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Tortola

$551+ 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 10/30. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — EIS
oct. 16 — oct. 231
jue. 10/16
jue. 10/23
1 adult, Economy
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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 septiembre 16, 2025.

Round-trip from

$551
(Kiwi.com)
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 septiembre 16, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
jue. 10/306:40 amORD - EIS
2 stops27h 15mMultiple Airlines
jue. 11/64:00 pmEIS - ORD
1 stop28h 00mMultiple Airlines
Deal found 9/15$551
This Kiwi.com deal was found by Cheapflights users on 9/14. 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. 9/226:30 amORD - EIS
2 stops10h 50mMultiple Airlines
vie. 9/264:00 pmEIS - ORD
1 stop8h 56mMultiple Airlines
Deal found 9/14$566
This Kiwi.com deal was found by Cheapflights users on 9/14. 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. 9/226:30 amORD - EIS
2 stops10h 50mMultiple Airlines
jue. 9/254:00 pmEIS - ORD
1 stop8h 56mMultiple Airlines
Deal found 9/14$569
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
dom. 9/2112:55 pmORD - EIS
1 stop21h 00mMultiple Airlines
vie. 9/264:00 pmEIS - ORD
2 stops25h 12mMultiple Airlines
Deal found 9/14$570
This Kiwi.com deal was found by Cheapflights users on 9/16. 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.
sáb. 10/113:00 pmORD - EIS
1 stop18h 55mMultiple Airlines
sáb. 10/1812:50 pmEIS - ORD
2 stops9h 43mMultiple Airlines
Deal found 9/16$574
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
dom. 9/215:10 amORD - EIS
2 stops9h 55mMultiple Airlines
jue. 9/254:00 pmEIS - ORD
1 stop8h 56mMultiple Airlines
Deal found 9/14$600
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
mar. 9/236:30 amORD - EIS
2 stops31h 45mMultiple Airlines
vie. 9/264:00 pmEIS - ORD
1 stop8h 56mMultiple Airlines
Deal found 9/14$604

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 septiembre 16, 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

lun. 1/5

1:35 pm-3:15 pm

2 stops23h 40m

Road Town Beef Island

mié. 1/14

12:10 pm-6:00 pm

1 stop7h 50m

$585

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

mié. 1/7

6:55 am-6:20 pm

1 stop9h 25m

Road Town Beef Island

mié. 1/14

8:55 am-6:00 pm

1 stop11h 05m

$587

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

mar. 1/6

4:35 pm-10:55 am

1 stop16h 20m

Road Town Beef Island

mié. 1/14

12:10 pm-9:59 pm

2 stops11h 49m

$601

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

mar. 1/6

4:35 pm-10:55 am

1 stop16h 20m

Road Town Beef Island

jue. 1/15

12:10 pm-12:12 am

2 stops14h 02m

$601

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

lun. 2/2

1:35 pm-3:15 pm

2 stops23h 40m

Road Town Beef Island

jue. 2/5

12:10 pm-6:00 pm

1 stop7h 50m

$618

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

lun. 1/5

1:35 pm-3:15 pm

2 stops23h 40m

Road Town Beef Island

jue. 1/15

12:10 pm-6:00 pm

1 stop7h 50m

$619

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

sáb. 10/11

7:43 pm-4:05 pm

2 stops19h 22m

Road Town Beef Island

sáb. 10/18

8:55 am-9:33 pm

2 stops13h 38m

$631

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

sáb. 2/7

10:18 am-10:55 am

2 stops22h 37m

Road Town Beef Island

dom. 2/15

8:55 am-6:00 pm

1 stop11h 05m

$661

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

lun. 1/5

1:35 pm-3:15 pm

2 stops23h 40m

Road Town Beef Island

vie. 1/16

12:10 pm-6:00 pm

1 stop7h 50m

$663

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

mar. 1/6

4:35 pm-10:55 am

1 stop16h 20m

Road Town Beef Island

vie. 1/16

12:10 pm-6:00 pm

1 stop7h 50m

$664

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 13 results
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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 septiembre 16, 2025.
Read through reviews of airlines operating flights from Chicago to Tortola, such as United Airlines and 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.
United Airlines
7.4
Good
8,924 reviews

Food

6.6

Comfort

7.3

Entertainment

7.1

Overall

7.4

Boarding

7.7

Crew

8.1

Reviews

1 / 20
4.0
Okay

Thomas,Mar 2025

SFO - TPE

When I asked for an extra snack, I got an unhappy look from the stewardess. Geez, does one extra snack really affect the bottom line??
United Airlines
7.4
Good
8,924 reviews
United Airlines
7.4
Good
8,924 reviews

Food

6.6

Comfort

7.3

Entertainment

7.1

Overall

7.4

Boarding

7.7

Crew

8.1

Reviews

1 / 20
4.0
Okay

Thomas,Mar 2025

SFO - TPE

When I asked for an extra snack, I got an unhappy look from the stewardess. Geez, does one extra snack really affect the bottom line??
American Airlines
7.2
Good
10,000 reviews
United Airlines
7.4
Good
8,924 reviews

Food

6.6

Comfort

7.3

Entertainment

7.1

Overall

7.4

Boarding

7.7

Crew

8.1

Reviews

1 / 20
4.0
Okay

Thomas,Mar 2025

SFO - TPE

When I asked for an extra snack, I got an unhappy look from the stewardess. Geez, does one extra snack really affect the bottom line??

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.

  • What is the cheapest month to book a flight from Chicago to Tortola?

    Currently, August is the cheapest month in which you can book a flight from Chicago to Tortola (average of $702). Flying from Chicago to Tortola in March is currently the most expensive (average of $966). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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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 septiembre 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$672Average$862FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$747Average$921FlexibilityNo cancel feeOn-time69%

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