ORD - EIS

$551 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 10/30. 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

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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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, Oct 30 - Thu, Nov 6
Multiple Airlines Logo
6:40 am - 10:55 amORD-EIS
27h 15m2 stops
Multiple Airlines Logo
4:00 pm - 6:00 pmEIS-ORD
28h 00m1 stop
$551Multiple Airlines
Find Deal
Sat, Oct 11 - Sat, Oct 18
Multiple Airlines Logo
3:00 pm - 10:55 amORD-EIS
18h 55m1 stop
Multiple Airlines Logo
12:50 pm - 9:33 pmEIS-ORD
9h 43m2 stops
$574Multiple Airlines
Find Deal
Mon, Jan 5 - Wed, Jan 14
Multiple Airlines Logo
1:35 pm - 3:15 pmORD-EIS
23h 40m2 stops
Multiple Airlines Logo
12:10 pm - 6:00 pmEIS-ORD
7h 50m1 stop
$585Multiple Airlines
Find Deal
Tue, Jan 6 - Wed, Jan 14
Multiple Airlines Logo
4:35 pm - 10:55 amORD-EIS
16h 20m1 stop
Multiple Airlines Logo
8:55 am - 6:00 pmEIS-ORD
11h 05m1 stop
$587Multiple Airlines
Find Deal
Tue, Jan 6 - Fri, Jan 16
American Airlines Logo
6:35 pm - 12:15 pmORD-EIS
15h 40m2 stops
American Airlines Logo
5:35 pm - 8:59 amEIS-ORD
17h 24m1 stop
$743American Airlines
Find Deal
Tue, Jan 6 - Thu, Jan 15
American Airlines Logo
6:24 pm - 2:45 pmORD-EIS
18h 21m1 stop
American Airlines Logo
3:35 pm - 12:30 amEIS-ORD
10h 55m1 stop
$744American Airlines
Find Deal
Tue, Jan 6 - Thu, Jan 15
American Airlines Logo
6:35 pm - 12:15 pmORD-EIS
15h 40m2 stops
American Airlines Logo
3:35 pm - 12:30 amEIS-ORD
10h 55m1 stop
$748American Airlines
Find Deal
Fri, Mar 6 - Sat, Mar 14
American Airlines Logo
1:59 pm - 9:55 pmORD-EIS
5h 56m1 stop
American Airlines Logo
7:00 am - 11:19 pmEIS-ORD
17h 19m1 stop
$784American Airlines
Find Deal
Sat, Jan 31 - Sun, Feb 8
United Airlines Logo
7:50 pm - 6:30 pmORD-EIS
20h 40m2 stops
United Airlines Logo
9:41 am - 2:25 pmEIS-ORD
30h 44m2 stops
$955United Airlines
Find Deal
Sat, Oct 4 - Thu, Oct 9
United Airlines Logo
8:52 am - 6:55 pmORD-EIS
9h 03m1 stop
United Airlines Logo
7:55 am - 8:03 pmEIS-ORD
13h 08m1 stop
$986United Airlines
Find Deal

Everything you should know

Top airlines
American Airlines
Cheapest • from $743 (round-trip)
United Airlines
Best reviews • 7.4 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Cheapest round-trip
$551
Multiple Airlines
Thu 10/30Thu 11/6
ORD - EIS • 2 stops
Cheapest one-way
$687
United Airlines
Fri 12/19
ORD - EIS • 1 stop
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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!
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 72 hours.

In the past 3 days, the cheapest round-trip tickets from Chicago to Road Town were found on American Airlines ($743) and United Airlines ($955).

Good to know

Low seasonSeptember
Cheapest flight$551
Best time to beat the crowds with an average 26% drop in price.
Most popular time to fly and prices are also 8% 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 $687 for a one-way ticket and $551 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 oneworld 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 $862 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 8929 reviews
7.3Comfort
7.7Boarding
7.1Entertainment
6.6Food
8.1Crew
Airline reviews

Once we got in the air the pilot made up some of the time of the delay. So that was really nice.

10.0 ExcellentAnonymous, Aug 2025ORD - MEM
Read more United Airlines reviews

Once we got in the air the pilot made up some of the time of the delay. So that was really nice.

We had a layover from YVR to Denver. We bought 4 bottles of Absolut Vodka at the YVR Duty Free for $116.20, after going through security and American Customs Pre Clearance at YVR, Vancouver. When we landed in Denver, United put us behind the American Customs as well as TSA again for some reason. We were forced to go through American Customs and TSA again. TSA confiscated our rightfully owned Duty Free Absolut Vodka bottles. Because United incorrectly forced our flight behind American border and TSA again, we missed the connecting flight. After United put us on a later flight, we eventually arrived in Chicago very late, with hardly any sleep. I am looking for compensation from United for our incorrectly confiscated Absolut Vodka bottles worth $116.20, as well as compensation for incorrectly putting us behind American Customs and TSA again, causing us to miss our connecting flight, making us arrive extremely late in Chicago.

Excellent flight. Boarding was efficient and departure was on time. Smooth flight with on time arrival. Deplaning was also efficient.

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

It was great, I’m very grateful for the pilots and crew flight attendants for everything.

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

The boarding of took of late.The presentation of the food was horrable as was the tast of the food was cold and tastless.

Delay and keep changing gates. I have to run around from B to C then to E.

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

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

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

This particular flight wasn't very full at the back, so there were three seats available for spreading out and getting relatively comfortable

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

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

Information on your arrival and departure airports

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