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Road Town

$568+ Cheap flights from Chicago (CHI) to Road Town (EIS)

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 10/4. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — EIS
Aug 26 — Sep 21
Tue 8/26
Tue 9/2
1 adult, Economy
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Cheap flight deals from Chicago to Road Town

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Road Town (EIS). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated August 21, 2025.

Round-trip from

$568
(Kiwi.com)
From Chicago (CHI) to Road Town Beef Island
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Find flight deals from Chicago to Road Town

Cheapest flights from Chicago to Road Town
Explore the most affordable flight options available from Chicago to Road Town. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 21, 2025.

This Kiwi.com deal was found by Cheapflights users on 8/20. 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.
Sat 10/48:00 amORD - EIS
2 stops25h 55mMultiple Airlines
Sat 10/114:00 pmEIS - ORD
1 stop21h 31mMultiple Airlines
Deal found 8/20$568
This Kiwi.com deal was found by Cheapflights users on 8/19. 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.
Sun 11/23:22 pmORD - EIS
1 stop20h 48mMultiple Airlines
Thu 11/68:55 amEIS - ORD
1 stop11h 05mMultiple Airlines
Deal found 8/19$580
This Kiwi.com deal was found by Cheapflights users on 8/18. 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.
Tue 10/143:22 pmORD - EIS
1 stop22h 53mMultiple Airlines
Mon 10/204:00 pmEIS - ORD
1 stop21h 31mMultiple Airlines
Deal found 8/18$586
This Kiwi.com deal was found by Cheapflights users on 8/19. 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 10/245:05 amORD - EIS
2 stops12h 15mMultiple Airlines
Thu 10/304:00 pmEIS - ORD
1 stop21h 31mMultiple Airlines
Deal found 8/19$591
This Kiwi.com deal was found by Cheapflights users on 8/18. 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 10/35:10 amORD - EIS
2 stops12h 10mMultiple Airlines
Fri 10/108:55 amEIS - ORD
1 stop28h 36mMultiple Airlines
Deal found 8/18$594
This Kiwi.com deal was found by Cheapflights users on 8/19. 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.
Thu 10/305:11 amORD - EIS
2 stops12h 09mMultiple Airlines
Sat 11/84:00 pmEIS - ORD
1 stop28h 00mMultiple Airlines
Deal found 8/19$597
This Kiwi.com deal was found by Cheapflights users on 8/19. 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 10/315:11 amORD - EIS
2 stops12h 09mMultiple Airlines
Sat 11/84:00 pmEIS - ORD
1 stop28h 00mMultiple Airlines
Deal found 8/19$600

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Road Town 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 August 21, 2025.
Use the filters below to find and compare flights from Chicago to Road Town that are best for you.

Fly from

Chicago

Fly to

Road Town

Route

Depart

Return

Price

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Sat 10/4

8:00 am-10:55 am

2 stops25h 55m

Road Town Beef Island

Sat 10/11

4:00 pm-12:31 pm

1 stop21h 31m

$568

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Fri 10/24

1:29 pm-6:20 pm

1 stop27h 51m

Road Town Beef Island

Thu 10/30

4:00 pm-12:31 pm

1 stop21h 31m

$580

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Sun 11/2

3:22 pm-2:10 pm

1 stop20h 48m

Road Town Beef Island

Thu 11/6

8:55 am-6:00 pm

1 stop11h 05m

$580

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Fri 10/3

12:55 pm-6:20 pm

1 stop28h 25m

Road Town Beef Island

Fri 10/10

4:00 pm-12:31 pm

1 stop21h 31m

$580

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Thu 10/30

4:21 pm-10:55 am

1 stop17h 34m

Road Town Beef Island

Sat 11/8

4:00 pm-6:00 pm

1 stop28h 00m

$586

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Tue 10/14

3:22 pm-3:15 pm

1 stop22h 53m

Road Town Beef Island

Mon 10/20

4:00 pm-12:31 pm

1 stop21h 31m

$586

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Fri 10/31

1:29 pm-10:55 am

1 stop20h 26m

Road Town Beef Island

Sat 11/8

4:00 pm-6:00 pm

1 stop28h 00m

$586

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Sat 1/31

4:35 pm-10:55 am

1 stop16h 20m

Road Town Beef Island

Sun 2/8

12:10 pm-6:00 pm

1 stop7h 50m

$592

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Fri 12/19

9:30 am-1:43 pm

1 stop26h 13m

$687

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/20

Best time to book a flight from Chicago to Road Town

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

Reviews of airlines servicing Road Town

Get insights into the airlines that provide service to Road Town. 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 Road Town. Reviews last updated August 21, 2025.
Peruse reviews from past customers who have flown with United Airlines and American Airlines from Chicago to Road Town to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
8,930 reviews

Overall

7.4

Boarding

7.7

Crew

8.1

Entertainment

7.1

Comfort

7.3

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
8,930 reviews
United Airlines
7.4
Good
8,930 reviews

Overall

7.4

Boarding

7.7

Crew

8.1

Entertainment

7.1

Comfort

7.3

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
8,930 reviews

Overall

7.4

Boarding

7.7

Crew

8.1

Entertainment

7.1

Comfort

7.3

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 Road Town. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Road Town from Chicago?

    If you book a flight to Road Town from Chicago, you will be flying to Beef Island, which is the city’s only airport. Road Town Beef Island (EIS) is located 5.2 mi from the center of Road Town. There are 0 flights from Chicago to Beef Island per day from 2 different airlines.

  • What are the cheapest airlines flying from Chicago to Road Town round-trip?

    American Airlines, at $672, was found to be the cheapest airline from Chicago to Road Town. An alternate airline flying to your destination would be United Airlines.

  • Can I find deals for flights from Chicago to Road Town that include hotel bookings?

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

  • How can I find direct flights from Chicago to Road Town?

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

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

    Yes. Cheapflights offers flight deals from Chicago to Road Town 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 Road Town?

    Currently, August is the cheapest month in which you can book a flight from Chicago to Road Town (average of $702). Flying from Chicago to Road Town in April is currently the most expensive (average of $959). 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 Road Town

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 Road Town

Discover the top 2 airlines that operate flights from Chicago to Road Town. 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 August 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$672Average$869FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$747Average$921FlexibilityNo cancel feeOn-time69%

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