ORD - EIS

$299 Find Cheap Flights from Chicago to Road Town

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Road Town departing on 6/2. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Road Town

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Road Town, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Road Town, as well as popular online travel agencies
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41.299.237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$528
Multiple Airlines
Sat 5/23Thu 5/28
ORD - EIS • 1 stop
Cheapest one-way
$299
Multiple Airlines
Tue 6/2
ORD - EIS • 3 stops
Nonstop flights
Not available
There are currently no direct flights between Chicago and Road Town. You'll need at least 1 connection.
Insights
Insights
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Insights
Top layover airports
San Juan (SJU)
Cheapest • Avg $1,078 (round-trip)
Miami (MIA)
Shortest trip • 8h 21m (one-way)
Insights
Insights
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Insights
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Road Town!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Chicago to Road Town (ORD-EIS)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Road Town that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Road Town

Sat, May 23 - Thu, May 28
Multiple Airlines Logo
12:59 pm - 2:05 pm
ORD
-
EIS
24h 06m
1 stop
Multiple Airlines Logo
9:00 am - 10:46 pm
EIS
-
ORD
14h 46m
1 stop
$528Multiple Airlines
Sat, May 23 - Thu, May 28
Multiple Airlines Logo
1:18 pm - 2:05 pm
ORD
-
EIS
47h 47m
2 stops
Multiple Airlines Logo
4:00 pm - 10:46 pm
EIS
-
ORD
7h 46m
1 stop
$576Multiple Airlines
Fri, May 22 - Thu, May 28
Multiple Airlines Logo
4:44 pm - 6:10 pm
ORD
-
EIS
24h 26m
1 stop
Multiple Airlines Logo
4:00 pm - 10:46 pm
EIS
-
ORD
7h 46m
1 stop
$589Multiple Airlines
Fri, May 22 - Thu, May 28
Multiple Airlines Logo
7:52 pm - 2:05 pm
ORD
-
EIS
41h 13m
2 stops
Multiple Airlines Logo
9:00 am - 10:46 pm
EIS
-
ORD
14h 46m
1 stop
$613Multiple Airlines
Wed, Jul 1 - Wed, Jul 8
Multiple Airlines Logo
12:44 am - 2:05 pm
ORD
-
EIS
12h 21m
1 stop
Multiple Airlines Logo
4:00 pm - 12:25 pm
EIS
-
ORD
21h 25m
2 stops
$614Multiple Airlines
Wed, Jul 1 - Wed, Jul 8
Multiple Airlines Logo
12:44 am - 10:55 am
ORD
-
EIS
9h 11m
1 stop
Multiple Airlines Logo
9:00 am - 11:27 pm
EIS
-
ORD
15h 27m
1 stop
$620Multiple Airlines
Thu, Jun 11 - Thu, Jun 18
Multiple Airlines Logo
12:31 pm - 10:55 am
ORD
-
EIS
21h 24m
2 stops
Multiple Airlines Logo
11:35 am - 11:38 pm
EIS
-
ORD
13h 03m
1 stop
$660Multiple Airlines
Fri, May 29 - Sat, Jun 6
Multiple Airlines Logo
7:52 pm - 10:55 am
ORD
-
EIS
14h 03m
2 stops
Multiple Airlines Logo
9:00 am - 3:15 pm
EIS
-
ORD
7h 15m
1 stop
$678Multiple Airlines
Thu, Jun 11 - Thu, Jun 18
Multiple Airlines Logo
4:44 pm - 10:55 am
ORD
-
EIS
17h 11m
1 stop
Multiple Airlines Logo
11:35 am - 11:38 pm
EIS
-
ORD
13h 03m
1 stop
$684Multiple Airlines
Mon, Jun 8 - Tue, Jun 16
Multiple Airlines Logo
12:44 am - 6:10 pm
ORD
-
EIS
16h 26m
1 stop
Multiple Airlines Logo
11:35 am - 12:43 pm
EIS
-
ORD
26h 08m
2 stops
$687Multiple Airlines
Booking Insights

KAYAK's insights & trends for Chicago to Road Town flights

Get data-powered insights and trends into flights from Chicago to Road Town to help you find the cheapest flights, the best time to fly and much more.

What is the most popular layover airport when flying from Chicago to Road Town?

Percentage of 1-stop round-trip flights from Chicago to Road Town chosen by KAYAK users via each layover airport in the last 12 months (only includes trips with the same layover airport on both legs).

Miami (MIA) is the top choice – 95% of KAYAK users who clicked on 1-stop flights from Chicago to Road Town picked an itinerary connecting there.

What is the cheapest layover airport when flying from Chicago to Road Town?

Average round-trip price for 1-stop flights from Chicago to Road Town clicked by KAYAK users in the last 12 months (only includes trips with the same layover airport on both legs).

Flights via San Juan (SJU) offer the most affordable fares, with an average round-trip price of $1,078.

Which layover airport offers the shortest total travel time from Chicago to Road Town?

Shortest average total travel time for 1-stop one-way flights from Chicago to Road Town via different layover airports, based on KAYAK user data from the last 12 months.

Consider flying via Miami (MIA) for the shortest journey. The average one-way travel time for flights connecting there is 8h 21m.

Which layover airport has the quickest connection when flying from Chicago to Road Town?

Average layover duration at different layover airports for 1-stop one-way flights from Chicago to Road Town, based on KAYAK user data from the last 12 months.

If you prefer a quick connection, Miami (MIA) often has the shortest layovers from Chicago to Road Town, with an average of 2h 26m.

Find deals

Good to know

Cheapest flight$299
Flight from Chicago to Road Town

When to book flights from Chicago to Road Town

Are your dates flexible? Find out the best times to travel from Chicago to Road Town based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Chicago to Road Town flights

  • What is the cheapest flight from Chicago O'Hare Intl Airport to Road Town?

    In the last 3 days, the lowest price for a flight from Chicago O'Hare Intl Airport to Road Town was $299 for a one-way ticket and $528 for a round-trip.

  • Do I need a passport to fly between Chicago and Road Town?

    Yes, you'll most likely have to show a valid passport before boarding the plane in Chicago and on arrival in Road Town.

  • Which aircraft models fly most regularly from Chicago to Road Town?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Chicago to Road Town?

    oneworld is the only airline alliance operating flights between Chicago and Road Town.

  • How does KAYAK find such low prices on flights from Chicago to Road Town?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Road Town.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Road Town?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Road Town from Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Road Town?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Road Town with an airline and back to Chicago with another airline. Booking your flights between Chicago and EIS can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Road Town?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Road Town from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airline flying from Chicago to Road Town

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Road Town. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Chicago to Road Town? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.1
American AirlinesOverall score based on 11678 reviews
7.2Comfort
7.9Crew
7.5Boarding
6.9Entertainment
6.4Food
Airline reviews

The airplane was an old model, the overhead didn’t have enough room for people’s items and made boarding and boarding disappointing and stressful. Crew allowed passengers to bring more than the permitted baggage sizes.

2.0 MediocreStella, Apr 2026
ORD - DCA
Read more American Airlines reviews

The airplane was an old model, the overhead didn’t have enough room for people’s items and made boarding and boarding disappointing and stressful. Crew allowed passengers to bring more than the permitted baggage sizes.

Original flight was on time, then late, then changed gates...4 times. Once our newest plane came in, it was fine.

I almost missed my flight and they helped me out enormously

Delays experienced in boarding/take off due to incoming plane delayed. However, the boarding time/depart time in the app was significantly delayed in providing these updates. Usually not updated until an hour after we should have already boarded. Poorly managed.

Moved to earlier flight which unexpectedly had maintenance issues initially indicated as quick fix to ultimately plane changes. Moved back to original flight, also delayed. In all cases customer updates and communication very unclear, no updates on drivers for delays.

Typical AA - late by 90+ mn. Gate changed twice... Changed the departure time 6 times No explanation, no communication on reasons for delay I travel with AA twice a year... and it is consistently very poor.. I will continue to use AA only when i have to.

The gate got changed several times and the flight was delayed over an hour. Awful experience

American continues to decline in their customer service and its beyond disappointing.

It was an older plane. First Class was not especially roomy or comfortable. It was a short flight so there were no meal but they did offer mixed nuts which used to be normal but now is rare. Crew member was very polite and professional.

Flight to Tampa was delayed taking off due to plane arriving late but no other issues

Everything you need to know for your flight from Chicago to Road Town

Information on your arrival and departure airports

Chicago (ORD)
Road Town (EIS)