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Tortola

$273+ 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 7/10. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — EIS
Jun 21 — Jun 281
Sat 6/21
Sat 6/28
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 June 16, 2025.

Round-trip from

$580
(Kiwi.com)

One-way from

$273
(Mytrip)

Popular in

March

Cheapest in

October

Average price

$958
From Chicago (CHI) to Tortola
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One-way flight from Chicago (CHI) to Tortola
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Highest demand for flights based on searches. 6% potential increase in price ($64 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($18 potential savings vs. average RT price).
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Average for round-trip flights in June 2025
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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 June 16, 2025.

This Kiwi.com deal was found by Cheapflights users on 6/14. 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.
Fri 7/186:23 pmORD - EIS
1 stop22h 57mMultiple Airlines
Tue 7/2212:10 pmEIS - ORD
2 stops19h 54mMultiple Airlines
Deal found 6/14$580
This American Airlines deal was found by Cheapflights users on 6/14. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/47:15 pmORD - EIS
1 stop16h 51mAmerican Airlines
Thu 10/94:30 pmEIS - ORD
1 stop8h 27mAmerican Airlines
Deal found 6/14$694
This United Airlines deal was found by Cheapflights users on 6/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/186:03 pmORD - EIS
1 stop23h 52mUnited Airlines
Tue 7/221:08 pmEIS - ORD
1 stop8h 07mUnited Airlines
Deal found 6/14$986

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 June 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

Fri 7/18

6:23 pm-6:20 pm

1 stop22h 57m

Road Town Beef Island

Tue 7/22

12:10 pm-7:04 am

2 stops19h 54m

$580

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Sat 10/4

7:15 pm-1:06 pm

1 stop16h 51m

Road Town Beef Island

Thu 10/9

4:30 pm-11:57 pm

1 stop8h 27m

$694

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Fri 7/18

6:03 pm-6:55 pm

1 stop23h 52m

Road Town Beef Island

Tue 7/22

1:08 pm-8:15 pm

1 stop8h 07m

$986

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Thu 7/10

6:23 pm-6:20 pm

1 stop22h 57m

$273

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Tue 7/29

6:57 pm-1:55 pm

1 stop17h 58m

$435

ChicagoRoad Town

MDW - EIS

MDWEIS

Chicago Midway

Thu 7/10

9:12 pm-11:05 am

3 stops36h 53m

$494

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Fri 6/27

6:03 pm-6:55 pm

1 stop23h 52m

$1,585

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/14

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

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

Currently, September is the cheapest month in which you can book a flight from Chicago to Tortola (average of $681). Flying from Chicago to Tortola in April is currently the most expensive (average of $943). 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.

Rainfall in Tortola by month

Plan your trip to Tortola by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Tortola ranges from 1.9 - 5.8 inches per month. October is typically the wettest month, when rainfall can reach 5.8 in. February is typically the driest time to visit Tortola when rainfall is around 1.9 in.

Temperature in Tortola by month

Plan your trip to Tortola by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Tortola, use this chart to help with planning. For those seeking warmer temperatures, August is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of February, when temperatures are typically at their lowest (around 75.2 F).

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 June 16, 2025.
United Airlines
7.4
Good
8,801 reviews

Overall

7.4

Crew

8.1

Boarding

7.7

Comfort

7.3

Entertainment

7.0

Food

6.6

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
8,801 reviews
United Airlines
7.4
Good
8,801 reviews

Overall

7.4

Crew

8.1

Boarding

7.7

Comfort

7.3

Entertainment

7.0

Food

6.6

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
8,801 reviews

Overall

7.4

Crew

8.1

Boarding

7.7

Comfort

7.3

Entertainment

7.0

Food

6.6

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, September is the cheapest month in which you can book a flight from Chicago to Tortola (average of $681). Flying from Chicago to Tortola in April is currently the most expensive (average of $943). 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 June 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$662Average$817FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$783Average$931FlexibilityNo cancel feeOn-time69%

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