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Cheap flights from Chicago 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 to the Cayman Islands departing on 2/7. 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.
Multiple Airlines Logo
5:32 pm - 1:53 pm
ORD
-
GCM
19h 21m
1 stop
Multiple Airlines Logo
11:30 am - 8:18 am
GCM
-
ORD
21h 48m
1 stop
$326Multiple Airlines
Wed, Feb 4 - Tue, Feb 10
Multiple Airlines Logo
5:32 pm - 1:53 pm
ORD
-
GCM
19h 21m
1 stop
Multiple Airlines Logo
7:00 am - 6:16 pm
GCM
-
ORD
12h 16m
1 stop
$329Multiple Airlines
Wed, Feb 4 - Fri, Feb 6
Multiple Airlines Logo
9:23 am - 4:05 pm
ORD
-
GCM
29h 42m
1 stop
Multiple Airlines Logo
2:34 pm - 11:47 pm
GCM
-
ORD
10h 13m
1 stop
$331Multiple Airlines
Tue, Feb 3 - Sat, Feb 7
Spirit Airlines Logo
12:44 pm - 1:53 pm
ORD
-
GCM
24h 09m
2 stops
Spirit Airlines Logo
2:34 pm - 11:47 pm
GCM
-
ORD
10h 13m
1 stop
$332Spirit Airlines
Sat, Jan 31 - Sat, Feb 7
Multiple Airlines Logo
5:15 am - 1:53 pm
ORD
-
GCM
7h 38m
1 stop
Multiple Airlines Logo
1:30 pm - 6:55 pm
GCM
-
ORD
54h 25m
2 stops
$333Multiple Airlines
Thu, Jan 29 - Sun, Feb 1
Spirit Airlines Logo
5:15 am - 1:43 pm
ORD
-
GCM
7h 28m
1 stop
Spirit Airlines Logo
2:49 pm - 7:54 am
GCM
-
ORD
18h 05m
2 stops
$335Spirit Airlines
Sun, Feb 22 - Thu, Feb 26
Southwest Logo
5:00 am - 12:55 pm
MDW
-
GCM
6h 55m
1 stop
Southwest Logo
1:50 pm - 9:00 pm
GCM
-
MDW
8h 10m
1 stop
$431Southwest
Mon, Feb 2 - Wed, Feb 11
Southwest Logo
7:50 pm - 12:55 pm
MDW
-
GCM
16h 05m
2 stops
Southwest Logo
1:50 pm - 9:00 pm
GCM
-
MDW
8h 10m
1 stop
$436Southwest
Mon, Feb 2 - Wed, Feb 11
Southwest Logo
5:00 am - 12:55 pm
MDW
-
GCM
6h 55m
1 stop
Southwest Logo
1:50 pm - 9:00 pm
GCM
-
MDW
8h 10m
1 stop
$441Southwest
Mon, Feb 2 - Wed, Feb 11
Southwest Logo
5:35 pm - 12:55 pm
MDW
-
GCM
18h 20m
2 stops
Southwest Logo
1:50 pm - 9:00 pm
GCM
-
MDW
8h 10m
1 stop
$446Southwest
Mon, Feb 2 - Wed, Feb 11

Southwest flights from Chicago to Cayman Islands

Our best Southwest deals on Chicago to Cayman Islands flight tickets
Southwest
Feb 2
MDW5:00 amChicago Midway
6h 55m
1 stop
GCM12:55 pmGeorge Town Owen Roberts Intl
Feb 11
GCM1:50 pmGeorge Town Owen Roberts Intl
8h 10m
1 stop
MDW9:00 pmChicago Midway
$431
Southwest
Feb 2
MDW7:50 pmChicago Midway
16h 05m
2 stops
GCM12:55 pmGeorge Town Owen Roberts Intl
Feb 11
GCM1:50 pmGeorge Town Owen Roberts Intl
8h 10m
1 stop
MDW9:00 pmChicago Midway
$436
Southwest
Feb 2
MDW5:00 amChicago Midway
6h 55m
1 stop
GCM12:55 pmGeorge Town Owen Roberts Intl
Feb 11
GCM1:50 pmGeorge Town Owen Roberts Intl
8h 10m
1 stop
MDW9:00 pmChicago Midway
$441

Spirit Airlines flights from Chicago to Cayman Islands

Our best Spirit Airlines deals on Chicago to Cayman Islands flight tickets
Spirit Airlines
Jan 31
ORD12:44 pmChicago O'Hare Intl
24h 09m
2 stops
GCM1:53 pmGeorge Town Owen Roberts Intl
Feb 7
GCM2:34 pmGeorge Town Owen Roberts Intl
10h 13m
1 stop
ORD11:47 pmChicago O'Hare Intl
$332
Spirit Airlines
Feb 22
ORD5:15 amChicago O'Hare Intl
7h 28m
1 stop
GCM1:43 pmGeorge Town Owen Roberts Intl
Feb 26
GCM2:49 pmGeorge Town Owen Roberts Intl
18h 05m
2 stops
ORD7:54 amChicago O'Hare Intl
$335
Spirit Airlines
Jan 28
ORD5:32 pmChicago O'Hare Intl
19h 21m
1 stop
GCM1:53 pmGeorge Town Owen Roberts Intl
Feb 7
GCM2:34 pmGeorge Town Owen Roberts Intl
7h 29m
1 stop
ORD9:03 pmChicago O'Hare Intl
$338

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 January 14, 2026.
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

Wed 2/4

5:32 pm-1:53 pm

1 stop19h 21m

George Town Owen Roberts Intl

Tue 2/10

11:30 am-8:18 am

1 stop21h 48m

$326

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 2/4

5:32 pm-1:53 pm

1 stop19h 21m

George Town Owen Roberts Intl

Fri 2/6

7:00 am-6:16 pm

1 stop12h 16m

$329

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Tue 2/3

9:23 am-4:05 pm

1 stop29h 42m

George Town Owen Roberts Intl

Sat 2/7

2:34 pm-11:47 pm

1 stop10h 13m

$331

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 1/31

12:44 pm-1:53 pm

2 stops24h 09m

George Town Owen Roberts Intl

Sat 2/7

2:34 pm-11:47 pm

1 stop10h 13m

$332

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Thu 1/29

5:15 am-1:53 pm

1 stop7h 38m

George Town Owen Roberts Intl

Sun 2/1

1:30 pm-6:55 pm

2 stops54h 25m

$333

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 2/22

5:15 am-1:43 pm

1 stop7h 28m

George Town Owen Roberts Intl

Thu 2/26

2:49 pm-7:54 am

2 stops18h 05m

$335

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Mon 2/2

5:00 am-12:55 pm

1 stop6h 55m

George Town Owen Roberts Intl

Wed 2/11

1:50 pm-9:00 pm

1 stop8h 10m

$431

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Mon 2/2

7:50 pm-12:55 pm

2 stops16h 05m

George Town Owen Roberts Intl

Wed 2/11

1:50 pm-9:00 pm

1 stop8h 10m

$436

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Mon 2/2

5:00 am-12:55 pm

1 stop6h 55m

George Town Owen Roberts Intl

Wed 2/11

1:50 pm-9:00 pm

1 stop8h 10m

$441

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Mon 2/2

5:35 pm-12:55 pm

2 stops18h 20m

George Town Owen Roberts Intl

Wed 2/11

1:50 pm-9:00 pm

1 stop8h 10m

$446

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 Thursday is the least expensive day to fly to Cayman Islands. Tickets to fly out on this day can be as low as $530. 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 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 $678 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 $486 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 60% 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

$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 in the past 72 hours is $288. The best round-trip flight deal from Chicago to Cayman Islands found on momondo in the last 72 hours is $497.
The fastest flight from Chicago to Cayman Islands takes 3h 59m
Direct flights go from Chicago to Cayman Islands every day.
There are 6 airports in Cayman Islands. From Chicago there are direct flights to 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
United AirlinesPriceFrom $341Free CancellationRating
7.4
9,156 reviews
Search United Airlines flights
American AirlinesPriceFrom $447Free CancellationRating
7.2
11,118 reviews
Search American Airlines 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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