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Cheap flights from Chicago to the Cayman Islands from $163

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
10:05 am - 12:10 pmORD  Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
25h 05m1 stop Toronto Pearson Intl
Air Canada Logo
1:10 pm - 9:08 amGCM  George Town Owen Roberts Intl-ORD Chicago O'Hare Intl
20h 58m1 stop Toronto Pearson Intl
$373Air Canada
Wed, Dec 2 - Tue, Dec 15
Air Canada Logo
10:05 am - 12:10 pmORD  Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
25h 05m1 stop Toronto Pearson Intl
Air Canada Logo
1:10 pm - 9:08 amGCM  George Town Owen Roberts Intl-ORD Chicago O'Hare Intl
20h 58m1 stop Toronto Pearson Intl
$378Air Canada
Sat, Dec 5 - Fri, Dec 11
Air Canada Logo
8:45 am - 12:10 pmORD  Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
26h 25m1 stop Toronto Pearson Intl
Air Canada Logo
1:10 pm - 9:08 amGCM  George Town Owen Roberts Intl-ORD Chicago O'Hare Intl
20h 58m1 stop Toronto Pearson Intl
$378Air Canada
Thu, Dec 3 - Thu, Dec 10
Air Canada Logo
1:55 pm - 12:10 pmORD  Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
21h 15m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl
Air Canada Logo
1:10 pm - 7:58 pmGCM  George Town Owen Roberts Intl-ORD Chicago O'Hare Intl
7h 48m1 stop Toronto Pearson Intl
$382Air Canada
Sat, Dec 5 - Fri, Dec 11
American Airlines Logo
9:45 pm - 11:00 amORD  Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
13h 15m1 stop Philadelphia
American Airlines Logo
2:30 pm - 7:30 amGCM  George Town Owen Roberts Intl-ORD Chicago O'Hare Intl
17h 00m1 stop Dallas/Fort Worth
$578American Airlines
Sun, Mar 28 - Thu, Apr 1
American Airlines Logo
6:49 pm - 12:04 pmORD  Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
16h 15m1 stop Charlotte Douglas
American Airlines Logo
4:07 pm - 1:05 amGCM  George Town Owen Roberts Intl-ORD Chicago O'Hare Intl
9h 58m1 stop Miami
$578American Airlines
Sun, Jan 31 - Thu, Feb 4
American Airlines Logo
8:59 pm - 12:04 pmORD  Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
14h 05m1 stop Charlotte Douglas
American Airlines Logo
12:59 pm - 7:29 pmGCM  George Town Owen Roberts Intl-ORD Chicago O'Hare Intl
7h 30m1 stop Charlotte Douglas
$602American Airlines
Mon, Feb 1 - Tue, Feb 9
United Airlines Logo
8:45 am - 12:45 pmORD  Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
4h 00mnonstop
United Airlines Logo
1:50 pm - 6:13 pmGCM  George Town Owen Roberts Intl-ORD Chicago O'Hare Intl
4h 23mnonstop
$603United Airlines
Tue, Apr 13 - Tue, Apr 20
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 - 7:51 amGCM  George Town Owen Roberts Intl-ORD Chicago O'Hare Intl
18h 26m1 stop Newark
$613United Airlines
Mon, Feb 1 - Tue, Feb 9
United Airlines Logo
8:45 am - 12:45 pmORD  Chicago O'Hare Intl-GCM George Town Owen Roberts Intl
4h 00mnonstop
United Airlines Logo
1:35 pm - 9:11 pmGCM  George Town Owen Roberts Intl-ORD Chicago O'Hare Intl
7h 36m1 stop Houston George Bush Intcntl
$613United Airlines
Tue, Apr 13 - Tue, Apr 20

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Delta flights from Chicago to Cayman Islands

Our best Delta deals on Chicago to Cayman Islands flight tickets
Delta
Feb 16
MDW6:00 amChicago Midway
5h 40m
1 stop
GCM12:40 pmGeorge Town Owen Roberts Intl
Feb 25
GCM2:05 pmGeorge Town Owen Roberts Intl
9h 05m
1 stop
MDW10:10 pmChicago Midway
$618
Delta
Nov 30
MDW1:31 pmChicago Midway
21h 54m
2 stops
GCM12:25 pmGeorge Town Owen Roberts Intl
Dec 9
GCM1:40 pmGeorge Town Owen Roberts Intl
10h 14m
1 stop
MDW10:54 pmChicago Midway
$622
Delta
Dec 24
MDW6:00 amChicago Midway
6h 12m
1 stop
GCM1:12 pmGeorge Town Owen Roberts Intl
Dec 31
GCM3:51 pmGeorge Town Owen Roberts Intl
7h 31m
1 stop
MDW10:22 pmChicago Midway
$658

American Airlines flights from Chicago to Cayman Islands

Our best American Airlines deals on Chicago to Cayman Islands flight tickets
American Airlines
Nov 1
ORD5:00 amChicago O'Hare Intl
5h 55m
1 stop
GCM11:55 amGeorge Town Owen Roberts Intl
Nov 6
GCM3:45 pmGeorge Town Owen Roberts Intl
9h 11m
1 stop
ORD11:56 pmChicago O'Hare Intl
$812
American Airlines
Nov 2
ORD6:00 amChicago O'Hare Intl
7h 45m
1 stop
GCM2:45 pmGeorge Town Owen Roberts Intl
Nov 6
GCM12:54 pmGeorge Town Owen Roberts Intl
12h 02m
1 stop
ORD11:56 pmChicago O'Hare Intl
$877
American Airlines
Nov 3
ORD9:50 amChicago O'Hare Intl
9h 08m
2 stops
GCM7:58 pmGeorge Town Owen Roberts Intl
Nov 8
GCM12:18 pmGeorge Town Owen Roberts Intl
11h 14m
1 stop
ORD10:32 pmChicago O'Hare Intl
$911

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

Depart

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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

Wed 12/2

10:05 am-12:10 pm

1 stop25h 05m

George Town Owen Roberts Intl

Tue 12/15

1:10 pm-9:08 am

1 stop20h 58m

$373

ChicagoGeorge Town

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

ORDGCM

Chicago O'Hare Intl

Sat 12/5

10:05 am-12:10 pm

1 stop25h 05m

George Town Owen Roberts Intl

Fri 12/11

1:10 pm-9:08 am

1 stop20h 58m

$378

ChicagoGeorge Town

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

ORDGCM

Chicago O'Hare Intl

Thu 12/3

8:45 am-12:10 pm

1 stop26h 25m

George Town Owen Roberts Intl

Thu 12/10

1:10 pm-9:08 am

1 stop20h 58m

$378

ChicagoGeorge Town

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

ORDGCM

Chicago O'Hare Intl

Sat 12/5

1:55 pm-12:10 pm

2 stops21h 15m

George Town Owen Roberts Intl

Fri 12/11

1:10 pm-7:58 pm

1 stop7h 48m

$382

ChicagoGeorge Town

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

ORDGCM

Chicago O'Hare Intl

Sun 3/28

9:45 pm-11:00 am

1 stop13h 15m

George Town Owen Roberts Intl

Thu 4/1

2:30 pm-7:30 am

1 stop17h 00m

$578

ChicagoGeorge Town

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

ORDGCM

Chicago O'Hare Intl

Sun 1/31

6:49 pm-12:04 pm

1 stop16h 15m

George Town Owen Roberts Intl

Thu 2/4

4:07 pm-1:05 am

1 stop9h 58m

$578

ChicagoGeorge Town

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

ORDGCM

Chicago O'Hare Intl

Mon 2/1

8:59 pm-12:04 pm

1 stop14h 05m

George Town Owen Roberts Intl

Tue 2/9

12:59 pm-7:29 pm

1 stop7h 30m

$602
Quickest round-trip

ChicagoGeorge Town

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

ORDGCM

Chicago O'Hare Intl

Tue 4/13

8:45 am-12:45 pm

Nonstop4h 00m

George Town Owen Roberts Intl

Tue 4/20

1:50 pm-6:13 pm

Nonstop4h 23m

$603

ChicagoGeorge Town

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

ORDGCM

Chicago O'Hare Intl

Mon 2/1

8:42 am-1:45 pm

Nonstop4h 03m

George Town Owen Roberts Intl

Tue 2/9

2:25 pm-7:51 am

1 stop18h 26m

$613

ChicagoGeorge Town

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

ORDGCM

Chicago O'Hare Intl

Tue 4/13

8:45 am-12:45 pm

Nonstop4h 00m

George Town Owen Roberts Intl

Tue 4/20

1:35 pm-9:11 pm

1 stop7h 36m

$613

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 April is also cheap. Prices for this month can be found on momondo for an average of $607.

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 $577. Be sure to avoid booking your departure on a Monday as prices are generally higher than usual. According to our data, the average ticket price to Cayman Islands on Monday is $717.

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 $691 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 51% 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

$163

Fastest flight time

4h 01m

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 $163. The best round-trip flight deal from Chicago to Cayman Islands found on momondo in the last 72 hours is $373.
The fastest flight from Chicago to Cayman Islands takes 4h 01m
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 $344Free CancellationRating
7.3
10,392 reviews
Search United Airlines flights
American AirlinesPriceFrom $447Free CancellationRating
7.0
12,179 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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