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Cheap flights from Chicago O'Hare Intl Airport to the Cayman Islands from $103

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 12/6. 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

Spirit Airlines Logo
5:59 pm - 11:00 amORD-GCM
16h 01m1 stop
Spirit Airlines Logo
11:55 am - 11:42 pmGCM-ORD
12h 47m1 stop
$330Spirit Airlines
Find Deal
Wed, Dec 10 - Sun, Dec 14
Spirit Airlines Logo
5:59 pm - 11:00 amORD-GCM
16h 01m1 stop
Spirit Airlines Logo
11:55 am - 9:00 pmGCM-ORD
10h 05m1 stop
$349Spirit Airlines
Find Deal
Wed, Feb 4 - Sat, Feb 7
Logo
1:59 pm - 12:25 pmORD-GCM
21h 26m2 stops
Logo
11:55 am - 9:00 pmGCM-ORD
10h 05m1 stop
$366
Find Deal
Wed, Dec 10 - Sun, Dec 14
Spirit Airlines Logo
5:59 pm - 11:00 amORD-GCM
16h 01m1 stop
Spirit Airlines Logo
11:55 am - 11:42 pmGCM-ORD
12h 47m1 stop
$385Spirit Airlines
Find Deal
Fri, Feb 20 - Sat, Feb 28
American Airlines Logo
6:00 am - 1:10 pmORD-GCM
7h 10m1 stop
American Airlines Logo
12:25 pm - 7:10 pmGCM-ORD
6h 45m1 stop
$446American Airlines
Find Deal
Tue, Oct 21 - Tue, Oct 28
American Airlines Logo
5:20 am - 1:10 pmORD-GCM
7h 50m2 stops
American Airlines Logo
8:25 am - 7:10 pmGCM-ORD
10h 45m2 stops
$450American Airlines
Find Deal
Tue, Oct 21 - Tue, Oct 28
Logo
5:59 pm - 11:00 amORD-GCM
16h 01m1 stop
Logo
1:30 pm - 8:05 amGCM-ORD
19h 35m2 stops
$451
Find Deal
Wed, Jan 21 - Sun, Jan 25
Delta Logo
5:32 am - 12:35 pmORD-GCM
6h 03m1 stop
Delta Logo
1:50 pm - 10:44 pmGCM-ORD
9h 54m1 stop
$486Delta
Find Deal
Mon, Dec 15 - Fri, Dec 19
Delta Logo
5:50 am - 12:35 pmORD-GCM
5h 45m1 stop
Delta Logo
2:00 pm - 11:54 pmGCM-ORD
10h 54m1 stop
$520Delta
Find Deal
Mon, Jan 12 - Wed, Jan 21
United Airlines Logo
8:45 am - 1:45 pmORD-GCM
4h 00mnonstop
United Airlines Logo
2:50 pm - 6:04 pmGCM-ORD
4h 14mnonstop
$527United Airlines
Find Deal
Thu, Jan 15 - Mon, Jan 19

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
Dec 10
ORD5:59 pmChicago O'Hare Intl
16h 01m
1 stop
GCM11:00 amGeorge Town Owen Roberts Intl
Dec 14
GCM11:55 amGeorge Town Owen Roberts Intl
12h 47m
1 stop
ORD11:42 pmChicago O'Hare Intl
$330
Find similar
Spirit Airlines
Feb 4
ORD5:59 pmChicago O'Hare Intl
16h 01m
1 stop
GCM11:00 amGeorge Town Owen Roberts Intl
Feb 7
GCM11:55 amGeorge Town Owen Roberts Intl
10h 05m
1 stop
ORD9:00 pmChicago O'Hare Intl
$349
Find similar
Spirit Airlines
Feb 20
ORD5:59 pmChicago O'Hare Intl
16h 01m
1 stop
GCM11:00 amGeorge Town Owen Roberts Intl
Feb 28
GCM11:55 amGeorge Town Owen Roberts Intl
12h 47m
1 stop
ORD11:42 pmChicago O'Hare Intl
$385
Find similar

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 25
ORD6:05 pmChicago O'Hare Intl
41h 20m
2 stops
GCM12:25 pmGeorge Town Owen Roberts Intl
Nov 28
GCM1:30 pmGeorge Town Owen Roberts Intl
22h 48m
2 stops
ORD11:18 amChicago O'Hare Intl
$414
Find similar
Air Canada
Jan 22
ORD8:15 pmChicago O'Hare Intl
15h 10m
1 stop
GCM12:25 pmGeorge Town Owen Roberts Intl
Jan 27
GCM1:30 pmGeorge Town Owen Roberts Intl
20h 43m
1 stop
ORD9:13 amChicago O'Hare Intl
$529
Find similar
Air Canada
Jan 22
ORD3:35 pmChicago O'Hare Intl
19h 50m
2 stops
GCM12:25 pmGeorge Town Owen Roberts Intl
Jan 27
GCM1:30 pmGeorge Town Owen Roberts Intl
19h 35m
2 stops
ORD8:05 amChicago O'Hare Intl
$534
Find similar

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 September 8, 2025.
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

Wed 12/10

5:59 pm-11:00 am

1 stop16h 01m

George Town Owen Roberts Intl

Sun 12/14

11:55 am-11:42 pm

1 stop12h 47m

$330

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 2/4

5:59 pm-11:00 am

1 stop16h 01m

George Town Owen Roberts Intl

Sat 2/7

11:55 am-9:00 pm

1 stop10h 05m

$349

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 12/10

1:59 pm-12:25 pm

2 stops21h 26m

George Town Owen Roberts Intl

Sun 12/14

11:55 am-9:00 pm

1 stop10h 05m

$366

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Fri 2/20

5:59 pm-11:00 am

1 stop16h 01m

George Town Owen Roberts Intl

Sat 2/28

11:55 am-11:42 pm

1 stop12h 47m

$385

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Tue 10/21

6:00 am-1:10 pm

1 stop7h 10m

George Town Owen Roberts Intl

Tue 10/28

12:25 pm-7:10 pm

1 stop6h 45m

$446

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Tue 10/21

5:20 am-1:10 pm

2 stops7h 50m

George Town Owen Roberts Intl

Tue 10/28

8:25 am-7:10 pm

2 stops10h 45m

$450

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 1/21

5:59 pm-11:00 am

1 stop16h 01m

George Town Owen Roberts Intl

Sun 1/25

1:30 pm-8:05 am

2 stops19h 35m

$451

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Mon 12/15

5:32 am-12:35 pm

1 stop6h 03m

George Town Owen Roberts Intl

Fri 12/19

1:50 pm-10:44 pm

1 stop9h 54m

$486

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Mon 1/12

5:50 am-12:35 pm

1 stop5h 45m

George Town Owen Roberts Intl

Wed 1/21

2:00 pm-11:54 pm

1 stop10h 54m

$520

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Thu 1/15

8:45 am-1:45 pm

Nonstop4h 00m

George Town Owen Roberts Intl

Mon 1/19

2:50 pm-6:04 pm

Nonstop4h 14m

$527

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 $629.

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

Our data shows that Monday is the least expensive day to fly to Cayman Islands. Tickets to fly out on this day can be as low as $668. Be sure to avoid booking your departure on a Friday as prices are generally higher than usual. According to our data, the average ticket price to Cayman Islands on Friday is $793.

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

According to our data, the cheapest time of day to fly to Cayman Islands is in the afternoon. momondo users have found flights departing from Chicago O'Hare Intl Airport to Cayman Islands in the afternoon for as low as $507. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are $732 on average. Flights to Cayman Islands from Chicago O'Hare Intl Airport in the morning are generally more expensive because this time of day is more convenient for travelers’ schedules.

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 $695 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 $608 on momondo.

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

There are 3 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?

No. A direct flight is the cheapest option for a flight between Chicago O'Hare Intl Airport to Cayman Islands.

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

$582

Fastest flight time

3h 45m

Direct flights

Every day

Airports in Cayman Islands

1 airport
The best one-way flight to Cayman Islands from Chicago O'Hare Intl Airport in the past 72 hours is $582. 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 3h 45m
Direct flights go from Chicago O'Hare Intl Airport to Cayman Islands every day.
There is 1 airport near Cayman Islands: 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
American AirlinesPriceFrom $530Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
DeltaPriceFrom $564Free CancellationRating
7.9
7,966 reviews
Search Delta flights
United AirlinesPriceFrom $584Free CancellationRating
7.4
8,944 reviews
Search United 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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