ORD - EIS

$287 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
$708
Typical prices: $840-$1,175
American Airlines
Sat 11/10Sun 11/18
ORD - EIS • 1 stop
Cheapest one-way
$287
Typical prices: $472-$658
Multiple Airlines
Mon 10/15
ORD - EIS • 2 stops
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
June
Cheapest • 9% price drop
January
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Miami (MIA)
Cheapest • Avg $988 (round-trip)
San Juan Luis Munoz Marin Intl (SJU)
Shortest trip • 8h 50m (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

Tue, Nov 10 - Wed, Nov 18
American Airlines Logo
5:00 am - 6:20 pmORD  Chicago O'Hare Intl-EIS Road Town Beef Island
11h 20m1 stop Miami
American Airlines Logo
7:00 pm - 9:30 amEIS  Road Town Beef Island-ORD Chicago O'Hare Intl
16h 30m1 stop Miami
$708American Airlines
Mon, Oct 12 - Mon, Oct 19
American Airlines Logo
5:05 am - 1:21 pmORD  Chicago O'Hare Intl-EIS Road Town Beef Island
7h 16m1 stop Miami
American Airlines Logo
2:01 pm - 9:30 pmEIS  Road Town Beef Island-ORD Chicago O'Hare Intl
8h 29m1 stop Miami
$709American Airlines
Mon, Oct 12 - Mon, Oct 19
American Airlines Logo
5:00 am - 3:10 pmORD  Chicago O'Hare Intl-EIS Road Town Beef Island
9h 10m2 stops Charlotte Douglas Miami
American Airlines Logo
3:50 pm - 7:27 amEIS  Road Town Beef Island-ORD Chicago O'Hare Intl
16h 37m2 stops Miami Washington, D.C. Reagan-National
$713American Airlines
Tue, Nov 10 - Wed, Nov 18
American Airlines Logo
5:19 am - 6:20 pmORD  Chicago O'Hare Intl-EIS Road Town Beef Island
11h 01m2 stops Charlotte Douglas Miami
American Airlines Logo
7:00 pm - 11:06 amEIS  Road Town Beef Island-ORD Chicago O'Hare Intl
18h 06m1 stop Miami
$713American Airlines
Tue, Nov 10 - Wed, Nov 18
American Airlines Logo
6:00 am - 6:20 pmORD  Chicago O'Hare Intl-EIS Road Town Beef Island
10h 20m2 stops Dallas/Fort Worth Miami
American Airlines Logo
7:00 pm - 11:06 amEIS  Road Town Beef Island-ORD Chicago O'Hare Intl
18h 06m1 stop Miami
$713American Airlines
Mon, Oct 12 - Mon, Oct 19
American Airlines Logo
5:00 am - 3:10 pmORD  Chicago O'Hare Intl-EIS Road Town Beef Island
9h 10m2 stops Charlotte Douglas Miami
American Airlines Logo
3:50 pm - 9:30 amEIS  Road Town Beef Island-ORD Chicago O'Hare Intl
18h 40m1 stop Miami
$713American Airlines
Fri, Nov 20 - Fri, Nov 27
Multiple Airlines Logo
5:45 am - 6:10 pmORD  Chicago O'Hare Intl-EIS Road Town Beef Island
34h 25m2 stops Baltimore/Washington San Juan Luis Munoz Marin Intl
Multiple Airlines Logo
4:00 pm - 7:16 amEIS  Road Town Beef Island-ORD Chicago O'Hare Intl
17h 16m1 stop San Juan Luis Munoz Marin Intl
$810Multiple Airlines
Fri, Nov 20 - Fri, Nov 27
Multiple Airlines Logo
7:53 pm - 6:10 pmORD  Chicago O'Hare Intl-EIS Road Town Beef Island
20h 17m1 stop San Juan Luis Munoz Marin Intl
Multiple Airlines Logo
4:00 pm - 7:16 amEIS  Road Town Beef Island-ORD Chicago O'Hare Intl
17h 16m1 stop San Juan Luis Munoz Marin Intl
$839Multiple Airlines
Sun, Sep 27 - Sun, Oct 4
Multiple Airlines Logo
6:00 am - 11:10 amORD  Chicago O'Hare Intl-EIS Road Town Beef Island
28h 10m2 stops Fort Lauderdale Simpson Bay Princess Juliana
Multiple Airlines Logo
7:15 am - 11:08 pmEIS  Road Town Beef Island-ORD Chicago O'Hare Intl
16h 53m3 stops Basseterre Robert Bradshaw Intl Simpson Bay Princess Juliana Fort Lauderdale
$839Multiple Airlines
Wed, Nov 25 - Sun, Nov 29
Multiple Airlines Logo
8:36 am - 10:55 amORD  Chicago O'Hare Intl-EIS Road Town Beef Island
24h 19m2 stops Fort Lauderdale San Juan Luis Munoz Marin Intl
Multiple Airlines Logo
9:00 am - 7:16 amEIS  Road Town Beef Island-ORD Chicago O'Hare Intl
24h 16m1 stop San Juan Luis Munoz Marin Intl
$874Multiple 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 from Chicago O'Hare Intl Airport to Road Town with more confidence.

How much is a round-trip flight from Chicago O'Hare Intl Airport to Road Town?

Round-trip flights from Chicago O'Hare Intl Airport to Road Town start at $708. Prices are below average for this route right now, with typical round-trip fares ranging from $840 to $1,175. The lowest price found in the past 5 days was $708 on American Airlines.

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

Wednesday is the cheapest day of the week to fly from Chicago O'Hare Intl Airport to Road Town, it is 10% cheaper than the average day. Saturday is the most expensive day with flight prices 31% higher than average. Based on deals found by KAYAK users in the last 12 months.

Find deals

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

Low season

August

Cheapest flight

$287
Best time to beat the crowds but there is an average 23% increase in price.
Most popular time to fly and prices are also 9% lower on average.
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 route details based on KAYAK data, including flight times, airports, airlines and booking questions.

  • 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).

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

    Only Economy Class is available on flights from Chicago O'Hare Intl Airport to Road Town.

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

    Connecting flights from Chicago O'Hare Intl Airport to Road Town most commonly pass through:

    • Miami (MIA) - 81% of one-stop connections
    • San Juan Luis Munoz Marin Intl (SJU) - 19% of one-stop connections
    Together, these airports account for 100% of one-stop bookings on this route.

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

    Yes. Being flexible with your travel dates can save you up to 32% on the Chicago O'Hare Intl Airport to Road Town route. 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 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 0h 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 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 $337, which is 40% below the typical average for this route.

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

    Flying via Miami (MIA) gives the shortest average 1-stop total travel time at 8h 40m, compared with 8h 50m 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 1 hour ahead of Chicago O'Hare Intl Airport (Atlantic Time vs Central Time). Plan for the time shift when scheduling connections or first-day activities.

  • 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 starting from around $24 for economy cars. Top options include:
    · Alamo
    · Hertz
    · Avis
    · Enterprise Rent-A-Car
    · National

  • 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 $840 to $1,175, with an average of $953 over the past 12 months. Anything below $840 counts as a good deal.

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 can be flexible, aim for a Wednesday departure instead of Saturday. On this route, Wednesday flights average $863 - about $389 less than Saturday (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 June. Fares historically average $863 round-trip in that month - typically $587 less than the most expensive month, which is May (based on the last 12 months).

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

Information on your arrival and departure airports

Chicago (ORD)
Road Town (EIS)