ORD - EIS

$504 Find Cheap Flights from Chicago to Road Town - Compare and Save

1 adult
1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$510
Typical prices: $863-$1,256
Multiple Airlines
Thu 2/22Mon 2/26
ORD - EIS • 1 stop
Cheapest one-way
$281
Typical prices: $428-$642
Multiple Airlines
Mon 1/8
ORD - EIS • 1 stop
Nonstop flights
Not available
There are currently no direct flights between Chicago O'Hare Intl Airport and Road Town. You'll need to take a connecting flight to reach the destination.
Insights
Insights
When to travel
August
Cheapest • 18% price drop
February
Most popular
Good to know
+1
Good to know
+1
Top layover airports
San Juan Luis Munoz Marin Intl (SJU)
Cheapest • Avg $1,081 (round-trip)
Saint Thomas Island Cyril E King (STT)
Shortest trip • 7h 19m (one-way)
Insights
Insights
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We hope you love your trip to Road Town!
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Flight Deals

Cheap Flights from Chicago to Road Town (ORD-EIS)

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Road Town

Mon, Feb 22 - Fri, Feb 26
Multiple Airlines Logo
12:17 am - 2:05 pmORD  Chicago O'Hare Intl-EIS Road Town Beef Island
11h 48m1 stop San Juan Luis Munoz Marin Intl
Multiple Airlines Logo
11:35 am - 1:36 amEIS  Road Town Beef Island-ORD Chicago O'Hare Intl
16h 01m1 stop San Juan Luis Munoz Marin Intl
$510Multiple Airlines
Mon, Feb 22 - Fri, Feb 26
Multiple Airlines Logo
12:17 am - 2:05 pmORD  Chicago O'Hare Intl-EIS Road Town Beef Island
11h 48m1 stop San Juan Luis Munoz Marin Intl
Multiple Airlines Logo
11:35 am - 11:50 amEIS  Road Town Beef Island-ORD Chicago O'Hare Intl
26h 15m2 stops San Juan Luis Munoz Marin Intl Atlanta Hartsfield-Jackson
$547Multiple Airlines
Tue, Jan 19 - Tue, Jan 26
Multiple Airlines Logo
10:21 pm - 10:55 amORD  Chicago O'Hare Intl-EIS Road Town Beef Island
10h 34m1 stop San Juan Luis Munoz Marin Intl
Multiple Airlines Logo
11:35 am - 9:13 amEIS  Road Town Beef Island-ORD Chicago O'Hare Intl
23h 38m2 stops San Juan Luis Munoz Marin Intl Tampa
$549Multiple Airlines
Thu, Dec 3 - Mon, Dec 7
Multiple Airlines Logo
9:34 pm - 2:05 pmORD  Chicago O'Hare Intl-EIS Road Town Beef Island
14h 31m2 stops Philadelphia San Juan Luis Munoz Marin Intl
Multiple Airlines Logo
4:00 pm - 3:30 pmEIS  Road Town Beef Island-ORD Chicago O'Hare Intl
25h 30m2 stops San Juan Luis Munoz Marin Intl Orlando
$623Multiple Airlines
Mon, Dec 7 - Mon, Dec 14
Multiple Airlines Logo
5:35 am - 2:05 pmORD  Chicago O'Hare Intl-EIS Road Town Beef Island
30h 30m2 stops Orlando San Juan Luis Munoz Marin Intl
Multiple Airlines Logo
11:35 am - 1:08 amEIS  Road Town Beef Island-ORD Chicago O'Hare Intl
15h 33m2 stops San Juan Luis Munoz Marin Intl Orlando
$625Multiple Airlines
Tue, Dec 1 - Sat, Dec 5
Multiple Airlines Logo
5:35 am - 10:55 amORD  Chicago O'Hare Intl-EIS Road Town Beef Island
27h 20m2 stops Orlando San Juan Luis Munoz Marin Intl
Multiple Airlines Logo
9:00 am - 1:08 amEIS  Road Town Beef Island-ORD Chicago O'Hare Intl
18h 08m2 stops San Juan Luis Munoz Marin Intl Orlando
$629Multiple Airlines
Fri, Jan 15 - Wed, Jan 20
Multiple Airlines Logo
10:21 pm - 10:55 amORD  Chicago O'Hare Intl-EIS Road Town Beef Island
10h 34m1 stop San Juan Luis Munoz Marin Intl
Multiple Airlines Logo
4:00 pm - 11:23 pmEIS  Road Town Beef Island-ORD Chicago O'Hare Intl
33h 23m2 stops San Juan Luis Munoz Marin Intl Atlanta Hartsfield-Jackson
$630Multiple Airlines
Thu, Jan 7 - Wed, Jan 13
Multiple Airlines Logo
7:10 am - 10:55 amORD  Chicago O'Hare Intl-EIS Road Town Beef Island
25h 45m2 stops Fort Lauderdale San Juan Luis Munoz Marin Intl
Multiple Airlines Logo
9:00 am - 9:01 pmEIS  Road Town Beef Island-ORD Chicago O'Hare Intl
14h 01m1 stop San Juan Luis Munoz Marin Intl
$646Multiple Airlines
Tue, Feb 2 - Tue, Feb 16
American Airlines Logo
5:00 am - 6:22 pmORD  Chicago O'Hare Intl-EIS Road Town Beef Island
11h 22m1 stop Miami
American Airlines Logo
7:39 pm - 11:10 amEIS  Road Town Beef Island-ORD Chicago O'Hare Intl
17h 31m1 stop Miami
$789American Airlines
Tue, Jan 26 - Tue, Feb 2
American Airlines Logo
7:00 am - 4:17 pmORD  Chicago O'Hare Intl-EIS Road Town Beef Island
7h 17m1 stop Miami
American Airlines Logo
4:58 pm - 1:05 amEIS  Road Town Beef Island-ORD Chicago O'Hare Intl
10h 07m1 stop Miami
$789American Airlines
Booking Insights

Price, demand and travel trends for Chicago O'Hare Intl Airport to Road Town flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

What's the cheapest day of the week to fly from Chicago O'Hare Intl Airport to Road Town?

Based on deals KAYAK users found in the last 12 months, Wednesday is the cheapest day of the week to fly from Chicago O'Hare Intl Airport to Road Town. It’s 14% cheaper than the average day, while Saturday is the most expensive, with prices 25% higher.

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Key details for Chicago O'Hare Intl Airport to Road Town flights

Low season

September

Cheapest flight

$281
Beat the crowds with an average 54% drop in travelers.
The most popular month to fly with an average 45% increase in travelers.
One-way flight from Chicago O'Hare Intl Airport 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

Your Chicago O'Hare Intl Airport to Road Town flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • What cabin classes can I book on flights from Chicago O'Hare Intl Airport to Road Town?

    Two cabin classes are available on flights from Chicago O'Hare Intl Airport to Road Town:

    • Economy Class
    • First Class

  • How long is a flight from Chicago O'Hare Intl Airport to Road Town?

    A nonstop flight from Chicago O'Hare Intl Airport to Road Town takes 00m, covering 2,126 miles.

  • Do I need a passport to fly from Chicago O'Hare Intl Airport to Road Town?

    Yes, a valid passport is required for this international route. Many destinations require at least six months of validity beyond your travel dates. Check your passport expiry well before booking.

  • How much should I expect to pay for a Chicago O'Hare Intl Airport to Road Town flight?

    Round-trip flights from Chicago O'Hare Intl Airport to Road Town range from $863 to $1,256, with an average of $998 over the past 12 months. Anything below $863 counts as a good deal.

  • Have flight prices from Chicago O'Hare Intl Airport to Road Town changed much recently?

    Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $510 to $4,855. That means the highest observed fare was about 10x higher than the lowest one.

  • How are flight prices from Chicago O'Hare Intl Airport to Road Town looking right now?

    One-way fares from Chicago O'Hare Intl Airport to Road Town are currently lower than usual. Average one-way flight prices are about $320, which is 39% below the typical average for this route.

  • What car rental options are available at Road Town Beef Island Airport (EIS)?

    Road Town Beef Island Airport (EIS) hosts 5 major car rental companies, with daily rates averaging $75 for economy cars. Top options include:

    • Alamo
    • Hertz
    • Avis
    • Enterprise Rent-A-Car
    • National

  • Which airports can I use when flying from Chicago O'Hare Intl Airport to Road Town?

    Flights from Chicago O'Hare Intl Airport to Road Town usually depart from Chicago O'Hare Intl (ORD) and arrive at Road Town Beef Island (EIS).

  • Which airports do connecting flights from Chicago O'Hare Intl Airport to Road Town pass through?

    One-stop flights from Chicago O'Hare Intl Airport to Road Town most commonly connect through:

    • Miami (MIA) - 82% of one-stop connections
    • San Juan Luis Munoz Marin Intl (SJU) - 16% of one-stop connections
    • Saint Thomas Island Cyril E King (STT) - 2% of one-stop connections

  • Can I save money by using flexible dates for flights from Chicago O'Hare Intl Airport to Road Town?

    Yes. Flexible dates can save you up to 32% on flights from Chicago O'Hare Intl Airport to Road Town. Wednesday is the cheapest departure day at $863 round-trip on average, while Saturday is the most expensive at $1,252, a difference of $389.

    KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

  • How much time can I save by choosing a different layover airport from Chicago O'Hare Intl Airport to Road Town?

    Flying via Saint Thomas Island Cyril E King (STT) gives the shortest average 1-stop total travel time at 7h 19m, compared with 8h 27m via Miami (MIA) and 8h 46m via San Juan Luis Munoz Marin Intl (SJU).

  • What is the time difference between Chicago O'Hare Intl Airport and Road Town?

    Road Town is 2 hours ahead of Chicago O'Hare Intl Airport (Atlantic Time vs Central Time). Plan for the time shift when scheduling connections or first-day activities.

Your guide to booking Chicago O'Hare Intl Airport to Road Town flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your dates are flexible, aim for a Wednesday departure and avoid flying on Saturday. On this route, Wednesday flights average $863, about $389 less than Saturday fares (31% savings) based on the last 12 months.
  • If you can choose when to travel, plan your Chicago O'Hare Intl Airport to Road Town trip for August. Fares historically average $818 round-trip in that month - typically $632 less than the most expensive month, which is May (based on the last 12 months).

More options for your flight from Chicago to Road Town

Complete your trip to Road Town with a hotel stay or car rental

Car rentals in Road Town
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