Latest deals
Insights
FAQs
Reviews
Price Alerts

Cheap flights from Chicago to Grand Cayman from $127

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 Grand Cayman departing on 1/28. 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 Grand Cayman

Cheap round-trip flights

Spirit Airlines Logo
5:59 pm - 11:00 amORD-GCM
16h 01m1 stop
Spirit Airlines Logo
11:55 am - 11:42 pmGCM-ORD
12h 47m1 stop
$357Spirit Airlines
Find Deal
Sat, Jan 24 - Sat, Jan 31
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
$433Spirit Airlines
Find Deal
Sat, Jan 17 - Sat, Jan 24
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
$443Spirit Airlines
Find Deal
Sat, Feb 14 - Sat, Feb 21
Southwest Logo
5:15 pm - 12:35 pmMDW-GCM
18h 20m2 stops
Southwest Logo
1:30 pm - 5:05 amGCM-MDW
16h 35m2 stops
$480Southwest
Find Deal
Wed, Nov 5 - Wed, Nov 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
$485Southwest
Find Deal
Fri, Feb 6 - Fri, Feb 13
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
Tue, Feb 17 - Tue, Feb 24
United Airlines Logo
7:35 am - 4:30 pmORD-GCM
7h 55m1 stop
United Airlines Logo
2:50 pm - 6:04 pmGCM-ORD
4h 14mnonstop
$510United Airlines
Find Deal
Sun, Dec 14 - Fri, Dec 19
American Airlines Logo
6:30 am - 4:31 pmORD-GCM
9h 01m2 stops
American Airlines Logo
2:00 pm - 5:10 pmGCM-ORD
4h 10mnonstop
$514American Airlines
Find Deal
Sun, Dec 14 - Fri, Dec 19
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
5:40 am - 12:30 pmORD-GCM
5h 50m1 stop
Delta Logo
1:55 pm - 11:58 pmGCM-ORD
11h 03m1 stop
$545Delta
Find Deal
Wed, Dec 24 - Mon, Dec 29

Delta flights from Chicago to Grand Cayman

Our best Delta deals on Chicago to Grand Cayman flight tickets
Delta
Dec 24
ORD5:40 amChicago O'Hare Intl
5h 50m
1 stop
GCM12:30 pmGeorge Town Owen Roberts Intl
Dec 31
GCM3:45 pmGeorge Town Owen Roberts Intl
9h 13m
1 stop
ORD11:58 pmChicago O'Hare Intl
$520
Find similar
Delta
Dec 24
ORD5:40 amChicago O'Hare Intl
5h 50m
1 stop
GCM12:30 pmGeorge Town Owen Roberts Intl
Dec 29
GCM1:55 pmGeorge Town Owen Roberts Intl
11h 03m
1 stop
ORD11:58 pmChicago O'Hare Intl
$545
Find similar
Delta
Nov 25
MDW6:00 amChicago Midway
5h 37m
1 stop
GCM12:37 pmGeorge Town Owen Roberts Intl
Dec 3
GCM2:02 pmGeorge Town Owen Roberts Intl
8h 42m
1 stop
MDW9:44 pmChicago Midway
$570
Find similar

Spirit Airlines flights from Chicago to Grand Cayman

Our best Spirit Airlines deals on Chicago to Grand Cayman flight tickets
Spirit Airlines
Jan 24
ORD5:59 pmChicago O'Hare Intl
16h 01m
1 stop
GCM11:00 amGeorge Town Owen Roberts Intl
Jan 31
GCM11:55 amGeorge Town Owen Roberts Intl
12h 47m
1 stop
ORD11:42 pmChicago O'Hare Intl
$357
Find similar
Spirit Airlines
Jan 17
ORD5:59 pmChicago O'Hare Intl
16h 01m
1 stop
GCM11:00 amGeorge Town Owen Roberts Intl
Jan 24
GCM11:55 amGeorge Town Owen Roberts Intl
10h 05m
1 stop
ORD9:00 pmChicago O'Hare Intl
$433
Find similar
Spirit Airlines
Feb 14
ORD5:59 pmChicago O'Hare Intl
16h 01m
1 stop
GCM11:00 amGeorge Town Owen Roberts Intl
Feb 21
GCM11:55 amGeorge Town Owen Roberts Intl
10h 05m
1 stop
ORD9:00 pmChicago O'Hare Intl
$443
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago to Grand Cayman 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 21, 2025.
Use the filters below to find and compare flights from Chicago to Grand Cayman 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

Sat 1/31

11:55 am-11:42 pm

1 stop12h 47m

$357

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 1/17

5:59 pm-11:00 am

1 stop16h 01m

George Town Owen Roberts Intl

Sat 1/24

11:55 am-9:00 pm

1 stop10h 05m

$433

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 2/14

5:59 pm-11:00 am

1 stop16h 01m

George Town Owen Roberts Intl

Sat 2/21

11:55 am-9:00 pm

1 stop10h 05m

$443

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Wed 11/5

5:15 pm-12:35 pm

2 stops18h 20m

George Town Owen Roberts Intl

Wed 11/12

1:30 pm-5:05 am

2 stops16h 35m

$480

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Fri 2/6

6:05 am-12:55 pm

1 stop5h 50m

George Town Owen Roberts Intl

Fri 2/13

1:50 pm-9:50 pm

1 stop9h 00m

$485

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Tue 2/17

8:10 am-12:56 pm

Nonstop3h 46m

George Town Owen Roberts Intl

Tue 2/24

2:00 pm-5:10 pm

Nonstop4h 10m

$505

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 12/14

7:35 am-4:30 pm

1 stop7h 55m

George Town Owen Roberts Intl

Fri 12/19

2:50 pm-6:04 pm

Nonstop4h 14m

$510

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 12/14

6:30 am-4:31 pm

2 stops9h 01m

George Town Owen Roberts Intl

Fri 12/19

2:00 pm-5:10 pm

Nonstop4h 10m

$514

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

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 12/24

5:40 am-12:30 pm

1 stop5h 50m

George Town Owen Roberts Intl

Mon 12/29

1:55 pm-11:58 pm

1 stop11h 03m

$545

Flights are sorted by cheapest round-trip flights first.

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

See travel insights to Grand Cayman from

How to get the cheapest flight ticket from Chicago to Grand Cayman

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 Grand Cayman?

The cheapest month to fly to Grand Cayman from Chicago is in October. Flight prices, which tend to average around $544, are often lower during this time because this is during the off-season. If you don’t want to visit Grand Cayman in October, then you should wait until September to fly from Chicago, when ticket prices are also cheap, with an average price of $569.

What is the cheapest day to depart on your flight to Grand Cayman?

The cheapest day to depart from Chicago to Grand Cayman is on a Monday when prices can be found for as low as $654. On the other hand, Friday is the most expensive day to depart from Chicago because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $878.

What is the cheapest time of day to depart on your flight to Grand Cayman?

Our most recent data shows that the best time of day to fly to Grand Cayman is in the afternoon. Flights from Chicago to Grand Cayman during this time can be as low as $507. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are $733 on average. Flights to Grand Cayman 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 Grand Cayman flight route?

Fly from Chicago O'Hare Intl to George Town Owen Roberts Intl for the best Chicago - Grand Cayman flight prices

How far in advance should I book a flight to Grand Cayman?

You are more likely to see cheaper flights to Grand Cayman from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Grand Cayman for around $699 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Grand Cayman from Chicago for as low as $610 on momondo.

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

There are 3 cabin classes available to choose from on Chicago to Grand Cayman 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 Grand Cayman flights?

No. A direct flight is the cheapest option for a flight between Chicago to Grand Cayman.

Cheap Chicago to Grand Cayman flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Grand Cayman

Fastest flight time

3h 46m

Direct flights

Mon, Wed, Thu, Fri, Sat and Sun

Airports in Grand Cayman

1 airport
The fastest flight from Chicago to Grand Cayman takes 3h 46m
Direct flights go from Chicago to Grand Cayman on Monday, Wednesday, Thursday, Friday, Saturday and Sunday. There are no airlines offering direct flights.
There is 1 airport near Grand Cayman: George Town Owen Roberts Intl (GCM)
Search flight deals

  • When did momondo last update prices for flights from Chicago to Grand Cayman?

    Prices for flights from Chicago to Grand Cayman are updated daily.

  • How many operators does momondo search for flights from Chicago to Grand Cayman?

  • How old do you have to be to fly from Chicago to Grand Cayman?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Grand Cayman.

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

    The necessary travel and health documents for your Grand Cayman trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Chicago to Grand Cayman?

Best airlines flying from Chicago to Grand Cayman

Compare and see reviews for airlines that fly from Chicago to Grand Cayman with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $473Free CancellationRating
7.9
7,981 reviews
Search Delta flights
American AirlinesPriceFrom $512Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $573Free CancellationRating
7.4
8,930 reviews
Search United Airlines flights

Why use momondo?

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

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Chicago to Grand Cayman. Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from Chicago to Grand Cayman with flexible booking policies on momondo?

All flight searches from Chicago to Grand Cayman on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Chicago to Grand Cayman?

Once all potential Chicago to Grand Cayman flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

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

If you are simply researching potential flights to Grand Cayman, momondo offers a useful price alert feature which will track prices for flights to Grand Cayman from Chicago and alert you when they change.

An easier way to manage your Grand Cayman 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 8/26
Tue 9/2
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Grand Cayman

Popular cities in Grand Cayman

Popular flights according to clicks in the last 7 days on momondo
Flights to George Townfrom $267
Flights to Cayman Bracfrom $341
Flights to Little Caymanfrom $393