Latest deals
Insights
FAQs
Reviews
Price Alerts

Cheap flights from Chicago to the Cayman Islands from $155

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 11/14. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Chicago to the Cayman Islands

Cheap round-trip flights

Spirit Airlines Logo
5:59 pm - 11:00 amORD-GCM
16h 01m1 stop
Spirit Airlines Logo
11:55 am - 9:00 pmGCM-ORD
10h 05m1 stop
$375Spirit Airlines
Find Deal
Sat, Jan 24 - Thu, Jan 29
Logo
5:59 pm - 11:00 amORD-GCM
16h 01m1 stop
Logo
1:30 pm - 9:13 amGCM-ORD
20h 43m1 stop
$423
Find Deal
Sat, Dec 6 - Fri, Dec 12
Southwest Logo
6:05 am - 12:55 pmORD-GCM
5h 50m1 stop
Southwest Logo
1:50 pm - 9:50 pmGCM-ORD
9h 00m1 stop
$434Southwest
Find Deal
Mon, Jan 26 - Tue, Feb 3
Southwest Logo
5:00 am - 12:55 pmMDW-GCM
6h 55m1 stop
Southwest Logo
1:50 pm - 9:00 pmGCM-MDW
8h 10m1 stop
$448Southwest
Find Deal
Mon, Jan 26 - Tue, Feb 3
American Airlines Logo
8:10 am - 12:56 pmORD-GCM
3h 46mnonstop
American Airlines Logo
2:00 pm - 5:10 pmGCM-ORD
4h 10mnonstop
$505American Airlines
Find Deal
Wed, Dec 31 - Wed, Jan 7
American Airlines Logo
6:35 pm - 12:05 pmORD-GCM
16h 30m1 stop
American Airlines Logo
2:00 pm - 5:10 pmGCM-ORD
4h 10mnonstop
$510American Airlines
Find Deal
Sun, Dec 14 - Fri, Dec 19
United Airlines Logo
8:45 am - 1:45 pmORD-GCM
4h 00mnonstop
United Airlines Logo
2:25 pm - 11:42 pmGCM-ORD
10h 17m1 stop
$515United Airlines
Find Deal
Mon, Jan 26 - Mon, Feb 2
Delta Logo
5:40 am - 12:30 pmORD-GCM
5h 50m1 stop
Delta Logo
3:45 pm - 11:58 pmGCM-ORD
9h 13m1 stop
$520Delta
Find Deal
Wed, Dec 24 - Wed, Dec 31
Delta Logo
6:00 am - 12:35 pmMDW-GCM
5h 35m1 stop
Delta Logo
2:00 pm - 9:46 pmGCM-MDW
8h 46m1 stop
$520Delta
Find Deal
Sun, Jan 25 - Thu, Jan 29
United Airlines Logo
8:45 am - 1:45 pmORD-GCM
4h 00mnonstop
United Airlines Logo
2:50 pm - 6:04 pmGCM-ORD
4h 14mnonstop
$530United Airlines
Find Deal
Fri, Feb 6 - Fri, Feb 13

Spirit Airlines flights from Chicago to Cayman Islands

Our best Spirit Airlines deals on Chicago to Cayman Islands flight tickets
Spirit Airlines
Jan 24
ORD5:59 pmChicago O'Hare Intl
16h 01m
1 stop
GCM11:00 amGeorge Town Owen Roberts Intl
Jan 29
GCM11:55 amGeorge Town Owen Roberts Intl
10h 05m
1 stop
ORD9:00 pmChicago O'Hare Intl
$375
Find similar
Spirit Airlines
Feb 7
ORD5:59 pmChicago O'Hare Intl
16h 01m
1 stop
GCM11:00 amGeorge Town Owen Roberts Intl
Feb 14
GCM11:55 amGeorge Town Owen Roberts Intl
10h 05m
1 stop
ORD9:00 pmChicago O'Hare Intl
$453
Find similar

Air Canada flights from Chicago to Cayman Islands

Our best Air Canada deals on Chicago to Cayman Islands flight tickets
Air Canada
Nov 20
ORD8:15 pmChicago O'Hare Intl
15h 05m
1 stop
GCM12:20 pmGeorge Town Owen Roberts Intl
Nov 23
GCM1:30 pmGeorge Town Owen Roberts Intl
26h 40m
1 stop
ORD3:10 pmChicago O'Hare Intl
$452
Find similar
Air Canada
Oct 29
ORD8:15 pmChicago O'Hare Intl
15h 05m
1 stop
GCM11:20 amGeorge Town Owen Roberts Intl
Nov 2
GCM1:30 pmGeorge Town Owen Roberts Intl
20h 43m
1 stop
ORD9:13 amChicago O'Hare Intl
$479
Find similar
Air Canada
Oct 30
ORD3:35 pmChicago O'Hare Intl
19h 45m
2 stops
GCM11:20 amGeorge Town Owen Roberts Intl
Nov 2
GCM1:30 pmGeorge Town Owen Roberts Intl
20h 43m
1 stop
ORD9:13 amChicago O'Hare Intl
$481
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 August 14, 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

Sat 1/24

5:59 pm-11:00 am

1 stop16h 01m

George Town Owen Roberts Intl

Thu 1/29

11:55 am-9:00 pm

1 stop10h 05m

$375

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 12/6

5:59 pm-11:00 am

1 stop16h 01m

George Town Owen Roberts Intl

Fri 12/12

1:30 pm-9:13 am

1 stop20h 43m

$423

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Mon 1/26

6:05 am-12:55 pm

1 stop5h 50m

George Town Owen Roberts Intl

Tue 2/3

1:50 pm-9:50 pm

1 stop9h 00m

$434

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Mon 1/26

5:00 am-12:55 pm

1 stop6h 55m

George Town Owen Roberts Intl

Tue 2/3

1:50 pm-9:00 pm

1 stop8h 10m

$448

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 12/31

8:10 am-12:56 pm

Nonstop3h 46m

George Town Owen Roberts Intl

Wed 1/7

2:00 pm-5:10 pm

Nonstop4h 10m

$505

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 12/14

6:35 pm-12:05 pm

1 stop16h 30m

George Town Owen Roberts Intl

Fri 12/19

2:00 pm-5:10 pm

Nonstop4h 10m

$510

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Mon 1/26

8:45 am-1:45 pm

Nonstop4h 00m

George Town Owen Roberts Intl

Mon 2/2

2:25 pm-11:42 pm

1 stop10h 17m

$515

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 12/24

5:40 am-12:30 pm

1 stop5h 50m

George Town Owen Roberts Intl

Wed 12/31

3:45 pm-11:58 pm

1 stop9h 13m

$520

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Sun 1/25

6:00 am-12:35 pm

1 stop5h 35m

George Town Owen Roberts Intl

Thu 1/29

2:00 pm-9:46 pm

1 stop8h 46m

$520

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Fri 2/6

8:45 am-1:45 pm

Nonstop4h 00m

George Town Owen Roberts Intl

Fri 2/13

2:50 pm-6:04 pm

Nonstop4h 14m

$530

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 $654. Be sure to avoid booking your departure on a Friday as prices are generally higher than usual. According to our data, the average ticket price to Cayman Islands on Friday is $878.

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 $732 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 $699 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 $610 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 28% 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

$155

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 $155. The best round-trip flight deal from Chicago to Cayman Islands found on momondo in the last 72 hours is $375.
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
DeltaPriceFrom $463Free CancellationRating
8.0
7,980 reviews
Search Delta flights
American AirlinesPriceFrom $512Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $573Free CancellationRating
7.4
8,916 reviews
Search United 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.

An easier way to manage your Cayman Islands trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Tue 8/19
Tue 8/26
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to the Cayman Islands

Popular cities in the Cayman Islands

Popular flights according to clicks in the last 7 days on momondo
Flights to George Townfrom $247
Flights to Cayman Bracfrom $368
Flights to Little Caymanfrom $377