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Grand Cayman

$178+ 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 7/22. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — GCM
Apr 29 — May 61
Tue 4/29
Tue 5/6
1 adult, Economy
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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 24, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$491
(Justfly.com)

One-way from

$178
(Kiwi.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.
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Provider most trusted by Cheapflights users for Chicago (CHI)-George Town Owen Roberts Intl flights.
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From Chicago (CHI) to Grand Cayman
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One-way flight from Chicago (CHI) to Grand Cayman
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Highest demand for flights based on searches. 8% potential increase in price ($62 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($20 potential savings vs. average RT price).
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Average for round-trip flights in April 2025
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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 24, 2025.

This Kiwi.com deal was found by Cheapflights users on 4/22. 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 10/253:11 pmORD - GCM
1 stop20h 29mMultiple Airlines
Sat 11/18:50 amGCM - ORD
1 stop13h 57mMultiple Airlines
Deal found 4/22$465
This Justfly.com deal was found by Cheapflights users on 4/23. 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 Justfly.com 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 stop20h 20mAir Canada
Deal found 4/23$491
This Southwest deal was found by Cheapflights users on 4/23. 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 5/145:55 amMDW - GCM
1 stop5h 55mSouthwest
Tue 5/2012:45 pmGCM - MDW
1 stop9h 20mSouthwest
Deal found 4/23$538
This Southwest deal was found by Cheapflights users on 4/22. 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.
Mon 11/174:25 pmORD - GCM
2 stops19h 10mSouthwest
Sat 11/222:15 pmGCM - ORD
1 stop8h 35mSouthwest
Deal found 4/22$576
This Delta deal was found by Cheapflights users on 4/22. 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.
Wed 7/25:35 amORD - GCM
1 stop5h 50mDelta
Thu 7/1012:50 pmGCM - ORD
1 stop8h 31mDelta
Deal found 4/22$610
This Delta deal was found by Cheapflights users on 4/23. 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.
Tue 6/36:00 amMDW - GCM
1 stop5h 20mDelta
Tue 6/1012:40 pmGCM - MDW
1 stop9h 05mDelta
Deal found 4/23$610
This American Airlines deal was found by Cheapflights users on 4/23. 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 20mAmerican Airlines
Tue 6/312:10 pmGCM - ORD
2 stops12h 01mAmerican Airlines
Deal found 4/23$614
This United Airlines deal was found by Cheapflights users on 4/23. 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 7/129:26 amORD - GCM
Nonstop4h 04mUnited Airlines
Sat 7/191:45 pmGCM - ORD
Nonstop4h 22mUnited Airlines
Deal found 4/23$645
This WestJet deal was found by Cheapflights users on 4/22. 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.
Wed 11/262:00 pmMDW - GCM
2 stops22h 49mWestJet
Sun 11/302:50 pmGCM - MDW
2 stops28h 08mWestJet
Deal found 4/22$3,401

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 24, 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 6/1

8:25 pm-11:55 am

1 stop15h 30m

George Town Owen Roberts Intl

Thu 6/5

12:50 pm-9:10 am

1 stop20h 20m

$491

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Tue 5/6

7:00 pm-4:10 pm

1 stop21h 10m

George Town Owen Roberts Intl

Fri 5/9

4:45 pm-8:07 pm

2 stops27h 22m

$492

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Wed 5/14

5:55 am-11:50 am

1 stop5h 55m

George Town Owen Roberts Intl

Tue 5/20

12:45 pm-10:05 pm

1 stop9h 20m

$538

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 7/2

5:35 am-11:25 am

1 stop5h 50m

George Town Owen Roberts Intl

Thu 7/10

12:50 pm-9:21 pm

1 stop8h 31m

$610

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Tue 6/3

6:00 am-11:20 am

1 stop5h 20m

George Town Owen Roberts Intl

Tue 6/10

12:40 pm-9:45 pm

1 stop9h 05m

$610

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 5/28

5:00 am-11:20 am

1 stop6h 20m

George Town Owen Roberts Intl

Tue 6/3

12:10 pm-12:11 am

2 stops12h 01m

$614

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 7/12

9:26 am-1:30 pm

Nonstop4h 04m

George Town Owen Roberts Intl

Sat 7/19

1:45 pm-6:07 pm

Nonstop4h 22m

$645

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Tue 7/22

7:00 am-4:10 pm

1 stop9h 10m

$178

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 6/22

10:00 am-11:55 am

1 stop25h 55m

$197

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Thu 5/29

7:50 pm-11:50 am

2 stops16h 00m

$223

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/22

Showing 1-10 of 18 results
1
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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 24, 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 24, 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
4,286 reviews

Boarding

8.2

Overall

8.0

Entertainment

7.6

Food

7.1

Crew

8.6

Comfort

8.0

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
4,286 reviews
Southwest
8.0
Very good
4,286 reviews

Boarding

8.2

Overall

8.0

Entertainment

7.6

Food

7.1

Crew

8.6

Comfort

8.0

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
7,920 reviews
Southwest
8.0
Very good
4,286 reviews

Boarding

8.2

Overall

8.0

Entertainment

7.6

Food

7.1

Crew

8.6

Comfort

8.0

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
8,685 reviews
Southwest
8.0
Very good
4,286 reviews

Boarding

8.2

Overall

8.0

Entertainment

7.6

Food

7.1

Crew

8.6

Comfort

8.0

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
4,286 reviews

Boarding

8.2

Overall

8.0

Entertainment

7.6

Food

7.1

Crew

8.6

Comfort

8.0

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
2,816 reviews
Southwest
8.0
Very good
4,286 reviews

Boarding

8.2

Overall

8.0

Entertainment

7.6

Food

7.1

Crew

8.6

Comfort

8.0

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 $223 and $293 on Southwest and Delta, respectively.

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

    On average you can expect to pay $574 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 $465.

  • 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

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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 24, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$463Average$668FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$468Average$659FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$502Average$707FlexibilityNo cancel feeOn-time69%

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