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Cheap flights from Chicago to Road Town from $255

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 1/1. 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
4:35 pm - 3:15 pmORD-EIS
20h 40m1 stop
Multiple Airlines Logo
4:00 pm - 6:10 pmEIS-ORD
28h 10m2 stops
$508Multiple Airlines
Find Deal
Sat, Jan 31 - Sun, Feb 8
Multiple Airlines Logo
5:20 am - 6:20 pmORD-EIS
11h 00m2 stops
Multiple Airlines Logo
8:55 am - 6:00 pmEIS-ORD
11h 05m1 stop
$541Multiple Airlines
Find Deal
Sun, Feb 1 - Sat, Feb 21
Multiple Airlines Logo
7:00 am - 3:15 pmORD-EIS
30h 15m2 stops
Multiple Airlines Logo
8:55 am - 6:00 pmEIS-ORD
11h 05m1 stop
$548Multiple Airlines
Find Deal
Mon, Feb 2 - Sat, Feb 21
Multiple Airlines Logo
4:35 pm - 10:55 amORD-EIS
16h 20m1 stop
Multiple Airlines Logo
4:00 pm - 6:00 pmEIS-ORD
28h 00m1 stop
$553Multiple Airlines
Find Deal
Sat, Jan 31 - Sun, Feb 8
Multiple Airlines Logo
5:20 am - 6:20 pmORD-EIS
11h 00m2 stops
Multiple Airlines Logo
8:55 am - 6:00 pmEIS-ORD
11h 05m1 stop
$558Multiple Airlines
Find Deal
Fri, Jan 30 - Sat, Feb 21
American Airlines Logo
5:45 am - 10:13 pmORD-EIS
14h 28m1 stop
American Airlines Logo
7:00 am - 4:09 pmEIS-ORD
10h 09m1 stop
$739American Airlines
Find Deal
Sat, Mar 7 - Thu, Mar 12
American Airlines Logo
5:00 am - 3:10 pmORD-EIS
8h 10m1 stop
American Airlines Logo
5:49 pm - 9:05 amEIS-ORD
17h 16m1 stop
$744American Airlines
Find Deal
Wed, Jan 28 - Wed, Feb 4
American Airlines Logo
9:54 am - 10:16 pmORD-EIS
10h 22m2 stops
American Airlines Logo
8:00 am - 6:01 pmEIS-ORD
12h 01m2 stops
$749American Airlines
Find Deal
Wed, Jan 28 - Wed, Feb 4
American Airlines Logo
12:07 pm - 10:16 pmORD-EIS
8h 09m1 stop
American Airlines Logo
5:49 pm - 9:05 amEIS-ORD
17h 16m1 stop
$794American Airlines
Find Deal
Tue, Jan 6 - Thu, Jan 15
United Airlines Logo
2:20 pm - 12:30 pmORD-EIS
20h 10m1 stop
United Airlines Logo
9:41 am - 2:25 pmEIS-ORD
30h 44m2 stops
$930United Airlines
Find Deal
Sat, Jan 17 - Mon, Jan 26

American Airlines flights from Chicago to Road Town

Our best American Airlines deals on Chicago to Road Town flight tickets
American Airlines
Mar 7
ORD5:45 amChicago O'Hare Intl
14h 28m
1 stop
EIS10:13 pmRoad Town Beef Island
Mar 12
EIS7:00 amRoad Town Beef Island
10h 09m
1 stop
ORD4:09 pmChicago O'Hare Intl
$739
Find similar
American Airlines
Jan 28
ORD5:00 amChicago O'Hare Intl
8h 10m
1 stop
EIS3:10 pmRoad Town Beef Island
Feb 4
EIS5:49 pmRoad Town Beef Island
17h 16m
1 stop
ORD9:05 amChicago O'Hare Intl
$744
Find similar
American Airlines
Jan 28
ORD9:54 amChicago O'Hare Intl
10h 22m
2 stops
EIS10:16 pmRoad Town Beef Island
Feb 4
EIS8:00 amRoad Town Beef Island
12h 01m
2 stops
ORD6:01 pmChicago O'Hare Intl
$749
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 November 4, 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

4:35 pm-3:15 pm

1 stop20h 40m

Road Town Beef Island

Sun 2/8

4:00 pm-6:10 pm

2 stops28h 10m

$508

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Sun 2/1

5:20 am-6:20 pm

2 stops11h 00m

Road Town Beef Island

Sat 2/21

8:55 am-6:00 pm

1 stop11h 05m

$541

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Mon 2/2

7:00 am-3:15 pm

2 stops30h 15m

Road Town Beef Island

Sat 2/21

8:55 am-6:00 pm

1 stop11h 05m

$548

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Sat 1/31

4:35 pm-10:55 am

1 stop16h 20m

Road Town Beef Island

Sun 2/8

4:00 pm-6:00 pm

1 stop28h 00m

$553

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Fri 1/30

5:20 am-6:20 pm

2 stops11h 00m

Road Town Beef Island

Sat 2/21

8:55 am-6:00 pm

1 stop11h 05m

$558

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Sat 3/7

5:45 am-10:13 pm

1 stop14h 28m

Road Town Beef Island

Thu 3/12

7:00 am-4:09 pm

1 stop10h 09m

$739

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Wed 1/28

5:00 am-3:10 pm

1 stop8h 10m

Road Town Beef Island

Wed 2/4

5:49 pm-9:05 am

1 stop17h 16m

$744

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Wed 1/28

9:54 am-10:16 pm

2 stops10h 22m

Road Town Beef Island

Wed 2/4

8:00 am-6:01 pm

2 stops12h 01m

$749

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Tue 1/6

12:07 pm-10:16 pm

1 stop8h 09m

Road Town Beef Island

Thu 1/15

5:49 pm-9:05 am

1 stop17h 16m

$794

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Sat 1/17

2:20 pm-12:30 pm

1 stop20h 10m

Road Town Beef Island

Mon 1/26

9:41 am-2:25 pm

2 stops30h 44m

$930

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 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 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
11,040 reviews
Search American Airlines flights
United AirlinesPriceFrom $747Free CancellationRating
7.4
9,002 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

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