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Grand Cayman

$180+ 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 2/4. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — GCM
Nov 12 — Nov 191
1 adult
Tue 11/12
Tue 11/19
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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 November 7, 2024.

This Kiwi.com deal was found by Cheapflights users on 11/7. 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.
Wed 12/44:19 pmORD - GCM
1 stop19h 41mMultiple Airlines
Tue 12/1011:30 amGCM - ORD
1 stop8h 37mMultiple Airlines
Deal found 11/7$514
This Priceline deal was found by Cheapflights users on 11/6. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/58:25 pmORD - GCM
1 stop16h 15mAir Canada
Fri 12/132:40 pmGCM - ORD
2 stops21h 14mAir Canada
Deal found 11/6$573
This American Airlines deal was found by Cheapflights users on 11/7. 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 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 1/71:00 pmGCM - ORD
2 stops12h 09mAmerican Airlines
Deal found 11/7$583
This United Airlines deal was found by Cheapflights users on 11/5. 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 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
Wed 1/12:50 pmGCM - ORD
Nonstop4h 16mUnited Airlines
Deal found 11/5$586
This Southwest deal was found by Cheapflights users on 11/5. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/155:10 amMDW - GCM
1 stop6h 45mSouthwest
Sun 12/221:50 pmGCM - MDW
1 stop9h 05mSouthwest
Deal found 11/5$590
This Kiwi.com deal was found by Cheapflights users on 11/5. 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.
Mon 12/169:57 pmMDW - GCM
1 stop17h 13mMultiple Airlines
Sun 12/222:00 pmGCM - MDW
1 stop19h 21mMultiple Airlines
Deal found 11/5$604
This Delta deal was found by Cheapflights users on 11/7. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/245:40 amORD - GCM
1 stop5h 47mDelta
Tue 12/313:47 pmGCM - ORD
1 stop9h 09mDelta
Deal found 11/7$608
This Delta deal was found by Cheapflights users on 11/7. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/246:00 amMDW - GCM
1 stop5h 27mDelta
Tue 12/313:47 pmGCM - MDW
1 stop7h 19mDelta
Deal found 11/7$608
This Mytrip deal was found by Cheapflights users on 11/6. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/49:30 amMDW - GCM
3 stops27h 19mWestJet
Sun 12/82:50 pmGCM - MDW
2 stops28h 42mWestJet
Deal found 11/6$779

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 2,537,365 searches. Data last updated November 7, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Tue 2/4

4:25 pm-4:10 pm

1 stop22h 45m

$180

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 2/5

6:08 pm-1:40 pm

2 stops18h 32m

$251

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 12/8

5:40 am-12:42 pm

1 stop6h 02m

$292

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 12/7

8:39 am-1:35 pm

Nonstop3h 56m

$358

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 12/21

8:34 pm-12:00 pm

2 stops14h 26m

$443

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Sat 11/16

6:00 am-12:37 pm

1 stop5h 37m

$392

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Mon 2/3

11:40 am-4:55 pm

3 stops28h 15m

$5,571

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Fri 1/17

7:25 am-9:20 pm

2 stops12h 55m

George Town Owen Roberts Intl

Tue 1/21

11:30 am-2:33 pm

1 stop28h 03m

$509

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 12/15

9:50 am-1:40 pm

1 stop26h 50m

George Town Owen Roberts Intl

Sun 12/22

4:00 pm-2:51 pm

1 stop23h 51m

$565

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 2/26

5:50 am-12:29 pm

1 stop5h 39m

George Town Owen Roberts Intl

Tue 3/11

12:50 pm-9:15 pm

1 stop8h 25m

$578

Flights are sorted by cheapest first

Deals found on 11/5

Showing 1-10 of 16 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 November 7, 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 November 7, 2024.
Southwest
8.1
Very good
5,083 reviews

Entertainment

7.7

Comfort

8.1

Boarding

8.3

Crew

8.7

Food

7.2

Overall

8.1

Reviews

1 / 10

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

Southwest
8.1
Very good
5,083 reviews
Southwest
8.1
Very good
5,083 reviews

Entertainment

7.7

Comfort

8.1

Boarding

8.3

Crew

8.7

Food

7.2

Overall

8.1

Reviews

1 / 10

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

Delta
8.0
Very good
8,828 reviews
Southwest
8.1
Very good
5,083 reviews

Entertainment

7.7

Comfort

8.1

Boarding

8.3

Crew

8.7

Food

7.2

Overall

8.1

Reviews

1 / 10

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

United Airlines
7.4
Good
9,206 reviews
Southwest
8.1
Very good
5,083 reviews

Entertainment

7.7

Comfort

8.1

Boarding

8.3

Crew

8.7

Food

7.2

Overall

8.1

Reviews

1 / 10

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

WestJet
7.3
Good
2,804 reviews
Southwest
8.1
Very good
5,083 reviews

Entertainment

7.7

Comfort

8.1

Boarding

8.3

Crew

8.7

Food

7.2

Overall

8.1

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
5,083 reviews

Entertainment

7.7

Comfort

8.1

Boarding

8.3

Crew

8.7

Food

7.2

Overall

8.1

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 Air Canada. According to our data, you can fly for as low as $251. Users have also found prices from $292 and $358 on Delta and United Airlines, respectively.

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

    On average you can expect to pay $577 for a flight from Chicago to Grand Cayman. The cheapest flight overall is $307 while the most popular route, (Chicago O'Hare Intl - George Town Owen Roberts Intl) is currently priced at $506.

  • 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
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 2,537,365 searches. Data last updated November 7, 2024.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$348Average$539FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$368Average$604FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$420Average$663FlexibilityNo cancel feeOn-time69%
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