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Cheap flights from Chicago to Road Town from $277

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 11/14. 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
0 bags

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Find the cheapest flights from Chicago to Road Town

Cheap round-trip flights

Logo
6:30 am - 4:05 pmORD-EIS
8h 35m2 stops
Logo
4:00 pm - 11:56 pmEIS-ORD
8h 56m1 stop
$579
Find Deal
Sun, Sep 14 - Sun, Sep 21
Logo
12:55 pm - 3:15 pmORD-EIS
25h 20m1 stop
Logo
8:55 am - 11:56 pmEIS-ORD
16h 01m1 stop
$585
Find Deal
Sun, Sep 14 - Sun, Sep 21
Logo
8:49 pm - 4:05 pmORD-EIS
42h 16m2 stops
Logo
4:00 pm - 11:56 pmEIS-ORD
8h 56m1 stop
$587
Find Deal
Fri, Sep 12 - Fri, Sep 19
American Airlines Logo
7:05 pm - 1:16 pmORD-EIS
17h 11m1 stop
American Airlines Logo
1:46 pm - 11:49 pmEIS-ORD
11h 03m1 stop
$754American Airlines
Find Deal
Wed, Aug 27 - Wed, Sep 3
American Airlines Logo
8:34 pm - 1:16 pmORD-EIS
15h 42m2 stops
American Airlines Logo
1:46 pm - 7:42 amEIS-ORD
18h 56m2 stops
$758American Airlines
Find Deal
Wed, Aug 27 - Wed, Sep 3
American Airlines Logo
7:15 pm - 1:06 pmORD-EIS
16h 51m1 stop
American Airlines Logo
2:00 pm - 9:22 pmEIS-ORD
8h 22m1 stop
$774American Airlines
Find Deal
Sat, Oct 4 - Thu, Oct 9
American Airlines Logo
8:29 pm - 1:06 pmORD-EIS
15h 37m2 stops
American Airlines Logo
2:00 pm - 11:53 pmEIS-ORD
10h 53m2 stops
$778American Airlines
Find Deal
Sat, Oct 4 - Thu, Oct 9
United Airlines Logo
8:55 am - 6:55 pmORD-EIS
8h 00m1 stop
United Airlines Logo
1:08 pm - 11:32 amEIS-ORD
24h 24m1 stop
$876United Airlines
Find Deal
Tue, Nov 11 - Tue, Nov 18
United Airlines Logo
9:00 am - 6:55 pmORD-EIS
32h 55m2 stops
United Airlines Logo
10:05 am - 2:54 pmEIS-ORD
29h 49m2 stops
$918United Airlines
Find Deal
Sat, Oct 25 - Thu, Oct 30
United Airlines Logo
9:00 am - 6:55 pmORD-EIS
32h 55m2 stops
United Airlines Logo
10:05 am - 2:54 pmEIS-ORD
29h 49m2 stops
$922United Airlines
Find Deal
Sat, Oct 25 - Thu, Oct 30

United Airlines flights from Chicago to Road Town

Our best United Airlines deals on Chicago to Road Town flight tickets
United Airlines
Nov 11
ORD8:55 amChicago O'Hare Intl
8h 00m
1 stop
EIS6:55 pmRoad Town Beef Island
Nov 18
EIS1:08 pmRoad Town Beef Island
24h 24m
1 stop
ORD11:32 amChicago O'Hare Intl
$876
Find similar
United Airlines
Oct 25
ORD9:00 amChicago O'Hare Intl
32h 55m
2 stops
EIS6:55 pmRoad Town Beef Island
Oct 30
EIS10:05 amRoad Town Beef Island
29h 49m
2 stops
ORD2:54 pmChicago O'Hare Intl
$918
Find similar
United Airlines
Oct 25
ORD9:00 amChicago O'Hare Intl
32h 55m
2 stops
EIS6:55 pmRoad Town Beef Island
Oct 30
EIS10:05 amRoad Town Beef Island
29h 49m
2 stops
ORD2:54 pmChicago O'Hare Intl
$922
Find similar

American Airlines flights from Chicago to Road Town

Our best American Airlines deals on Chicago to Road Town flight tickets
American Airlines
Aug 27
ORD7:05 pmChicago O'Hare Intl
17h 11m
1 stop
EIS1:16 pmRoad Town Beef Island
Sep 3
EIS1:46 pmRoad Town Beef Island
11h 03m
1 stop
ORD11:49 pmChicago O'Hare Intl
$754
Find similar
American Airlines
Aug 27
ORD8:34 pmChicago O'Hare Intl
15h 42m
2 stops
EIS1:16 pmRoad Town Beef Island
Sep 3
EIS1:46 pmRoad Town Beef Island
18h 56m
2 stops
ORD7:42 amChicago O'Hare Intl
$758
Find similar
American Airlines
Oct 4
ORD7:15 pmChicago O'Hare Intl
16h 51m
1 stop
EIS1:06 pmRoad Town Beef Island
Oct 9
EIS2:00 pmRoad Town Beef Island
8h 22m
1 stop
ORD9:22 pmChicago O'Hare Intl
$774
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 July 31, 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

Sun 9/14

6:30 am-4:05 pm

2 stops8h 35m

Road Town Beef Island

Sun 9/21

4:00 pm-11:56 pm

1 stop8h 56m

$579

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Sun 9/14

12:55 pm-3:15 pm

1 stop25h 20m

Road Town Beef Island

Sun 9/21

8:55 am-11:56 pm

1 stop16h 01m

$585

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Fri 9/12

8:49 pm-4:05 pm

2 stops42h 16m

Road Town Beef Island

Fri 9/19

4:00 pm-11:56 pm

1 stop8h 56m

$587

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Wed 8/27

7:05 pm-1:16 pm

1 stop17h 11m

Road Town Beef Island

Wed 9/3

1:46 pm-11:49 pm

1 stop11h 03m

$754

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Wed 8/27

8:34 pm-1:16 pm

2 stops15h 42m

Road Town Beef Island

Wed 9/3

1:46 pm-7:42 am

2 stops18h 56m

$758

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Sat 10/4

7:15 pm-1:06 pm

1 stop16h 51m

Road Town Beef Island

Thu 10/9

2:00 pm-9:22 pm

1 stop8h 22m

$774

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Sat 10/4

8:29 pm-1:06 pm

2 stops15h 37m

Road Town Beef Island

Thu 10/9

2:00 pm-11:53 pm

2 stops10h 53m

$778

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Tue 11/11

8:55 am-6:55 pm

1 stop8h 00m

Road Town Beef Island

Tue 11/18

1:08 pm-11:32 am

1 stop24h 24m

$876

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Sat 10/25

9:00 am-6:55 pm

2 stops32h 55m

Road Town Beef Island

Thu 10/30

10:05 am-2:54 pm

2 stops29h 49m

$918

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Sat 10/25

9:00 am-6:55 pm

2 stops32h 55m

Road Town Beef Island

Thu 10/30

10:05 am-2:54 pm

2 stops29h 49m

$922

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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 month to fly to Road Town?

The month of October is, on average, the cheapest month to fly to Road Town from Chicago, with most prices found around $741. If you don’t want to visit Road Town in October, then you should wait until February to fly from Chicago, when ticket prices are also cheap, with an average price of $743.

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.

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

Best Price Found

$277

Fastest flight time

8h 00m

Direct flights

None

Airports in Road Town

1 airport
The best one-way flight to Road Town from Chicago in the past 72 hours is $277. The best round-trip flight deal from Chicago to Road Town found on momondo in the last 72 hours is $579.
The fastest flight from Chicago to Road Town takes 8h 00m
There are no direct flights from Chicago to Road Town. Popular non-direct route for this connection is Chicago O'Hare Intl Airport - Road Town Beef Island Airport.
There is 1 airport near Road Town: Road Town Beef Island (EIS)
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 00m, 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 $662Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $747Free CancellationRating
7.4
8,900 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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