ORD - EIS

$288 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 4/18. 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
$508
Multiple Airlines
Mon 2/23Mon 3/2
ORD - EIS • 1 stop
Cheapest one-way
$288
Multiple Airlines
Sat 4/18
ORD - EIS • 2 stops
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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

Mon, Feb 23 - Mon, Mar 2
Multiple Airlines Logo
12:17 pm - 3:15 pm
ORD
-
EIS
24h 58m1 stop
Multiple Airlines Logo
12:10 pm - 3:52 pm
EIS
-
ORD
29h 42m2 stops
$508Multiple Airlines
Wed, Feb 25 - Mon, Mar 2
Multiple Airlines Logo
12:17 pm - 10:55 am
ORD
-
EIS
20h 38m1 stop
Multiple Airlines Logo
12:10 pm - 9:39 am
EIS
-
ORD
47h 29m2 stops
$512Multiple Airlines
Tue, Feb 24 - Tue, Mar 3
Multiple Airlines Logo
12:17 pm - 10:55 am
ORD
-
EIS
20h 38m1 stop
Multiple Airlines Logo
12:10 pm - 3:52 pm
EIS
-
ORD
29h 42m2 stops
$514Multiple Airlines
Fri, Jan 23 - Thu, Jan 29
Multiple Airlines Logo
11:55 am - 10:55 am
ORD
-
EIS
45h 00m2 stops
Multiple Airlines Logo
8:55 am - 4:37 pm
EIS
-
ORD
9h 42m1 stop
$532Multiple Airlines
Sat, Feb 28 - Sat, Mar 7
Multiple Airlines Logo
12:17 pm - 10:55 am
ORD
-
EIS
20h 38m1 stop
Multiple Airlines Logo
4:00 pm - 1:21 pm
EIS
-
ORD
23h 21m2 stops
$533Multiple Airlines
Wed, Feb 25 - Wed, Mar 4
Multiple Airlines Logo
7:23 pm - 10:55 am
ORD
-
EIS
37h 32m2 stops
Multiple Airlines Logo
4:00 pm - 3:48 pm
EIS
-
ORD
25h 48m1 stop
$534Multiple Airlines
Sun, Apr 5 - Thu, Apr 9
Multiple Airlines Logo
7:30 pm - 10:55 am
ORD
-
EIS
14h 25m1 stop
Multiple Airlines Logo
9:00 am - 12:29 am
EIS
-
ORD
16h 29m2 stops
$536Multiple Airlines
Mon, Feb 23 - Mon, Mar 2
Multiple Airlines Logo
12:17 pm - 3:15 pm
ORD
-
EIS
24h 58m1 stop
Multiple Airlines Logo
12:10 pm - 3:48 pm
EIS
-
ORD
29h 38m1 stop
$540Multiple Airlines
Wed, Feb 25 - Wed, Mar 4
Multiple Airlines Logo
12:17 pm - 10:55 am
ORD
-
EIS
20h 38m1 stop
Multiple Airlines Logo
8:55 am - 3:48 pm
EIS
-
ORD
8h 53m1 stop
$546Multiple Airlines
Sat, Feb 28 - Sun, Mar 8
Multiple Airlines Logo
12:17 pm - 10:55 am
ORD
-
EIS
20h 38m1 stop
Multiple Airlines Logo
4:00 pm - 3:28 pm
EIS
-
ORD
24h 28m2 stops
$558Multiple 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 fly non-stop between Chicago O'Hare Intl Airport and Road Town?

Airline and price data is aggregated from results in KAYAK’s search results from the last 2 weeks for round-trip flights from Chicago O'Hare Intl Airport to Road Town.

There are 2 airlines that fly nonstop from Chicago O'Hare Intl Airport to Road Town. They are American Airlines and United Airlines. The cheapest airline for this route is American Airlines, with the best round-trip deal found costing $718. On average, the best prices for this route can be found at American Airlines.

Good to know

Low seasonSeptember
Cheapest flight$288
Best time to beat the crowds with an average 30% drop in price.
Most popular time to fly and prices are also 14% 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 $288 for a one-way ticket and $508 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?

    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 $906 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 $889 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.

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 9145 reviews
7.7Boarding
7.3Comfort
8.1Crew
7.1Entertainment
6.6Food
Airline reviews

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

6.0 GoodPatricia, Jan 2026
ORD - LAS
Read more United Airlines reviews

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.

The movies offered were great. Staff were very pleasant and very efficient.

After a delay at the gate, C3, at Ohare on Sunday, I left my Blk ski coat on the bench at the gate, lost! Please review my lob claim, thx.

Very nice flight love the small aircraft. We had a wonderful flight attendant. Nice to see someone that really enjoys her job. Don't have her name but had a southern accent.

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

The plane was late, when we did board the plane was as cold as a freezer. I was freezing the entire flight, no blankets. Lost miserable flight I’ve ever had.

My wife and I love to travel, so we fly a lot. We've already logged 381,075 miles and with practically every major airline. But this flight was very disappointing. It started off well, with no delays and a new plane. But when lunchtime approached, all that good impression was ruined. Instead of white tablecloths, we were offered small, dark placemats, which, as it turned out, were perfectly adequate for the food. All the food offered—and my wife and I only took fish, and the meat—was not just bad, it was downright disgusting and not heated enough. The same applies to the appetizers. This was the first time in many years of traveling that we've been offered such disgusting food.

Lost luggage stuck no clothes and no word after 2 days leaving on cruise no stuff or clothes

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

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

Information on your arrival and departure airports