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Cheap flights from Chicago to Road Town from $551

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 10/30. 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
6:40 am - 10:55 amORD-EIS
27h 15m2 stops
Logo
4:00 pm - 6:00 pmEIS-ORD
28h 00m1 stop
$551
Find Deal
Thu, Oct 30 - Thu, Nov 6
Logo
1:35 pm - 3:15 pmORD-EIS
23h 40m2 stops
Logo
12:10 pm - 6:00 pmEIS-ORD
7h 50m1 stop
$585
Find Deal
Mon, Jan 5 - Wed, Jan 14
Logo
4:35 pm - 10:55 amORD-EIS
16h 20m1 stop
Logo
8:55 am - 6:00 pmEIS-ORD
11h 05m1 stop
$587
Find Deal
Tue, Jan 6 - Wed, Jan 14
American Airlines Logo
6:35 pm - 12:15 pmORD-EIS
15h 40m2 stops
American Airlines Logo
2:50 pm - 12:10 amEIS-ORD
11h 20m2 stops
$743American Airlines
Find Deal
Tue, Jan 6 - Fri, Jan 16
American Airlines Logo
1:59 pm - 9:55 pmORD-EIS
5h 56m1 stop
American Airlines Logo
7:00 am - 11:19 pmEIS-ORD
17h 19m1 stop
$784American Airlines
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Fri, Mar 6 - Sat, Mar 14
American Airlines Logo
10:40 am - 9:55 pmORD-EIS
9h 15m2 stops
American Airlines Logo
8:00 am - 10:01 pmEIS-ORD
16h 01m1 stop
$788American Airlines
Find Deal
Sun, Mar 1 - Sat, Mar 7
American Airlines Logo
5:00 am - 5:04 pmORD-EIS
10h 04m2 stops
American Airlines Logo
2:04 pm - 11:56 pmEIS-ORD
11h 52m2 stops
$798American Airlines
Find Deal
Mon, Nov 17 - Tue, Nov 25
United Airlines Logo
7:50 pm - 6:30 pmORD-EIS
20h 40m2 stops
United Airlines Logo
9:41 am - 2:25 pmEIS-ORD
30h 44m2 stops
$955United Airlines
Find Deal
Sat, Jan 31 - Sun, Feb 8
United Airlines Logo
8:55 am - 6:55 pmORD-EIS
9h 00m1 stop
United Airlines Logo
8:15 am - 11:32 amEIS-ORD
29h 17m1 stop
$974United Airlines
Find Deal
Tue, Oct 28 - Tue, Nov 4
United Airlines Logo
8:52 am - 6:55 pmORD-EIS
9h 03m1 stop
United Airlines Logo
7:55 am - 8:03 pmEIS-ORD
13h 08m1 stop
$986United Airlines
Find Deal
Sat, Oct 4 - Thu, Oct 9

American Airlines flights from Chicago to Road Town

Our best American Airlines deals on Chicago to Road Town flight tickets
American Airlines
Jan 6
ORD6:35 pmChicago O'Hare Intl
15h 40m
2 stops
EIS12:15 pmRoad Town Beef Island
Jan 16
EIS2:50 pmRoad Town Beef Island
11h 20m
2 stops
ORD12:10 amChicago O'Hare Intl
$743
Find similar
American Airlines
Mar 6
ORD1:59 pmChicago O'Hare Intl
5h 56m
1 stop
EIS9:55 pmRoad Town Beef Island
Mar 14
EIS7:00 amRoad Town Beef Island
17h 19m
1 stop
ORD11:19 pmChicago O'Hare Intl
$784
Find similar
American Airlines
Mar 1
ORD10:40 amChicago O'Hare Intl
9h 15m
2 stops
EIS9:55 pmRoad Town Beef Island
Mar 7
EIS8:00 amRoad Town Beef Island
16h 01m
1 stop
ORD10:01 pmChicago O'Hare Intl
$788
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
ORD7:50 pmChicago O'Hare Intl
20h 40m
2 stops
EIS6:30 pmRoad Town Beef Island
Feb 8
EIS9:41 amRoad Town Beef Island
30h 44m
2 stops
ORD2:25 pmChicago O'Hare Intl
$955
Find similar
United Airlines
Oct 28
ORD8:55 amChicago O'Hare Intl
9h 00m
1 stop
EIS6:55 pmRoad Town Beef Island
Nov 4
EIS8:15 amRoad Town Beef Island
29h 17m
1 stop
ORD11:32 amChicago O'Hare Intl
$974
Find similar
United Airlines
Oct 4
ORD8:52 amChicago O'Hare Intl
9h 03m
1 stop
EIS6:55 pmRoad Town Beef Island
Oct 9
EIS7:55 amRoad Town Beef Island
13h 08m
1 stop
ORD8:03 pmChicago O'Hare Intl
$986
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 September 15, 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

Thu 10/30

6:40 am-10:55 am

2 stops27h 15m

Road Town Beef Island

Thu 11/6

4:00 pm-6:00 pm

1 stop28h 00m

$551

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Mon 1/5

1:35 pm-3:15 pm

2 stops23h 40m

Road Town Beef Island

Wed 1/14

12:10 pm-6:00 pm

1 stop7h 50m

$585

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Tue 1/6

4:35 pm-10:55 am

1 stop16h 20m

Road Town Beef Island

Wed 1/14

8:55 am-6:00 pm

1 stop11h 05m

$587

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Tue 1/6

6:35 pm-12:15 pm

2 stops15h 40m

Road Town Beef Island

Fri 1/16

2:50 pm-12:10 am

2 stops11h 20m

$743

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Fri 3/6

1:59 pm-9:55 pm

1 stop5h 56m

Road Town Beef Island

Sat 3/14

7:00 am-11:19 pm

1 stop17h 19m

$784

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Sun 3/1

10:40 am-9:55 pm

2 stops9h 15m

Road Town Beef Island

Sat 3/7

8:00 am-10:01 pm

1 stop16h 01m

$788

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Mon 11/17

5:00 am-5:04 pm

2 stops10h 04m

Road Town Beef Island

Tue 11/25

2:04 pm-11:56 pm

2 stops11h 52m

$798

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Sat 1/31

7:50 pm-6:30 pm

2 stops20h 40m

Road Town Beef Island

Sun 2/8

9:41 am-2:25 pm

2 stops30h 44m

$955

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Tue 10/28

8:55 am-6:55 pm

1 stop9h 00m

Road Town Beef Island

Tue 11/4

8:15 am-11:32 am

1 stop29h 17m

$974

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Sat 10/4

8:52 am-6:55 pm

1 stop9h 03m

Road Town Beef Island

Thu 10/9

7:55 am-8:03 pm

1 stop13h 08m

$986

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 13 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 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

Direct flights

None
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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  • 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 5h 56m, 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 $672Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $747Free CancellationRating
7.4
8,929 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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