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Cheap flights from Chicago to Road Town from $414

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Road Town departing on 9/14. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Chicago to Road Town

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
7:53 pm - 6:10 pm-
20h 17m
Multiple Airlines Logo
9:00 am - 1:09 am-
18h 09m
$770Multiple Airlines
Thu, Nov 26 - Sat, Dec 5
Multiple Airlines Logo
7:53 pm - 10:55 am-
13h 02m
Multiple Airlines Logo
4:00 pm - 1:11 pm-
23h 11m
$806Multiple Airlines
Wed, Nov 25 - Sun, Dec 6
American Airlines Logo
6:14 am - 3:10 pm-
7h 56m
American Airlines Logo
2:01 pm - 12:38 am-
11h 37m
$808American Airlines
Mon, Oct 12 - Thu, Oct 15
American Airlines Logo
6:00 am - 6:20 pm-
10h 20m
American Airlines Logo
5:38 pm - 12:44 am-
9h 06m
$808American Airlines
Mon, Nov 9 - Mon, Nov 16
American Airlines Logo
7:00 am - 3:10 pm-
7h 10m
American Airlines Logo
2:01 pm - 12:38 am-
11h 37m
$808American Airlines
Mon, Oct 12 - Thu, Oct 15
American Airlines Logo
5:05 am - 3:10 pm-
9h 05m
American Airlines Logo
2:01 pm - 12:08 am-
11h 07m
$813American Airlines
Mon, Oct 12 - Thu, Oct 15
American Airlines Logo
7:00 pm - 1:52 pm-
17h 52m
American Airlines Logo
2:32 pm - 12:33 am-
11h 01m
$813American Airlines
Wed, Sep 23 - Wed, Sep 30
American Airlines Logo
7:00 am - 3:10 pm-
7h 10m
American Airlines Logo
3:50 pm - 7:27 am-
16h 37m
$813American Airlines
Mon, Oct 12 - Thu, Oct 15
American Airlines Logo
5:00 am - 3:10 pm-
9h 10m
American Airlines Logo
2:01 pm - 12:08 am-
11h 07m
$813American Airlines
Mon, Oct 12 - Thu, Oct 15
American Airlines Logo
6:00 am - 6:20 pm-
10h 20m
American Airlines Logo
2:47 pm - 12:01 am-
11h 14m
$813American Airlines
Mon, Nov 9 - Mon, Nov 16

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American Airlines flights from Chicago to Road Town

Our best American Airlines deals on Chicago to Road Town flight tickets
American Airlines
Oct 12
ORD7:00 amChicago O'Hare Intl
7h 10m
1 stop
EIS3:10 pmRoad Town Beef Island
Oct 15
EIS2:01 pmRoad Town Beef Island
11h 37m
1 stop
ORD12:38 amChicago O'Hare Intl
$808
American Airlines
Oct 12
ORD5:00 amChicago O'Hare Intl
9h 10m
2 stops
EIS3:10 pmRoad Town Beef Island
Oct 15
EIS2:01 pmRoad Town Beef Island
11h 07m
2 stops
ORD12:08 amChicago O'Hare Intl
$813
American Airlines
Sep 23
ORD1:59 pmChicago O'Hare Intl
22h 53m
1 stop
EIS1:52 pmRoad Town Beef Island
Sep 30
EIS2:32 pmRoad Town Beef Island
9h 58m
1 stop
ORD11:30 pmChicago O'Hare Intl
$814

United Airlines flights from Chicago to Road Town

Our best United Airlines deals on Chicago to Road Town flight tickets
United Airlines
Aug 23
ORD8:55 amChicago O'Hare Intl
29h 43m
1 stop
EIS3:38 pmRoad Town Beef Island
Aug 27
EIS12:20 pmRoad Town Beef Island
8h 45m
1 stop
ORD8:05 pmChicago O'Hare Intl
$880
United Airlines
Sep 1
ORD8:55 amChicago O'Hare Intl
9h 05m
1 stop
EIS7:00 pmRoad Town Beef Island
Sep 5
EIS9:20 amRoad Town Beef Island
11h 45m
1 stop
ORD8:05 pmChicago O'Hare Intl
$940
United Airlines
Aug 23
ORD5:30 amChicago O'Hare Intl
33h 08m
2 stops
EIS3:38 pmRoad Town Beef Island
Aug 27
EIS12:20 pmRoad Town Beef Island
8h 45m
1 stop
ORD8:05 pmChicago O'Hare Intl
$1,010

momondo 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, momondo users made 832,500 searches. Data last updated August 4, 2026.
Use the filters below to find and compare flights from Chicago to Road Town that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Thu 11/26

7:53 pm-6:10 pm

1 stop20h 17m

Road Town Beef Island

Sat 12/5

9:00 am-1:09 am

2 stops18h 09m

$770

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Wed 11/25

7:53 pm-10:55 am

1 stop13h 02m

Road Town Beef Island

Sun 12/6

4:00 pm-1:11 pm

2 stops23h 11m

$806

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Mon 10/12

6:14 am-3:10 pm

1 stop7h 56m

Road Town Beef Island

Thu 10/15

2:01 pm-12:38 am

1 stop11h 37m

$808

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Mon 11/9

6:00 am-6:20 pm

1 stop10h 20m

Road Town Beef Island

Mon 11/16

5:38 pm-12:44 am

1 stop9h 06m

$808
Quickest round-trip

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Mon 10/12

7:00 am-3:10 pm

1 stop7h 10m

Road Town Beef Island

Thu 10/15

2:01 pm-12:38 am

1 stop11h 37m

$808

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Mon 10/12

5:05 am-3:10 pm

1 stop9h 05m

Road Town Beef Island

Thu 10/15

2:01 pm-12:08 am

2 stops11h 07m

$813

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Wed 9/23

7:00 pm-1:52 pm

1 stop17h 52m

Road Town Beef Island

Wed 9/30

2:32 pm-12:33 am

1 stop11h 01m

$813

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Mon 10/12

7:00 am-3:10 pm

1 stop7h 10m

Road Town Beef Island

Thu 10/15

3:50 pm-7:27 am

2 stops16h 37m

$813

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Mon 10/12

5:00 am-3:10 pm

2 stops9h 10m

Road Town Beef Island

Thu 10/15

2:01 pm-12:08 am

2 stops11h 07m

$813

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Mon 11/9

6:00 am-6:20 pm

1 stop10h 20m

Road Town Beef Island

Mon 11/16

2:47 pm-12:01 am

2 stops11h 14m

$813

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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How to get the cheapest flight ticket from Chicago to Road Town

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Can stopping save me money on Chicago to Road Town flights?

You could potentially save up to 31% on your flight if you consider stops on a Chicago to Road Town flight.

When to book flights from Chicago to Road Town

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago to Road Town according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago to Road Town (CHI to EIS) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Road Town

Fastest flight time

8h 05m

Direct flights

None
The fastest flight from Chicago to Road Town takes 8h 05m
There are no direct flights from Chicago to Road Town. There are no popular flight routes from Chicago to Road Town.
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Frequently asked questions about flying from Chicago to Road Town

  • How far is Chicago to Road Town Beef Island by plane?

    A flight from Chicago to Road Town Beef Island will travel around 2109.0 mi. Flights usually cover this in 8h 05m, depending on flying conditions and air traffic around both airports.

  • When did momondo last update prices for flights from Chicago to Road Town Beef Island Airport?

    Prices for flights from Chicago to Road Town Beef Island Airport refresh daily.

  • How many operators does momondo search for flights from Chicago to Road Town Beef Island Airport?

  • How old do you have to be to fly from Chicago to Road Town Beef Island Airport?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago to Road Town Beef Island Airport.

  • What documentation or ID do you need to fly to Road Town Beef Island Airport?

    The travel and health documents you'll need for your trip to Road Town Beef Island Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Road Town Beef Island Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular airline from Chicago to Road Town?

Best airlines flying from Chicago to Road Town

Compare and see reviews for airlines that fly from Chicago to Road Town with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $788Free CancellationRating
7.1
11,856 reviews
Search American Airlines flights

Traveling to a place near Road Town?

Book flights to Road Town if you plan to visit one of these locations
Jost Van Dyke
Scrub Island

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Road Town?

Finding the right flight to Road Town from Chicago is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Road Town quick and easy, saving you time and money.

Can I find flights from Chicago to Road Town with flexible booking policies on momondo?

momondo does allow users to show only those flights to Road Town from Chicago which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from Chicago to Road Town?

momondo provides multiple filters to help you find the best flight to Road Town from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Chicago to Road Town right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Chicago to Road Town now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Road Town and let you know when they change.

An easier way to manage your Road Town trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
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