ORD - EIS

$323 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 5/16. 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.
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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

 
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.

Recent round-trip flight deals from Chicago to Road Town

KAYAK's recommended round-trip deals from the most popular airlines that fly from Chicago to Road Town.
Discover the best prices for you by selecting your travel dates on KAYAK.
 Logo
11:30 am - 10:55 amORD-EIS
22h 25m1 stop
 Logo
4:00 pm - 10:25 amEIS-ORD
19h 25m1 stop
Thu, May 29 - Thu, Jun 5
 Logo
12:31 pm - 10:55 amORD-EIS
21h 24m1 stop
 Logo
8:55 am - 6:43 pmEIS-ORD
10h 48m2 stops
Sat, Oct 25 - Wed, Oct 29
 Logo
11:30 am - 6:20 pmORD-EIS
29h 50m1 stop
 Logo
4:00 pm - 8:50 amEIS-ORD
17h 50m2 stops
Thu, May 29 - Thu, Jun 5
United Airlines Logo
8:52 am - 11:30 amORD-EIS
25h 38m1 stop
United Airlines Logo
3:10 pm - 8:11 pmEIS-ORD
30h 01m1 stop
$682United Airlines
Find Deal
Sat, Oct 25 - Wed, Oct 29
American Airlines Logo
5:20 am - 3:20 pmORD-EIS
9h 00m2 stops
American Airlines Logo
4:20 pm - 8:17 amEIS-ORD
16h 57m2 stops
$723American Airlines
Find Deal
Mon, Aug 11 - Sat, Aug 16
United Airlines Logo
8:52 am - 10:50 amORD-EIS
24h 58m1 stop
United Airlines Logo
3:10 pm - 8:11 pmEIS-ORD
30h 01m1 stop
$779United Airlines
Find Deal
Fri, Oct 24 - Thu, Oct 30
United Airlines Logo
8:49 am - 8:10 pmORD-EIS
10h 21m1 stop
United Airlines Logo
11:25 am - 10:21 amEIS-ORD
23h 56m2 stops
$869United Airlines
Find Deal
Sat, Jul 19 - Sat, Jul 26
American Airlines Logo
5:00 am - 3:19 pmORD-EIS
9h 19m2 stops
American Airlines Logo
2:43 pm - 1:09 amEIS-ORD
11h 26m2 stops
$1,610American Airlines
Find Deal
Thu, May 29 - Thu, Jun 5
American Airlines Logo
5:15 am - 3:50 pmORD-EIS
9h 35m2 stops
American Airlines Logo
2:38 pm - 12:59 amEIS-ORD
11h 21m2 stops
$2,493American Airlines
Find Deal
Sat, Jul 19 - Sat, Jul 26
American Airlines Logo
6:51 am - 3:19 pmORD-EIS
7h 28m1 stop
American Airlines Logo
12:35 pm - 11:56 pmEIS-ORD
12h 21m2 stops
$2,816American Airlines
Find Deal
Sat, May 17 - Sat, May 24
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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 August and December, where the average cost of round-trip tickets is $1,546 and $1,156 respectively.

Good to know

Low seasonAugust
High seasonApril
Cheapest flight$323
Best time to beat the crowds but there is an average 68% increase in price.
Most popular time to fly and prices are also 6% 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 $323 for a one-way ticket and $558 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 $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 $812 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.

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 8696 reviews
7.7Boarding
6.6Food
7.1Entertainment
8.1Crew
7.3Comfort
Airline reviews

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

8.0 ExcellentAnonymous, Apr 2025ORD - SFO
Read more United Airlines reviews

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

They switched out gate from terminal 1 to terminal two ten minutes before boarding. So we had to make a 20 min crazy fast walk to a different terminal. Then we boarded the plane and waited for over 40 minutes until push back. Brutal

My flight was scheduled for about 6:05 departure. There were 11 gate changes from 4-7pm and the flight was 3 hours delayed due to operational issues. The plane taxied around the airport for about half an hour before stopping to be de-iced. It would have been nice if we were alerted of the plan to de-ice prior to the 30 minute drive around the airport. The flight attendant was friendly, which was the only redeeming thing about this flight. As a former flight attendant for United, I was extremely disappointed.

Delays took 2hours and thirty minutes making me miss my connecting flight and make me sit in the Chicago airport for 9 hours

Had a short delay once we boarded the aircraft in Chicago, but it was fixed in no time flat then we were on our way. The pilot was able to make up the time lost and we landed 5 minute later then schedualed . Great service

Our seats were all the way in back of the plane,

The seats on this flight were almost roomy enough to be the basic amount needed for human existence. I think my favorite part of this flight was it landed at an A gate, which was the most palatial part of Sea-Tac I've ever seen - a massive improvement from the S gates.

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

My boarding pass wouldn't pull up in the app very easily and had to really dig through my email. That caused a delay in TSA..

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

Information on your arrival and departure airports

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