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Cheap flights from Chicago O'Hare Intl Airport to the Cayman Islands from $129

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago O'Hare Intl Airport to the Cayman Islands departing on 9/16. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Chicago O'Hare Intl Airport to the Cayman Islands

Cheap round-trip flights

Enter your travel dates to find the best prices.
Air Canada Logo
8:40 pm - 9:45 am-
13h 05m
Air Canada Logo
12:25 pm - 8:00 am-
19h 35m
$351Air Canada
Fri, Sep 11 - Thu, Sep 17
Air Canada Logo
8:40 pm - 9:45 am-
13h 05m
Air Canada Logo
12:25 pm - 8:00 am-
19h 35m
$352Air Canada
Fri, Sep 11 - Thu, Sep 17
Air Canada Logo
9:55 am - 9:45 am-
23h 50m
Air Canada Logo
12:25 pm - 1:23 pm-
24h 58m
$356Air Canada
Fri, Sep 11 - Thu, Sep 17
Air Canada Logo
9:50 am - 11:30 am-
25h 40m
Air Canada Logo
12:25 pm - 1:13 pm-
24h 48m
$357Air Canada
Sun, Oct 18 - Sat, Oct 24
United Airlines Logo
8:45 am - 1:45 pm-
4h 00mnonstop
United Airlines Logo
2:50 pm - 6:04 pm-
4h 14mnonstop
$617United Airlines
Sun, Jan 17 - Fri, Jan 22
United Airlines Logo
8:42 am - 1:42 pm-
4h 00mnonstop
United Airlines Logo
2:55 pm - 6:13 pm-
4h 18mnonstop
$617United Airlines
Sun, Jan 3 - Wed, Jan 13
American Airlines Logo
7:10 pm - 11:47 am-
15h 37m
American Airlines Logo
3:25 pm - 6:49 pm-
4h 24mnonstop
$621American Airlines
Sun, Jan 3 - Wed, Jan 13
American Airlines Logo
8:55 pm - 11:57 am-
14h 02m
American Airlines Logo
3:25 pm - 6:49 pm-
4h 24mnonstop
$621American Airlines
Sun, Jan 3 - Wed, Jan 13
American Airlines Logo
9:31 am - 2:35 pm-
4h 04mnonstop
American Airlines Logo
3:25 pm - 6:49 pm-
4h 24mnonstop
$622American Airlines
Wed, Jan 6 - Tue, Jan 12
United Airlines Logo
8:45 am - 1:45 pm-
4h 00mnonstop
United Airlines Logo
2:25 pm - 11:42 pm-
10h 17m
$627United Airlines
Sun, Jan 17 - Fri, Jan 22

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Air Canada flights from Chicago O'Hare Intl Airport to Cayman Islands

Our best Air Canada deals on Chicago O'Hare Intl Airport to Cayman Islands flight tickets
Air Canada
Sep 11
ORD8:40 pmChicago O'Hare Intl
13h 05m
1 stop
GCM9:45 amGeorge Town Owen Roberts Intl
Sep 17
GCM12:25 pmGeorge Town Owen Roberts Intl
19h 35m
1 stop
ORD8:00 amChicago O'Hare Intl
$351
Air Canada
Sep 11
ORD8:40 pmChicago O'Hare Intl
13h 05m
1 stop
GCM9:45 amGeorge Town Owen Roberts Intl
Sep 17
GCM12:25 pmGeorge Town Owen Roberts Intl
19h 35m
1 stop
ORD8:00 amChicago O'Hare Intl
$352
Air Canada
Sep 11
ORD9:55 amChicago O'Hare Intl
23h 50m
1 stop
GCM9:45 amGeorge Town Owen Roberts Intl
Sep 17
GCM12:25 pmGeorge Town Owen Roberts Intl
24h 58m
1 stop
ORD1:23 pmChicago O'Hare Intl
$356

American Airlines flights from Chicago O'Hare Intl Airport to Cayman Islands

Our best American Airlines deals on Chicago O'Hare Intl Airport to Cayman Islands flight tickets
American Airlines
Aug 16
ORD8:53 pmChicago O'Hare Intl
14h 34m
1 stop
GCM11:27 amGeorge Town Owen Roberts Intl
Aug 23
GCM2:10 pmGeorge Town Owen Roberts Intl
9h 20m
1 stop
ORD11:30 pmChicago O'Hare Intl
$821
American Airlines
Aug 16
ORD8:53 pmChicago O'Hare Intl
14h 07m
2 stops
GCM11:00 amGeorge Town Owen Roberts Intl
Aug 23
GCM2:10 pmGeorge Town Owen Roberts Intl
9h 20m
1 stop
ORD11:30 pmChicago O'Hare Intl
$826
American Airlines
Aug 14
ORD5:00 amChicago O'Hare Intl
6h 00m
1 stop
GCM11:00 amGeorge Town Owen Roberts Intl
Aug 17
GCM2:10 pmGeorge Town Owen Roberts Intl
10h 25m
1 stop
ORD12:35 amChicago O'Hare Intl
$861

momondo Fare Finder

 
Customize your flight search to find flights from Chicago O'Hare Intl Airport to Cayman Islands that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated August 5, 2026.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to the Cayman Islands that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Fri 9/11

8:40 pm-9:45 am

1 stop13h 05m

George Town Owen Roberts Intl

Thu 9/17

12:25 pm-8:00 am

1 stop19h 35m

$351

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Fri 9/11

8:40 pm-9:45 am

1 stop13h 05m

George Town Owen Roberts Intl

Thu 9/17

12:25 pm-8:00 am

1 stop19h 35m

$352

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Fri 9/11

9:55 am-9:45 am

1 stop23h 50m

George Town Owen Roberts Intl

Thu 9/17

12:25 pm-1:23 pm

1 stop24h 58m

$356

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 10/18

9:50 am-11:30 am

1 stop25h 40m

George Town Owen Roberts Intl

Sat 10/24

12:25 pm-1:13 pm

1 stop24h 48m

$357
Quickest round-trip

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 1/17

8:45 am-1:45 pm

Nonstop4h 00m

George Town Owen Roberts Intl

Fri 1/22

2:50 pm-6:04 pm

Nonstop4h 14m

$617

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 1/3

8:42 am-1:42 pm

Nonstop4h 00m

George Town Owen Roberts Intl

Wed 1/13

2:55 pm-6:13 pm

Nonstop4h 18m

$617

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 1/3

7:10 pm-11:47 am

1 stop15h 37m

George Town Owen Roberts Intl

Wed 1/13

3:25 pm-6:49 pm

Nonstop4h 24m

$621

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 1/3

8:55 pm-11:57 am

1 stop14h 02m

George Town Owen Roberts Intl

Wed 1/13

3:25 pm-6:49 pm

Nonstop4h 24m

$621

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 1/6

9:31 am-2:35 pm

Nonstop4h 04m

George Town Owen Roberts Intl

Tue 1/12

3:25 pm-6:49 pm

Nonstop4h 24m

$622

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 1/17

8:45 am-1:45 pm

Nonstop4h 00m

George Town Owen Roberts Intl

Fri 1/22

2:25 pm-11:42 pm

1 stop10h 17m

$627

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to the Cayman Islands from

How to get the cheapest flight ticket from Chicago O'Hare Intl Airport to Cayman Islands

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Cayman Islands?

If you aren’t able to travel to Cayman Islands during the month of February, then flying in January is also cheap. Prices for this month can be found on momondo for an average of $555.

What is the cheapest day to depart on your flight to Cayman Islands?

Our data shows that Thursday is the least expensive day to fly to Cayman Islands. Tickets to fly out on this day can be as low as $531. Be sure to avoid booking your departure on a Sunday as prices are generally higher than usual. According to our data, the average ticket price to Cayman Islands on Sunday is $731.

What is the cheapest Chicago O'Hare Intl to Cayman Islands flight route?

Fly from Chicago O'Hare Intl to George Town Owen Roberts Intl for the best Chicago O'Hare Intl - Cayman Islands flight prices

How far in advance should I book a flight from Chicago O'Hare Intl Airport to the Cayman Islands?

You are more likely to see cheaper flights to Cayman Islands from Chicago O'Hare Intl Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Cayman Islands for around $682 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Cayman Islands from Chicago O'Hare Intl Airport for as low as $492 on momondo.

What cabin class options are available on Chicago O'Hare Intl Airport to Cayman Islands flights?

There are 3 cabin classes available to choose from on Chicago O'Hare Intl Airport to Cayman Islands flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Chicago O'Hare Intl Airport to Cayman Islands flights?

You could potentially save up to 10% on your flight if you consider stops on a Chicago O'Hare Intl Airport to Cayman Islands flight.

Cheap Chicago O'Hare Intl Airport to Cayman Islands flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago O'Hare Intl Airport to Cayman Islands

Best Price Found

$751

Fastest flight time

4h 00m

Direct flights

Every day

Airports in Cayman Islands

6 airports
The best flight deal from Chicago O'Hare Intl Airport to Cayman Islands found on momondo in the last 72 hours is $751
The fastest flight from Chicago O'Hare Intl Airport to Cayman Islands takes 4h 00m
Direct flights go from Chicago O'Hare Intl Airport to Cayman Islands every day.
There are 6 airports in Cayman Islands. From Chicago O'Hare Intl Airport there are direct flights to George Town Owen Roberts Intl (GCM).
Search flight deals

Frequently asked questions about flying from Chicago O'Hare Intl Airport to the Cayman Islands

  • When did momondo last update prices for flights from Chicago O'Hare Intl Airport to Cayman Islands?

    Prices for flights from Chicago O'Hare Intl Airport to Cayman Islands refresh daily.

  • How many operators does momondo search for flights from Chicago O'Hare Intl Airport to Cayman Islands?

  • How old do you have to be to fly from Chicago O'Hare Intl Airport to Cayman Islands?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago O'Hare Intl Airport to Cayman Islands.

  • What documentation or ID do you need to fly to Cayman Islands?

    The required travel and health documents for your Cayman Islands trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Cayman Islands. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

  • What is the most popular plane model from Chicago O'Hare Intl Airport to Cayman Islands?

Best airlines flying from Chicago O'Hare Intl Airport to Cayman Islands

Compare and see reviews for airlines that fly from Chicago O'Hare Intl Airport to Cayman Islands with momondo
Airline
Rating
Free Cancellation
Price
United AirlinesPriceFrom $341Free CancellationRating
7.4
10,058 reviews
Search United Airlines flights
American AirlinesPriceFrom $447Free CancellationRating
7.1
11,848 reviews
Search American Airlines flights

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Cayman Islands?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Chicago to Cayman Islands for you.

Can I find flights from Chicago to Cayman Islands with flexible booking policies on momondo?

Yes. All flights to Cayman Islands from Chicago on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Chicago to Cayman Islands?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Chicago to Cayman Islands.

I’m not ready to book a flight from Chicago to Cayman Islands right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Chicago to Cayman Islands flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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