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Cheap flights from Chicago O'Hare Intl Airport to the Cayman Islands from $94

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 3/12. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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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.
Multiple Airlines Logo
6:40 pm - 10:10 am
ORD
-
GCM
15h 30m
1 stop
Multiple Airlines Logo
11:30 am - 6:54 pm
GCM
-
ORD
31h 24m
3 stops
$458Multiple Airlines
Thu, Apr 9 - Wed, Apr 15
Multiple Airlines Logo
8:00 am - 10:25 am
ORD
-
GCM
26h 25m
1 stop
Multiple Airlines Logo
5:05 pm - 8:25 am
GCM
-
ORD
15h 20m
1 stop
$459Multiple Airlines
Sun, Mar 15 - Sun, Mar 22
Multiple Airlines Logo
6:22 pm - 11:30 am
ORD
-
GCM
41h 08m
2 stops
Multiple Airlines Logo
2:05 pm - 10:17 am
GCM
-
ORD
20h 12m
2 stops
$460Multiple Airlines
Tue, May 26 - Tue, Jun 2
Multiple Airlines Logo
6:10 pm - 12:20 pm
ORD
-
GCM
18h 10m
1 stop
Multiple Airlines Logo
1:15 pm - 8:09 pm
GCM
-
ORD
6h 54m
1 stop
$461Multiple Airlines
Fri, Mar 13 - Sat, Mar 21
Multiple Airlines Logo
6:10 pm - 12:20 pm
ORD
-
GCM
18h 10m
1 stop
Multiple Airlines Logo
1:52 pm - 12:13 am
GCM
-
ORD
10h 21m
2 stops
$462Multiple Airlines
Fri, Mar 13 - Thu, Mar 19
Multiple Airlines Logo
6:10 pm - 12:57 pm
ORD
-
GCM
18h 47m
1 stop
Multiple Airlines Logo
5:05 pm - 2:20 pm
GCM
-
ORD
21h 15m
2 stops
$463Multiple Airlines
Wed, Apr 8 - Fri, Apr 17
Air Canada Logo
3:45 pm - 10:10 am
ORD
-
GCM
18h 25m
2 stops
Air Canada Logo
11:55 am - 7:58 am
GCM
-
ORD
20h 03m
2 stops
$464Air Canada
Thu, Apr 9 - Thu, Apr 16
Multiple Airlines Logo
4:51 pm - 4:05 pm
ORD
-
GCM
23h 14m
1 stop
Multiple Airlines Logo
1:15 pm - 8:09 pm
GCM
-
ORD
6h 54m
1 stop
$465Multiple Airlines
Mon, Mar 16 - Sat, Mar 21
Multiple Airlines Logo
5:05 am - 12:57 pm
ORD
-
GCM
7h 52m
1 stop
Multiple Airlines Logo
4:45 pm - 11:17 pm
GCM
-
ORD
30h 32m
3 stops
$466Multiple Airlines
Thu, Mar 12 - Mon, Mar 16
Multiple Airlines Logo
3:55 pm - 11:25 am
ORD
-
GCM
19h 30m
1 stop
Multiple Airlines Logo
1:15 pm - 8:01 am
GCM
-
ORD
18h 46m
2 stops
$467Multiple Airlines
Wed, Mar 25 - Sat, Mar 28

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

Our best Spirit Airlines deals on Chicago O'Hare Intl Airport to Cayman Islands flight tickets
Spirit Airlines
Mar 13
ORD12:45 pmChicago O'Hare Intl
23h 35m
3 stops
GCM12:20 pmGeorge Town Owen Roberts Intl
Mar 19
GCM1:52 pmGeorge Town Owen Roberts Intl
9h 25m
1 stop
ORD11:17 pmChicago O'Hare Intl
$475
Spirit Airlines
Apr 8
ORD6:10 pmChicago O'Hare Intl
18h 47m
1 stop
GCM12:57 pmGeorge Town Owen Roberts Intl
Apr 12
GCM1:52 pmGeorge Town Owen Roberts Intl
21h 25m
1 stop
ORD11:17 amChicago O'Hare Intl
$479
Spirit Airlines
Mar 15
ORD5:05 amChicago O'Hare Intl
7h 52m
1 stop
GCM12:57 pmGeorge Town Owen Roberts Intl
Mar 19
GCM1:52 pmGeorge Town Owen Roberts Intl
34h 30m
3 stops
ORD12:22 amChicago O'Hare Intl
$481

Delta flights from Chicago O'Hare Intl Airport to Cayman Islands

Our best Delta deals on Chicago O'Hare Intl Airport to Cayman Islands flight tickets
Delta
Mar 31
ORD5:30 amChicago O'Hare Intl
6h 17m
1 stop
GCM11:47 amGeorge Town Owen Roberts Intl
Apr 7
GCM1:12 pmGeorge Town Owen Roberts Intl
10h 42m
1 stop
ORD11:54 pmChicago O'Hare Intl
$499
Delta
Apr 6
ORD5:40 pmChicago O'Hare Intl
18h 07m
2 stops
GCM11:47 amGeorge Town Owen Roberts Intl
Apr 14
GCM1:25 pmGeorge Town Owen Roberts Intl
20h 54m
2 stops
ORD10:19 amChicago O'Hare Intl
$504

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 February 26, 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

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Thu 4/9

6:40 pm-10:10 am

1 stop15h 30m

George Town Owen Roberts Intl

Wed 4/15

11:30 am-6:54 pm

3 stops31h 24m

$458

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 3/15

8:00 am-10:25 am

1 stop26h 25m

George Town Owen Roberts Intl

Sun 3/22

5:05 pm-8:25 am

1 stop15h 20m

$459

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Tue 5/26

6:22 pm-11:30 am

2 stops41h 08m

George Town Owen Roberts Intl

Tue 6/2

2:05 pm-10:17 am

2 stops20h 12m

$460

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Fri 3/13

6:10 pm-12:20 pm

1 stop18h 10m

George Town Owen Roberts Intl

Sat 3/21

1:15 pm-8:09 pm

1 stop6h 54m

$461

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Fri 3/13

6:10 pm-12:20 pm

1 stop18h 10m

George Town Owen Roberts Intl

Thu 3/19

1:52 pm-12:13 am

2 stops10h 21m

$462

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 4/8

6:10 pm-12:57 pm

1 stop18h 47m

George Town Owen Roberts Intl

Fri 4/17

5:05 pm-2:20 pm

2 stops21h 15m

$463

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Thu 4/9

3:45 pm-10:10 am

2 stops18h 25m

George Town Owen Roberts Intl

Thu 4/16

11:55 am-7:58 am

2 stops20h 03m

$464

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Mon 3/16

4:51 pm-4:05 pm

1 stop23h 14m

George Town Owen Roberts Intl

Sat 3/21

1:15 pm-8:09 pm

1 stop6h 54m

$465

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Thu 3/12

5:05 am-12:57 pm

1 stop7h 52m

George Town Owen Roberts Intl

Mon 3/16

4:45 pm-11:17 pm

3 stops30h 32m

$466

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 3/25

3:55 pm-11:25 am

1 stop19h 30m

George Town Owen Roberts Intl

Sat 3/28

1:15 pm-8:01 am

2 stops18h 46m

$467

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 January, then flying in February is also cheap. Prices for this month can be found on momondo for an average of $530.

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 $526. 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 $770.

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 to 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 $670 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 $461 on momondo.

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

There are 2 cabin classes available to choose from on Chicago O'Hare Intl 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

$324

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 $324. The best round-trip flight deal from Chicago O'Hare Intl Airport to Cayman Islands found on momondo in the last 72 hours is $530.
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

  • 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
9,348 reviews
Search United Airlines flights
American AirlinesPriceFrom $438Free CancellationRating
7.2
11,352 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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Find better results for your trip to the Cayman Islands

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