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Grand Cayman

$179+ 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 1/21. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — GCM
Dec 27 — Jan 31
Fri 12/27
Fri 1/3
1 adult, Economy
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Cheap flight deals from Chicago to Grand Cayman

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Grand Cayman (zzLAW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated December 22, 2024.

Round-trip from

$578
(Expedia)

One-way from

$179
(Kiwi.com)
From Chicago (CHI) to Grand Cayman
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One-way flight from Chicago (CHI) to Grand Cayman
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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 December 22, 2024.

This Kiwi.com deal was found by Cheapflights users on 12/21. 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 12/315:07 pmORD - GCM
1 stop22h 03mMultiple Airlines
Tue 1/711:30 amGCM - ORD
1 stop29h 42mMultiple Airlines
Deal found 12/21$704
This Southwest deal was found by Cheapflights users on 12/20. 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 12/216:15 amORD - GCM
1 stop6h 05mSouthwest
Sat 12/282:15 pmGCM - ORD
1 stop9h 20mSouthwest
Deal found 12/20$784
This American Airlines deal was found by Cheapflights users on 12/21. 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.
Tue 12/315:02 amORD - GCM
2 stops8h 28mAmerican Airlines
Tue 1/73:15 pmGCM - ORD
1 stop18h 44mAmerican Airlines
Deal found 12/21$844
This Air Canada deal was found by Cheapflights users on 12/21. 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 12/228:25 pmORD - GCM
1 stop16h 15mAir Canada
Sun 12/294:00 pmGCM - ORD
1 stop17h 57mAir Canada
Deal found 12/21$855
This Delta deal was found by Cheapflights users on 12/21. 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 12/307:05 amORD - GCM
1 stop6h 27mDelta
Wed 1/13:47 pmGCM - ORD
1 stop9h 09mDelta
Deal found 12/21$858
This Kiwi.com deal was found by Cheapflights users on 12/20. 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 12/265:52 pmMDW - GCM
1 stop20h 53mMultiple Airlines
Sun 12/297:00 amGCM - MDW
1 stop7h 36mMultiple Airlines
Deal found 12/20$904
This United Airlines deal was found by Cheapflights users on 12/20. 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.
Tue 12/248:48 amORD - GCM
Nonstop3h 57mUnited Airlines
Sun 12/292:50 pmGCM - ORD
Nonstop4h 16mUnited Airlines
Deal found 12/20$929
This Southwest deal was found by Cheapflights users on 12/21. 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 12/235:00 amMDW - GCM
1 stop6h 55mSouthwest
Thu 1/21:50 pmGCM - MDW
2 stops10h 25mSouthwest
Deal found 12/21$959
This Delta deal was found by Cheapflights users on 12/21. 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 12/246:00 amMDW - GCM
1 stop7h 32mDelta
Tue 12/311:52 pmGCM - MDW
1 stop9h 14mDelta
Deal found 12/21$963
This KAYAK deal was found by Cheapflights users on 12/20. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/2511:48 amMDW - GCM
2 stops25h 01mWestJet
Sun 12/292:50 pmGCM - MDW
2 stops32h 16mWestJet
Deal found 12/20$4,006

Find flights from Chicago to Grand Cayman within your budget

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 22, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Tue 1/28

1:55 pm-1:40 pm

2 stops46h 45m

George Town Owen Roberts Intl

Sun 2/2

4:00 pm-1:11 pm

1 stop22h 11m

$578

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 2/5

3:56 pm-6:40 pm

2 stops25h 44m

George Town Owen Roberts Intl

Wed 2/12

11:30 am-10:37 am

1 stop24h 07m

$580

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Wed 3/19

3:14 pm-6:45 pm

1 stop27h 31m

George Town Owen Roberts Intl

Mon 3/24

2:00 pm-11:00 pm

1 stop9h 00m

$583

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Sat 5/3

6:40 am-12:10 pm

1 stop5h 30m

George Town Owen Roberts Intl

Thu 5/8

12:45 pm-10:40 pm

1 stop9h 55m

$584

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Tue 3/18

8:48 am-12:45 pm

Nonstop3h 57m

George Town Owen Roberts Intl

Thu 3/27

1:25 pm-10:00 pm

1 stop8h 35m

$594

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 2/26

5:45 am-12:38 pm

1 stop5h 53m

George Town Owen Roberts Intl

Wed 3/5

2:04 pm-11:49 pm

1 stop10h 45m

$598

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Tue 3/25

6:00 am-11:25 am

1 stop5h 25m

George Town Owen Roberts Intl

Tue 4/1

12:50 pm-10:27 pm

1 stop9h 37m

$598

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Tue 2/4

5:00 am-12:00 pm

1 stop6h 00m

George Town Owen Roberts Intl

Tue 2/11

1:00 pm-10:04 pm

2 stops10h 04m

$601

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Thu 4/10

5:25 pm-11:50 am

2 stops18h 25m

George Town Owen Roberts Intl

Sat 4/19

1:10 pm-9:30 pm

1 stop8h 20m

$689

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Sun 3/23

10:24 am-12:43 pm

2 stops26h 19m

George Town Owen Roberts Intl

Sun 3/30

1:50 pm-2:15 pm

2 stops24h 25m

$3,075

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/20

Showing 1-10 of 20 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.

Travel insights for flights from Chicago to Grand Cayman

Get recent, data-driven insights about flights from Chicago to Grand Cayman including ideal travel times, pricing trends, and more.

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 December 22, 2024.

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 22, 2024.

The most flights from CHI to zzLAW are scheduled on a Saturday (2 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (1 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 22, 2024.
Get a feel of what it's like to fly with United Airlines, American Airlines and Air Canada 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
8.1
Very good
4,804 reviews

Boarding

8.2

Overall

8.1

Crew

8.7

Comfort

8.1

Entertainment

7.7

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,804 reviews
Southwest
8.1
Very good
4,804 reviews

Boarding

8.2

Overall

8.1

Crew

8.7

Comfort

8.1

Entertainment

7.7

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,594 reviews
Southwest
8.1
Very good
4,804 reviews

Boarding

8.2

Overall

8.1

Crew

8.7

Comfort

8.1

Entertainment

7.7

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

United Airlines
7.4
Good
9,028 reviews
Southwest
8.1
Very good
4,804 reviews

Boarding

8.2

Overall

8.1

Crew

8.7

Comfort

8.1

Entertainment

7.7

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

WestJet
7.3
Good
2,812 reviews
Southwest
8.1
Very good
4,804 reviews

Boarding

8.2

Overall

8.1

Crew

8.7

Comfort

8.1

Entertainment

7.7

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
4,804 reviews

Boarding

8.2

Overall

8.1

Crew

8.7

Comfort

8.1

Entertainment

7.7

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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 $214. Users have also found prices from $233 and $292 on Sun Country Air and Delta, respectively.

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

    On average you can expect to pay $528 for a flight from Chicago to Grand Cayman. The cheapest flight overall is $314 while the most popular route, (Chicago O'Hare Intl - George Town Owen Roberts Intl) is currently priced at $509.

  • 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
St. Louis to George Town flights
Midway to George Town flights
O'Hare Intl to Cayman Brac flights
Moline to George Town 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 December 22, 2024.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$351Average$501FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$367Average$613FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$429Average$683FlexibilityNo cancel feeOn-time69%
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