ORD - EIS

$527 Find Cheap Flights from Chicago to Road Town

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Road Town departing on 3/18. 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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Everything you should know

Cheapest round-trip
$522
Typical prices: $794-$1,133
Multiple Airlines
Wed 3/18Wed 3/25
ORD - EIS • 1 stop
Cheapest one-way
Multiple Airlines
Mon 2/9
ORD - EIS • multi-stop
Top airlines
American Airlines
Cheapest • from $760 (round-trip)
United Airlines
Best reviews • 7.4 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
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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

Wed, Mar 18 - Wed, Mar 25
Multiple Airlines Logo
8:56 pm - 2:10 pm
ORD
-
EIS
16h 14m
1 stop
Multiple Airlines Logo
8:55 am - 7:51 pm
EIS
-
ORD
11h 56m
2 stops
$522Multiple Airlines
Tue, Mar 3 - Mon, Mar 9
Multiple Airlines Logo
12:17 pm - 3:15 pm
ORD
-
EIS
24h 58m
1 stop
Multiple Airlines Logo
4:00 pm - 9:39 am
EIS
-
ORD
42h 39m
2 stops
$523Multiple Airlines
Mon, May 4 - Mon, May 11
Multiple Airlines Logo
12:22 pm - 2:05 pm
ORD
-
EIS
24h 43m
1 stop
Multiple Airlines Logo
4:00 pm - 6:15 pm
EIS
-
ORD
27h 15m
2 stops
$527Multiple Airlines
Sat, Apr 18 - Sat, Apr 25
Multiple Airlines Logo
3:52 pm - 10:55 am
ORD
-
EIS
18h 03m
2 stops
Multiple Airlines Logo
9:00 am - 4:37 pm
EIS
-
ORD
8h 37m
1 stop
$528Multiple Airlines
Sat, Apr 18 - Sat, Apr 25
Multiple Airlines Logo
1:27 pm - 10:55 am
ORD
-
EIS
44h 28m
2 stops
Multiple Airlines Logo
9:00 am - 4:37 pm
EIS
-
ORD
8h 37m
1 stop
$532Multiple Airlines
Sat, Apr 18 - Sat, Apr 25
Multiple Airlines Logo
12:22 pm - 2:05 pm
ORD
-
EIS
24h 43m
1 stop
Multiple Airlines Logo
9:00 am - 6:15 pm
EIS
-
ORD
10h 15m
2 stops
$533Multiple Airlines
Sat, Apr 18 - Sat, Apr 25
Multiple Airlines Logo
12:22 pm - 10:55 am
ORD
-
EIS
21h 33m
1 stop
Multiple Airlines Logo
9:00 am - 4:37 pm
EIS
-
ORD
8h 37m
1 stop
$545Multiple Airlines
Wed, Mar 18 - Mon, Mar 30
Multiple Airlines Logo
8:56 pm - 10:55 am
ORD
-
EIS
12h 59m
1 stop
Multiple Airlines Logo
4:00 pm - 7:51 pm
EIS
-
ORD
28h 51m
2 stops
$554Multiple Airlines
Sat, Apr 18 - Sat, Apr 25
Multiple Airlines Logo
12:22 pm - 2:05 pm
ORD
-
EIS
24h 43m
1 stop
Multiple Airlines Logo
9:00 am - 4:37 pm
EIS
-
ORD
8h 37m
1 stop
$555Multiple Airlines
Sat, Apr 18 - Sat, Apr 25
Multiple Airlines Logo
12:22 pm - 2:05 pm
ORD
-
EIS
24h 43m
1 stop
Multiple Airlines Logo
9:00 am - 4:37 pm
EIS
-
ORD
8h 37m
1 stop
$556Multiple 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.

How much is a round-trip flight from Chicago O'Hare Intl Airport to Road Town?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago O'Hare Intl Airport to Road Town departing in March.

Good to know

Low seasonSeptember
Cheapest flight$522
Best time to beat the crowds with an average 30% drop in price.
Most popular time to fly and prices are also 7% lower on average.
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 $527 for a round-trip ticket.

  • 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?

    Star Alliance, and oneworld are the airline alliances operating flights between Chicago and Road Town, with Star Alliance being the most commonly used for this route.

  • Which is the best airline for flights from Chicago to Road Town, United Airlines or American Airlines?

    The two airlines most popular with KAYAK users for flights from Chicago to Road Town are United Airlines and American Airlines. With an average price for the route of $921 and an overall rating of 7.4, United Airlines is the most popular choice. American Airlines is also a great choice for the route, with an average price of $883 and an overall rating of 7.2.

  • 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.

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

    In the past 3 days, the cheapest round-trip tickets from Chicago to Road Town were found on American Airlines ($760) and United Airlines ($892).

Reviews of the top airlines 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.
7.4
United AirlinesOverall score based on 9259 reviews
6.6Food
7.1Entertainment
8.1Crew
7.7Boarding
7.3Comfort
Airline reviews

Not being stranded in Chicago for her airport to 11:30 tomorrow morning the 3rd

2.0 MediocreRonald, Feb 2026
ORD - BWI
Read more United Airlines reviews

Not being stranded in Chicago for her airport to 11:30 tomorrow morning the 3rd

I was fully checked in the prior night and i was unchecked and then didn’t have a seat when I boarded. Instead of an aisle seat, I was out in the middle seat of the very last row of the plane.

In overall it was a good experience, the only down point was that the entertainment screen was working properly.

They lost my luggage, so, not happy. The crew was nice but my suitcases never made it, still trying to find out what happened!

I understand weather is an issue, but making us chase our plane down at five scheduled gates across three terminals in an airport the size of O'Hare was unfair. They'd have probably been better off to leave gates as TBD until the inbound plane is in final approach instead of running us all over the place. Also, props to the consistently-unprepared ground crew in Richmond for once again leaving my lane parked short of the gate because they couldn't have a crew in place on time with 2 hours notice...

cabin crew was OK, food was OK, the trip from the US to Munich was actually pretty bad comfort wise. Noisy aircraft, lights never dimmed even in Business class (night flight) barely sufficient amenities for the price. I have millions of miles with United but TBH American is gaining ground and Delta has always been marginally better then United although on paper United has more longes and cheaper upgrades.

Essy to get on. The hostess gave very little pop, the plane was late getting in, and we are still waiting for our bags. This sucks. :/

Not United Airlines' fault. It's ORL airport's fault.

Great flight. On time boarding. Smooth flight and on time arrival at EWR. The flight crew was marvelous and there was a great selection of movies on the entertainment system. Our bags were at the carousel before we got there. Another excellent flight from United.

I liked the snacks and the flight attendants were friendly.

Delayed an hour due to operational issues. Minimal apologies or care for the significant inconvenience caused. Landed at nearly 1am and they still couldn’t find ground staff to get us off the plane promptly.

The aircraft had several problems - from excess fuel to non operational ac. Two hours of delay in Chicago could have been avoided with proper planning and aircraft maintenance.

Crew in Columbia was not prepared for landing. It was a bit of a disaster and getting bags took forever.

We were upgraded to First Class and it was a great flight

We experienced gate changes and a long delay. My seat was dirty when I boarded and I had to use wipes to clean it myself. There was an unpleasant and overpowering cleaning product scent on the plane as well that lingered through the flight.

My carry on baggage was damaged. Entire trip, I had to carry the baggage. When complained to the boarding crew, they got mad at me and still asked me to valet check in the cabin baggage. Rude boarding crew!!!

Crew were all friendly and helpful. It was a short flight so just a beverage service with a cookie. After we were boarded the plane took about 45 minutes to leave the gate but it was New Year’s Eve so not shocking there was some delay. Overall good experience and very grateful.

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

The boarding by groups is pointless. The first two groups worked fine, but almost Noone boarded in goups three thru five leaving the vast majority boarding when group six was called. It defeated the purpose of spreading out the crowd.

We loved the steward on the plane. He made the night enjoyable

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

Information on your arrival and departure airports