Latest deals
Insights
FAQs
Reviews
Price Alerts

Cheap flights from Chicago O'Hare Intl Airport to the Cayman Islands from $148

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
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 - 9:23 amGCM  George Town Owen Roberts Intl-ORD Chicago O'Hare Intl
21h 13m1 stop Toronto Pearson Intl
$383Air Canada
Tue, Nov 10 - Thu, Nov 19
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
$383Air Canada
Sun, Dec 13 - Wed, Dec 16
Air Canada Logo
10:15 am - 12:10 pmORD  Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
24h 55m1 stop Toronto Pearson Intl
Air Canada Logo
1:10 pm - 9:23 amGCM  George Town Owen Roberts Intl-ORD Chicago O'Hare Intl
21h 13m1 stop Toronto Pearson Intl
$383Air Canada
Thu, Nov 19 - Thu, Nov 26
Air Canada Logo
8:45 am - 12:10 pmORD  Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
26h 25m1 stop Toronto Pearson Intl
Air Canada Logo
1:10 pm - 3:38 pmGCM  George Town Owen Roberts Intl-ORD Chicago O'Hare Intl
27h 28m1 stop Toronto Pearson Intl
$419Air Canada
Thu, Dec 3 - Mon, Dec 7
United Airlines Logo
6:00 am - 3:30 pmORD  Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
9h 30m1 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
$587United Airlines
Wed, Mar 17 - Tue, Mar 23
American Airlines Logo
9:25 am - 2:30 pmORD  Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
4h 05mnonstop
American Airlines Logo
3:36 pm - 6:46 pmGCM  George Town Owen Roberts Intl-ORD Chicago O'Hare Intl
4h 10mnonstop
$588American Airlines
Wed, Feb 24 - Tue, Mar 2
American Airlines Logo
5:18 am - 12:04 pmORD  Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
5h 46m1 stop Charlotte Douglas
American Airlines Logo
3:36 pm - 6:46 pmGCM  George Town Owen Roberts Intl-ORD Chicago O'Hare Intl
4h 10mnonstop
$592American Airlines
Wed, Feb 24 - Tue, Mar 2
American Airlines Logo
4:50 pm - 11:31 amORD  Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
17h 41m1 stop Philadelphia
American Airlines Logo
12:59 pm - 7:29 pmGCM  George Town Owen Roberts Intl-ORD Chicago O'Hare Intl
7h 30m1 stop Charlotte Douglas
$597American Airlines
Sun, Jan 3 - Wed, Jan 13
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
1:25 pm - 10:58 pmGCM  George Town Owen Roberts Intl-ORD Chicago O'Hare Intl
9h 33m1 stop Newark
$598United Airlines
Wed, Mar 17 - Tue, Mar 23
United Airlines Logo
8:42 am - 1:45 pmORD  Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
4h 03mnonstop
United Airlines Logo
2:55 pm - 6:13 pmGCM  George Town Owen Roberts Intl-ORD Chicago O'Hare Intl
4h 18mnonstop
$623United Airlines
Wed, Jan 13 - Sun, Jan 17

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

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
Nov 10
ORD4:30 pmChicago O'Hare Intl
18h 40m
1 stop
GCM12:10 pmGeorge Town Owen Roberts Intl
Nov 19
GCM1:10 pmGeorge Town Owen Roberts Intl
21h 13m
1 stop
ORD9:23 amChicago O'Hare Intl
$383
Air Canada
Nov 30
ORD4:30 pmChicago O'Hare Intl
18h 40m
1 stop
GCM12:10 pmGeorge Town Owen Roberts Intl
Dec 3
GCM1:10 pmGeorge Town Owen Roberts Intl
7h 48m
1 stop
ORD7:58 pmChicago O'Hare Intl
$419
Air Canada
Oct 28
ORD1:55 pmChicago O'Hare Intl
45h 15m
2 stops
GCM11:10 amGeorge Town Owen Roberts Intl
Nov 6
GCM1:10 pmGeorge Town Owen Roberts Intl
27h 28m
1 stop
ORD3:38 pmChicago O'Hare Intl
$422

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
Oct 15
ORD5:05 amChicago O'Hare Intl
8h 05m
1 stop
GCM1:10 pmGeorge Town Owen Roberts Intl
Oct 26
GCM2:10 pmGeorge Town Owen Roberts Intl
7h 20m
1 stop
ORD9:30 pmChicago O'Hare Intl
$701
American Airlines
Oct 17
ORD8:55 pmChicago O'Hare Intl
14h 35m
1 stop
GCM11:30 amGeorge Town Owen Roberts Intl
Oct 24
GCM3:15 pmGeorge Town Owen Roberts Intl
8h 44m
1 stop
ORD11:59 pmChicago O'Hare Intl
$702
American Airlines
Oct 15
ORD8:05 amChicago O'Hare Intl
10h 55m
2 stops
GCM7:00 pmGeorge Town Owen Roberts Intl
Oct 26
GCM2:10 pmGeorge Town Owen Roberts Intl
7h 20m
1 stop
ORD9:30 pmChicago O'Hare Intl
$706

momondo Fare Finder

 
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 Chicago O'Hare Intl - GCM George Town Owen Roberts Intl

ORDGCM

Chicago O'Hare Intl

Tue 11/10

4:30 pm-12:10 pm

1 stop18h 40m

George Town Owen Roberts Intl

Thu 11/19

1:10 pm-9:23 am

1 stop21h 13m

$383

ChicagoGeorge Town

ORD Chicago O'Hare Intl - GCM George Town Owen Roberts Intl

ORDGCM

Chicago O'Hare Intl

Sun 12/13

4:30 pm-12:10 pm

1 stop18h 40m

George Town Owen Roberts Intl

Wed 12/16

1:10 pm-9:08 am

1 stop20h 58m

$383

ChicagoGeorge Town

ORD Chicago O'Hare Intl - GCM George Town Owen Roberts Intl

ORDGCM

Chicago O'Hare Intl

Thu 11/19

10:15 am-12:10 pm

1 stop24h 55m

George Town Owen Roberts Intl

Thu 11/26

1:10 pm-9:23 am

1 stop21h 13m

$383

ChicagoGeorge Town

ORD Chicago O'Hare Intl - GCM George Town Owen Roberts Intl

ORDGCM

Chicago O'Hare Intl

Thu 12/3

8:45 am-12:10 pm

1 stop26h 25m

George Town Owen Roberts Intl

Mon 12/7

1:10 pm-3:38 pm

1 stop27h 28m

$419

ChicagoGeorge Town

ORD Chicago O'Hare Intl - GCM George Town Owen Roberts Intl

ORDGCM

Chicago O'Hare Intl

Wed 3/17

6:00 am-3:30 pm

1 stop9h 30m

George Town Owen Roberts Intl

Tue 3/23

1:55 pm-6:13 pm

Nonstop4h 18m

$587
Quickest round-trip

ChicagoGeorge Town

ORD Chicago O'Hare Intl - GCM George Town Owen Roberts Intl

ORDGCM

Chicago O'Hare Intl

Wed 2/24

9:25 am-2:30 pm

Nonstop4h 05m

George Town Owen Roberts Intl

Tue 3/2

3:36 pm-6:46 pm

Nonstop4h 10m

$588

ChicagoGeorge Town

ORD Chicago O'Hare Intl - GCM George Town Owen Roberts Intl

ORDGCM

Chicago O'Hare Intl

Wed 2/24

5:18 am-12:04 pm

1 stop5h 46m

George Town Owen Roberts Intl

Tue 3/2

3:36 pm-6:46 pm

Nonstop4h 10m

$592

ChicagoGeorge Town

ORD Chicago O'Hare Intl - GCM George Town Owen Roberts Intl

ORDGCM

Chicago O'Hare Intl

Sun 1/3

4:50 pm-11:31 am

1 stop17h 41m

George Town Owen Roberts Intl

Wed 1/13

12:59 pm-7:29 pm

1 stop7h 30m

$597

ChicagoGeorge Town

ORD Chicago O'Hare Intl - GCM George Town Owen Roberts Intl

ORDGCM

Chicago O'Hare Intl

Wed 3/17

6:50 am-3:30 pm

1 stop8h 40m

George Town Owen Roberts Intl

Tue 3/23

1:25 pm-10:58 pm

1 stop9h 33m

$598

ChicagoGeorge Town

ORD Chicago O'Hare Intl - GCM George Town Owen Roberts Intl

ORDGCM

Chicago O'Hare Intl

Wed 1/13

8:42 am-1:45 pm

Nonstop4h 03m

George Town Owen Roberts Intl

Sun 1/17

2:55 pm-6:13 pm

Nonstop4h 18m

$623

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 January, then flying in February is also cheap. Prices for this month can be found on momondo for an average of $607.

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

Our data shows that Wednesday is the least expensive day to fly to Cayman Islands. Tickets to fly out on this day can be as low as $577. Be sure to avoid booking your departure on a Monday as prices are generally higher than usual. According to our data, the average ticket price to Cayman Islands on Monday is $682.

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 $698 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 $533 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 9% 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

$148

Fastest flight time

4h 00m

Direct flights

Every day

Airports in Cayman Islands

6 airports
The best one-way flight to Cayman Islands from Chicago O'Hare Intl Airport in the past 72 hours is $148. The best round-trip flight deal from Chicago O'Hare Intl Airport to Cayman Islands found on momondo in the last 72 hours is $383.
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
10,283 reviews
Search United Airlines flights
American AirlinesPriceFrom $447Free CancellationRating
7.0
12,132 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.

An easier way to manage your Cayman Islands trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Tue 11/3
Tue 11/10
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to the Cayman Islands

Popular cities in the Cayman Islands

Flights to George Townfrom $317
Flights to Cayman Bracfrom $395
Flights to Little Caymanfrom $391