HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Grand Cayman

$72+ Cheap flights from Chicago (CHI) to Grand Cayman

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/25. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — GCM
Jan 27 — Feb 31
Tue 1/27
Tue 2/3
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to Grand Cayman with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Chicago to Grand Cayman

Cheapest flights from Chicago to Grand Cayman
Explore the most affordable flight options available from Chicago to Grand Cayman. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 28, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:05 pmORD - GCM
1 stop26h 10mMultiple Airlines
Wed 1/711:30 amGCM - ORD
1 stop21h 48mMultiple Airlines
Deal found 12/26$447
This Kiwi.com deal was found by Cheapflights users on 12/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:05 pmORD - GCM
1 stop16h 30mMultiple Airlines
Wed 1/1411:30 amGCM - ORD
1 stop21h 48mMultiple Airlines
Deal found 12/26$456
This Kiwi.com deal was found by Cheapflights users on 12/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:05 pmORD - GCM
1 stop16h 30mMultiple Airlines
Thu 1/12:40 pmGCM - ORD
1 stop10h 50mMultiple Airlines
Deal found 12/26$561
This Kiwi.com deal was found by Cheapflights users on 12/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:05 pmORD - GCM
1 stop16h 30mMultiple Airlines
Tue 1/611:30 amGCM - ORD
2 stops28h 27mMultiple Airlines
Deal found 12/26$569
This Kiwi.com deal was found by Cheapflights users on 12/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:05 pmORD - GCM
1 stop16h 30mMultiple Airlines
Sat 1/35:56 pmGCM - ORD
2 stops17h 24mMultiple Airlines
Deal found 12/26$578
This Kiwi.com deal was found by Cheapflights users on 12/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/313:32 pmMDW - GCM
1 stop19h 03mMultiple Airlines
Wed 1/1411:30 amGCM - MDW
2 stops11h 49mMultiple Airlines
Deal found 12/26$609
This Kiwi.com deal was found by Cheapflights users on 12/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:05 pmORD - GCM
1 stop16h 30mMultiple Airlines
Sun 1/42:40 pmGCM - ORD
2 stops28h 53mMultiple Airlines
Deal found 12/27$612
This Kiwi.com deal was found by Cheapflights users on 12/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/302:01 pmMDW - GCM
2 stops25h 04mMultiple Airlines
Tue 1/611:30 amGCM - MDW
1 stop27h 36mMultiple Airlines
Deal found 12/26$628
This Southwest deal was found by Cheapflights users on 12/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/315:05 amMDW - GCM
1 stop6h 30mSouthwest
Wed 1/141:50 pmGCM - MDW
1 stop8h 10mSouthwest
Deal found 12/26$679
This Kiwi.com deal was found by Cheapflights users on 12/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/296:15 amMDW - GCM
1 stop14h 00mMultiple Airlines
Tue 1/611:30 amGCM - MDW
1 stop27h 36mMultiple Airlines
Deal found 12/26$728
This Kiwi.com deal was found by Cheapflights users on 12/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/313:32 pmMDW - GCM
1 stop19h 03mMultiple Airlines
Sat 1/35:56 pmGCM - MDW
2 stops29h 16mMultiple Airlines
Deal found 12/27$757
This Kiwi.com deal was found by Cheapflights users on 12/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/296:15 amMDW - GCM
1 stop14h 00mMultiple Airlines
Sun 1/42:40 pmGCM - MDW
2 stops23h 41mMultiple Airlines
Deal found 12/26$820

Find flight deals from Chicago to Grand Cayman

Keep the following information in mind while searching for Chicago to Grand Cayman flight deals. Data was last updated December 28, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$325
(Kiwi.com)

One-way from

$72
(Priceline)

Popular in

December

Cheapest in

October

Average price

$807
Provider with most accurate pricing for Chicago (CHI)-George Town Owen Roberts Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-George Town Owen Roberts Intl flights.
Search Deals
From Chicago (CHI) to Grand Cayman
Search Deals
One-way flight from Chicago (CHI) to Grand Cayman
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($42 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($14 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

Cheapflights 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, Cheapflights users made 2,558,603 searches. Data last updated December 28, 2025.
Use the filters below to find and compare flights from Chicago to Grand Cayman that are best for you.

Fly from

Chicago

Fly to

Grand Cayman

Route

Depart

Return

Price

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 1/18

6:00 pm-12:25 pm

2 stops17h 25m

George Town Owen Roberts Intl

Fri 1/23

1:30 pm-10:06 am

1 stop21h 36m

$366

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 2/7

6:00 pm-12:25 pm

2 stops17h 25m

George Town Owen Roberts Intl

Thu 2/12

1:30 pm-12:48 pm

2 stops24h 18m

$406

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Thu 2/12

3:00 pm-9:15 pm

2 stops29h 15m

George Town Owen Roberts Intl

Thu 2/19

7:00 am-1:56 pm

1 stop7h 56m

$412

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 2/15

8:45 am-1:45 pm

Nonstop4h 00m

George Town Owen Roberts Intl

Fri 2/20

2:50 pm-6:04 pm

Nonstop4h 14m

$438

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Tue 2/17

5:25 am-12:29 pm

1 stop6h 04m

George Town Owen Roberts Intl

Wed 2/18

1:54 pm-11:56 pm

1 stop11h 02m

$452

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 1/25

6:50 am-12:40 pm

2 stops28h 50m

George Town Owen Roberts Intl

Wed 1/28

2:05 pm-9:41 am

2 stops20h 36m

$457

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Tue 2/17

5:25 am-12:29 pm

1 stop6h 04m

George Town Owen Roberts Intl

Fri 2/20

3:55 pm-8:44 pm

2 stops29h 49m

$457

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 2/18

5:25 am-12:29 pm

1 stop6h 04m

George Town Owen Roberts Intl

Fri 2/20

3:55 pm-1:20 pm

2 stops22h 25m

$457

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Mon 1/26

1:58 pm-12:40 pm

2 stops21h 42m

George Town Owen Roberts Intl

Tue 2/3

2:05 pm-9:41 am

2 stops20h 36m

$457

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 1/21

6:00 pm-12:40 pm

2 stops17h 40m

George Town Owen Roberts Intl

Tue 2/3

2:05 pm-9:41 am

2 stops20h 36m

$457

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/25

Showing 1-10 of 26 results
1
2
3

Best time to book a flight from Chicago to Grand Cayman

Have a flexible travel schedule? Discover the best time to fly to Grand Cayman from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Grand Cayman

What is the cheapest month to book a flight from Chicago to Grand Cayman?

Currently, December is the cheapest month in which you can book a flight from Chicago to Grand Cayman (average of $322). Flying from Chicago to Grand Cayman in September is currently the most expensive (average of $650). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CHI to LAW?

Find hourly flight availability from Chicago to Grand Cayman. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 28, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago to Grand Cayman as you normally would.

Weekly flight availability from Chicago to Grand Cayman

Explore weekly flight availability from Chicago to Grand Cayman. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated December 28, 2025.

The most flights from CHI to zzLAW are scheduled on a Monday (2 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (2 on average).

Reviews of airlines servicing Grand Cayman

Get insights into the airlines that provide service to Grand Cayman. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Grand Cayman. Reviews last updated December 28, 2025.
Read reviews from past customers who have flown Southwest, Delta, and United Airlines from Chicago to Grand Cayman. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,256 reviews

Boarding

8.1

Food

7.0

Comfort

8.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,256 reviews
Southwest
8.0
Very good
4,256 reviews

Boarding

8.1

Food

7.0

Comfort

8.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Delta
7.9
Good
8,019 reviews
Southwest
8.0
Very good
4,256 reviews

Boarding

8.1

Food

7.0

Comfort

8.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
United Airlines
7.4
Good
9,113 reviews
Southwest
8.0
Very good
4,256 reviews

Boarding

8.1

Food

7.0

Comfort

8.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
American Airlines
7.2
Good
11,073 reviews
Southwest
8.0
Very good
4,256 reviews

Boarding

8.1

Food

7.0

Comfort

8.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Related info for your journey

Find useful and relevant information for your journey from Chicago to Grand Cayman. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Chicago to Grand Cayman?

    A quick flight from Chicago to Grand Cayman can take about 4h. Air Canada provides one of the quickest options available for as low as $438. The distance between Chicago and Grand Cayman is about 1613 mi. This flight may include one or multiple stops.

  • What are the cheapest flights from Chicago to Grand Cayman?

    On average you can expect to pay $487 for a flight from Chicago to Grand Cayman. The cheapest flight overall is $288 while the most popular route, (Chicago O'Hare Intl - George Town Owen Roberts Intl) is currently priced at $247.

  • Can I find deals for flights from Chicago to Grand Cayman that include hotel bookings?

    Yes. In addition to deals on Chicago to Grand Cayman flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Grand Cayman?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Grand Cayman.

  • Can I find deals for business class flights from Chicago to Grand Cayman?

    Yes. Cheapflights offers flight deals from Chicago to Grand Cayman by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to Grand Cayman?

    Currently, December is the cheapest month in which you can book a flight from Chicago to Grand Cayman (average of $322). Flying from Chicago to Grand Cayman in September is currently the most expensive (average of $650). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Chicago to Grand Cayman

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to George Town flights
Midway to George Town flights
St. Louis to George Town flights
O'Hare Intl to Cayman Brac flights
Moline to George Town flights

Top 2 airlines flying from Chicago to Grand Cayman

Discover the top 2 airlines that operate flights from Chicago to Grand Cayman. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$341Average$658FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$449Average$723FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.