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

American Airlines, at $707, was found to be the cheapest airline from Chicago to Road Town. An alternate airline flying to your destination would be United Airlines.

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.

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).

What is the cheapest time of day to fly from CHI to EIS?

When flying from Chicago to Road Town, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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.

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.

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.

$238+ Flights from Chicago to Road Town

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Cheap 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 December 27, 2025.

Fri 12/269:09 pmORD - EIS

2 stops43h 11mMultiple Airlines

Tue 12/3012:10 pmEIS - ORD

1 stop13h 15mMultiple Airlines

Deal found 12/25

$1,043

Fri 12/261:24 pmORD - EIS

2 stops24h 51mUnited Airlines

Tue 12/308:15 amEIS - ORD

2 stops32h 05mUnited Airlines

Deal found 12/25

$1,160

Tue 12/305:45 amORD - EIS

1 stop7h 30mMultiple Airlines

Sun 1/48:55 amEIS - ORD

1 stop16h 30mMultiple Airlines

Deal found 12/27

$1,240

Sun 12/2812:32 pmORD - EIS

1 stop7h 42mAmerican Airlines

Sat 1/38:00 amEIS - ORD

1 stop12h 34mAmerican Airlines

Deal found 12/25

$1,654

Tue 12/307:26 pmORD - EIS

1 stop14h 49mAmerican Airlines

Sun 1/45:28 pmEIS - ORD

1 stop17h 19mAmerican Airlines

Deal found 12/27

$1,749

Sun 12/2810:35 amORD - EIS

2 stops29h 55mUnited Airlines

Sat 1/39:41 amEIS - ORD

2 stops30h 39mUnited Airlines

Deal found 12/25

$1,892

Best flights from Chicago to Road Town
Discover carefully curated flight deals from Chicago to Road Town that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated December 27, 2025.

Mon 1/2612:05 pmORD - EIS

2 stops44h 50mMultiple Airlines

Mon 2/24:00 pmEIS - ORD

1 stop26h 37mMultiple Airlines

Deal found 12/27

$488

Fri 4/105:24 pmORD - EIS

1 stop16h 51mAmerican Airlines

Mon 4/209:00 amEIS - ORD

1 stop14h 39mAmerican Airlines

Deal found 12/26

$739

Fri 3/69:30 amORD - EIS

1 stop25h 04mUnited Airlines

Sat 3/149:41 amEIS - ORD

1 stop27h 11mUnited Airlines

Deal found 12/27

$771

Sun 2/159:18 amORD - EIS

2 stops31h 02mMultiple Airlines

Mon 2/234:00 pmEIS - ORD

1 stop25h 48mMultiple Airlines

Deal found 12/26

$528

Thu 2/512:17 pmORD - EIS

1 stop20h 38mMultiple Airlines

Thu 2/128:55 amEIS - ORD

1 stop8h 53mMultiple Airlines

Deal found 12/26

$632

Thu 5/79:55 amORD - EIS

2 stops10h 15mAmerican Airlines

Fri 5/159:00 amEIS - ORD

2 stops9h 40mAmerican Airlines

Deal found 12/25

$744

Fri 4/106:00 amORD - EIS

2 stops11h 10mMultiple Airlines

Mon 4/204:00 pmEIS - ORD

1 stop25h 37mMultiple Airlines

Deal found 12/26

$654

Mon 5/118:25 amORD - EIS

2 stops11h 45mAmerican Airlines

Mon 5/184:20 pmEIS - ORD

1 stop17h 28mAmerican Airlines

Deal found 12/26

$749

Thu 5/712:22 pmORD - EIS

1 stop28h 48mMultiple Airlines

Fri 5/1511:35 amEIS - ORD

2 stops12h 37mMultiple Airlines

Deal found 12/25

$674

Last-minute flights from Chicago to Road Town
Discover last-minute flight deals from Chicago to Road Town. Data last updated December 27, 2025 and is based on user searches.

Fri 12/269:09 pmORD - EIS

2 stops43h 11mMultiple Airlines

Tue 12/3012:10 pmEIS - ORD

1 stop13h 15mMultiple Airlines

Deal found 12/25

$1,043

Fri 12/261:24 pmORD - EIS

2 stops24h 51mUnited Airlines

Tue 12/308:15 amEIS - ORD

2 stops32h 05mUnited Airlines

Deal found 12/25

$1,160

Tue 1/67:00 amORD - EIS

1 stop8h 09mAmerican Airlines

Thu 1/158:00 amEIS - ORD

1 stop18h 30mAmerican Airlines

Deal found 12/25

$1,144

Fri 1/168:10 amORD - EIS

1 stop12h 06mAmerican Airlines

Sun 1/255:49 pmEIS - ORD

1 stop17h 16mAmerican Airlines

Deal found 12/26

$1,074

Sat 1/175:00 amORD - EIS

1 stop15h 16mAmerican Airlines

Mon 1/265:49 pmEIS - ORD

1 stop17h 16mAmerican Airlines

Deal found 12/27

$1,024

Mon 1/2612:05 pmORD - EIS

2 stops44h 50mMultiple Airlines

Mon 2/24:00 pmEIS - ORD

1 stop26h 37mMultiple Airlines

Deal found 12/27

$488

Mon 1/269:54 amORD - EIS

2 stops10h 22mAmerican Airlines

Mon 2/28:00 amEIS - ORD

2 stops12h 01mAmerican Airlines

Deal found 12/27

$899

Sat 1/317:00 amORD - EIS

1 stop13h 16mAmerican Airlines

Sun 2/88:00 amEIS - ORD

1 stop18h 30mAmerican Airlines

Deal found 12/26

$1,204

One-way flights from Chicago to Road Town
Search for one-way flight options from Chicago to Road Town. Find affordable one-way fares based on user searches. Data last updated December 27, 2025.

Wed 1/2112:17 pmORD - EIS

1 stop23h 53mMultiple Airlines

Deal found 12/26

$238

Thu 2/54:19 pmORD - EIS

3 stops19h 51mMultiple Airlines

Deal found 12/26

$266

Thu 2/51:00 pmMDW - EIS

2 stops23h 10mMultiple Airlines

Deal found 12/26

$274

Find flight deals from Chicago to Road Town

Most accurate provider	eDreams 3 stars
Most trusted provider	eDreams 3 stars
Round-trip from	$528 (Kiwi.com)
One-way from	$238 (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

Fly from

Fly to

Route

Depart

Return

Price

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Mon 1/26

12:05 pm-10:55 am

2 stops44h 50m

Road Town Beef Island

Mon 2/2

4:00 pm-4:37 pm

1 stop26h 37m

$488

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Sun 2/15

9:18 am-6:20 pm

2 stops31h 02m

Road Town Beef Island

Mon 2/23

4:00 pm-3:48 pm

1 stop25h 48m

$528

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Thu 2/5

12:17 pm-10:55 am

1 stop20h 38m

Road Town Beef Island

Thu 2/12

8:55 am-3:48 pm

1 stop8h 53m

$632

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Fri 4/10

6:00 am-6:10 pm

2 stops11h 10m

Road Town Beef Island

Mon 4/20

4:00 pm-4:37 pm

1 stop25h 37m

$654

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Thu 5/7

12:22 pm-6:10 pm

1 stop28h 48m

Road Town Beef Island

Fri 5/15

11:35 am-11:12 pm

2 stops12h 37m

$674

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Fri 4/10

5:24 pm-11:15 am

1 stop16h 51m

Road Town Beef Island

Mon 4/20

9:00 am-10:39 pm

1 stop14h 39m

$739

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Thu 5/7

9:55 am-9:10 pm

2 stops10h 15m

Road Town Beef Island

Fri 5/15

9:00 am-5:40 pm

2 stops9h 40m

$744

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Mon 5/11

8:25 am-9:10 pm

2 stops11h 45m

Road Town Beef Island

Mon 5/18

4:20 pm-8:48 am

1 stop17h 28m

$749

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Fri 3/6

9:30 am-12:34 pm

1 stop25h 04m

Road Town Beef Island

Sat 3/14

9:41 am-11:52 am

1 stop27h 11m

$771

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Wed 1/21

12:17 pm-2:10 pm

1 stop23h 53m

$238

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/26

Showing 1-10 of 12 results

Compare providers for flights from Chicago to Road Town

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 December.

Provider	Price Accuracy	Trust Score*
FlightHub	Price Accuracy3 stars	Trust Score*1 star
AranGrant	Price Accuracy2 stars	Trust Score*3 stars
eDreams	Price Accuracy3 stars	Trust 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

How often are flights from Chicago to Road Town delayed?

About 50% of weekly flights between Chicago and Road Town have experienced delays in the past year, with the average delay time being 41 minutes.

What is the most punctual flight time for Chicago to Road Town flights?

Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the morning tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Thursday tends to have the lowest number of delays on this route, whereas Monday has historically faced a higher average of delays compared to other days of the week.

Reviews of airlines servicing Road Town

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

11,067 reviews

Reviews

1 / 20

10.0

Excellent

Jeremy,Dec 2025

OKC - CLT

Was an okay flight. Had extra seat empty beside me so was able to stretch a bit

American Airlines

7.2

Good

11,067 reviews

American Airlines

7.2

Good

11,067 reviews

Reviews

1 / 20

10.0

Excellent

Jeremy,Dec 2025

OKC - CLT

Was an okay flight. Had extra seat empty beside me so was able to stretch a bit

Related info for your journey

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 $707, 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

Alternative routes for Chicago to Road Town

O'Hare Intl to Road Town flights

St. Louis to Road Town flights

Top 2 airlines flying from Chicago to Road Town

Airline	Cheapest	Average	Flexibility	On-time
American Airlines	Cheapest$707	Average$885	FlexibilityNo cancel fee	On-time71%
United Airlines	Cheapest$747	Average$906	FlexibilityNo cancel fee	On-time69%

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$238+ 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 1/21. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Chicago to Road Town with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Cheap flight deals from Chicago to Road Town

Cheapest flights from Chicago to Road TownExplore 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 December 27, 2025.

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 December 27, 2025.

Find flight deals from Chicago to Road Town

Most accurate provider

Most trusted provider

Round-trip from

One-way from

Cheapflights Fare Finder

Use the filters below to find and compare flights from Chicago to Road Town that are best for you.

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 December.

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.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Road Town

How often are flights from Chicago to Road Town delayed?

What is the most punctual flight time for Chicago to Road Town flights?

What day of the week experiences the fewest flight delays on this route?

Reviews of airlines servicing Road Town

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.

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?

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

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

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

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

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.

Top 2 airlines flying from Chicago to Road Town

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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 December 27, 2025.