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Cheap flights from Chicago O'Hare Intl Airport to the Cayman Islands from $56

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 1/31. 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
1:55 pm - 12:25 pm
ORD
-
GCM
45h 30m2 stops
Multiple Airlines Logo
2:49 pm - 11:46 pm
GCM
-
ORD
9h 57m1 stop
$323Multiple Airlines
mié., ene. 21 - dom., ene. 25
Spirit Airlines Logo
4:43 pm - 1:43 pm
ORD
-
GCM
20h 00m1 stop
Spirit Airlines Logo
2:49 pm - 7:54 am
GCM
-
ORD
18h 05m2 stops
$324Spirit Airlines
mié., feb. 18 - dom., feb. 22
Multiple Airlines Logo
4:43 pm - 1:43 pm
ORD
-
GCM
20h 00m1 stop
Multiple Airlines Logo
4:45 pm - 9:39 am
GCM
-
ORD
17h 54m1 stop
$325Multiple Airlines
mié., feb. 18 - lun., feb. 23
Spirit Airlines Logo
9:23 am - 1:53 pm
ORD
-
GCM
27h 30m3 stops
Spirit Airlines Logo
2:34 pm - 9:12 am
GCM
-
ORD
19h 38m2 stops
$327Spirit Airlines
sáb., ene. 24 - sáb., ene. 31
Multiple Airlines Logo
10:07 am - 1:53 pm
ORD
-
GCM
26h 46m2 stops
Multiple Airlines Logo
4:45 pm - 8:18 am
GCM
-
ORD
16h 33m1 stop
$329Multiple Airlines
mié., feb. 4 - lun., feb. 9
Multiple Airlines Logo
5:15 am - 1:53 pm
ORD
-
GCM
7h 38m1 stop
Multiple Airlines Logo
2:49 pm - 9:27 pm
GCM
-
ORD
31h 38m2 stops
$333Multiple Airlines
jue., feb. 5 - dom., feb. 8
Multiple Airlines Logo
10:07 am - 1:43 pm
ORD
-
GCM
26h 36m2 stops
Multiple Airlines Logo
11:30 am - 9:39 am
GCM
-
ORD
23h 09m1 stop
$334Multiple Airlines
mié., feb. 11 - mié., feb. 25
Spirit Airlines Logo
5:15 am - 1:53 pm
ORD
-
GCM
7h 38m1 stop
Spirit Airlines Logo
2:49 pm - 11:47 pm
GCM
-
ORD
9h 58m1 stop
$335Spirit Airlines
jue., ene. 22 - dom., feb. 1
Multiple Airlines Logo
8:43 pm - 1:38 pm
ORD
-
GCM
15h 55m1 stop
Multiple Airlines Logo
7:00 am - 3:18 pm
GCM
-
ORD
9h 18m1 stop
$338Multiple Airlines
vie., feb. 6 - vie., feb. 13
Multiple Airlines Logo
5:15 am - 1:53 pm
ORD
-
GCM
7h 38m1 stop
Multiple Airlines Logo
5:10 pm - 9:22 am
GCM
-
ORD
17h 12m1 stop
$339Multiple Airlines
jue., feb. 5 - mié., feb. 11

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
Jan 22
ORD8:45 pmChicago O'Hare Intl
14h 40m
1 stop
GCM12:25 pmGeorge Town Owen Roberts Intl
Jan 26
GCM1:30 pmGeorge Town Owen Roberts Intl
20h 43m
1 stop
ORD9:13 amChicago O'Hare Intl
$359
Air Canada
Jan 17
ORD3:55 pmChicago O'Hare Intl
19h 30m
1 stop
GCM12:25 pmGeorge Town Owen Roberts Intl
Jan 20
GCM1:30 pmGeorge Town Owen Roberts Intl
20h 43m
1 stop
ORD9:13 amChicago O'Hare Intl
$360
Air Canada
Apr 26
ORD8:20 pmChicago O'Hare Intl
14h 50m
1 stop
GCM11:10 amGeorge Town Owen Roberts Intl
May 2
GCM12:25 pmGeorge Town Owen Roberts Intl
20h 35m
1 stop
ORD9:00 amChicago O'Hare Intl
$361

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
Feb 18
ORD4:43 pmChicago O'Hare Intl
20h 00m
1 stop
GCM1:43 pmGeorge Town Owen Roberts Intl
Feb 22
GCM2:49 pmGeorge Town Owen Roberts Intl
18h 05m
2 stops
ORD7:54 amChicago O'Hare Intl
$324
Spirit Airlines
Jan 24
ORD9:23 amChicago O'Hare Intl
27h 30m
3 stops
GCM1:53 pmGeorge Town Owen Roberts Intl
Jan 31
GCM2:34 pmGeorge Town Owen Roberts Intl
19h 38m
2 stops
ORD9:12 amChicago O'Hare Intl
$327
Spirit Airlines
Jan 22
ORD5:15 amChicago O'Hare Intl
7h 38m
1 stop
GCM1:53 pmGeorge Town Owen Roberts Intl
Feb 1
GCM2:49 pmGeorge Town Owen Roberts Intl
9h 58m
1 stop
ORD11:47 pmChicago O'Hare Intl
$335

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 enero 8, 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

mié. 1/21

1:55 pm-12:25 pm

2 stops45h 30m

George Town Owen Roberts Intl

dom. 1/25

2:49 pm-11:46 pm

1 stop9h 57m

$323

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

mié. 2/18

4:43 pm-1:43 pm

1 stop20h 00m

George Town Owen Roberts Intl

dom. 2/22

2:49 pm-7:54 am

2 stops18h 05m

$324

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

mié. 2/18

4:43 pm-1:43 pm

1 stop20h 00m

George Town Owen Roberts Intl

lun. 2/23

4:45 pm-9:39 am

1 stop17h 54m

$325

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

sáb. 1/24

9:23 am-1:53 pm

3 stops27h 30m

George Town Owen Roberts Intl

sáb. 1/31

2:34 pm-9:12 am

2 stops19h 38m

$327

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

mié. 2/4

10:07 am-1:53 pm

2 stops26h 46m

George Town Owen Roberts Intl

lun. 2/9

4:45 pm-8:18 am

1 stop16h 33m

$329

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

jue. 2/5

5:15 am-1:53 pm

1 stop7h 38m

George Town Owen Roberts Intl

dom. 2/8

2:49 pm-9:27 pm

2 stops31h 38m

$333

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

mié. 2/11

10:07 am-1:43 pm

2 stops26h 36m

George Town Owen Roberts Intl

mié. 2/25

11:30 am-9:39 am

1 stop23h 09m

$334

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

jue. 1/22

5:15 am-1:53 pm

1 stop7h 38m

George Town Owen Roberts Intl

dom. 2/1

2:49 pm-11:47 pm

1 stop9h 58m

$335

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

vie. 2/6

8:43 pm-1:38 pm

1 stop15h 55m

George Town Owen Roberts Intl

vie. 2/13

7:00 am-3:18 pm

1 stop9h 18m

$338

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

jue. 2/5

5:15 am-1:53 pm

1 stop7h 38m

George Town Owen Roberts Intl

mié. 2/11

5:10 pm-9:22 am

1 stop17h 12m

$339

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 Thursday is the least expensive day to fly to Cayman Islands. Tickets to fly out on this day can be as low as $547. 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 $775.

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 $679 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 $486 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?

You could potentially save up to 60% 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

$288

Fastest flight time

3h 59m

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 $288. The best round-trip flight deal from Chicago O'Hare Intl Airport to Cayman Islands found on momondo in the last 72 hours is $497.
The fastest flight from Chicago O'Hare Intl Airport to Cayman Islands takes 3h 59m
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
9,139 reviews
Search United Airlines flights
American AirlinesPriceFrom $448Free CancellationRating
7.2
11,095 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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