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$279+ Cheap flights from Grand Cayman to Chicago (CHI)

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 12/4. Fares are subject to change and may not be available on all flights or dates of travel.
GCM — CHI
Nov 12 — Nov 191
1 adult
Tue 11/12
Tue 11/19
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Find flight deals from Grand Cayman to Chicago

Cheapest flights from Grand Cayman to Chicago
Explore the most affordable flight options available from Grand Cayman to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 7, 2024.

This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/192:50 pmGCM - ORD
Nonstop4h 16mUnited Airlines
Mon 12/238:48 amORD - GCM
Nonstop3h 57mUnited Airlines
Deal found 11/6$594
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/191:52 pmGCM - ORD
1 stop8h 28mDelta
Mon 12/235:40 amORD - GCM
1 stop7h 52mDelta
Deal found 11/6$599
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1911:30 amGCM - MDW
1 stop21h 51mMultiple Airlines
Mon 12/236:00 amMDW - GCM
1 stop11h 40mMultiple Airlines
Deal found 11/6$624
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.
Thu 12/194:00 pmGCM - ORD
1 stop23h 51mMultiple Airlines
Mon 12/239:08 pmORD - GCM
2 stops18h 02mMultiple Airlines
Deal found 11/6$657
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/193:47 pmGCM - MDW
2 stops18h 03mDelta
Mon 12/236:25 pmMDW - GCM
2 stops17h 02mDelta
Deal found 11/6$1,164

Find flights from Grand Cayman to Chicago within your budget

Customize your flight search to find flights from Grand Cayman to Chicago 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

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Wed 12/4

11:30 am-7:07 pm

1 stop8h 37m

$279

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Wed 12/18

1:50 pm-10:00 pm

2 stops9h 10m

$320

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Thu 1/16

2:40 pm-10:13 pm

1 stop8h 33m

$325

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Wed 12/25

3:47 pm-10:06 pm

1 stop7h 19m

$392

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Wed 1/15

1:00 pm-12:09 am

2 stops12h 09m

$401

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Sat 12/28

2:40 pm-5:56 pm

Nonstop4h 16m

$412

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Tue 12/24

7:00 am-3:13 pm

1 stop9h 13m

$296

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Mon 12/9

2:50 pm-11:37 am

3 stops21h 47m

$614

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Wed 12/18

1:57 pm-9:05 pm

1 stop8h 08m

$392

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Thu 12/19

2:50 pm-6:06 pm

Nonstop4h 16m

Chicago O'Hare Intl

Mon 12/23

8:48 am-1:45 pm

Nonstop3h 57m

$594

Flights are sorted by cheapest first

Deals found on 11/5

Showing 1-10 of 15 results
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Best time to book a flight from Grand Cayman to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Grand Cayman 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 Grand Cayman to Chicago

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

What is the cheapest month to book a flight from Grand Cayman to Chicago?

Currently, September is the cheapest month in which you can book a flight from Grand Cayman to Chicago (average of $232). Flying from Grand Cayman to Chicago in June is currently the most expensive (average of $308). 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 LAW to CHI?

Find hourly flight availability from Grand Cayman to Chicago. 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.

When flying from Grand Cayman to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated November 7, 2024.
Southwest
8.1
Very good
5,083 reviews

Boarding

8.3

Entertainment

7.7

Overall

8.1

Food

7.2

Crew

8.7

Comfort

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

Boarding

8.3

Entertainment

7.7

Overall

8.1

Food

7.2

Crew

8.7

Comfort

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

Boarding

8.3

Entertainment

7.7

Overall

8.1

Food

7.2

Crew

8.7

Comfort

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

Boarding

8.3

Entertainment

7.7

Overall

8.1

Food

7.2

Crew

8.7

Comfort

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

Boarding

8.3

Entertainment

7.7

Overall

8.1

Food

7.2

Crew

8.7

Comfort

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

Boarding

8.3

Entertainment

7.7

Overall

8.1

Food

7.2

Crew

8.7

Comfort

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 Grand Cayman to Chicago. 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 Grand Cayman to Chicago one-way?

    The cheapest airlines for a one-way flight from Grand Cayman to Chicago are Southwest ($320), Air Canada ($325), and Delta ($392).

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

    Looking for the cheapest flight from Grand Cayman to Chicago? While on average our users pay $504, our data indicates the cheapest price to be $177. The most popular route (George Town Owen Roberts Intl - Chicago O'Hare Intl), is priced around $594.

  • Can I find deals for flights from Grand Cayman to Chicago that include hotel bookings?

    Yes. In addition to deals on Grand Cayman to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Grand Cayman to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Grand Cayman to Chicago.

  • Can I find deals for business class flights from Grand Cayman to Chicago?

    Yes. Cheapflights offers flight deals from Grand Cayman to Chicago 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 Grand Cayman to Chicago?

    Currently, September is the cheapest month in which you can book a flight from Grand Cayman to Chicago (average of $232). Flying from Grand Cayman to Chicago in June is currently the most expensive (average of $308). 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 Grand Cayman to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
George Town to O'Hare Intl flights

Top airline flying from Grand Cayman to Chicago

Discover the top airline that operate flights from Grand Cayman to Chicago. 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
United AirlinesCheapest$451Average$558FlexibilityNo cancel feeOn-time69%
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