ORD - EIS

$414 Find Cheap Flights from Chicago to Road Town - Compare and Save

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 8/14. 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

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Everything you should know

Cheapest round-trip
$539
Multiple Airlines
Sat 8/15Sun 8/23
ORD - EIS • 1 stop
Cheapest one-way
$414
American Airlines
Fri 8/14
ORD - EIS • 2 stops
Top airlines
Cheapest • from $788 (round-trip)
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
Cheapest • Avg $1,121 (round-trip)
Shortest trip • 8h 09m (one-way)
Insights
Insights
Insights
Insights
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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, Aug 15 - Sun, Aug 23
Multiple Airlines Logo
12:44 am - 10:55 am
ORD
-
EIS
9h 11m
1 stop
Multiple Airlines Logo
4:00 pm - 12:50 pm
EIS
-
ORD
45h 50m
2 stops
$539Multiple Airlines
Sat, Aug 15 - Mon, Aug 24
Multiple Airlines Logo
12:44 am - 10:55 am
ORD
-
EIS
9h 11m
1 stop
Multiple Airlines Logo
4:00 pm - 12:50 pm
EIS
-
ORD
45h 50m
2 stops
$542Multiple Airlines
Sat, Aug 15 - Mon, Aug 24
Multiple Airlines Logo
12:44 am - 10:55 am
ORD
-
EIS
9h 11m
1 stop
Multiple Airlines Logo
4:00 pm - 11:27 pm
EIS
-
ORD
8h 27m
1 stop
$558Multiple Airlines
Fri, Aug 14 - Sat, Aug 22
Multiple Airlines Logo
12:44 am - 10:55 am
ORD
-
EIS
9h 11m
1 stop
Multiple Airlines Logo
4:00 pm - 11:27 pm
EIS
-
ORD
8h 27m
1 stop
$563Multiple Airlines
Sat, Aug 15 - Mon, Aug 24
Multiple Airlines Logo
12:44 am - 2:05 pm
ORD
-
EIS
12h 21m
1 stop
Multiple Airlines Logo
4:00 pm - 11:27 pm
EIS
-
ORD
8h 27m
1 stop
$566Multiple Airlines
Wed, Aug 26 - Wed, Sep 9
Multiple Airlines Logo
12:44 am - 10:55 am
ORD
-
EIS
9h 11m
1 stop
Multiple Airlines Logo
4:00 pm - 8:21 am
EIS
-
ORD
17h 21m
2 stops
$579Multiple Airlines
Sat, Aug 15 - Sun, Aug 23
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
$615Multiple Airlines
Fri, Aug 14 - Sat, Aug 22
Multiple Airlines Logo
12:44 am - 2:05 pm
ORD
-
EIS
12h 21m
1 stop
Multiple Airlines Logo
9:00 am - 11:08 pm
EIS
-
ORD
15h 08m
2 stops
$620Multiple Airlines
Thu, Aug 13 - Fri, Aug 21
Multiple Airlines Logo
12:44 am - 10:55 am
ORD
-
EIS
9h 11m
1 stop
Multiple Airlines Logo
4:00 pm - 12:50 pm
EIS
-
ORD
45h 50m
2 stops
$629Multiple Airlines
Thu, Aug 13 - Fri, Aug 21
Multiple Airlines Logo
12:44 am - 2:05 pm
ORD
-
EIS
12h 21m
1 stop
Multiple Airlines Logo
4:00 pm - 11:27 pm
EIS
-
ORD
8h 27m
1 stop
$631Multiple 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 5 days.

In the past 5 days, the cheapest round-trip tickets from Chicago to Road Town were found on American Airlines ($788) and United Airlines ($940).

Good to know

Cheapest flight$414
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 5 days, the lowest price for a flight from Chicago O'Hare Intl Airport to Road Town was $414 for a one-way ticket and $539 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 11764 reviews
6.4Food
7.5Boarding
7.9Crew
6.8Entertainment
7.2Comfort
Airline reviews

The seat was not even cleaned. It has full of cookie crums probably from last flight's passenger. Its basic expectation that, seats are clean.

2.0 MediocreOnkar Pravin, Jul 2026
ORD - DFW
Read more American Airlines reviews

The seat was not even cleaned. It has full of cookie crums probably from last flight's passenger. Its basic expectation that, seats are clean.

Very turbulent flight, no drinks, very little service, unorganized boarding, gate changed multiple times

The flight was delayed significantly. Communication during the flight was abrupt and caused some panic as we were navigating turbulence. It was also too loud and every announcement felt startling. The flight attendants did not offer any assurances and I felt unsettled most of the flight. The seats, floor and tray table was very dirty. The seat next to me was broken and the passenger sitting there was very uncomfortable. He had a spring in his back and his seat made terrible squeaking noises through the flight.

Significant delays on my trip to Chicago and my trip back to NY

Delayed by 5 hours and I had to wit in the airport for more than 6+ hours.

I’ve got 31F seat and window seat . My 2 co passengers was AA crew members and they were very rude attitude and when I was going to use bathroom their gestures was very different and awkward and the guy beside me completely occupied the hand rest and I was really uncomfortable

It was so much better than expected, Ohare is not such a pleasant experience but American Airlines with the new, clean aeroplane and free Wi-Fi was outstanding and the crew so pleasant and helpful.

It wa sort of on time; the cab was left with some trash

My pillow had a shoe print on it, when I asked if I can have another pillow, I was told “I’m sorry but it is one pillow per guest, do YOU want to turn it inside out” to which I responded , no thanks I will go without. This is generally not ok, but For the price tag I paid flying business this is absolutely unacceptable. Hopefully American Airlines can update their accommodations to bedding that is not tossed on the ground and stepped on, or at least have a couple of extra pillows in hand, incase someone had decided to step on the pillows for what ever reason

Horrible. Got delayed many hours because their pilot wasn't trained for night landing at the airport and a rain delay made it a night landing. We have to wait hours for a qualified crew. They give us 12 dollar meal vouchers but most everything in the airport was closed and definitely more expensive than the vouchers.

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

Information on your arrival and departure airports