ORD - EIS

$237 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 4/12. 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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41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$574
Multiple Airlines
Sat 4/11Sat 4/18
ORD - EIS • 1 stop
Cheapest one-way
$237
Multiple Airlines
Sun 4/12
ORD - EIS • 2 stops
Nonstop flights
Not available
There are currently no direct flights between Chicago and Road Town. You'll need at least 1 connection.
Insights
Insights
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Insights
Top layover airports
Cheapest • Avg $1,069 (round-trip)
Shortest trip • 8h 19m (one-way)
Insights
Insights
Insights
Insights
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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

Sat, Apr 11 - Sat, Apr 18
Multiple Airlines Logo
8:56 pm - 10:55 am
ORD
-
EIS
12h 59m
1 stop
Multiple Airlines Logo
9:00 am - 11:59 pm
EIS
-
ORD
15h 59m
2 stops
$574Multiple Airlines
Mon, Apr 27 - Mon, May 4
Multiple Airlines Logo
10:00 am - 2:05 pm
ORD
-
EIS
27h 05m
1 stop
Multiple Airlines Logo
4:00 pm - 11:13 pm
EIS
-
ORD
32h 13m
2 stops
$578Multiple Airlines
Wed, May 6 - Wed, May 20
Multiple Airlines Logo
5:05 am - 10:55 am
ORD
-
EIS
28h 50m
2 stops
Multiple Airlines Logo
4:00 pm - 10:46 pm
EIS
-
ORD
7h 46m
1 stop
$599Multiple Airlines
Sat, Apr 25 - Sat, May 2
Multiple Airlines Logo
10:00 am - 6:10 pm
ORD
-
EIS
7h 10m
1 stop
Multiple Airlines Logo
4:00 pm - 8:03 pm
EIS
-
ORD
29h 03m
2 stops
$606Multiple Airlines
Sun, Apr 5 - Mon, Apr 13
Multiple Airlines Logo
8:56 pm - 10:55 am
ORD
-
EIS
12h 59m
1 stop
Multiple Airlines Logo
4:00 pm - 5:45 am
EIS
-
ORD
14h 45m
1 stop
$610Multiple Airlines
Wed, Apr 29 - Wed, May 6
Multiple Airlines Logo
7:15 pm - 10:55 am
ORD
-
EIS
38h 40m
2 stops
Multiple Airlines Logo
4:00 pm - 6:50 pm
EIS
-
ORD
27h 50m
1 stop
$611Multiple Airlines
Sat, Apr 11 - Sat, Apr 18
Multiple Airlines Logo
7:17 am - 10:55 am
ORD
-
EIS
26h 38m
2 stops
Multiple Airlines Logo
9:00 am - 12:24 am
EIS
-
ORD
16h 24m
2 stops
$614Multiple Airlines
Sat, Apr 11 - Sat, Apr 18
Multiple Airlines Logo
8:56 pm - 10:55 am
ORD
-
EIS
12h 59m
1 stop
Multiple Airlines Logo
9:00 am - 8:49 pm
EIS
-
ORD
12h 49m
1 stop
$632Multiple Airlines
Sun, Aug 2 - Tue, Aug 11
Multiple Airlines Logo
12:59 am - 10:55 am
ORD
-
EIS
8h 56m
1 stop
Multiple Airlines Logo
4:00 pm - 9:04 pm
EIS
-
ORD
30h 04m
1 stop
$636Multiple Airlines
Fri, May 22 - Wed, May 27
Multiple Airlines Logo
8:05 am - 6:10 pm
ORD
-
EIS
9h 05m
2 stops
Multiple Airlines Logo
9:00 am - 3:08 pm
EIS
-
ORD
7h 08m
1 stop
$646Multiple 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.

What is the most popular layover airport when flying from Chicago to Road Town?

Percentage of 1-stop round-trip flights from Chicago to Road Town chosen by KAYAK users via each layover airport in the last 12 months (only includes trips with the same layover airport on both legs).

Miami (MIA) is the top choice – 76% of KAYAK users who clicked on 1-stop flights from Chicago to Road Town picked an itinerary connecting there.

What is the cheapest layover airport when flying from Chicago to Road Town?

Average round-trip price for 1-stop flights from Chicago to Road Town clicked by KAYAK users in the last 12 months (only includes trips with the same layover airport on both legs).

Flights via San Juan (SJU) offer the most affordable fares, with an average round-trip price of $1,069.

Which layover airport offers the shortest total travel time from Chicago to Road Town?

Shortest average total travel time for 1-stop one-way flights from Chicago to Road Town via different layover airports, based on KAYAK user data from the last 12 months.

Consider flying via Miami (MIA) for the shortest journey. The average one-way travel time for flights connecting there is 8h 19m.

Which layover airport has the quickest connection when flying from Chicago to Road Town?

Average layover duration at different layover airports for 1-stop one-way flights from Chicago to Road Town, based on KAYAK user data from the last 12 months.

If you prefer a quick connection, Miami (MIA) often has the shortest layovers from Chicago to Road Town, with an average of 2h 27m.

Good to know

Cheapest flight$237
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 $237 for a one-way ticket and $574 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 $972 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 $894 and an overall rating of 7.1.

  • 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 9428 reviews
7.3Comfort
8.1Crew
7.1Entertainment
6.6Food
7.7Boarding
Airline reviews

This trip did not start off well. The inbound flight was delayed about 20 minutes. Then, after initial onboarding, the passengers had to deplane due to a mechanical problem. That took about 30 minutes to fix and be cleared. Then, reboarding was chaotic. It took a long time to sort passengers and two passengers on standby were ticketed but there was no seat. So, they had to deplane. One of the flight crew was trying to help passengers figure out a place to put their carry-on bags and that took more time. In the end, our scheduled 10:30 am departure did not actually take off until about 12:05 pm CST. The flight itself was long but we got to Houston. Some passengers missed their connecting flights and had to rebook. Not the best of flights I've had.

4.0 OkayDr. Joseph, Feb 2026
ORD - IAH
Read more United Airlines reviews

This trip did not start off well. The inbound flight was delayed about 20 minutes. Then, after initial onboarding, the passengers had to deplane due to a mechanical problem. That took about 30 minutes to fix and be cleared. Then, reboarding was chaotic. It took a long time to sort passengers and two passengers on standby were ticketed but there was no seat. So, they had to deplane. One of the flight crew was trying to help passengers figure out a place to put their carry-on bags and that took more time. In the end, our scheduled 10:30 am departure did not actually take off until about 12:05 pm CST. The flight itself was long but we got to Houston. Some passengers missed their connecting flights and had to rebook. Not the best of flights I've had.

We were delayed for about an hour from taking off due to traffic control procedures at the destination airport. But once in the air, the flight went well. The crew members were great and provided cabin service despite moderate turbulence during much of the flight.

Short flight, but no drink/snack service. The flights both going and coming were delayed.

Not being stranded in Chicago for her airport to 11:30 tomorrow morning the 3rd

I was fully checked in the prior night and i was unchecked and then didn’t have a seat when I boarded. Instead of an aisle seat, I was out in the middle seat of the very last row of the plane.

In overall it was a good experience, the only down point was that the entertainment screen was working properly.

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. :/

The gate got changed several times and the flight was delayed over an hour. Awful experience

American continues to decline in their customer service and its beyond disappointing.

It was an older plane. First Class was not especially roomy or comfortable. It was a short flight so there were no meal but they did offer mixed nuts which used to be normal but now is rare. Crew member was very polite and professional.

Flight to Tampa was delayed taking off due to plane arriving late but no other issues

Horrible. Got delayed many hours because their pilot wasn't trained for night landing at the airport and a rain delay made it a night landing. We have to wait hours for a qualified crew. They give us 12 dollar meal vouchers but most everything in the airport was closed and definitely more expensive than the vouchers.

As previously stated the delay I experienced flying from Wichita to Chicago caused a host of issues. When I finally was able to be booked on the last remaining American flight from Chicago to Cincinnati, the gate changed four times with the last change occurring very near the scheduled boarding time. While I didn't have a problem moving from gate to gate, I did notice and make note of others that had mobility issues and had to move each time for the gate change.

Maintenance took a very long time and then we were in a holding pattern. While a one-off maintenance issue is standard, there were delays on both of my flights for this trip based on maintenance issues with the planes, which delayed both flights over 45 minutes. Thankfully, I didn't have any connections but it wasn't an experience that would make me pick AA if I have other options.

No Snacks or Entertainment. The flight was short, snacks should still be given.

See prior comment about how Kayak mishandled my reservation and delayed my arrival by 6 hours.

Boarding delayed 20 minutes for no reason, no wifi, in flight entertainment, or snacks / waters?

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

Information on your arrival and departure airports