31m

Road Town Beef Island

ven. 2/13

4:00 pm-3:48 pm

1 stop25h 48m

$553

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

mer. 5/27

12:22 pm-10:55 am

1 stop21h 33m

Road Town Beef Island

lun. 6/1

4:00 pm-4:37 pm

1 stop25h 37m

$570

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

jeu. 3/12

7:30 pm-2:10 pm

1 stop17h 40m

Road Town Beef Island

mar. 3/17

12:10 pm-10:39 pm

2 stops11h 29m

$573

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

sam. 4/4

7:30 pm-10:55 am

1 stop14h 25m

Road Town Beef Island

lun. 4/13

11:35 am-12:29 am

2 stops13h 54m

$576

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

mer. 4/8

12:22 pm-2:05 pm

1 stop24h 43m

Road Town Beef Island

lun. 4/13

11:35 am-12:29 am

2 stops13h 54m

$576

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

mer. 3/11

4:18 pm-10:55 am

2 stops17h 37m

Road Town Beef Island

ven. 3/20

4:00 pm-5:45 am

1 stop14h 45m

$590

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

sam. 4/4

7:30 pm-2:05 pm

1 stop17h 35m

Road Town Beef Island

ven. 4/10

4:00 pm-12:29 am

2 stops33h 29m

$606

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/7

Showing 1-10 of 13 results
1
2

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 janvier 8, 2026.
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
11,094 reviews

Entertainment

6.9

Boarding

7.5

Food

6.4

Overall

7.2

Comfort

7.2

Crew

8.0

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
11,094 reviews
American Airlines
7.2
Good
11,094 reviews

Entertainment

6.9

Boarding

7.5

Food

6.4

Overall

7.2

Comfort

7.2

Crew

8.0

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 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.

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 janvier 8, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$718Average$889FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$747Average$906FlexibilityNo cancel feeOn-time69%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.