CHI - GCM

$145 Find Cheap Flights from Chicago to George Town - Compare and Save

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Everything you should know

Cheapest round-trip
$377
Typical prices: $528-$775
Air Canada
Sat 12/1Sat 12/15
ORD - GCM • 1 stop
Cheapest non-stop
$587
Typical prices: $527-$781
American Airlines
Fri 2/23Fri 3/2
ORD - GCM • Non-stop
Nonstop flights
You can fly direct with United Airlines and American Airlines. Average duration is 4h 05m
Direct flights
+1
Direct flights
+1
Top routes
Cheapest • 1% average savings
Most popular
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 4 weeks in advance save around 22% compared to booking last minute.
Insights
Insights
When to travel
Cheapest • 13% price drop
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Cheapest • Avg $430 (round-trip)
Shortest trip • 6h 28m (one-way)
Insights
Insights
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We hope you love your trip to George Town!
Flight Deals
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Expert advice
Flight Deals

Cheap Flights from Chicago to George Town (CHI-GCM)

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

Recent round-trip flight deals from Chicago to George Town

Sat, Dec 5 - Tue, Dec 8
Air Canada Logo
4:30 pm - 12:10 pmORD  Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
18h 40m1 stop Toronto Pearson Intl
Air Canada Logo
1:10 pm - 9:08 amGCM  George Town Owen Roberts Intl-ORD Chicago O'Hare Intl
20h 58m1 stop Toronto Pearson Intl
$377Air Canada
Tue, Dec 1 - Tue, Dec 15
Air Canada Logo
4:30 pm - 12:10 pmORD  Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
18h 40m1 stop Toronto Pearson Intl
Air Canada Logo
1:10 pm - 9:08 amGCM  George Town Owen Roberts Intl-ORD Chicago O'Hare Intl
20h 58m1 stop Toronto Pearson Intl
$377Air Canada
Thu, Nov 26 - Thu, Dec 3
Air Canada Logo
4:30 pm - 12:10 pmORD  Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
18h 40m1 stop Toronto Pearson Intl
Air Canada Logo
1:10 pm - 9:08 amGCM  George Town Owen Roberts Intl-ORD Chicago O'Hare Intl
20h 58m1 stop Toronto Pearson Intl
$377Air Canada
Sat, Nov 28 - Thu, Dec 3
Air Canada Logo
4:40 pm - 12:10 pmORD  Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
18h 30m1 stop Toronto Pearson Intl
Air Canada Logo
1:10 pm - 9:08 amGCM  George Town Owen Roberts Intl-ORD Chicago O'Hare Intl
20h 58m1 stop Toronto Pearson Intl
$377Air Canada
Sun, Dec 13 - Thu, Dec 17
American Airlines Logo
6:17 pm - 11:55 amORD  Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
16h 38m1 stop Miami
American Airlines Logo
5:45 pm - 9:25 pmGCM  George Town Owen Roberts Intl-ORD Chicago O'Hare Intl
4h 40mnonstop
$567American Airlines
Sun, Mar 28 - Thu, Apr 1
American Airlines Logo
10:25 pm - 1:21 pmORD  Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
14h 56m1 stop Dallas/Fort Worth
American Airlines Logo
2:21 pm - 7:40 amGCM  George Town Owen Roberts Intl-ORD Chicago O'Hare Intl
17h 19m1 stop Dallas/Fort Worth
$578American Airlines
Tue, Feb 23 - Tue, Mar 2
American Airlines Logo
9:50 am - 2:54 pmORD  Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
4h 04mnonstop
American Airlines Logo
3:54 pm - 7:24 pmGCM  George Town Owen Roberts Intl-ORD Chicago O'Hare Intl
4h 30mnonstop
$587American Airlines
Wed, Mar 17 - Tue, Mar 23
United Airlines Logo
6:50 am - 3:30 pmORD  Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
8h 40m1 stop Houston George Bush Intcntl
United Airlines Logo
1:55 pm - 6:13 pmGCM  George Town Owen Roberts Intl-ORD Chicago O'Hare Intl
4h 18mnonstop
$627United Airlines
Wed, Mar 17 - Tue, Mar 23
United Airlines Logo
7:45 am - 3:30 pmORD  Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
7h 45m1 stop Houston George Bush Intcntl
United Airlines Logo
1:55 pm - 6:13 pmGCM  George Town Owen Roberts Intl-ORD Chicago O'Hare Intl
4h 18mnonstop
$627United Airlines
Wed, Dec 23 - Tue, Dec 29
United Airlines Logo
8:52 am - 4:35 pmORD  Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
6h 43m1 stop Washington, D.C. Dulles Intl
United Airlines Logo
2:55 pm - 6:13 pmGCM  George Town Owen Roberts Intl-ORD Chicago O'Hare Intl
4h 18mnonstop
$627United Airlines
Booking Insights

Price, demand and travel trends for Chicago to George Town flights

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

How much is a round-trip flight from Chicago to George Town?

Round-trip flights from Chicago to George Town typically range from $528 to $775. The lowest price found in the past 5 days was $377, on Air Canada.

What is the cheapest Chicago to George Town flight route?

There's little price difference between Chicago to George Town routes. They average around $662 round-trip, based on KAYAK data over the past 12 months.

What's the cheapest day of the week to fly from Chicago to George Town?

Based on deals KAYAK users found in the last 12 months, Wednesday is the cheapest day of the week to fly from Chicago to George Town. It’s 11% cheaper than the average day, while Saturday is the most expensive, with prices 2% higher.

What’s the cheapest month to fly from Chicago to George Town?

•February is the cheapest month to fly from Chicago to George Town at $570 round-trip.
•July ($776) and November ($753) are the most expensive months.
•The price difference between flying in the cheapest and most expensive months is 36% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

When are flights from Chicago to George Town the cheapest?

Flights from Chicago to George Town are cheapest 4 weeks before departure. Booking in this window typically costs about 22% less than the average last-minute fare (within 2 weeks of the flight), based on KAYAK data.

Expert advice

Expert advice for your flight from Chicago to George Town

 
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on United Airlines

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Harriet Baskas

Harriet Baskas

Expert on American Airlines

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Key details for Chicago to George Town flights

Low season

August

Cheapest flight

$145
Beat the crowds with an average 79% drop in travelers.
The most popular month to fly with an average 111% increase in travelers.
One-way flight from Chicago O'Hare Intl Airport to George Town

When to book flights from Chicago to George Town

Are your dates flexible? Find out the best times to travel from Chicago to George 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 to George Town flight questions, answered

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

  • What are the earliest and latest flights from Chicago to George Town?

    These are the earliest and latest flight times available from Chicago to George Town:

    • Earliest: departs at 8:42 am and lands at 12:47 pm
    • Latest: departs at 11:38 am and lands at 3:43 pm.

    The flight takes about 4h 05m.

  • What cabin classes can I book on flights from Chicago to George Town?

    Two cabin classes are available on flights from Chicago to George Town:

    • Economy Class
    • Business Class

  • How long is a flight from Chicago to George Town?

    A nonstop flight from Chicago to George Town takes 4h 05m, covering 1,602 miles.

  • Do I need a passport to fly from Chicago to George 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 to George Town flight?

    Round-trip flights from Chicago to George Town range from $528 to $775, with an average of $654 over the past 12 months. Anything below $528 counts as a good deal.

  • How expensive are last-minute Chicago to George Town flights?

    Last-minute fares on this route (booked within two weeks of departure) run 3% above the $654 route average. Book 4 weeks before departure for the lowest fares.

  • How much can I save by taking a layover when flying from Chicago to George Town?

    On this route, layover flights are cheaper than nonstop options on average. Layover fares average $430 round-trip via Fort Lauderdale (FLL), compared to $647 for nonstop.

  • What is the standard checked-bag allowance on flights from Chicago to George Town?

    There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $35–$100 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

  • How are flight departures from Chicago to George Town spread across the day?

    Morning is the busiest departure period on Chicago to George Town flights, with 100% of flights leaving in that window. Afternoon departures account for 0%, evening flights for 0%, and night flights for 0%.

  • Which airlines offer Wi-Fi on Chicago to George Town flights?

    Two airlines offer in-flight Wi-Fi on Chicago to George Town flights:

    • American Airlines
    • JetBlue

    Pricing varies by airline and fare class. Some plans are included with the ticket or loyalty program; others are paid add-ons priced by flight length.

  • How are flight prices from Chicago to George Town looking right now?

    One-way fares from Chicago to George Town are currently lower than usual. Average one-way flight prices are about $250, which is 31% below the typical average for this route.

  • What car rental options are available at George Town Owen Roberts Intl Airport (GCM)?

    George Town Owen Roberts Intl Airport (GCM) hosts 5 major car rental companies, with daily rates averaging $42 for economy cars. Top options include:

    • Europcar
    • Hertz
    • Firefly
    • Alamo
    • Budget

  • Which airports can I use when flying from Chicago to George Town?

    Flights from Chicago to George Town may depart from several airports in Chicago area, including Chicago Midway (MDW), Chicago O'Hare Intl (ORD) and Chicago Greater Rockford (RFD). Flights usually arrive at George Town Owen Roberts Intl (GCM).

  • Which airports do connecting flights from Chicago to George Town pass through?

    One-stop flights from Chicago to George Town most commonly connect through:

    • Miami (MIA) - 29% of one-stop connections
    • Orlando (MCO) - 20% of one-stop connections
    • Fort Lauderdale (FLL) - 13% of one-stop connections
    • Atlanta Hartsfield-Jackson (ATL) - 12% of one-stop connections

  • Can I save money by using flexible dates for flights from Chicago to George Town?

    Yes. Flexible dates can save you up to 13% on flights from Chicago to George Town. Wednesday is the cheapest departure day at $586 round-trip on average, while Saturday is the most expensive at $668, a difference of $82.

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

  • What airlines fly from Chicago to George Town?

    2 airlines operate flights between Chicago and George Town. The airlines offering nonstop flights on this route include:

    • United Airlines
    • American Airlines

  • How much time can I save by choosing a different layover airport from Chicago to George Town?

    Flying via Charlotte Douglas (CLT) gives the shortest average 1-stop total travel time at 6h 28m, compared with 6h 53m via Orlando (MCO) and 7h 02m via Atlanta Hartsfield-Jackson (ATL).

  • Which airlines offer extra legroom and free seat selection on Chicago to George Town flights?

    Among airlines operating Chicago to George Town flights:

    • United Airlines: offers extra legroom; offers free seat selection
    • American Airlines: offers extra legroom; offers free seat selection

    Extra legroom and free seat selection availability depends on fare class and route.

  • Which airlines include bags at no extra cost on Chicago to George Town flights?

    Here are some options for this route, based on selected ticket types and cabin classes:

    • United Airlines: a cabin bag and a checked bag in Economy Class
    • American Airlines: a cabin bag and a checked bag in Economy Class
    • JetBlue: a cabin bag in Economy Class class

    Bag allowance can vary by ticket type, cabin class, route and airline, so always check the fare details before booking.

Your guide to booking Chicago to George 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 $586, about $82 less than Saturday fares (12% savings) based on the last 12 months.
  • For the best chance at a low fare, aim to book around 4 weeks before you fly. On this route, that window historically saves about 22% versus last-minute pricing (KAYAK booking data, last 12 months).
  • If you can choose when to travel, plan your Chicago to George Town trip for February. Fares historically average $570 round-trip in that month - typically $206 less than the most expensive month, which is July (based on the last 12 months).
  • If you have the time, taking a 1-stop flight through Fort Lauderdale Airport (FLL) can be cheaper than flying direct. The cheapest layover option averages $430 round-trip on this route - about $217 less than direct flights (based on the last 12 months).
  • If you're arriving late at night and need somewhere to stay, check out these hotels close to George Town Owen Roberts Intl Airport.

    • One Gt Grand Cayman

Prefer to fly direct from Chicago to George Town?

 
Find which airlines fly direct from Chicago to George Town Owen Roberts Intl Airport, which days they fly and book direct flights.

Direct departures

Chicago to George Town Owen Roberts Intl

Monday

American Airlines,United Airlines

American Airlines,United Airlines

Tuesday

American Airlines,United Airlines

American Airlines,United Airlines

Wednesday

American Airlines,United Airlines

American Airlines,United Airlines

Thursday

American Airlines,United Airlines

American Airlines,United Airlines

Friday

American Airlines,United Airlines

American Airlines,United Airlines

Saturday

American Airlines,United Airlines

American Airlines,United Airlines

Sunday

American Airlines,United Airlines

American Airlines,United Airlines

See more direct flights

Direct returns

George Town Owen Roberts Intl to Chicago

Monday

American Airlines,United Airlines

American Airlines,United Airlines

Tuesday

American Airlines,United Airlines

American Airlines,United Airlines

Wednesday

American Airlines,United Airlines

American Airlines,United Airlines

Thursday

American Airlines,United Airlines

American Airlines,United Airlines

Friday

American Airlines,United Airlines

American Airlines,United Airlines

Saturday

American Airlines,United Airlines

American Airlines,United Airlines

Sunday

American Airlines,United Airlines

American Airlines,United Airlines

See more direct flights

More options for your flight from Chicago to George Town

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