HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Road Town

$255+ Cheap flights from Chicago (CHI) to Road Town (EIS)

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 1/1. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — EIS
Dec 3 — Dec 101
Wed 12/3
Wed 12/10
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to Road Town 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 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 November 3, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$508
(Kiwi.com)

One-way from

$255
(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 Road Town Beef Island
Search Deals
One-way flight from Chicago (CHI) to Road Town Beef Island
Search Deals

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 November 3, 2025.

This Trip.com deal was found by Cheapflights users on 11/2. 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.
Wed 12/175:40 amORD - EIS
1 stop10h 40mMultiple Airlines
Wed 12/2412:50 pmEIS - ORD
1 stop12h 35mMultiple Airlines
Deal found 11/2$564
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 11/2511:48 amORD - EIS
2 stops28h 32mMultiple Airlines
Tue 12/212:10 pmEIS - ORD
1 stop9h 13mMultiple Airlines
Deal found 11/2$658
This Kiwi.com deal was found by Cheapflights users on 11/1. 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 12/269:31 pmORD - EIS
2 stops39h 44mMultiple Airlines
Wed 12/314:00 pmEIS - ORD
1 stop9h 25mMultiple Airlines
Deal found 11/1$844
This Kiwi.com deal was found by Cheapflights users on 11/1. 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 12/255:45 amORD - EIS
1 stop8h 20mMultiple Airlines
Wed 12/318:55 amEIS - ORD
1 stop16h 30mMultiple Airlines
Deal found 11/1$846

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 November 3, 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

Wed 2/4

4:35 pm-10:55 am

1 stop16h 20m

Road Town Beef Island

Sun 2/8

4:00 pm-6:10 pm

2 stops28h 10m

$508

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Wed 12/17

5:40 am-6:20 pm

1 stop10h 40m

Road Town Beef Island

Wed 12/24

12:50 pm-11:25 pm

1 stop12h 35m

$564

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Sat 2/21

10:15 am-2:10 pm

2 stops49h 55m

Road Town Beef Island

Sat 2/28

8:55 am-6:00 pm

1 stop11h 05m

$580

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Tue 11/25

5:00 am-6:20 pm

3 stops35h 20m

Road Town Beef Island

Tue 12/2

12:10 pm-12:08 pm

3 stops25h 58m

$776

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Sat 1/31

2:47 pm-4:05 pm

3 stops23h 18m

Road Town Beef Island

Sun 2/8

8:55 am-9:44 am

2 stops26h 49m

$793

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Thu 1/1

5:45 am-6:20 pm

1 stop10h 35m

$255

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Fri 12/19

5:00 am-10:14 pm

1 stop15h 14m

$547

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Tue 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 11/2

Compare providers for flights from Chicago to Road Town

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Road Town in November.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*1 star
AranGrantPrice Accuracy2 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago-Road Town flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago-Road Town flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Chicago-Road Town flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Road Town flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Road Town flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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 November 3, 2025.
Peruse reviews from past customers who have flown with 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.
American Airlines
7.2
Good
11,038 reviews

Entertainment

6.9

Food

6.4

Crew

8.0

Overall

7.2

Boarding

7.5

Comfort

7.2

Reviews

1 / 20
2.0
Mediocre

Jeremy,Sep 2025

SAN - PHL

Terrible. Bad customer service and unacceptable delay on the tarmac
American Airlines
7.2
Good
11,038 reviews
American Airlines
7.2
Good
11,038 reviews

Entertainment

6.9

Food

6.4

Crew

8.0

Overall

7.2

Boarding

7.5

Comfort

7.2

Reviews

1 / 20
2.0
Mediocre

Jeremy,Sep 2025

SAN - PHL

Terrible. Bad customer service and unacceptable delay on the tarmac

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 $693, 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.

See more FAQs

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 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 November 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$693Average$878FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$747Average$921FlexibilityNo 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.