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Grand Cayman

$56+ 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 1/31. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — GCM
févr. 7 — févr. 141
sam. 2/7
sam. 2/14
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 janvier 8, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$323
(Expedia)

One-way from

$56
(Orbitz)

Popular in

December

Cheapest in

October

Average price

$575
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. 5% potential increase in price ($35 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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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 janvier 8, 2026.

This Expedia deal was found by Cheapflights users on 1/7. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer. 1/211:55 pmORD - GCM
2 stops45h 30mMultiple Airlines
dim. 1/252:49 pmGCM - ORD
1 stop9h 57mMultiple Airlines
Deal found 1/7$323
This Kiwi.com deal was found by Cheapflights users on 1/5. 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.
mer. 2/184:43 pmORD - GCM
1 stop20h 00mSpirit Airlines
dim. 2/222:49 pmGCM - ORD
2 stops18h 05mSpirit Airlines
Deal found 1/5$324
This Kiwi.com deal was found by Cheapflights users on 1/5. 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.
mer. 2/184:43 pmORD - GCM
1 stop20h 00mMultiple Airlines
lun. 2/234:45 pmGCM - ORD
1 stop17h 54mMultiple Airlines
Deal found 1/5$325
This Mytrip deal was found by Cheapflights users on 1/7. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sam. 1/249:23 amORD - GCM
3 stops27h 30mSpirit Airlines
sam. 1/312:34 pmGCM - ORD
2 stops19h 38mSpirit Airlines
Deal found 1/7$327
This Kiwi.com deal was found by Cheapflights users on 1/8. 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.
mer. 2/410:07 amORD - GCM
2 stops26h 46mMultiple Airlines
lun. 2/94:45 pmGCM - ORD
1 stop16h 33mMultiple Airlines
Deal found 1/8$329
This Kiwi.com deal was found by Cheapflights users on 1/7. 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.
jeu. 2/55:15 amORD - GCM
1 stop7h 38mMultiple Airlines
dim. 2/82:49 pmGCM - ORD
2 stops31h 38mMultiple Airlines
Deal found 1/7$333
This Kiwi.com deal was found by Cheapflights users on 1/6. 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.
mer. 2/1110:07 amORD - GCM
2 stops26h 36mMultiple Airlines
mer. 2/2511:30 amGCM - ORD
1 stop23h 09mMultiple Airlines
Deal found 1/6$334
This FlightHub deal was found by Cheapflights users on 1/8. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 1/225:15 amORD - GCM
1 stop7h 38mSpirit Airlines
dim. 2/12:49 pmGCM - ORD
1 stop9h 58mSpirit Airlines
Deal found 1/8$335
This Kiwi.com deal was found by Cheapflights users on 1/6. 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.
ven. 2/68:43 pmORD - GCM
1 stop15h 55mMultiple Airlines
ven. 2/137:00 amGCM - ORD
1 stop9h 18mMultiple Airlines
Deal found 1/6$338
This Mytrip deal was found by Cheapflights users on 1/7. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 2/55:15 amORD - GCM
1 stop7h 38mMultiple Airlines
mer. 2/115:10 pmGCM - ORD
1 stop17h 12mMultiple Airlines
Deal found 1/7$339
This Kiwi.com deal was found by Cheapflights users on 1/7. 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.
mer. 2/45:32 pmORD - GCM
1 stop19h 21mMultiple Airlines
mer. 2/1111:30 amGCM - ORD
1 stop23h 09mMultiple Airlines
Deal found 1/7$340
This FlightHub deal was found by Cheapflights users on 1/7. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sam. 5/25:15 amORD - GCM
1 stop7h 28mSpirit Airlines
sam. 5/91:40 pmGCM - ORD
1 stop10h 01mSpirit Airlines
Deal found 1/7$341

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 janvier 8, 2026.
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

dim. 1/18

3:35 pm-12:25 pm

2 stops19h 50m

George Town Owen Roberts Intl

ven. 1/23

1:30 pm-8:05 am

2 stops19h 35m

$422

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

mar. 2/17

5:25 am-12:29 pm

1 stop6h 04m

George Town Owen Roberts Intl

ven. 2/20

1:54 pm-9:01 pm

1 stop8h 07m

$453

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

dim. 2/8

6:00 am-12:40 pm

1 stop5h 40m

George Town Owen Roberts Intl

jeu. 2/26

1:54 pm-10:31 pm

1 stop9h 37m

$453

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

dim. 2/1

6:00 am-12:40 pm

1 stop5h 40m

George Town Owen Roberts Intl

jeu. 2/5

2:05 pm-10:22 pm

1 stop9h 17m

$453

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

mer. 2/4

7:55 pm-12:55 pm

2 stops16h 00m

George Town Owen Roberts Intl

mer. 2/11

1:50 pm-10:05 pm

2 stops9h 15m

$455

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

lun. 2/23

8:45 am-1:45 pm

Nonstop4h 00m

George Town Owen Roberts Intl

sam. 2/28

2:50 pm-6:04 pm

Nonstop4h 14m

$469

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

ven. 2/6

8:45 am-1:45 pm

Nonstop4h 00m

George Town Owen Roberts Intl

ven. 2/13

2:50 pm-6:04 pm

Nonstop4h 14m

$469

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

dim. 4/19

8:45 am-12:45 pm

Nonstop4h 00m

George Town Owen Roberts Intl

jeu. 4/23

1:50 pm-6:13 pm

Nonstop4h 23m

$473

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

mer. 2/4

5:00 am-12:55 pm

1 stop6h 55m

George Town Owen Roberts Intl

lun. 2/9

1:50 pm-8:55 pm

1 stop8h 05m

$480

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

dim. 4/19

5:05 am-11:55 am

1 stop6h 50m

George Town Owen Roberts Intl

jeu. 4/23

1:05 pm-11:40 pm

1 stop10h 35m

$484

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/8

Showing 1-10 of 34 results
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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 $321). 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 janvier 8, 2026.

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 janvier 8, 2026.
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
4,248 reviews

Crew

8.6

Overall

8.0

Food

7.0

Boarding

8.1

Entertainment

7.5

Comfort

8.0

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
4,248 reviews
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Overall

8.0

Food

7.0

Boarding

8.1

Entertainment

7.5

Comfort

8.0

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
8,025 reviews
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Overall

8.0

Food

7.0

Boarding

8.1

Entertainment

7.5

Comfort

8.0

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
9,139 reviews
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Overall

8.0

Food

7.0

Boarding

8.1

Entertainment

7.5

Comfort

8.0

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
11,095 reviews
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Overall

8.0

Food

7.0

Boarding

8.1

Entertainment

7.5

Comfort

8.0

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 6h 04m. Air Canada provides one of the quickest options available for as low as $453. 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 $507 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 $237.

  • 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 $321). 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

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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 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 janvier 8, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$341Average$632FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$448Average$738FlexibilityNo cancel feeOn-time71%

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