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Cheap flights from Chicago to the Cayman Islands from $124

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 to the Cayman Islands departing on 12/9. 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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0 bags

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Find the cheapest flights from Chicago to the Cayman Islands

Cheap round-trip flights

Enter your travel dates to find the best prices.
United Airlines Logo
8:45 am - 1:45 pmORD-GCM
4h 00mnonstop
United Airlines Logo
2:50 pm - 6:04 pmGCM-ORD
4h 14mnonstop
$326United Airlines
Find Deal
Sun, Jan 18 - Thu, Jan 22
American Airlines Logo
9:24 am - 2:35 pmORD-GCM
4h 11mnonstop
American Airlines Logo
8:45 am - 6:10 pmGCM-ORD
10h 25m1 stop
$336American Airlines
Find Deal
Wed, Dec 31 - Wed, Jan 7
Spirit Airlines Logo
5:05 am - 1:40 pmORD-GCM
7h 35m1 stop
Spirit Airlines Logo
2:35 pm - 9:00 pmGCM-ORD
7h 25m1 stop
$339Spirit Airlines
Find Deal
Sat, Feb 21 - Thu, Feb 26
American Airlines Logo
8:30 am - 8:18 pmORD-GCM
10h 48m1 stop
American Airlines Logo
8:45 am - 11:09 pmGCM-ORD
15h 24m1 stop
$340American Airlines
Find Deal
Wed, Dec 31 - Wed, Jan 7
United Airlines Logo
7:35 am - 4:30 pmORD-GCM
7h 55m1 stop
United Airlines Logo
2:50 pm - 6:04 pmGCM-ORD
4h 14mnonstop
$342United Airlines
Find Deal
Sun, Dec 14 - Thu, Dec 18
Delta Logo
5:30 am - 12:37 pmORD-GCM
6h 07m1 stop
Delta Logo
1:52 pm - 9:14 pmGCM-ORD
8h 22m1 stop
$345Delta
Find Deal
Tue, Dec 23 - Tue, Dec 30
Delta Logo
5:30 am - 12:37 pmORD-GCM
6h 07m1 stop
Delta Logo
1:52 pm - 7:38 pmGCM-ORD
6h 46m1 stop
$352Delta
Find Deal
Tue, Dec 23 - Wed, Dec 24
Spirit Airlines Logo
5:05 am - 1:40 pmORD-GCM
7h 35m1 stop
Spirit Airlines Logo
2:35 pm - 11:42 pmGCM-ORD
10h 07m1 stop
$360Spirit Airlines
Find Deal
Sun, Feb 22 - Sat, Feb 28
Southwest Logo
6:05 am - 12:35 pmORD-GCM
5h 30m1 stop
Southwest Logo
1:40 pm - 9:50 pmGCM-ORD
9h 10m1 stop
$408Southwest
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Mon, Nov 17 - Fri, Nov 21
Southwest Logo
5:50 am - 12:35 pmMDW-GCM
5h 45m1 stop
Southwest Logo
1:30 pm - 8:30 pmGCM-MDW
8h 00m1 stop
$417Southwest
Find Deal
Mon, Nov 10 - Thu, Nov 13

Spirit Airlines flights from Chicago to Cayman Islands

Our best Spirit Airlines deals on Chicago to Cayman Islands flight tickets
Spirit Airlines
Feb 21
ORD5:05 amChicago O'Hare Intl
7h 35m
1 stop
GCM1:40 pmGeorge Town Owen Roberts Intl
Feb 26
GCM2:35 pmGeorge Town Owen Roberts Intl
7h 25m
1 stop
ORD9:00 pmChicago O'Hare Intl
$339
Find similar
Spirit Airlines
Feb 22
ORD5:05 amChicago O'Hare Intl
7h 35m
1 stop
GCM1:40 pmGeorge Town Owen Roberts Intl
Feb 28
GCM2:35 pmGeorge Town Owen Roberts Intl
10h 07m
1 stop
ORD11:42 pmChicago O'Hare Intl
$360
Find similar

Delta flights from Chicago to Cayman Islands

Our best Delta deals on Chicago to Cayman Islands flight tickets
Delta
Dec 23
ORD5:30 amChicago O'Hare Intl
6h 07m
1 stop
GCM12:37 pmGeorge Town Owen Roberts Intl
Dec 30
GCM1:52 pmGeorge Town Owen Roberts Intl
8h 22m
1 stop
ORD9:14 pmChicago O'Hare Intl
$345
Find similar
Delta
Dec 23
ORD5:30 amChicago O'Hare Intl
6h 07m
1 stop
GCM12:37 pmGeorge Town Owen Roberts Intl
Dec 24
GCM1:52 pmGeorge Town Owen Roberts Intl
6h 46m
1 stop
ORD7:38 pmChicago O'Hare Intl
$352
Find similar
Delta
Dec 22
ORD9:41 amChicago O'Hare Intl
25h 56m
2 stops
GCM12:37 pmGeorge Town Owen Roberts Intl
Dec 30
GCM3:42 pmGeorge Town Owen Roberts Intl
6h 32m
1 stop
ORD9:14 pmChicago O'Hare Intl
$357
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago 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 October 9, 2025.
Use the filters below to find and compare flights from Chicago 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

Sun 1/18

8:45 am-1:45 pm

Nonstop4h 00m

George Town Owen Roberts Intl

Thu 1/22

2:50 pm-6:04 pm

Nonstop4h 14m

$326

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 12/31

9:24 am-2:35 pm

Nonstop4h 11m

George Town Owen Roberts Intl

Wed 1/7

8:45 am-6:10 pm

1 stop10h 25m

$336

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 2/21

5:05 am-1:40 pm

1 stop7h 35m

George Town Owen Roberts Intl

Thu 2/26

2:35 pm-9:00 pm

1 stop7h 25m

$339

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 12/31

8:30 am-8:18 pm

1 stop10h 48m

George Town Owen Roberts Intl

Wed 1/7

8:45 am-11:09 pm

1 stop15h 24m

$340

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 12/14

7:35 am-4:30 pm

1 stop7h 55m

George Town Owen Roberts Intl

Thu 12/18

2:50 pm-6:04 pm

Nonstop4h 14m

$342

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Tue 12/23

5:30 am-12:37 pm

1 stop6h 07m

George Town Owen Roberts Intl

Tue 12/30

1:52 pm-9:14 pm

1 stop8h 22m

$345

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Tue 12/23

5:30 am-12:37 pm

1 stop6h 07m

George Town Owen Roberts Intl

Wed 12/24

1:52 pm-7:38 pm

1 stop6h 46m

$352

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 2/22

5:05 am-1:40 pm

1 stop7h 35m

George Town Owen Roberts Intl

Sat 2/28

2:35 pm-11:42 pm

1 stop10h 07m

$360

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Mon 11/17

6:05 am-12:35 pm

1 stop5h 30m

George Town Owen Roberts Intl

Fri 11/21

1:40 pm-9:50 pm

1 stop9h 10m

$408

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Mon 11/10

5:50 am-12:35 pm

1 stop5h 45m

George Town Owen Roberts Intl

Thu 11/13

1:30 pm-8:30 pm

1 stop8h 00m

$417

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 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 October, then flying in September is also cheap. Prices for this month can be found on momondo for an average of $569.

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 $593. 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 $780.

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 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 $731 on average. Flights to Cayman Islands from Chicago in the morning are generally more expensive because this time of day is more convenient for travelers’ schedules.

What is the cheapest Chicago to Cayman Islands flight route?

Fly from Chicago O'Hare Intl to George Town Owen Roberts Intl for the best Chicago - 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 when booking weeks ahead of your departure date. In general, you can expect to find flights to Cayman Islands for around $714 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 for as low as $563 on momondo.

What cabin class options are available on Chicago to Cayman Islands flights?

There are 3 cabin classes available to choose from on Chicago 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 to Cayman Islands flights?

You could potentially save up to 45% on your flight if you consider stops on a Chicago to Cayman Islands flight.

Cheap Chicago to Cayman Islands flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Cayman Islands

Best Price Found

$251

Fastest flight time

3h 46m

Direct flights

Every day

Airports in Cayman Islands

1 airport
The best one-way flight to Cayman Islands from Chicago in the past 72 hours is $251. The best round-trip flight deal from Chicago to Cayman Islands found on momondo in the last 72 hours is $530.
The fastest flight from Chicago to Cayman Islands takes 3h 46m
Direct flights go from Chicago 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 to Cayman Islands?

    Prices for flights from Chicago to Cayman Islands refresh daily.

  • How many operators does momondo search for flights from Chicago to Cayman Islands?

  • How old do you have to be to fly from Chicago to Cayman Islands?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Cayman Islands.

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

    The travel and health documents you'll need for your trip to Cayman Islands may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Cayman Islands. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Chicago to Cayman Islands?

Best airlines flying from Chicago to Cayman Islands

Compare and see reviews for airlines that fly from Chicago to Cayman Islands with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $505Free CancellationRating
7.2
11,043 reviews
Search American Airlines flights
United AirlinesPriceFrom $530Free CancellationRating
7.4
8,968 reviews
Search United Airlines flights
DeltaPriceFrom $564Free CancellationRating
7.9
7,969 reviews
Search Delta flights

Why use momondo?

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

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Chicago to Cayman Islands. momondo saves you time and could save you money on your trip.

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?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Cayman Islands from Chicago.

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

Yes momondo offers price alerts on flights to Cayman Islands from Chicago. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

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Find better results for your trip to the Cayman Islands

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