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Road Town

$256+ 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 10/25. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — EIS
may. 10 — may. 171
sáb. 5/10
sáb. 5/17
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 mayo 5, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$568
(Kiwi.com)

One-way from

$256
(Kiwi.com)

Popular in

March

Cheapest in

October

Average price

$897
Provider with most accurate pricing for Chicago (CHI)-Road Town Beef Island flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Road Town Beef Island flights.
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From Chicago (CHI) to Road Town Beef Island
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One-way flight from Chicago (CHI) to Road Town Beef Island
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Highest demand for flights based on searches. 18% potential increase in price ($217 potential increase over avg. RT price).
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Cheapest flight prices on average. 7% potential price decrease ($66 potential savings vs. average RT price).
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Average for round-trip flights in May 2025
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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 mayo 5, 2025.

This Kiwi.com deal was found by Cheapflights users on 5/4. 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.
vie. 5/2311:30 amORD - EIS
1 stop27h 35mMultiple Airlines
sáb. 5/314:00 pmEIS - ORD
2 stops17h 50mMultiple Airlines
Deal found 5/4$568
This United Airlines deal was found by Cheapflights users on 5/3. 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.
lun. 9/298:52 amORD - EIS
1 stop28h 43mUnited Airlines
jue. 10/212:05 pmEIS - ORD
1 stop8h 58mUnited Airlines
Deal found 5/3$682
This American Airlines deal was found by Cheapflights users on 5/4. 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.
sáb. 8/238:34 pmORD - EIS
2 stops15h 41mAmerican Airlines
sáb. 8/301:55 pmEIS - ORD
2 stops10h 53mAmerican Airlines
Deal found 5/4$723

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 mayo 5, 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

vie. 5/23

11:30 am-4:05 pm

1 stop27h 35m

Road Town Beef Island

sáb. 5/31

4:00 pm-8:50 am

2 stops17h 50m

$568

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

lun. 9/29

8:52 am-2:35 pm

1 stop28h 43m

Road Town Beef Island

jue. 10/2

12:05 pm-8:03 pm

1 stop8h 58m

$682

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

sáb. 8/23

8:34 pm-1:15 pm

2 stops15h 41m

Road Town Beef Island

sáb. 8/30

1:55 pm-11:48 pm

2 stops10h 53m

$723

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

sáb. 10/25

12:31 pm-10:55 am

1 stop21h 24m

$256

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

sáb. 10/25

8:47 am-2:35 pm

2 stops28h 48m

$327

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

mié. 6/18

10:05 pm-2:03 pm

2 stops14h 58m

$829

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/4

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 May.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*2 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice 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 AranGrant to be most consistent on Cheapflights vs. AranGrant Users can find the same prices on Chicago-Road Town flight deals on Cheapflights vs. AranGrant >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 AranGrant the most. AranGrant 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

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

Currently, September is the cheapest month in which you can book a flight from Chicago to Road Town (average of $700). Flying from Chicago to Road Town in April is currently the most expensive (average of $947). 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 Road Town by month

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

In terms of precipitation, rainfall in Road Town 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 Road Town when rainfall is around 1.9 in.

Temperature in Road Town by month

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

If weather is an important factor for your trip to Road Town, 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 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 mayo 5, 2025.
United Airlines
7.4
Good
8,702 reviews

Boarding

7.7

Entertainment

7.1

Food

6.6

Overall

7.4

Crew

8.1

Comfort

7.3

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
8,702 reviews
United Airlines
7.4
Good
8,702 reviews

Boarding

7.7

Entertainment

7.1

Food

6.6

Overall

7.4

Crew

8.1

Comfort

7.3

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
8,702 reviews

Boarding

7.7

Entertainment

7.1

Food

6.6

Overall

7.4

Crew

8.1

Comfort

7.3

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?

    United Airlines, at $682, was found to be the cheapest airline from Chicago to Road Town. An alternate airline flying to your destination would be American Airlines. United Airlines is priced at 27% lower than the current average price of a flight leaving 3 months from now.

  • 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, September is the cheapest month in which you can book a flight from Chicago to Road Town (average of $700). Flying from Chicago to Road Town in April is currently the most expensive (average of $947). 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 mayo 5, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$666Average$812FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$747Average$931FlexibilityNo cancel feeOn-time69%

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