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Cheap flights from Chicago to Road Town from $284

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 5/22. 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

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
12:33 am - 6:10 pm
ORD
-
EIS
16h 37m
1 stop
Multiple Airlines Logo
4:00 pm - 10:46 pm
EIS
-
ORD
7h 46m
1 stop
$594Multiple Airlines
Fri, May 22 - Thu, May 28
Multiple Airlines Logo
12:33 am - 6:10 pm
ORD
-
EIS
16h 37m
1 stop
Multiple Airlines Logo
4:00 pm - 12:37 pm
EIS
-
ORD
21h 37m
2 stops
$596Multiple Airlines
Fri, May 22 - Thu, May 28
Multiple Airlines Logo
12:44 am - 10:55 am
ORD
-
EIS
9h 11m
1 stop
Multiple Airlines Logo
4:00 pm - 11:05 pm
EIS
-
ORD
32h 05m
2 stops
$636Multiple Airlines
Sat, Aug 8 - Sat, Aug 15
Multiple Airlines Logo
7:30 am - 6:10 pm
ORD
-
EIS
9h 40m
1 stop
Multiple Airlines Logo
4:00 pm - 12:25 pm
EIS
-
ORD
21h 25m
2 stops
$638Multiple Airlines
Tue, Jun 30 - Mon, Jul 6
Multiple Airlines Logo
3:55 pm - 2:05 pm
ORD
-
EIS
21h 10m
2 stops
Multiple Airlines Logo
11:35 am - 3:11 pm
EIS
-
ORD
28h 36m
1 stop
$653Multiple Airlines
Tue, May 19 - Mon, May 25
Multiple Airlines Logo
10:16 am - 2:05 pm
ORD
-
EIS
26h 49m
2 stops
Multiple Airlines Logo
4:00 pm - 11:27 pm
EIS
-
ORD
8h 27m
1 stop
$658Multiple Airlines
Fri, Aug 7 - Wed, Aug 12
Multiple Airlines Logo
4:44 pm - 10:55 am
ORD
-
EIS
17h 11m
1 stop
Multiple Airlines Logo
11:35 am - 9:21 am
EIS
-
ORD
22h 46m
2 stops
$665Multiple Airlines
Sun, Jun 14 - Sun, Jun 21
Multiple Airlines Logo
1:04 pm - 10:55 am
ORD
-
EIS
20h 51m
1 stop
Multiple Airlines Logo
11:35 am - 11:05 pm
EIS
-
ORD
36h 30m
2 stops
$676Multiple Airlines
Thu, Jul 2 - Wed, Jul 8
Multiple Airlines Logo
7:30 am - 6:10 pm
ORD
-
EIS
9h 40m
1 stop
Multiple Airlines Logo
4:00 pm - 11:27 pm
EIS
-
ORD
8h 27m
1 stop
$714Multiple Airlines
Tue, Jun 30 - Mon, Jul 6
Multiple Airlines Logo
4:44 pm - 10:55 am
ORD
-
EIS
17h 11m
1 stop
Multiple Airlines Logo
11:35 am - 3:11 pm
EIS
-
ORD
28h 36m
1 stop
$721Multiple Airlines
Tue, May 19 - Mon, May 25

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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
Jun 25
ORD6:59 amChicago O'Hare Intl
13h 59m
1 stop
EIS9:58 pmRoad Town Beef Island
Jul 2
EIS5:06 pmRoad Town Beef Island
8h 20m
1 stop
ORD12:26 amChicago O'Hare Intl
$788
American Airlines
Jun 25
ORD9:52 amChicago O'Hare Intl
11h 06m
2 stops
EIS9:58 pmRoad Town Beef Island
Jul 2
EIS5:06 pmRoad Town Beef Island
17h 02m
1 stop
ORD9:08 amChicago O'Hare Intl
$793
American Airlines
Jun 24
ORD9:52 amChicago O'Hare Intl
11h 06m
2 stops
EIS9:58 pmRoad Town Beef Island
Jul 1
EIS8:19 amRoad Town Beef Island
11h 30m
2 stops
ORD6:49 pmChicago O'Hare Intl
$798

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 May 5, 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

Fri 5/22

12:33 am-6:10 pm

1 stop16h 37m

Road Town Beef Island

Thu 5/28

4:00 pm-10:46 pm

1 stop7h 46m

$594

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Fri 5/22

12:33 am-6:10 pm

1 stop16h 37m

Road Town Beef Island

Thu 5/28

4:00 pm-12:37 pm

2 stops21h 37m

$596

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Sat 8/8

12:44 am-10:55 am

1 stop9h 11m

Road Town Beef Island

Sat 8/15

4:00 pm-11:05 pm

2 stops32h 05m

$636

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Tue 6/30

7:30 am-6:10 pm

1 stop9h 40m

Road Town Beef Island

Mon 7/6

4:00 pm-12:25 pm

2 stops21h 25m

$638

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Tue 5/19

3:55 pm-2:05 pm

2 stops21h 10m

Road Town Beef Island

Mon 5/25

11:35 am-3:11 pm

1 stop28h 36m

$653

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Fri 8/7

10:16 am-2:05 pm

2 stops26h 49m

Road Town Beef Island

Wed 8/12

4:00 pm-11:27 pm

1 stop8h 27m

$658

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Sun 6/14

4:44 pm-10:55 am

1 stop17h 11m

Road Town Beef Island

Sun 6/21

11:35 am-9:21 am

2 stops22h 46m

$665

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Thu 7/2

1:04 pm-10:55 am

1 stop20h 51m

Road Town Beef Island

Wed 7/8

11:35 am-11:05 pm

2 stops36h 30m

$676
Quickest round-trip

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Tue 6/30

7:30 am-6:10 pm

1 stop9h 40m

Road Town Beef Island

Mon 7/6

4:00 pm-11:27 pm

1 stop8h 27m

$714

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

Tue 5/19

4:44 pm-10:55 am

1 stop17h 11m

Road Town Beef Island

Mon 5/25

11:35 am-3:11 pm

1 stop28h 36m

$721

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

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

You could potentially save up to 60% 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 $693Free CancellationRating
7.1
11,667 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

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