ORD - EIS

$255 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 12/15. 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
$491
Multiple Airlines
Wed 2/18Sun 2/22
ORD - EIS • 1 stop
Cheapest one-way
$255
Multiple Airlines
Mon 12/15
ORD - EIS • 2 stops
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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

Wed, Feb 18 - Sun, Feb 22
Multiple Airlines Logo
12:22 pm - 10:55 amORD-EIS
20h 33m1 stop
Multiple Airlines Logo
4:00 pm - 2:10 pmEIS-ORD
24h 10m2 stops
$491Multiple Airlines
Find Deal
Sun, Jan 18 - Fri, Jan 23
Multiple Airlines Logo
7:45 am - 10:55 amORD-EIS
25h 10m2 stops
Multiple Airlines Logo
4:00 pm - 4:37 pmEIS-ORD
26h 37m1 stop
$496Multiple Airlines
Find Deal
Sat, Jan 10 - Sat, Jan 17
Multiple Airlines Logo
8:27 pm - 10:55 amORD-EIS
36h 28m2 stops
Multiple Airlines Logo
8:55 am - 4:37 pmEIS-ORD
9h 42m1 stop
$515Multiple Airlines
Find Deal
Mon, Jan 5 - Mon, Jan 12
Multiple Airlines Logo
1:44 pm - 10:55 amORD-EIS
43h 11m2 stops
Multiple Airlines Logo
4:00 pm - 4:37 pmEIS-ORD
26h 37m1 stop
$529Multiple Airlines
Find Deal
Tue, Jan 20 - Sat, Jan 24
Multiple Airlines Logo
12:22 pm - 10:55 amORD-EIS
20h 33m1 stop
Multiple Airlines Logo
8:55 am - 4:37 pmEIS-ORD
9h 42m1 stop
$532Multiple Airlines
Find Deal
Mon, Jan 19 - Sat, Jan 24
Multiple Airlines Logo
12:00 pm - 3:15 pmORD-EIS
25h 15m2 stops
Multiple Airlines Logo
8:55 am - 4:37 pmEIS-ORD
9h 42m1 stop
$533Multiple Airlines
Find Deal
Mon, Jan 5 - Mon, Jan 12
Multiple Airlines Logo
5:45 am - 6:20 pmORD-EIS
10h 35m1 stop
Multiple Airlines Logo
4:00 pm - 4:37 pmEIS-ORD
26h 37m1 stop
$536Multiple Airlines
Find Deal
Wed, Dec 3 - Wed, Dec 10
Multiple Airlines Logo
11:40 am - 2:10 pmORD-EIS
24h 30m2 stops
Multiple Airlines Logo
8:55 am - 10:53 pmEIS-ORD
15h 58m1 stop
$538Multiple Airlines
Find Deal
Sun, Jan 18 - Fri, Jan 23
Multiple Airlines Logo
12:22 pm - 10:55 amORD-EIS
20h 33m1 stop
Multiple Airlines Logo
4:00 pm - 4:37 pmEIS-ORD
26h 37m1 stop
$541Multiple Airlines
Find Deal
Mon, Feb 9 - Sun, Feb 15
Multiple Airlines Logo
11:51 am - 3:15 pmORD-EIS
25h 24m2 stops
Multiple Airlines Logo
4:00 pm - 4:37 pmEIS-ORD
26h 37m1 stop
$542Multiple Airlines
Find Deal
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 $693. On average, the best prices for this route can be found at American Airlines.

Good to know

Low seasonSeptember
Cheapest flight$255
Best time to beat the crowds with an average 27% drop in price.
Most popular time to fly and prices are also 18% 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 $255 for a one-way ticket and $491 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 $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 $878 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 9014 reviews
7.3Comfort
7.1Entertainment
7.7Boarding
8.1Crew
6.6Food
Airline reviews

Seats in waiting area and on plane hard as rock. Fast internet on the flight was great! Crew was kind.

10.0 ExcellentClaire, Nov 2025ORD - YOW
Read more United Airlines reviews

Seats in waiting area and on plane hard as rock. Fast internet on the flight was great! Crew was kind.

Always wish for more healthy, gluten free options. We have to bring our own.

Having a long layover, I was very appreciative of the ability to stand by for an earlier flight. Other airlines like Delta have refused this to me in the past, just to be mean (because my ticket class wasn't high enough). United went out of their way to help me get to my destination early, which I really appreciated given that it was the third leg of a 24+ hour journey for me.

Other than a way way too cold cabinets for the entire flight, all was great

One bag is incorrect and not acceptable for an international flight. The food was not just good. I won't fly with them again.

Excellent flight. Smooth, efficient boarding. Quick flight. Arrived early at STL.

Not the fault of United—weather, reroute around weather, time sitting on tarmac, arrived couple hours late, too late for train into city necessitating a much pricier cab but weather…can’t be helped.

I will never book a flight through Cheap fare. They booked me from Portland Main . And would not give me a refund, so I bought 2 tickets one for 299. From Portland Main to ORD. Then I had to buy a ticket from Oregon PDX to ORD that was another 440. So Just so you know they even told me it was there fault but no refund. Bad bussniess. I did inform United but they said they couldn't help me due to the fact I booked through Cheap Tickets. Never again. And I'm spreding the word. I let everyone know at my 50th class reunion

The flight attendants were rude. Seemed like they didn’t want to be there. Except for one girl that was really nice. Seats are sooooo uncomfortable. They give you a piece of paper and a thin cushion for a pillow and blanket that does nothing. Airlines have gone way downhill, especially United international flights. Food was disguting. Definitely flying ANA next time.

Crew and customer service were excellent. This flight also had plenty of leg room and seat mounted screens for entertainment. A very pleasant flight all around!

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!

After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"

After a two hour delay, my flight was CANCELLED! No pilot available. Such BS.

Amazing food, great staff, with one noticable detail missing ...but no seat entertainment in any of aircraft ...I am not a fan

I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

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

Information on your arrival and departure airports