ORD - EIS

$248 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 8/9. 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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Flights 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

Fri, Aug 15 - Fri, Aug 22
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11:15 am - 6:20 pmORD-EIS
30h 05m2 stops
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4:00 pm - 11:43 pmEIS-ORD
8h 43m1 stop
Fri, Aug 15 - Fri, Aug 22
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11:15 am - 6:20 pmORD-EIS
30h 05m2 stops
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4:00 pm - 11:43 pmEIS-ORD
8h 43m1 stop
Mon, Aug 18 - Fri, Aug 22
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12:55 pm - 3:15 pmORD-EIS
25h 20m1 stop
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4:00 pm - 11:43 pmEIS-ORD
8h 43m1 stop
Fri, Aug 15 - Fri, Aug 22
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4:26 pm - 6:20 pmORD-EIS
24h 54m2 stops
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4:00 pm - 11:43 pmEIS-ORD
8h 43m1 stop
Sat, Jul 12 - Wed, Jul 16
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6:40 am - 6:20 pmORD-EIS
10h 40m1 stop
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12:10 pm - 10:16 amEIS-ORD
23h 06m1 stop
Mon, Aug 18 - Fri, Aug 22
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6:56 am - 6:20 pmORD-EIS
10h 24m2 stops
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8:55 am - 11:59 pmEIS-ORD
16h 04m2 stops
Mon, Aug 18 - Fri, Aug 22
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6:56 am - 6:20 pmORD-EIS
10h 24m2 stops
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4:00 pm - 11:43 pmEIS-ORD
8h 43m1 stop
Sat, Aug 16 - Sat, Aug 23
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12:55 pm - 10:55 amORD-EIS
21h 00m1 stop
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4:00 pm - 11:43 pmEIS-ORD
8h 43m1 stop
Sat, Oct 4 - Thu, Oct 9
American Airlines Logo
5:00 am - 1:06 pmORD-EIS
7h 06m1 stop
American Airlines Logo
1:59 pm - 10:31 pmEIS-ORD
9h 32m1 stop
$774American Airlines
Find Deal
Sat, Oct 4 - Thu, Oct 9
American Airlines Logo
8:29 pm - 1:06 pmORD-EIS
15h 37m2 stops
American Airlines Logo
1:59 pm - 11:53 pmEIS-ORD
10h 54m2 stops
$778American Airlines
Find Deal
Useful Info

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.

What is the cheapest month to fly from Chicago O'Hare Intl Airport to Road Town?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago O'Hare Intl Airport to Road Town, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago O'Hare Intl Airport to Road Town is September, where tickets cost $716 (return) on average. On the other hand, the most expensive months are December and August, where the average cost of round-trip tickets is $2,217 and $1,546 respectively.

Good to know

Low seasonAugust
High seasonApril
Cheapest flight$248
Best time to beat the crowds but there is an average 52% increase in price.
Most popular time to fly and prices are also 15% 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 $248 for a one-way ticket and $573 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, and Star Alliance 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 $931 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 $817 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 8861 reviews
7.3Comfort
7.0Entertainment
7.7Boarding
6.6Food
8.1Crew
Airline reviews

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

8.0 ExcellentStacie, Jun 2025ORD - ALB
Read more United Airlines reviews

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!

Flight was great. Efficient boarding. Short flight. Early arrival. Friendly flight crew. The entertainment system did not work well. Could not access it until the aircraft reached 10K feet or more. Lots of glitches.

A bit rush for transit. Food and entertainment are not available

Boarding was a little difficult. The gate area at O'Hare was very small and crowded due to multiple gates in the area. Could not hear the intercom, so had to rely on signage to see when my group was boarding and the signage was blocked by passengers standing in the gate. Flight was great and we arrived in Montreal on time.

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

I do prefer to fly United and have always had excellent service, except for bad weather. Flights are on time and staff is alway curtious and helpful

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.

You were more on time than United. I'm so over united delays.

The meals were mediocre and the alcohol selection was poor. I enjoyed the selection of movies and other entertainment.

I chatted with the captain before the flight, and similarly during the welcome announcement, he warned of a turbulent flight that may impact the in-flight service. However, once at altitude, he announced that the weather changed and he immediately turned off the seatbelt sign. But it appeared the cabin crew had already decided to take off this flight. They remained seated and then just chatted in the galley. The flight was fully catered, but only first class received service.

My flight attendant was attentive! The elderly person next to me was flatulent and the flight attendant could see that I was in distress and brought me some face masks

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

Information on your arrival and departure airports

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