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Grand Cayman

$167+ 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 1/22. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — GCM
nov. 25 — dic. 21
lun. 11/25
lun. 12/2
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 noviembre 20, 2024.

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 noviembre 20, 2024.

This Mytrip deal was found by Cheapflights users on 11/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/116:37 pmORD - GCM
1 stop17h 23mMultiple Airlines
dom. 12/154:00 pmGCM - ORD
2 stops17h 02mMultiple Airlines
Deal found 11/20$562
This Southwest deal was found by Cheapflights users on 11/19. 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.
lun. 12/96:00 amMDW - GCM
1 stop5h 55mSouthwest
jue. 12/121:50 pmGCM - MDW
2 stops9h 30mSouthwest
Deal found 11/19$575
This United Airlines deal was found by Cheapflights users on 11/19. 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.
mié. 12/187:35 amORD - GCM
1 stop7h 50mUnited Airlines
mié. 12/252:50 pmGCM - ORD
Nonstop4h 16mUnited Airlines
Deal found 11/19$608
This Priceline deal was found by Cheapflights users on 11/19. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 12/59:50 amORD - GCM
1 stop26h 50mAir Canada
dom. 12/84:00 pmGCM - ORD
1 stop28h 32mAir Canada
Deal found 11/19$617
This Delta deal was found by Cheapflights users on 11/19. 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.
mar. 12/317:05 amORD - GCM
1 stop6h 16mDelta
jue. 1/92:09 pmGCM - ORD
1 stop10h 50mDelta
Deal found 11/19$618
This Delta deal was found by Cheapflights users on 11/19. 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.
lun. 12/306:00 amMDW - GCM
1 stop5h 27mDelta
mié. 1/82:09 pmGCM - MDW
1 stop9h 11mDelta
Deal found 11/19$618
This American Airlines deal was found by Cheapflights users on 11/19. 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.
mar. 12/316:55 pmORD - GCM
1 stop16h 05mAmerican Airlines
mar. 1/71:00 pmGCM - ORD
2 stops10h 04mAmerican Airlines
Deal found 11/19$623
This Southwest deal was found by Cheapflights users on 11/19. 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.
mar. 11/265:45 amORD - GCM
1 stop6h 10mSouthwest
mar. 12/31:50 pmGCM - ORD
2 stops9h 10mSouthwest
Deal found 11/19$659
This Kiwi.com deal was found by Cheapflights users on 11/19. 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.
vie. 12/65:01 amMDW - GCM
1 stop9h 44mMultiple Airlines
mié. 12/1111:30 amGCM - MDW
1 stop28h 42mMultiple Airlines
Deal found 11/19$661
This Mytrip deal was found by Cheapflights users on 11/19. 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.
mié. 12/49:30 amMDW - GCM
3 stops27h 19mWestJet
dom. 12/82:50 pmGCM - MDW
2 stops28h 42mWestJet
Deal found 11/19$795

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 2,629,791 searches. Data last updated noviembre 20, 2024.

Fly from

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Fly to

Any airport

Route

Depart

Return

Price

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

mié. 1/22

5:06 pm-1:00 pm

1 stop18h 54m

George Town Owen Roberts Intl

mar. 1/28

11:30 am-12:45 pm

2 stops26h 15m

$462

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

mié. 2/19

7:25 am-4:10 pm

1 stop7h 45m

George Town Owen Roberts Intl

vie. 2/28

4:45 pm-8:44 am

1 stop16h 59m

$488

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

jue. 1/2

5:45 am-12:55 pm

1 stop6h 10m

George Town Owen Roberts Intl

mié. 1/8

1:50 pm-10:20 pm

2 stops9h 30m

$531

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

mié. 1/1

6:00 am-12:55 pm

1 stop5h 55m

George Town Owen Roberts Intl

mié. 1/8

1:50 pm-9:20 am

2 stops20h 30m

$572

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

mar. 3/18

8:48 am-12:45 pm

Nonstop3h 57m

George Town Owen Roberts Intl

mar. 3/25

1:50 pm-6:06 pm

Nonstop4h 16m

$574

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

sáb. 2/1

6:30 pm-12:35 pm

1 stop17h 05m

George Town Owen Roberts Intl

mié. 2/19

3:20 pm-9:41 pm

1 stop7h 21m

$588

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

dom. 1/12

6:00 am-12:44 pm

1 stop5h 44m

George Town Owen Roberts Intl

mar. 1/14

2:09 pm-10:20 pm

1 stop9h 11m

$588

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

sáb. 1/11

3:35 pm-3:00 pm

2 stops22h 25m

George Town Owen Roberts Intl

dom. 1/19

4:00 pm-10:54 am

2 stops19h 54m

$594

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

vie. 2/21

6:15 am-2:35 pm

1 stop7h 20m

George Town Owen Roberts Intl

mié. 2/26

2:09 pm-11:59 pm

1 stop10h 50m

$613

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

mié. 12/4

9:30 am-1:49 pm

3 stops27h 19m

George Town Owen Roberts Intl

dom. 12/8

2:50 pm-6:32 pm

2 stops28h 42m

$795

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/19

Showing 1-10 of 23 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.

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 June is currently the most expensive (average of $560). 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 noviembre 20, 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.

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 noviembre 20, 2024.
Get a feel of what it's like to fly with Delta, Air Canada and WestJet 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
5,014 reviews

Crew

8.7

Comfort

8.1

Overall

8.1

Boarding

8.2

Entertainment

7.7

Food

7.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Southwest
8.1
Very good
5,014 reviews
Southwest
8.1
Very good
5,014 reviews

Crew

8.7

Comfort

8.1

Overall

8.1

Boarding

8.2

Entertainment

7.7

Food

7.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Delta
8.0
Very good
8,756 reviews
Southwest
8.1
Very good
5,014 reviews

Crew

8.7

Comfort

8.1

Overall

8.1

Boarding

8.2

Entertainment

7.7

Food

7.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

United Airlines
7.4
Good
9,171 reviews
Southwest
8.1
Very good
5,014 reviews

Crew

8.7

Comfort

8.1

Overall

8.1

Boarding

8.2

Entertainment

7.7

Food

7.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

WestJet
7.3
Good
2,811 reviews
Southwest
8.1
Very good
5,014 reviews

Crew

8.7

Comfort

8.1

Overall

8.1

Boarding

8.2

Entertainment

7.7

Food

7.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
5,014 reviews

Crew

8.7

Comfort

8.1

Overall

8.1

Boarding

8.2

Entertainment

7.7

Food

7.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

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 Southwest. According to our data, you can fly for as low as $225. Users have also found prices from $261 and $272 on Air Canada and Sun Country Air, respectively.

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

    On average you can expect to pay $570 for a flight from Chicago to Grand Cayman. The cheapest flight overall is $296 while the most popular route, (Chicago O'Hare Intl - George Town Owen Roberts Intl) is currently priced at $462.

  • 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 June is currently the most expensive (average of $560). 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
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 2,629,791 searches. Data last updated noviembre 20, 2024.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$348Average$476FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$368Average$606FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$420Average$671FlexibilityNo cancel feeOn-time69%
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