Latest deals
Insights
FAQs
Reviews
Price Alerts

Cheap flights from Chicago O'Hare Intl Airport to the Cayman Islands from $85

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 O'Hare Intl Airport to the Cayman Islands departing on 12/7. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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 O'Hare Intl Airport to the Cayman Islands

Cheap round-trip flights

Enter your travel dates to find the best prices.
Spirit Airlines Logo
7:10 am - 4:55 pmORD-GCM
8h 45m1 stop
Spirit Airlines Logo
5:56 pm - 12:09 amGCM-ORD
7h 13m1 stop
$272Spirit Airlines
Find Deal
Sat, Dec 6 - Sat, Dec 13
Spirit Airlines Logo
7:00 am - 1:40 pmORD-GCM
5h 40m1 stop
Spirit Airlines Logo
2:35 pm - 8:54 pmGCM-ORD
7h 19m1 stop
$305Spirit Airlines
Find Deal
Sat, Jan 24 - Thu, Jan 29
Multiple Airlines Logo
3:26 pm - 1:45 pmORD-GCM
21h 19m1 stop
Multiple Airlines Logo
2:40 pm - 11:02 pmGCM-ORD
9h 22m1 stop
$329Multiple Airlines
Find Deal
Sat, Dec 6 - Sun, Dec 14
United Airlines Logo
8:45 am - 1:45 pmORD-GCM
4h 00mnonstop
United Airlines Logo
2:50 pm - 6:04 pmGCM-ORD
4h 14mnonstop
$338United Airlines
Find Deal
Sat, Nov 29 - Sat, Dec 6
Multiple Airlines Logo
12:15 pm - 4:55 pmORD-GCM
27h 40m2 stops
Multiple Airlines Logo
5:56 pm - 12:09 amGCM-ORD
7h 13m1 stop
$340Multiple Airlines
Find Deal
Fri, Dec 5 - Sat, Dec 13
United Airlines Logo
8:45 am - 1:45 pmORD-GCM
4h 00mnonstop
United Airlines Logo
2:50 pm - 6:04 pmGCM-ORD
4h 14mnonstop
$342United Airlines
Find Deal
Sat, Jan 24 - Thu, Jan 29
American Airlines Logo
7:11 am - 2:28 pmORD-GCM
6h 17m1 stop
American Airlines Logo
1:01 pm - 8:26 pmGCM-ORD
8h 25m1 stop
$344American Airlines
Find Deal
Sat, Nov 29 - Sat, Dec 6
American Airlines Logo
6:35 pm - 11:59 amORD-GCM
16h 24m1 stop
American Airlines Logo
3:35 pm - 6:45 pmGCM-ORD
4h 10mnonstop
$347American Airlines
Find Deal
Sun, Dec 14 - Sun, Dec 21
Delta Logo
7:53 pm - 12:35 pmORD-GCM
15h 42m1 stop
Delta Logo
3:42 pm - 9:14 pmGCM-ORD
6h 32m1 stop
$352Delta
Find Deal
Sun, Dec 14 - Sat, Dec 20
Delta Logo
8:55 am - 12:35 pmORD-GCM
26h 40m2 stops
Delta Logo
3:42 pm - 9:01 amGCM-ORD
18h 19m2 stops
$357Delta
Find Deal
Sun, Dec 14 - Sun, Dec 21

Spirit Airlines flights from Chicago O'Hare Intl Airport to Cayman Islands

Our best Spirit Airlines deals on Chicago O'Hare Intl Airport to Cayman Islands flight tickets
Spirit Airlines
Dec 6
ORD7:10 amChicago O'Hare Intl
8h 45m
1 stop
GCM4:55 pmGeorge Town Owen Roberts Intl
Dec 13
GCM5:56 pmGeorge Town Owen Roberts Intl
7h 13m
1 stop
ORD12:09 amChicago O'Hare Intl
$272
Find similar
Spirit Airlines
Jan 24
ORD7:00 amChicago O'Hare Intl
5h 40m
1 stop
GCM1:40 pmGeorge Town Owen Roberts Intl
Jan 29
GCM2:35 pmGeorge Town Owen Roberts Intl
7h 19m
1 stop
ORD8:54 pmChicago O'Hare Intl
$305
Find similar
Spirit Airlines
Dec 6
ORD3:26 pmChicago O'Hare Intl
21h 19m
1 stop
GCM1:45 pmGeorge Town Owen Roberts Intl
Dec 11
GCM2:40 pmGeorge Town Owen Roberts Intl
10h 29m
1 stop
ORD12:09 amChicago O'Hare Intl
$311
Find similar

United Airlines flights from Chicago O'Hare Intl Airport to Cayman Islands

Our best United Airlines deals on Chicago O'Hare Intl Airport to Cayman Islands flight tickets
United Airlines
Nov 29
ORD8:45 amChicago O'Hare Intl
4h 00m
GCM1:45 pmGeorge Town Owen Roberts Intl
Dec 6
GCM2:50 pmGeorge Town Owen Roberts Intl
4h 14m
ORD6:04 pmChicago O'Hare Intl
$338
Find similar
United Airlines
Jan 24
ORD8:45 amChicago O'Hare Intl
4h 00m
GCM1:45 pmGeorge Town Owen Roberts Intl
Jan 29
GCM2:50 pmGeorge Town Owen Roberts Intl
4h 14m
ORD6:04 pmChicago O'Hare Intl
$342
Find similar
United Airlines
Jan 24
ORD5:37 amChicago O'Hare Intl
9h 43m
1 stop
GCM4:20 pmGeorge Town Owen Roberts Intl
Jan 29
GCM2:50 pmGeorge Town Owen Roberts Intl
4h 14m
ORD6:04 pmChicago O'Hare Intl
$346
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago O'Hare Intl Airport 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 November 5, 2025.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport 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 12/6

7:10 am-4:55 pm

1 stop8h 45m

George Town Owen Roberts Intl

Sat 12/13

5:56 pm-12:09 am

1 stop7h 13m

$272

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 1/24

7:00 am-1:40 pm

1 stop5h 40m

George Town Owen Roberts Intl

Thu 1/29

2:35 pm-8:54 pm

1 stop7h 19m

$305

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 12/6

3:26 pm-1:45 pm

1 stop21h 19m

George Town Owen Roberts Intl

Sun 12/14

2:40 pm-11:02 pm

1 stop9h 22m

$329

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 11/29

8:45 am-1:45 pm

Nonstop4h 00m

George Town Owen Roberts Intl

Sat 12/6

2:50 pm-6:04 pm

Nonstop4h 14m

$338

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Fri 12/5

12:15 pm-4:55 pm

2 stops27h 40m

George Town Owen Roberts Intl

Sat 12/13

5:56 pm-12:09 am

1 stop7h 13m

$340

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 1/24

8:45 am-1:45 pm

Nonstop4h 00m

George Town Owen Roberts Intl

Thu 1/29

2:50 pm-6:04 pm

Nonstop4h 14m

$342

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 11/29

7:11 am-2:28 pm

1 stop6h 17m

George Town Owen Roberts Intl

Sat 12/6

1:01 pm-8:26 pm

1 stop8h 25m

$344

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 12/14

6:35 pm-11:59 am

1 stop16h 24m

George Town Owen Roberts Intl

Sun 12/21

3:35 pm-6:45 pm

Nonstop4h 10m

$347

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 12/14

7:53 pm-12:35 pm

1 stop15h 42m

George Town Owen Roberts Intl

Sat 12/20

3:42 pm-9:14 pm

1 stop6h 32m

$352

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 12/14

8:55 am-12:35 pm

2 stops26h 40m

George Town Owen Roberts Intl

Sun 12/21

3:42 pm-9:01 am

2 stops18h 19m

$357

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 O'Hare Intl Airport 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 $613.

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 $593. 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 $780.

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 O'Hare Intl Airport 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 $718 on average. Flights to Cayman Islands from Chicago O'Hare Intl Airport in the morning are generally more expensive because this time of day is more convenient for travelers’ schedules.

What is the cheapest Chicago O'Hare Intl to Cayman Islands flight route?

Fly from Chicago O'Hare Intl to George Town Owen Roberts Intl for the best Chicago O'Hare Intl - 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 O'Hare Intl Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Cayman Islands for around $707 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 O'Hare Intl Airport for as low as $519 on momondo.

What cabin class options are available on Chicago O'Hare Intl to Cayman Islands flights?

There are 3 cabin classes available to choose from on Chicago O'Hare Intl 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 O'Hare Intl Airport to Cayman Islands flights?

No. A direct flight is the cheapest option for a flight between Chicago O'Hare Intl Airport to Cayman Islands.

Cheap Chicago O'Hare Intl Airport to Cayman Islands flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago O'Hare Intl Airport to Cayman Islands

Best Price Found

$582

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 O'Hare Intl Airport in the past 72 hours is $582. The best round-trip flight deal from Chicago O'Hare Intl Airport to Cayman Islands found on momondo in the last 72 hours is $448.
The fastest flight from Chicago O'Hare Intl Airport to Cayman Islands takes 3h 46m
Direct flights go from Chicago O'Hare Intl Airport 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 O'Hare Intl Airport to Cayman Islands?

    Prices for flights from Chicago O'Hare Intl Airport to Cayman Islands refresh daily.

  • How many operators does momondo search for flights from Chicago O'Hare Intl Airport to Cayman Islands?

  • How old do you have to be to fly from Chicago O'Hare Intl Airport to Cayman Islands?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago O'Hare Intl Airport to Cayman Islands.

  • What documentation or ID do you need to fly to Cayman Islands?

    The required travel and health documents for your Cayman Islands trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Cayman Islands. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

  • What is the most popular plane model from Chicago O'Hare Intl Airport to Cayman Islands?

Best airlines flying from Chicago O'Hare Intl Airport to Cayman Islands

Compare and see reviews for airlines that fly from Chicago O'Hare Intl Airport to Cayman Islands with momondo
Airline
Rating
Free Cancellation
Price
United AirlinesPriceFrom $434Free CancellationRating
7.4
9,002 reviews
Search United Airlines flights
American AirlinesPriceFrom $488Free CancellationRating
7.2
11,042 reviews
Search American Airlines flights
DeltaPriceFrom $564Free CancellationRating
7.9
8,004 reviews
Search Delta flights

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Cayman Islands?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Chicago to Cayman Islands for you.

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?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Chicago to Cayman Islands.

I’m not ready to book a flight from Chicago to Cayman Islands right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Chicago to Cayman Islands flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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
Fri 12/5
Fri 12/12
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 $201
Flights to Cayman Bracfrom $332
Flights to Little Caymanfrom $392