Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Chicago to Road Town from $251

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 4/3. 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
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

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
8:00 am - 6:10 pm
ORD
-
EIS
9h 10m
1 stop
Multiple Airlines Logo
11:35 am - 11:13 pm
EIS
-
ORD
12h 38m
2 stops
$548Multiple Airlines
mar., may. 5 - mar., may. 12
Multiple Airlines Logo
3:52 pm - 2:05 pm
ORD
-
EIS
21h 13m
2 stops
Multiple Airlines Logo
9:00 am - 6:50 pm
EIS
-
ORD
10h 50m
1 stop
$550Multiple Airlines
sáb., may. 2 - sáb., may. 9
Multiple Airlines Logo
3:55 pm - 2:05 pm
ORD
-
EIS
21h 10m
2 stops
Multiple Airlines Logo
4:00 pm - 6:50 pm
EIS
-
ORD
27h 50m
1 stop
$552Multiple Airlines
mié., may. 20 - mié., may. 27
Multiple Airlines Logo
7:55 am - 10:55 am
ORD
-
EIS
26h 00m
2 stops
Multiple Airlines Logo
4:00 pm - 5:45 am
EIS
-
ORD
14h 45m
1 stop
$561Multiple Airlines
vie., abr. 10 - dom., abr. 12
Multiple Airlines Logo
7:55 am - 10:55 am
ORD
-
EIS
26h 00m
2 stops
Multiple Airlines Logo
4:00 pm - 5:45 am
EIS
-
ORD
14h 45m
1 stop
$562Multiple Airlines
vie., abr. 10 - dom., abr. 12
Multiple Airlines Logo
12:29 am - 10:55 am
ORD
-
EIS
9h 26m
1 stop
Multiple Airlines Logo
4:00 pm - 10:26 pm
EIS
-
ORD
7h 26m
1 stop
$563Multiple Airlines
vie., ago. 7 - mar., ago. 18
Multiple Airlines Logo
8:05 am - 6:10 pm
ORD
-
EIS
9h 05m
2 stops
Multiple Airlines Logo
9:00 am - 3:08 pm
EIS
-
ORD
7h 08m
1 stop
$564Multiple Airlines
mar., may. 26 - mié., jun. 3
Multiple Airlines Logo
5:30 pm - 2:05 pm
ORD
-
EIS
19h 35m
2 stops
Multiple Airlines Logo
9:00 am - 6:50 pm
EIS
-
ORD
10h 50m
1 stop
$567Multiple Airlines
dom., may. 17 - sáb., may. 23
Multiple Airlines Logo
8:56 pm - 10:55 am
ORD
-
EIS
12h 59m
1 stop
Multiple Airlines Logo
4:00 pm - 5:45 am
EIS
-
ORD
14h 45m
1 stop
$572Multiple Airlines
vie., abr. 10 - dom., abr. 12
Multiple Airlines Logo
8:56 pm - 10:55 am
ORD
-
EIS
12h 59m
1 stop
Multiple Airlines Logo
4:00 pm - 5:45 am
EIS
-
ORD
14h 45m
1 stop
$573Multiple Airlines
vie., abr. 10 - dom., abr. 12

American Airlines flights from Chicago to Road Town

Our best American Airlines deals on Chicago to Road Town flight tickets
American Airlines
Mar 25
ORD6:59 pmChicago O'Hare Intl
14h 53m
1 stop
EIS10:52 amRoad Town Beef Island
Apr 1
EIS3:22 pmRoad Town Beef Island
8h 55m
1 stop
ORD11:17 pmChicago O'Hare Intl
$1,013
American Airlines
Mar 25
ORD5:00 amChicago O'Hare Intl
10h 01m
2 stops
EIS4:01 pmRoad Town Beef Island
Apr 1
EIS4:41 pmRoad Town Beef Island
8h 57m
1 stop
ORD12:38 amChicago O'Hare Intl
$1,018
American Airlines
Mar 25
ORD7:00 amChicago O'Hare Intl
13h 03m
1 stop
EIS9:03 pmRoad Town Beef Island
Apr 1
EIS8:48 amRoad Town Beef Island
8h 26m
1 stop
ORD4:14 pmChicago O'Hare Intl
$1,101

JetBlue flights from Chicago to Road Town

Our best JetBlue deals on Chicago to Road Town flight tickets
JetBlue
Mar 25
ORD11:00 amChicago O'Hare Intl
24h 19m
2 stops
EIS12:19 pmRoad Town Beef Island
Apr 1
EIS4:43 pmRoad Town Beef Island
16h 22m
2 stops
ORD8:05 amChicago O'Hare Intl
$1,298
JetBlue
Mar 25
ORD11:00 amChicago O'Hare Intl
24h 19m
2 stops
EIS12:19 pmRoad Town Beef Island
Apr 1
EIS4:43 pmRoad Town Beef Island
16h 22m
2 stops
ORD8:05 amChicago O'Hare Intl
$1,308
JetBlue
Apr 3
ORD8:55 amChicago O'Hare Intl
24h 58m
2 stops
EIS10:53 amRoad Town Beef Island
Apr 11
EIS11:21 amRoad Town Beef Island
21h 47m
2 stops
ORD8:08 amChicago O'Hare Intl
$1,327

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 marzo 22, 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

mar. 5/5

8:00 am-6:10 pm

1 stop9h 10m

Road Town Beef Island

mar. 5/12

11:35 am-11:13 pm

2 stops12h 38m

$548

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

sáb. 5/2

3:52 pm-2:05 pm

2 stops21h 13m

Road Town Beef Island

sáb. 5/9

9:00 am-6:50 pm

1 stop10h 50m

$550

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

mié. 5/20

3:55 pm-2:05 pm

2 stops21h 10m

Road Town Beef Island

mié. 5/27

4:00 pm-6:50 pm

1 stop27h 50m

$552

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

vie. 4/10

7:55 am-10:55 am

2 stops26h 00m

Road Town Beef Island

dom. 4/12

4:00 pm-5:45 am

1 stop14h 45m

$561

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

vie. 4/10

7:55 am-10:55 am

2 stops26h 00m

Road Town Beef Island

dom. 4/12

4:00 pm-5:45 am

1 stop14h 45m

$562

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

vie. 8/7

12:29 am-10:55 am

1 stop9h 26m

Road Town Beef Island

mar. 8/18

4:00 pm-10:26 pm

1 stop7h 26m

$563
Quickest round-trip

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

mar. 5/26

8:05 am-6:10 pm

2 stops9h 05m

Road Town Beef Island

mié. 6/3

9:00 am-3:08 pm

1 stop7h 08m

$564

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

dom. 5/17

5:30 pm-2:05 pm

2 stops19h 35m

Road Town Beef Island

sáb. 5/23

9:00 am-6:50 pm

1 stop10h 50m

$567

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

vie. 4/10

8:56 pm-10:55 am

1 stop12h 59m

Road Town Beef Island

dom. 4/12

4:00 pm-5:45 am

1 stop14h 45m

$572

ChicagoRoad Town

ORD - EIS

ORDEIS

Chicago O'Hare Intl

vie. 4/10

8:56 pm-10:55 am

1 stop12h 59m

Road Town Beef Island

dom. 4/12

4:00 pm-5:45 am

1 stop14h 45m

$573

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 19 resultsSorted by cheapest first
1
2

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 47% 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

9h 10m

Direct flights

None
The fastest flight from Chicago to Road Town takes 9h 10m
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 9h 10m, 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
11,489 reviews
Search American Airlines flights
United AirlinesPriceFrom $747Free CancellationRating
7.4
9,455 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.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
mar. 4/21
mar. 4/28
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to the British Virgin Islands

Airports servicing British Virgin Islands

Anegada Airport
Virgin Gorda Airport