HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Grand Cayman

$169+ 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 6/1. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — GCM
May 4 — May 111
Sun 5/4
Sun 5/11
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

Keep the following information in mind while searching for Chicago to Grand Cayman flight deals. Data was last updated April 29, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$473
(Kiwi.com)

One-way from

$195
(Trip.com)

Popular in

March

Cheapest in

September

Average price

$648
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. 8% potential increase in price ($62 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($20 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2025
Search Deals

Find 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 April 29, 2025.

This Kiwi.com deal was found by Cheapflights users on 4/29. 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.
Sat 10/43:11 pmORD - GCM
1 stop20h 29mMultiple Airlines
Wed 10/811:30 amGCM - ORD
1 stop11h 17mMultiple Airlines
Deal found 4/29$464
This Air Canada deal was found by Cheapflights users on 4/29. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/18:25 pmORD - GCM
1 stop15h 30mAir Canada
Thu 6/512:50 pmGCM - ORD
1 stop9h 15mAir Canada
Deal found 4/29$511
This Southwest deal was found by Cheapflights users on 4/28. 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.
Thu 12/46:00 pmMDW - GCM
2 stops17h 35mSouthwest
Mon 12/81:30 pmGCM - MDW
2 stops16h 35mSouthwest
Deal found 4/28$542
This Southwest deal was found by Cheapflights users on 4/29. 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.
Sat 9/66:00 amORD - GCM
1 stop6h 10mSouthwest
Sat 9/131:10 pmGCM - ORD
1 stop8h 20mSouthwest
Deal found 4/29$576
This Delta deal was found by Cheapflights users on 4/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/145:35 amORD - GCM
1 stop5h 50mDelta
Tue 7/2212:40 pmGCM - ORD
1 stop8h 50mDelta
Deal found 4/29$610
This Delta deal was found by Cheapflights users on 4/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/36:00 amMDW - GCM
1 stop5h 25mDelta
Fri 8/812:40 pmGCM - MDW
1 stop9h 01mDelta
Deal found 4/27$610
This American Airlines deal was found by Cheapflights users on 4/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/285:00 amORD - GCM
1 stop6h 10mAmerican Airlines
Tue 6/312:10 pmGCM - ORD
2 stops11h 46mAmerican Airlines
Deal found 4/29$614
This United Airlines deal was found by Cheapflights users on 4/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/269:26 amORD - GCM
Nonstop4h 04mUnited Airlines
Sat 8/21:45 pmGCM - ORD
Nonstop4h 22mUnited Airlines
Deal found 4/29$645
This WestJet deal was found by Cheapflights users on 4/29. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/131:40 pmORD - GCM
2 stops47h 05mWestJet
Tue 7/221:45 pmGCM - ORD
2 stops26h 59mWestJet
Deal found 4/29$792
This Kiwi.com deal was found by Cheapflights users on 4/28. 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.
Thu 6/129:12 pmMDW - GCM
2 stops39h 33mMultiple Airlines
Thu 6/1912:40 pmGCM - MDW
1 stop9h 52mMultiple Airlines
Deal found 4/28$834

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 April 29, 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

Sat 10/4

3:11 pm-11:40 am

1 stop20h 29m

George Town Owen Roberts Intl

Wed 10/8

11:30 am-10:47 pm

1 stop11h 17m

$464

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 6/1

8:25 pm-11:55 am

1 stop15h 30m

George Town Owen Roberts Intl

Thu 6/5

12:50 pm-10:05 pm

1 stop9h 15m

$511

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Fri 7/18

9:45 pm-10:35 am

1 stop12h 50m

George Town Owen Roberts Intl

Mon 7/21

12:45 pm-11:40 pm

1 stop10h 55m

$562

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 9/6

6:00 am-12:10 pm

1 stop6h 10m

George Town Owen Roberts Intl

Sat 9/13

1:10 pm-9:30 pm

1 stop8h 20m

$576

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Mon 7/14

5:35 am-11:25 am

1 stop5h 50m

George Town Owen Roberts Intl

Wed 7/23

12:40 pm-9:30 pm

1 stop8h 50m

$610

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Sun 8/3

6:00 am-11:25 am

1 stop5h 25m

George Town Owen Roberts Intl

Fri 8/8

12:40 pm-9:41 pm

1 stop9h 01m

$610

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 5/28

5:00 am-11:10 am

1 stop6h 10m

George Town Owen Roberts Intl

Tue 6/3

12:10 pm-11:56 pm

2 stops11h 46m

$614

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 7/26

9:26 am-1:30 pm

Nonstop4h 04m

George Town Owen Roberts Intl

Sat 8/2

1:45 pm-6:07 pm

Nonstop4h 22m

$645

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 7/13

1:40 pm-12:45 pm

2 stops47h 05m

George Town Owen Roberts Intl

Tue 7/22

1:45 pm-4:44 pm

2 stops26h 59m

$792

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Thu 6/12

9:12 pm-12:45 pm

2 stops39h 33m

George Town Owen Roberts Intl

Thu 6/19

12:40 pm-10:32 pm

1 stop9h 52m

$834

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

Showing 1-10 of 22 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, January is the cheapest month in which you can book a flight from Chicago to Grand Cayman (average of $467). Flying from Chicago to Grand Cayman in March is currently the most expensive (average of $594). 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 April 29, 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.

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 April 29, 2025.
Get a feel of what it's like to fly with Southwest, Delta and United Airlines from Chicago to Grand Cayman by reading reviews from past customers. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,295 reviews

Overall

8.0

Crew

8.6

Food

7.1

Boarding

8.2

Comfort

8.0

Entertainment

7.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Southwest
8.0
Very good
4,295 reviews
Southwest
8.0
Very good
4,295 reviews

Overall

8.0

Crew

8.6

Food

7.1

Boarding

8.2

Comfort

8.0

Entertainment

7.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Delta
8.0
Very good
7,936 reviews
Southwest
8.0
Very good
4,295 reviews

Overall

8.0

Crew

8.6

Food

7.1

Boarding

8.2

Comfort

8.0

Entertainment

7.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
United Airlines
7.4
Good
8,696 reviews
Southwest
8.0
Very good
4,295 reviews

Overall

8.0

Crew

8.6

Food

7.1

Boarding

8.2

Comfort

8.0

Entertainment

7.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,295 reviews

Overall

8.0

Crew

8.6

Food

7.1

Boarding

8.2

Comfort

8.0

Entertainment

7.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
WestJet
7.2
Good
2,823 reviews
Southwest
8.0
Very good
4,295 reviews

Overall

8.0

Crew

8.6

Food

7.1

Boarding

8.2

Comfort

8.0

Entertainment

7.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

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.

  • What are the cheapest airlines to fly from Chicago to Grand Cayman one-way?

    For one-way options, check prices for Air Canada. According to our data, you can fly for as low as $197. Users have also found prices from $231 and $289 on Southwest and Delta, respectively.

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

    On average you can expect to pay $605 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 $537.

  • 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, January is the cheapest month in which you can book a flight from Chicago to Grand Cayman (average of $467). Flying from Chicago to Grand Cayman in March is currently the most expensive (average of $594). 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
Moline to George Town flights
O'Hare Intl to Cayman Brac flights

Top 3 airlines flying from Chicago to Grand Cayman

Discover the top 3 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 April 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$463Average$668FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$467Average$662FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$501Average$705FlexibilityNo cancel feeOn-time69%

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.