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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 1/14. Fares are subject to change and may not be available on all flights or dates of travel.
GCM — CHI
Nov 25 — Dec 21
Mon 11/25
Mon 12/2
1 adult, Economy
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Cheap flight deals from Cayman Islands to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Cayman Islands (KY0) to Chicago (CHI). 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 November 20, 2024.

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 20, 2024.

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.
Tue 12/247:00 amGCM - ORD
1 stop10h 12mMultiple Airlines
Sun 1/1210:19 amORD - GCM
2 stops28h 51mMultiple Airlines
Deal found 11/19$506
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.
Thu 12/192:50 pmGCM - ORD
Nonstop4h 16mUnited Airlines
Tue 12/245:00 amORD - GCM
1 stop10h 25mUnited Airlines
Deal found 11/19$594
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.
Thu 12/263:47 pmGCM - MDW
1 stop7h 19mDelta
Mon 12/306:00 amMDW - GCM
1 stop5h 27mDelta
Deal found 11/19$609
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.
Thu 12/261:00 pmGCM - ORD
2 stops11h 37mAmerican Airlines
Mon 12/305:00 amORD - GCM
1 stop8h 30mAmerican Airlines
Deal found 11/19$623
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.
Thu 12/1911:30 amGCM - MDW
1 stop21h 51mMultiple Airlines
Tue 12/242:20 pmMDW - GCM
2 stops24h 50mMultiple Airlines
Deal found 11/19$637
This WestJet 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/192:50 pmGCM - MDW
2 stops43h 33mWestJet
Tue 12/2410:08 amMDW - GCM
2 stops50h 41mWestJet
Deal found 11/19$1,732

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

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Route

Depart

Return

Price

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Tue 12/24

7:00 am-4:12 pm

1 stop10h 12m

Chicago O'Hare Intl

Sun 1/12

10:19 am-4:10 pm

2 stops28h 51m

$506

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Tue 1/14

2:09 pm-10:20 pm

1 stop9h 11m

Chicago Midway

Mon 1/20

6:00 am-12:44 pm

1 stop5h 44m

$579

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

Tue 12/24

5:00 am-4:25 pm

1 stop10h 25m

$594

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Fri 1/24

2:09 pm-8:48 pm

1 stop7h 39m

Chicago O'Hare Intl

Thu 1/30

5:45 am-12:44 pm

1 stop5h 59m

$604

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Thu 12/26

1:00 pm-11:37 pm

2 stops11h 37m

Chicago O'Hare Intl

Mon 12/30

5:00 am-2:30 pm

1 stop8h 30m

$623

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Thu 12/19

11:30 am-8:21 am

1 stop21h 51m

Chicago Midway

Tue 12/24

2:20 pm-4:10 pm

2 stops24h 50m

$637

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Thu 12/19

2:50 pm-9:23 am

2 stops43h 33m

Chicago Midway

Tue 12/24

10:08 am-1:49 pm

2 stops50h 41m

$1,732

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Tue 1/14

11:30 am-11:47 am

2 stops25h 17m

$287

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Tue 1/14

11:30 am-5:57 pm

2 stops31h 27m

$293

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Fri 12/20

1:50 pm-10:00 pm

1 stop9h 10m

$316

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/19

Showing 1-10 of 17 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 20, 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 20, 2024.
Southwest
8.1
Very good
5,014 reviews

Boarding

8.2

Comfort

8.1

Crew

8.7

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

Boarding

8.2

Comfort

8.1

Crew

8.7

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

Boarding

8.2

Comfort

8.1

Crew

8.7

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
9,171 reviews
Southwest
8.1
Very good
5,014 reviews

Boarding

8.2

Comfort

8.1

Crew

8.7

Overall

8.1

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

Boarding

8.2

Comfort

8.1

Crew

8.7

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
5,014 reviews

Boarding

8.2

Comfort

8.1

Crew

8.7

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.

  • 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 ($316), Air Canada ($322), and United Airlines ($387).

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

    On average you can expect to pay $573 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 $582.

  • 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.

  • 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 2,629,791 searches. Data last updated November 20, 2024.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$451Average$558FlexibilityNo cancel feeOn-time69%
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