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Cheap flights from Road Town to Chicago from $455

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Road Town to Chicago departing on 12/12. 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

Find the cheapest flights from Road Town to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
4:00 pm - 12:50 pm
EIS
-
ORD
45h 50m
2 stops
Multiple Airlines Logo
12:44 am - 10:55 am
ORD
-
EIS
9h 11m
1 stop
$578Multiple Airlines
Sun, Aug 23 - Sat, Aug 29
Multiple Airlines Logo
4:00 pm - 11:27 pm
EIS
-
ORD
8h 27m
1 stop
Multiple Airlines Logo
12:44 am - 10:55 am
ORD
-
EIS
9h 11m
1 stop
$691Multiple Airlines
Sun, Aug 23 - Sat, Aug 29
American Airlines Logo
12:36 pm - 11:44 pm
EIS
-
ORD
12h 08m
2 stops
American Airlines Logo
8:53 pm - 2:06 pm
ORD
-
EIS
16h 13m
2 stops
$923American Airlines
Sun, Aug 23 - Sun, Aug 30

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Customize your flight search to find flights from Road Town to Chicago 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 July 28, 2026.
Use the filters below to find and compare flights from Road Town to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Road TownChicago

EIS - ORD

EISORD

Road Town Beef Island

Sun 8/23

4:00 pm-12:50 pm

2 stops45h 50m

Chicago O'Hare Intl

Sat 8/29

12:44 am-10:55 am

1 stop9h 11m

$578
Quickest round-trip

Road TownChicago

EIS - ORD

EISORD

Road Town Beef Island

Sun 8/23

4:00 pm-11:27 pm

1 stop8h 27m

Chicago O'Hare Intl

Sat 8/29

12:44 am-10:55 am

1 stop9h 11m

$691

Road TownChicago

EIS - ORD

EISORD

Road Town Beef Island

Sun 8/23

12:36 pm-11:44 pm

2 stops12h 08m

Chicago O'Hare Intl

Sun 8/30

8:53 pm-2:06 pm

2 stops16h 13m

$923
Cheapest one-way

Road TownChicago

EIS - ORD

EISORD

Road Town Beef Island

Sat 12/12

4:00 pm-1:09 am

2 stops11h 09m

$455

Road TownChicago

EIS - ORD

EISORD

Road Town Beef Island

Sun 12/6

4:00 pm-1:09 am

2 stops11h 09m

$456

Road TownChicago

EIS - ORD

EISORD

Road Town Beef Island

Sat 12/12

9:00 am-1:09 am

2 stops18h 09m

$464

Road TownChicago

EIS - ORD

EISORD

Road Town Beef Island

Sat 12/12

4:00 pm-8:16 pm

3 stops30h 16m

$504

Road TownChicago

EIS - MDW

EISMDW

Road Town Beef Island

Sat 12/12

4:00 pm-12:59 pm

2 stops22h 59m

$542

Road TownChicago

EIS - ORD

EISORD

Road Town Beef Island

Sun 12/6

9:00 am-1:09 am

3 stops18h 09m

$557

Road TownChicago

EIS - MDW

EISMDW

Road Town Beef Island

Sat 12/12

4:00 pm-7:02 pm

3 stops29h 02m

$564

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 12 resultsSorted by cheapest first
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How to get the cheapest flight ticket from Road Town to Chicago

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 Road Town to Chicago flights?

You could potentially save up to 50% on your flight if you consider stops on a Road Town to Chicago flight.

When to book flights from Road Town to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Road Town to Chicago according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Road Town to Chicago (EIS to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Road Town to Chicago

Fastest flight time

10h 23m

Direct flights

None
The fastest flight from Road Town to Chicago takes 10h 23m
There are no direct flights from Road Town to Chicago. There are no popular flight routes from Road Town to Chicago.
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Frequently asked questions about flying from Road Town to Chicago

  • How far is Road Town Beef Island to Chicago by plane?

    Chicago is 2109.0 mi away from Road Town Beef Island. A reasonable flight in good conditions will take 10h 23m.

  • When did momondo last update prices for flights from Road Town Beef Island Airport to Chicago?

    Prices for flights from Road Town Beef Island Airport to Chicago are updated daily.

  • How old do you have to be to fly from Road Town Beef Island Airport to Chicago?

    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 Road Town Beef Island Airport to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The required travel and health documents for your Chicago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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Hammond
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Benton Harbor
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Saint Joseph
Valparaiso
Schererville
Munster
Chesterton
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Porter
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Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Road Town to Chicago?

It is quick and easy to find Road Town to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

Can I find flights from Road Town to Chicago with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for Road Town to Chicago flights to just show those with flexible booking policies.

How can momondo help me find flights from Road Town to Chicago?

Once you have performed a search for Road Town to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

I’m not ready to book a flight from Road Town to Chicago right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Road Town and alert you when they change.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport