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Cheap flights from Chicago to Road Town from $243

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 5/28. 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
10:55 am - 10:55 am
ORD
-
EIS
23h 00m
2 stops
Multiple Airlines Logo
9:00 am - 4:37 pm
EIS
-
ORD
8h 37m
1 stop
$509Multiple Airlines
พ., เม.ย. 8 - พ., เม.ย. 15
Multiple Airlines Logo
10:55 am - 10:55 am
ORD
-
EIS
23h 00m
2 stops
Multiple Airlines Logo
4:00 pm - 5:45 am
EIS
-
ORD
14h 45m
1 stop
$510Multiple Airlines
อ., เม.ย. 7 - จ., เม.ย. 13
Multiple Airlines Logo
4:51 pm - 10:55 am
ORD
-
EIS
41h 04m
2 stops
Multiple Airlines Logo
9:00 am - 4:37 pm
EIS
-
ORD
8h 37m
1 stop
$513Multiple Airlines
ส., เม.ย. 11 - ส., เม.ย. 18
Multiple Airlines Logo
8:56 pm - 2:05 pm
ORD
-
EIS
16h 09m
1 stop
Multiple Airlines Logo
4:00 pm - 9:50 am
EIS
-
ORD
42h 50m
2 stops
$515Multiple Airlines
จ., เม.ย. 6 - อา., เม.ย. 12
Multiple Airlines Logo
8:56 pm - 2:05 pm
ORD
-
EIS
16h 09m
1 stop
Multiple Airlines Logo
4:00 pm - 6:15 pm
EIS
-
ORD
27h 15m
2 stops
$522Multiple Airlines
จ., เม.ย. 6 - อ., เม.ย. 14
Multiple Airlines Logo
10:55 am - 10:55 am
ORD
-
EIS
23h 00m
2 stops
Multiple Airlines Logo
4:00 pm - 5:45 am
EIS
-
ORD
14h 45m
1 stop
$525Multiple Airlines
ส., เม.ย. 11 - จ., เม.ย. 13
Multiple Airlines Logo
4:18 pm - 10:55 am
ORD
-
EIS
17h 37m
2 stops
Multiple Airlines Logo
8:55 am - 5:45 am
EIS
-
ORD
21h 50m
1 stop
$535Multiple Airlines
พ., มี.ค. 11 - อา., มี.ค. 15
Multiple Airlines Logo
8:56 pm - 10:55 am
ORD
-
EIS
12h 59m
1 stop
Multiple Airlines Logo
4:00 pm - 4:37 pm
EIS
-
ORD
25h 37m
1 stop
$537Multiple Airlines
พ., เม.ย. 8 - พ., เม.ย. 15
Multiple Airlines Logo
8:56 pm - 6:10 pm
ORD
-
EIS
20h 14m
1 stop
Multiple Airlines Logo
4:00 pm - 5:45 am
EIS
-
ORD
14h 45m
1 stop
$538Multiple Airlines
จ., เม.ย. 6 - อา., เม.ย. 12
Multiple Airlines Logo
12:22 pm - 10:55 am
ORD
-
EIS
21h 33m
1 stop
Multiple Airlines Logo
12:10 pm - 5:45 am
EIS
-
ORD
18h 35m
1 stop
$539Multiple Airlines
พ., มี.ค. 11 - อา., มี.ค. 15

American Airlines flights from Chicago to Road Town

Our best American Airlines deals on Chicago to Road Town flight tickets
American Airlines
Jun 10
ORD5:00 amChicago O'Hare Intl
14h 59m
1 stop
EIS8:59 pmRoad Town Beef Island
Jun 17
EIS5:08 pmRoad Town Beef Island
17h 11m
1 stop
ORD9:19 amChicago O'Hare Intl
$715
American Airlines
Jun 10
ORD7:50 amChicago O'Hare Intl
12h 09m
2 stops
EIS8:59 pmRoad Town Beef Island
Jun 17
EIS5:08 pmRoad Town Beef Island
17h 11m
1 stop
ORD9:19 amChicago O'Hare Intl
$720
American Airlines
Feb 11
ORD12:07 pmChicago O'Hare Intl
8h 09m
1 stop
EIS10:16 pmRoad Town Beef Island
Feb 27
EIS1:40 pmRoad Town Beef Island
12h 57m
1 stop
ORD12:37 amChicago O'Hare Intl
$1,205

United Airlines flights from Chicago to Road Town

Our best United Airlines deals on Chicago to Road Town flight tickets
United Airlines
Feb 11
ORD8:54 amChicago O'Hare Intl
31h 36m
2 stops
EIS6:30 pmRoad Town Beef Island
Feb 27
EIS11:21 amRoad Town Beef Island
29h 17m
2 stops
ORD2:38 pmChicago O'Hare Intl
$1,076
United Airlines
Feb 7
ORD10:35 amChicago O'Hare Intl
23h 55m
2 stops
EIS12:30 pmRoad Town Beef Island
Feb 15
EIS8:15 amRoad Town Beef Island
18h 11m
2 stops
ORD12:26 amChicago O'Hare Intl
$1,475

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 กุมภาพันธ์ 3, 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

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

พ. 4/8

10:55 am-10:55 am

2 stops23h 00m

Road Town Beef Island

พ. 4/15

9:00 am-4:37 pm

1 stop8h 37m

$509

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

อ. 4/7

10:55 am-10:55 am

2 stops23h 00m

Road Town Beef Island

จ. 4/13

4:00 pm-5:45 am

1 stop14h 45m

$510

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

ส. 4/11

4:51 pm-10:55 am

2 stops41h 04m

Road Town Beef Island

ส. 4/18

9:00 am-4:37 pm

1 stop8h 37m

$513

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

จ. 4/6

8:56 pm-2:05 pm

1 stop16h 09m

Road Town Beef Island

อา. 4/12

4:00 pm-9:50 am

2 stops42h 50m

$515

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

จ. 4/6

8:56 pm-2:05 pm

1 stop16h 09m

Road Town Beef Island

อ. 4/14

4:00 pm-6:15 pm

2 stops27h 15m

$522

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

ส. 4/11

10:55 am-10:55 am

2 stops23h 00m

Road Town Beef Island

จ. 4/13

4:00 pm-5:45 am

1 stop14h 45m

$525

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

พ. 3/11

4:18 pm-10:55 am

2 stops17h 37m

Road Town Beef Island

อา. 3/15

8:55 am-5:45 am

1 stop21h 50m

$535

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

พ. 4/8

8:56 pm-10:55 am

1 stop12h 59m

Road Town Beef Island

พ. 4/15

4:00 pm-4:37 pm

1 stop25h 37m

$537

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

จ. 4/6

8:56 pm-6:10 pm

1 stop20h 14m

Road Town Beef Island

อา. 4/12

4:00 pm-5:45 am

1 stop14h 45m

$538

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

พ. 3/11

12:22 pm-10:55 am

1 stop21h 33m

Road Town Beef Island

อา. 3/15

12:10 pm-5:45 am

1 stop18h 35m

$539

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 16 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 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

10h 05m

Direct flights

None
The fastest flight from Chicago to Road Town takes 10h 05m
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 10h 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 $718Free CancellationRating
7.2
11,216 reviews
Search American Airlines flights
United AirlinesPriceFrom $747Free CancellationRating
7.4
9,236 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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