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Cheap flights from Chicago to the Cayman Islands from $133

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 6/10. 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 to the Cayman Islands

Cheap round-trip flights

Enter your travel dates to find the best prices.
Air Canada Logo
8:20 pm - 10:00 am
ORD
-
GCM
13h 40m
1 stop
Air Canada Logo
12:25 pm - 9:00 am
GCM
-
ORD
20h 35m
1 stop
$365Air Canada
Fri, Jun 5 - Mon, Jun 8
Air Canada Logo
8:20 pm - 10:00 am
ORD
-
GCM
13h 40m
1 stop
Air Canada Logo
12:25 pm - 10:18 am
GCM
-
ORD
21h 53m
2 stops
$368Air Canada
Fri, Jun 5 - Mon, Jun 8
Air Canada Logo
8:40 pm - 10:00 am
ORD
-
GCM
13h 20m
1 stop
Air Canada Logo
12:25 pm - 8:00 am
GCM
-
ORD
19h 35m
1 stop
$370Air Canada
Fri, Jun 19 - Mon, Jun 22
Air Canada Logo
10:41 am - 10:00 am
ORD
-
GCM
23h 19m
2 stops
Air Canada Logo
12:25 pm - 12:11 pm
GCM
-
ORD
23h 46m
2 stops
$375Air Canada
Fri, Jun 5 - Mon, Jun 8
Multiple Airlines Logo
9:55 am - 11:25 am
ORD
-
GCM
25h 30m
1 stop
Multiple Airlines Logo
7:00 am - 9:00 am
GCM
-
ORD
26h 00m
2 stops
$391Multiple Airlines
Sun, Jun 7 - Fri, Jun 12
Delta Logo
6:05 am - 11:34 am
MDW
-
GCM
5h 29m
1 stop
Delta Logo
12:59 pm - 10:17 pm
GCM
-
MDW
9h 18m
1 stop
$573Delta
Sun, Jun 7 - Fri, Jun 12
Multiple Airlines Logo
11:59 am - 5:20 pm
MDW
-
GCM
29h 21m
2 stops
Multiple Airlines Logo
1:45 pm - 9:45 am
GCM
-
MDW
20h 00m
1 stop
$578Multiple Airlines
Sat, May 23 - Sat, May 30
Delta Logo
6:00 am - 11:41 am
MDW
-
GCM
5h 41m
1 stop
Delta Logo
12:56 pm - 9:46 pm
GCM
-
MDW
8h 50m
1 stop
$581Delta
Sat, Aug 22 - Wed, Aug 26
Southwest Logo
6:00 am - 12:10 pm
MDW
-
GCM
6h 10m
1 stop
Southwest Logo
1:05 pm - 9:25 pm
GCM
-
MDW
8h 20m
1 stop
$593Southwest
Wed, May 27 - Wed, Jun 3
Southwest Logo
6:00 am - 12:10 pm
MDW
-
GCM
6h 10m
1 stop
Southwest Logo
1:05 pm - 9:20 am
GCM
-
MDW
20h 15m
2 stops
$598Southwest
Wed, May 27 - Wed, Jun 3

Air Canada flights from Chicago to Cayman Islands

Our best Air Canada deals on Chicago to Cayman Islands flight tickets
Air Canada
Jun 5
ORD8:20 pmChicago O'Hare Intl
13h 40m
1 stop
GCM10:00 amGeorge Town Owen Roberts Intl
Jun 8
GCM12:25 pmGeorge Town Owen Roberts Intl
20h 35m
1 stop
ORD9:00 amChicago O'Hare Intl
$365
Air Canada
Jun 5
ORD8:20 pmChicago O'Hare Intl
13h 40m
1 stop
GCM10:00 amGeorge Town Owen Roberts Intl
Jun 8
GCM12:25 pmGeorge Town Owen Roberts Intl
21h 53m
2 stops
ORD10:18 amChicago O'Hare Intl
$368
Air Canada
Jun 19
ORD8:40 pmChicago O'Hare Intl
13h 20m
1 stop
GCM10:00 amGeorge Town Owen Roberts Intl
Jun 22
GCM12:25 pmGeorge Town Owen Roberts Intl
19h 35m
1 stop
ORD8:00 amChicago O'Hare Intl
$370

American Airlines flights from Chicago to Cayman Islands

Our best American Airlines deals on Chicago to Cayman Islands flight tickets
American Airlines
Aug 22
ORD7:00 pmChicago O'Hare Intl
16h 00m
1 stop
GCM11:00 amGeorge Town Owen Roberts Intl
Aug 26
GCM2:10 pmGeorge Town Owen Roberts Intl
8h 50m
1 stop
ORD11:00 pmChicago O'Hare Intl
$481
American Airlines
Apr 26
ORD5:00 amChicago O'Hare Intl
8h 10m
2 stops
GCM1:10 pmGeorge Town Owen Roberts Intl
Apr 29
GCM12:00 pmGeorge Town Owen Roberts Intl
9h 21m
2 stops
ORD9:21 pmChicago O'Hare Intl
$840
American Airlines
May 2
ORD8:46 pmChicago O'Hare Intl
14h 45m
1 stop
GCM11:31 amGeorge Town Owen Roberts Intl
May 9
GCM2:10 pmGeorge Town Owen Roberts Intl
7h 28m
1 stop
ORD9:38 pmChicago O'Hare Intl
$841

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 April 21, 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

Cheapest round-trip

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Fri 6/5

8:20 pm-10:00 am

1 stop13h 40m

George Town Owen Roberts Intl

Mon 6/8

12:25 pm-9:00 am

1 stop20h 35m

$365

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Fri 6/5

8:20 pm-10:00 am

1 stop13h 40m

George Town Owen Roberts Intl

Mon 6/8

12:25 pm-10:18 am

2 stops21h 53m

$368

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Fri 6/19

8:40 pm-10:00 am

1 stop13h 20m

George Town Owen Roberts Intl

Mon 6/22

12:25 pm-8:00 am

1 stop19h 35m

$370

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Fri 6/5

10:41 am-10:00 am

2 stops23h 19m

George Town Owen Roberts Intl

Mon 6/8

12:25 pm-12:11 pm

2 stops23h 46m

$375

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 6/7

9:55 am-11:25 am

1 stop25h 30m

George Town Owen Roberts Intl

Fri 6/12

7:00 am-9:00 am

2 stops26h 00m

$391

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Sun 6/7

6:05 am-11:34 am

1 stop5h 29m

George Town Owen Roberts Intl

Fri 6/12

12:59 pm-10:17 pm

1 stop9h 18m

$573

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Sat 5/23

11:59 am-5:20 pm

2 stops29h 21m

George Town Owen Roberts Intl

Sat 5/30

1:45 pm-9:45 am

1 stop20h 00m

$578

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Sat 8/22

6:00 am-11:41 am

1 stop5h 41m

George Town Owen Roberts Intl

Wed 8/26

12:56 pm-9:46 pm

1 stop8h 50m

$581
Quickest round-trip

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Wed 5/27

6:00 am-12:10 pm

1 stop6h 10m

George Town Owen Roberts Intl

Wed 6/3

1:05 pm-9:25 pm

1 stop8h 20m

$593

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Wed 5/27

6:00 am-12:10 pm

1 stop6h 10m

George Town Owen Roberts Intl

Wed 6/3

1:05 pm-9:20 am

2 stops20h 15m

$598

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 February, then flying in October is also cheap. Prices for this month can be found on momondo for an average of $534.

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 $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 $770.

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 $669 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 $492 on momondo.

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

There are 2 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 31% 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

$348

Fastest flight time

4h 00m

Direct flights

Tue and Sun

Airports in Cayman Islands

6 airports
The best one-way flight to Cayman Islands from Chicago in the past 72 hours is $348. The best round-trip flight deal from Chicago to Cayman Islands found on momondo in the last 72 hours is $695.
The fastest flight from Chicago to Cayman Islands takes 4h 00m
Direct flights go from Chicago to Cayman Islands on Tuesday and Sunday. There are no airlines offering direct flights.
There are 6 airports in Cayman Islands. From Chicago there are direct flights to George Town Owen Roberts Intl (GCM).
Search flight deals

Frequently asked questions about flying from Chicago to the Cayman Islands

  • 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
9,613 reviews
Search United Airlines flights
American AirlinesPriceFrom $438Free CancellationRating
7.1
11,645 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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Popular flights according to clicks in the last 7 days on momondo
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