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$287+ Cheap flights from the Cayman Islands 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 10 — Nov 171
1 adult
Sun 11/10
Sun 11/17
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Find flight deals from Cayman Islands to Chicago

Cheapest flights from Cayman Islands to Chicago
Explore the most affordable flight options available from Cayman Islands to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 5, 2024.

This Kiwi.com deal was found by Cheapflights users on 11/4. 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 12/511:30 amGCM - ORD
2 stops13h 21mMultiple Airlines
Wed 12/118:02 pmORD - GCM
1 stop24h 18mMultiple Airlines
Deal found 11/4$477
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.
Fri 12/204:45 pmGCM - MDW
1 stop23h 28mMultiple Airlines
Fri 12/276:00 amMDW - GCM
1 stop8h 45mMultiple Airlines
Deal found 11/5$792
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.
Fri 12/202:50 pmGCM - ORD
Nonstop4h 16mUnited Airlines
Fri 12/277:25 amORD - GCM
1 stop8h 00mUnited Airlines
Deal found 11/5$1,016
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/203:47 pmGCM - MDW
2 stops18h 03mDelta
Fri 12/276:25 pmMDW - GCM
2 stops17h 02mDelta
Deal found 11/5$1,684

Find flights from Cayman Islands to Chicago within your budget

Customize your flight search to find flights from Cayman Islands 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 2,554,862 searches. Data last updated November 5, 2024.

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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

$287

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Tue 2/4

1:50 pm-10:20 pm

2 stops9h 30m

$320

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Thu 2/6

2:40 pm-9:01 am

1 stop19h 21m

$324

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Wed 1/1

3:47 pm-11:56 pm

1 stop9h 09m

$392

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Thu 1/2

5:40 pm-7:45 am

1 stop15h 05m

$397

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Wed 11/27

5:35 pm-12:16 am

1 stop7h 41m

$432

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Sat 1/4

8:00 pm-7:05 pm

1 stop24h 05m

$450

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Sat 3/22

8:50 am-7:18 pm

1 stop10h 28m

$449

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Sat 12/28

6:50 pm-5:00 pm

2 stops23h 10m

$3,711

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Thu 12/5

11:30 am-11:51 pm

2 stops13h 21m

Chicago O'Hare Intl

Wed 12/11

8:02 pm-9:20 pm

1 stop24h 18m

$477

Flights are sorted by cheapest first

Deals found on 11/3

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

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

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

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

Currently, September is the cheapest month in which you can book a flight from Cayman Islands to Chicago (average of $232). Flying from Cayman Islands 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 KY to CHI?

Find hourly flight availability from Cayman Islands 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 5, 2024.

When flying from Cayman Islands 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 5, 2024.
Southwest
8.1
Very good
5,082 reviews

Boarding

8.3

Crew

8.7

Comfort

8.1

Overall

8.1

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
5,082 reviews
Southwest
8.1
Very good
5,082 reviews

Boarding

8.3

Crew

8.7

Comfort

8.1

Overall

8.1

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
8,830 reviews
Southwest
8.1
Very good
5,082 reviews

Boarding

8.3

Crew

8.7

Comfort

8.1

Overall

8.1

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
9,215 reviews
Southwest
8.1
Very good
5,082 reviews

Boarding

8.3

Crew

8.7

Comfort

8.1

Overall

8.1

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
5,082 reviews

Boarding

8.3

Crew

8.7

Comfort

8.1

Overall

8.1

Entertainment

7.7

Food

7.2

Reviews

1 / 10

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

Air Canada
7.0
Good
8,130 reviews
Southwest
8.1
Very good
5,082 reviews

Boarding

8.3

Crew

8.7

Comfort

8.1

Overall

8.1

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 Cayman Islands to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • Can I find flights from Cayman Islands to Chicago for under $500 on Cheapflights?

    Yes, there are multiple flights from Cayman Islands to Chicago for under $500. The cheapest flight booked recently is on Multiple Airlines for just $477, but on average you can expect to pay $959.

  • Are there nonstop flights from Cayman Islands to Chicago for under $1,400 on Cheapflights?

    Cheapflights has at least 1 direct flight from Cayman Islands to Chicago under $1,400. A good price for a nonstop flight from Cayman Islands to Chicago is less than $1,321.

  • What are the cheapest airlines to fly from Cayman Islands to Chicago one-way?

    The cheapest airlines for a one-way flight from Cayman Islands to Chicago are Southwest ($320), Air Canada ($324), and Delta ($392).

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

    On average you can expect to pay $504 for a flight from Cayman Islands to Chicago. The cheapest flight overall is $177 while the most popular route, (George Town Owen Roberts Intl - Chicago O'Hare Intl) is currently priced at $477.

  • What does GCM to ORD mean?

    GCM stands for George Town Owen Roberts Intl Airport, while ORD stands for Chicago O'Hare Intl Airport. These codes are often called IATA codes, a set of identifiers established by IATA (International Air Transport Association) that is widely used by airlines and the aviation industry. While you’re still figuring out your travel plans, it’s not a bad idea to learn the names and codes of other airports around these areas: Chicago Midway Airport (MDW), Chicago Greater Rockford Airport (RFD).

  • Can I find deals for flights from Cayman Islands to Chicago that include extra baggage allowance?

    The amount of baggage you can bring on your Cayman Islands to Chicago flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from Cayman Islands to Chicago with specific airlines?

    Yes, Cheapflights allows you to browse and filter Cayman Islands to Chicago flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Cayman Islands 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.

  • Can I find deals for flights from Cayman Islands to Chicago that allow pets onboard?

    Many airlines flying from Cayman Islands to Chicago offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from Cayman Islands to Chicago?

    Yes, you can often find last-minute deals on Cayman Islands to Chicago flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the Cayman Islands to Chicago flight deals updated?

    The Cayman Islands to Chicago flight deals you see on this page were last updated on 11/5.

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

    Currently, September is the cheapest month in which you can book a flight from Cayman Islands to Chicago (average of $232). Flying from Cayman Islands 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 Cayman Islands to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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Top airline flying from Cayman Islands to Chicago

Discover the top airline that operate flights from Cayman Islands 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 2,554,862 searches. Data last updated November 5, 2024.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$451Average$558FlexibilityNo cancel feeOn-time69%
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