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Cheap flights from Chicago to the Cayman Islands from $125

1 adult
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

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
8:40 pm - 9:45 amORD  Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
13h 05m1 stop Toronto Pearson Intl
Air Canada Logo
12:25 pm - 9:00 amGCM  George Town Owen Roberts Intl-ORD Chicago O'Hare Intl
20h 35m1 stop Toronto Pearson Intl
$349Air Canada
Fri, Oct 2 - Mon, Oct 5
Air Canada Logo
9:50 am - 9:45 amORD  Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
23h 55m1 stop Toronto Pearson Intl
Air Canada Logo
10:40 am - 1:23 pmGCM  George Town Owen Roberts Intl-ORD Chicago O'Hare Intl
26h 43m1 stop Toronto Pearson Intl
$349Air Canada
Fri, Sep 25 - Sat, Oct 3
Air Canada Logo
3:40 pm - 9:45 amORD  Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
18h 05m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl
Air Canada Logo
12:25 pm - 9:00 amGCM  George Town Owen Roberts Intl-ORD Chicago O'Hare Intl
20h 35m1 stop Toronto Pearson Intl
$352Air Canada
Fri, Oct 2 - Mon, Oct 5
Air Canada Logo
8:45 am - 11:25 amORD  Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
50h 40m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl
Air Canada Logo
10:40 am - 7:48 pmGCM  George Town Owen Roberts Intl-ORD Chicago O'Hare Intl
9h 08m1 stop Toronto Pearson Intl
$352Air Canada
Sat, Sep 26 - Sat, Oct 3
American Airlines Logo
6:00 am - 2:45 pmORD  Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
7h 45m1 stop Miami
American Airlines Logo
12:55 pm - 12:44 amGCM  George Town Owen Roberts Intl-ORD Chicago O'Hare Intl
12h 49m1 stop Miami
$537American Airlines
Mon, Nov 9 - Wed, Nov 11
American Airlines Logo
9:06 pm - 11:23 amORD  Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
13h 17m1 stop Charlotte Douglas
American Airlines Logo
3:45 pm - 12:01 amGCM  George Town Owen Roberts Intl-ORD Chicago O'Hare Intl
9h 16m2 stops Miami Charlotte Douglas
$542American Airlines
Mon, Nov 9 - Wed, Nov 11
American Airlines Logo
9:25 am - 2:30 pmORD  Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
4h 05mnonstop
American Airlines Logo
3:36 pm - 6:46 pmGCM  George Town Owen Roberts Intl-ORD Chicago O'Hare Intl
4h 10mnonstop
$563American Airlines
Tue, Feb 23 - Thu, Mar 4
United Airlines Logo
8:42 am - 1:45 pmORD  Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
4h 03mnonstop
United Airlines Logo
2:55 pm - 6:13 pmGCM  George Town Owen Roberts Intl-ORD Chicago O'Hare Intl
4h 18mnonstop
$617United Airlines
Wed, Feb 10 - Wed, Feb 17
United Airlines Logo
8:42 am - 1:45 pmORD  Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
4h 03mnonstop
United Airlines Logo
2:25 pm - 9:47 pmGCM  George Town Owen Roberts Intl-ORD Chicago O'Hare Intl
8h 22m1 stop Newark
$627United Airlines
Wed, Feb 10 - Wed, Feb 17
United Airlines Logo
8:42 am - 1:45 pmORD  Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
4h 03mnonstop
United Airlines Logo
2:55 pm - 6:13 pmGCM  George Town Owen Roberts Intl-ORD Chicago O'Hare Intl
4h 18mnonstop
$642United Airlines
Thu, Dec 31 - Thu, Jan 7

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Air Canada flights from Chicago to Cayman Islands

Our best Air Canada deals on Chicago to Cayman Islands flight tickets
Air Canada
Sep 11
ORD3:45 pmChicago O'Hare Intl
18h 00m
1 stop
GCM9:45 amGeorge Town Owen Roberts Intl
Sep 17
GCM12:25 pmGeorge Town Owen Roberts Intl
24h 58m
1 stop
ORD1:23 pmChicago O'Hare Intl
$335
Air Canada
Sep 25
ORD9:50 amChicago O'Hare Intl
23h 55m
1 stop
GCM9:45 amGeorge Town Owen Roberts Intl
Oct 3
GCM10:40 amGeorge Town Owen Roberts Intl
26h 43m
1 stop
ORD1:23 pmChicago O'Hare Intl
$349
Air Canada
Sep 25
ORD2:20 pmChicago O'Hare Intl
19h 25m
1 stop
GCM9:45 amGeorge Town Owen Roberts Intl
Oct 3
GCM10:40 amGeorge Town Owen Roberts Intl
47h 32m
2 stops
ORD10:12 amChicago O'Hare Intl
$352

Southwest flights from Chicago to Cayman Islands

Our best Southwest deals on Chicago to Cayman Islands flight tickets
Southwest
Nov 18
MDW5:20 amChicago Midway
6h 15m
1 stop
GCM12:35 pmGeorge Town Owen Roberts Intl
Nov 21
GCM2:20 pmGeorge Town Owen Roberts Intl
9h 40m
1 stop
MDW11:00 pmChicago Midway
$485
Southwest
Nov 9
MDW6:05 pmChicago Midway
17h 30m
2 stops
GCM12:35 pmGeorge Town Owen Roberts Intl
Nov 11
GCM1:30 pmGeorge Town Owen Roberts Intl
10h 10m
2 stops
MDW10:40 pmChicago Midway
$489
Southwest
Nov 18
MDW5:20 amChicago Midway
6h 15m
1 stop
GCM12:35 pmGeorge Town Owen Roberts Intl
Nov 21
GCM2:20 pmGeorge Town Owen Roberts Intl
11h 00m
2 stops
MDW12:20 amChicago Midway
$490

momondo Fare Finder

 
Use the filters below to find and compare flights from Chicago to the Cayman Islands that are best for you.

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Route

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Price

Cheapest round-trip

ChicagoGeorge Town

ORD Chicago O'Hare Intl - GCM George Town Owen Roberts Intl

ORDGCM

Chicago O'Hare Intl

Fri 10/2

8:40 pm-9:45 am

1 stop13h 05m

George Town Owen Roberts Intl

Mon 10/5

12:25 pm-9:00 am

1 stop20h 35m

$349

ChicagoGeorge Town

ORD Chicago O'Hare Intl - GCM George Town Owen Roberts Intl

ORDGCM

Chicago O'Hare Intl

Fri 9/25

9:50 am-9:45 am

1 stop23h 55m

George Town Owen Roberts Intl

Sat 10/3

10:40 am-1:23 pm

1 stop26h 43m

$349

ChicagoGeorge Town

ORD Chicago O'Hare Intl - GCM George Town Owen Roberts Intl

ORDGCM

Chicago O'Hare Intl

Fri 10/2

3:40 pm-9:45 am

2 stops18h 05m

George Town Owen Roberts Intl

Mon 10/5

12:25 pm-9:00 am

1 stop20h 35m

$352

ChicagoGeorge Town

ORD Chicago O'Hare Intl - GCM George Town Owen Roberts Intl

ORDGCM

Chicago O'Hare Intl

Sat 9/26

8:45 am-11:25 am

2 stops50h 40m

George Town Owen Roberts Intl

Sat 10/3

10:40 am-7:48 pm

1 stop9h 08m

$352

ChicagoGeorge Town

ORD Chicago O'Hare Intl - GCM George Town Owen Roberts Intl

ORDGCM

Chicago O'Hare Intl

Mon 11/9

6:00 am-2:45 pm

1 stop7h 45m

George Town Owen Roberts Intl

Wed 11/11

12:55 pm-12:44 am

1 stop12h 49m

$537

ChicagoGeorge Town

ORD Chicago O'Hare Intl - GCM George Town Owen Roberts Intl

ORDGCM

Chicago O'Hare Intl

Mon 11/9

9:06 pm-11:23 am

1 stop13h 17m

George Town Owen Roberts Intl

Wed 11/11

3:45 pm-12:01 am

2 stops9h 16m

$542
Quickest round-trip

ChicagoGeorge Town

ORD Chicago O'Hare Intl - GCM George Town Owen Roberts Intl

ORDGCM

Chicago O'Hare Intl

Tue 2/23

9:25 am-2:30 pm

Nonstop4h 05m

George Town Owen Roberts Intl

Thu 3/4

3:36 pm-6:46 pm

Nonstop4h 10m

$563

ChicagoGeorge Town

ORD Chicago O'Hare Intl - GCM George Town Owen Roberts Intl

ORDGCM

Chicago O'Hare Intl

Wed 2/10

8:42 am-1:45 pm

Nonstop4h 03m

George Town Owen Roberts Intl

Wed 2/17

2:55 pm-6:13 pm

Nonstop4h 18m

$617

ChicagoGeorge Town

ORD Chicago O'Hare Intl - GCM George Town Owen Roberts Intl

ORDGCM

Chicago O'Hare Intl

Wed 2/10

8:42 am-1:45 pm

Nonstop4h 03m

George Town Owen Roberts Intl

Wed 2/17

2:25 pm-9:47 pm

1 stop8h 22m

$627

ChicagoGeorge Town

ORD Chicago O'Hare Intl - GCM George Town Owen Roberts Intl

ORDGCM

Chicago O'Hare Intl

Thu 12/31

8:42 am-1:45 pm

Nonstop4h 03m

George Town Owen Roberts Intl

Thu 1/7

2:55 pm-6:13 pm

Nonstop4h 18m

$642

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 January is also cheap. Prices for this month can be found on momondo for an average of $560.

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 $532. Be sure to avoid booking your departure on a Saturday as prices are generally higher than usual. According to our data, the average ticket price to Cayman Islands on Saturday is $670.

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 from Chicago to the 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 $693 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 $533 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 7% 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

$125

Fastest flight time

4h 00m

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 $125. The best round-trip flight deal from Chicago to Cayman Islands found on momondo in the last 72 hours is $349.
The fastest flight from Chicago to Cayman Islands takes 4h 00m
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

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
10,173 reviews
Search United Airlines flights
American AirlinesPriceFrom $438Free CancellationRating
7.1
12,042 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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