ORD - EIS

$306 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 7/14. 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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 24% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest round-trip
$694
Multiple Airlines
Thu 7/2Thu 7/9
ORD - EIS • 2 stops
Cheapest one-way
$306
Multiple Airlines
Tue 7/14
ORD - EIS • 1 stop
Top airlines
American Airlines
Cheapest • from $788 (round-trip)
American Airlines
Best reviews • 7.1 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Not available
There are currently no direct flights between Chicago and Road Town. You'll need at least 1 connection.
Insights
Insights
Insights
Insights
Top layover airports
San Juan (SJU)
Cheapest • Avg $1,078 (round-trip)
Miami (MIA)
Shortest trip • 8h 21m (one-way)
Insights
Insights
Insights
Insights
Start a new search
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

Thu, Jul 2 - Thu, Jul 9
Multiple Airlines Logo
7:52 am - 6:10 pm
ORD
-
EIS
33h 18m
2 stops
Multiple Airlines Logo
11:35 am - 11:27 pm
EIS
-
ORD
12h 52m
1 stop
$694Multiple Airlines
Thu, Jul 2 - Thu, Jul 9
Multiple Airlines Logo
4:59 pm - 10:55 am
ORD
-
EIS
16h 56m
2 stops
Multiple Airlines Logo
4:00 pm - 11:27 pm
EIS
-
ORD
8h 27m
1 stop
$766Multiple Airlines
Wed, Jul 8 - Thu, Jul 16
Multiple Airlines Logo
12:44 am - 2:05 pm
ORD
-
EIS
12h 21m
1 stop
Multiple Airlines Logo
4:00 pm - 12:15 pm
EIS
-
ORD
45h 15m
2 stops
$783Multiple Airlines
Wed, Jul 8 - Thu, Jul 16
Multiple Airlines Logo
12:44 am - 2:05 pm
ORD
-
EIS
12h 21m
1 stop
Multiple Airlines Logo
9:00 am - 11:27 pm
EIS
-
ORD
15h 27m
1 stop
$787Multiple Airlines
Thu, Jul 23 - Tue, Jul 28
American Airlines Logo
6:10 am - 10:01 pm
ORD
-
EIS
14h 51m
1 stop
American Airlines Logo
8:20 am - 11:30 pm
EIS
-
ORD
16h 10m
1 stop
$788American Airlines
Thu, Jul 23 - Tue, Jul 28
American Airlines Logo
9:00 am - 10:01 pm
ORD
-
EIS
12h 01m
2 stops
American Airlines Logo
1:00 pm - 12:29 am
EIS
-
ORD
12h 29m
2 stops
$793American Airlines
Mon, Oct 19 - Mon, Oct 26
American Airlines Logo
5:05 pm - 2:50 pm
ORD
-
EIS
20h 45m
1 stop
American Airlines Logo
3:05 pm - 10:31 pm
EIS
-
ORD
8h 26m
1 stop
$806American Airlines
Mon, Oct 19 - Mon, Oct 26
American Airlines Logo
5:05 pm - 2:50 pm
ORD
-
EIS
20h 45m
1 stop
American Airlines Logo
4:45 pm - 8:24 am
EIS
-
ORD
16h 39m
2 stops
$810American Airlines
Wed, Nov 4 - Wed, Nov 11
American Airlines Logo
4:40 pm - 5:05 pm
ORD
-
EIS
22h 25m
1 stop
American Airlines Logo
5:45 pm - 9:25 am
EIS
-
ORD
17h 40m
1 stop
$811American Airlines
Wed, Nov 4 - Wed, Nov 11
American Airlines Logo
4:40 pm - 5:05 pm
ORD
-
EIS
22h 25m
1 stop
American Airlines Logo
5:45 pm - 7:05 am
EIS
-
ORD
15h 20m
2 stops
$816American 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.

Which airlines provide the cheapest flights from Chicago to Road Town?

The cheapest round-trip price for the route for each airline clicked by KAYAK users in the last 7 days.

In the past 7 days, the cheapest round-trip tickets from Chicago to Road Town were found on American Airlines ($788) and United Airlines ($1,086).

Find deals

Good to know

Cheapest flight$306
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 7 days, the lowest price for a flight from Chicago O'Hare Intl Airport to Road Town was $306 for a one-way ticket and $694 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 11630 reviews
7.2Comfort
7.5Boarding
6.4Food
7.9Crew
6.9Entertainment
Airline reviews

Our flight was cancelled while we are on our way to the airport. So, no notice. We were rescheduled to another airline with a 2 hour later takeoff and so arrived at our destination on time. We pre-paid American Airlines $190 to upgrade our seats. No refund. So no use for AA or Kayak.

2.0 MediocreWilliam, May 2026
ORD - LHR
Read more American Airlines reviews

Our flight was cancelled while we are on our way to the airport. So, no notice. We were rescheduled to another airline with a 2 hour later takeoff and so arrived at our destination on time. We pre-paid American Airlines $190 to upgrade our seats. No refund. So no use for AA or Kayak.

Terrible, horrible, disappointing- without telling us they changed planes and moved and separated our seats to opposite sides - said they changed seats putting us together - got to airport to find no, they did not - we sat opposing sides of plane - food overly salty to inedible, never saw stewardess but once - it was terrible

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.

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)