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Cheap flights from Chicago to Road Town from $515

This is the cheapest round-trip flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Road Town departing on 1/31. 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
0 bags

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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
12:17 pm - 10:55 am
ORD
-
EIS
20h 38m1 stop
Multiple Airlines Logo
8:55 am - 9:10 am
EIS
-
ORD
26h 15m2 stops
$515Multiple Airlines
Sat, Jan 31 - Sat, Feb 7
Multiple Airlines Logo
12:22 pm - 2:10 pm
ORD
-
EIS
23h 48m1 stop
Multiple Airlines Logo
4:00 pm - 9:39 am
EIS
-
ORD
43h 39m2 stops
$546Multiple Airlines
Wed, Feb 18 - Sun, Feb 22
Multiple Airlines Logo
12:17 pm - 10:55 am
ORD
-
EIS
20h 38m1 stop
Multiple Airlines Logo
8:55 am - 4:37 pm
EIS
-
ORD
9h 42m1 stop
$558Multiple Airlines
Sat, Jan 31 - Sat, Feb 7
Multiple Airlines Logo
12:17 pm - 10:55 am
ORD
-
EIS
20h 38m1 stop
Multiple Airlines Logo
12:10 pm - 3:48 pm
EIS
-
ORD
29h 38m1 stop
$559Multiple Airlines
Thu, Feb 26 - Tue, Mar 3
Multiple Airlines Logo
7:13 pm - 6:20 pm
ORD
-
EIS
21h 07m3 stops
Multiple Airlines Logo
7:15 am - 11:47 pm
EIS
-
ORD
18h 32m3 stops
$604Multiple Airlines
Tue, Feb 24 - Wed, Mar 4
Multiple Airlines Logo
12:44 pm - 10:55 am
ORD
-
EIS
20h 11m2 stops
Multiple Airlines Logo
8:55 am - 11:47 pm
EIS
-
ORD
16h 52m2 stops
$610Multiple Airlines
Sat, Jan 31 - Sat, Feb 7
Multiple Airlines Logo
8:16 pm - 6:20 pm
ORD
-
EIS
20h 04m2 stops
Multiple Airlines Logo
7:15 am - 11:47 pm
EIS
-
ORD
18h 32m3 stops
$626Multiple Airlines
Tue, Feb 24 - Wed, Mar 4
Multiple Airlines Logo
12:22 pm - 2:10 pm
ORD
-
EIS
23h 48m1 stop
Multiple Airlines Logo
4:00 pm - 3:48 pm
EIS
-
ORD
25h 48m1 stop
$642Multiple Airlines
Wed, Feb 18 - Sun, Feb 22
Multiple Airlines Logo
7:13 pm - 6:20 pm
ORD
-
EIS
21h 07m3 stops
Multiple Airlines Logo
8:55 am - 3:48 pm
EIS
-
ORD
8h 53m1 stop
$663Multiple Airlines
Tue, Feb 24 - Wed, Mar 4
Multiple Airlines Logo
10:48 am - 10:55 am
ORD
-
EIS
22h 07m2 stops
Multiple Airlines Logo
12:10 pm - 2:17 pm
EIS
-
ORD
28h 07m3 stops
$698Multiple Airlines
Sat, Jan 31 - Sat, Feb 7

American Airlines flights from Chicago to Road Town

Our best American Airlines deals on Chicago to Road Town flight tickets
American Airlines
Mar 6
ORD8:30 amChicago O'Hare Intl
11h 42m
1 stop
EIS10:12 pmRoad Town Beef Island
Mar 14
EIS8:48 amRoad Town Beef Island
15h 29m
1 stop
ORD11:17 pmChicago O'Hare Intl
$884
Find similar
American Airlines
Feb 27
ORD5:45 amChicago O'Hare Intl
14h 27m
1 stop
EIS10:12 pmRoad Town Beef Island
Mar 8
EIS11:32 amRoad Town Beef Island
14h 03m
1 stop
ORD12:35 amChicago O'Hare Intl
$889
Find similar
American Airlines
Feb 27
ORD12:32 pmChicago O'Hare Intl
7h 40m
1 stop
EIS10:12 pmRoad Town Beef Island
Mar 8
EIS11:32 amRoad Town Beef Island
10h 50m
2 stops
ORD9:22 pmChicago O'Hare Intl
$894
Find similar

United Airlines flights from Chicago to Road Town

Our best United Airlines deals on Chicago to Road Town flight tickets
United Airlines
Jan 31
ORD8:55 amChicago O'Hare Intl
29h 20m
1 stop
EIS4:15 pmRoad Town Beef Island
Feb 7
EIS11:21 amRoad Town Beef Island
10h 59m
1 stop
ORD8:20 pmChicago O'Hare Intl
$1,004
Find similar
United Airlines
Mar 13
ORD9:30 amChicago O'Hare Intl
26h 04m
1 stop
EIS12:34 pmRoad Town Beef Island
Mar 22
EIS3:00 pmRoad Town Beef Island
28h 45m
1 stop
ORD6:45 pmChicago O'Hare Intl
$1,049
Find similar
United Airlines
Mar 13
ORD9:30 amChicago O'Hare Intl
26h 04m
1 stop
EIS12:34 pmRoad Town Beef Island
Mar 22
EIS3:00 pmRoad Town Beef Island
34h 26m
2 stops
ORD12:26 amChicago O'Hare Intl
$1,081
Find similar

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 December 18, 2025.
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

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Sat 1/31

12:17 pm-10:55 am

1 stop20h 38m

Road Town Beef Island

Sat 2/7

8:55 am-9:10 am

2 stops26h 15m

$515

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Wed 2/18

12:22 pm-2:10 pm

1 stop23h 48m

Road Town Beef Island

Sun 2/22

4:00 pm-9:39 am

2 stops43h 39m

$546

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Sat 1/31

12:17 pm-10:55 am

1 stop20h 38m

Road Town Beef Island

Sat 2/7

8:55 am-4:37 pm

1 stop9h 42m

$558

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Thu 2/26

12:17 pm-10:55 am

1 stop20h 38m

Road Town Beef Island

Tue 3/3

12:10 pm-3:48 pm

1 stop29h 38m

$559

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Tue 2/24

7:13 pm-6:20 pm

3 stops21h 07m

Road Town Beef Island

Wed 3/4

7:15 am-11:47 pm

3 stops18h 32m

$604

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Sat 1/31

12:44 pm-10:55 am

2 stops20h 11m

Road Town Beef Island

Sat 2/7

8:55 am-11:47 pm

2 stops16h 52m

$610

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Tue 2/24

8:16 pm-6:20 pm

2 stops20h 04m

Road Town Beef Island

Wed 3/4

7:15 am-11:47 pm

3 stops18h 32m

$626

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Wed 2/18

12:22 pm-2:10 pm

1 stop23h 48m

Road Town Beef Island

Sun 2/22

4:00 pm-3:48 pm

1 stop25h 48m

$642

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Tue 2/24

7:13 pm-6:20 pm

3 stops21h 07m

Road Town Beef Island

Wed 3/4

8:55 am-3:48 pm

1 stop8h 53m

$663

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Sat 1/31

10:48 am-10:55 am

2 stops22h 07m

Road Town Beef Island

Sat 2/7

12:10 pm-2:17 pm

3 stops28h 07m

$698

Flights are sorted by cheapest round-trip flights first.

Sorted by cheapest first

See travel insights to Road Town from

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

What is the cheapest day to depart on your flight to Road Town?

Our data shows that Tuesday is the least expensive day to fly to Road Town. Tickets to fly out on this day can be as low as $752. If your travel schedule is flexible, try to avoid departing on a Saturday because tickets tend to average around $1,203. These prices are subject to change though, so be sure to set up a Price Alert for flights to Road Town.

What is the cheapest time of day to depart on your flight to Road Town?

Flying to Road Town from Chicago in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $867 when looking at flights departing in the afternoon. Flights at noon are often more expensive with an average ticket price of $931.

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

You could potentially save up to 42% 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 09m

Direct flights

None
The fastest flight from Chicago to Road Town takes 8h 09m
There are no direct flights from Chicago to Road Town. There are no popular flight routes from Chicago to Road Town.
Search flight deals

  • 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 09m, 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 $693Free CancellationRating
7.2
11,054 reviews
Search American Airlines flights
United AirlinesPriceFrom $747Free CancellationRating
7.4
9,091 reviews
Search United 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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