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$293+ 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 7/11. Fares are subject to change and may not be available on all flights or dates of travel.
GCM — CHI
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
1 adult, Economy
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Cheap flight deals from Cayman Islands to Chicago

Keep the following information in mind while searching for Cayman Islands to Chicago flight deals. Data was last updated June 12, 2025.

Round-trip from

$570
(American Airlines)

One-way from

$293
(Mytrip)

Popular in

March

Cheapest in

September

Average price

$654

Good round-trip deal

$599 or less

Good one-way deal

$303 or less
From Cayman Islands to Chicago (CHI)
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One-way flight from Cayman Islands to Chicago (CHI)
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Highest demand for flights based on searches. 37% potential increase in price ($372 potential increase over avg. RT price).
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Cheapest flight prices on average. 7% potential price decrease ($42 potential savings vs. average RT price).
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Average for round-trip flights in June 2025
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Price to beat on a round-trip flight from Cayman Islands to Chicago (CHI).
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Price to beat on a one-way flight from Cayman Islands to Chicago (CHI).
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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 June 12, 2025.

This American Airlines deal was found by Cheapflights users on 6/12. 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.
Wed 8/612:10 pmGCM - ORD
1 stop11h 47mAmerican Airlines
Wed 8/205:00 amORD - GCM
1 stop6h 10mAmerican Airlines
Deal found 6/12$570
This United Airlines deal was found by Cheapflights users on 6/11. 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.
Sat 7/261:45 pmGCM - ORD
Nonstop4h 22mUnited Airlines
Sat 8/27:35 pmORD - GCM
1 stop16h 55mUnited Airlines
Deal found 6/11$625
This Mytrip deal was found by Cheapflights users on 6/11. 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.
Sat 7/268:50 amGCM - ORD
2 stops23h 00mMultiple Airlines
Sat 8/29:10 pmORD - GCM
2 stops20h 10mMultiple Airlines
Deal found 6/11$728
This Delta deal was found by Cheapflights users on 6/11. 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.
Sat 7/261:07 pmGCM - MDW
1 stop8h 35mDelta
Sat 8/26:00 amMDW - GCM
1 stop5h 42mDelta
Deal found 6/11$1,168

Cheapflights Fare Finder

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 2,558,603 searches. Data last updated June 12, 2025.
Use the filters below to find and compare flights from the Cayman Islands to Chicago that are best for you.

Fly from

Cayman Islands

Fly to

Chicago

Route

Depart

Return

Price

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Wed 8/6

12:10 pm-11:57 pm

1 stop11h 47m

Chicago O'Hare Intl

Wed 8/20

5:00 am-11:10 am

1 stop6h 10m

$570

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Sat 7/26

1:45 pm-6:07 pm

Nonstop4h 22m

Chicago O'Hare Intl

Sat 8/2

7:35 pm-12:30 pm

1 stop16h 55m

$625

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Sat 7/26

8:50 am-7:50 am

2 stops23h 00m

Chicago O'Hare Intl

Sat 8/2

9:10 pm-5:20 pm

2 stops20h 10m

$728

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Sat 7/26

1:07 pm-9:42 pm

1 stop8h 35m

Chicago Midway

Sat 8/2

6:00 am-11:42 am

1 stop5h 42m

$1,168

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Fri 7/11

4:45 pm-4:11 pm

1 stop23h 26m

$293

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Fri 11/21

1:30 pm-9:50 pm

1 stop9h 20m

$321

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Fri 7/11

12:45 pm-11:40 pm

1 stop10h 55m

$365

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Fri 11/21

1:35 pm-8:00 am

2 stops19h 25m

$383

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Fri 7/4

1:35 pm-11:11 am

1 stop21h 36m

$438

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Fri 7/4

12:10 pm-10:45 pm

2 stops10h 35m

$447

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

Showing 1-10 of 12 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.

Cheapflights Insights

Everything you need to know about your flight from the Cayman Islands to Chicago

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 June 12, 2025.

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 June 12, 2025.
Southwest
8.0
Very good
4,287 reviews

Entertainment

7.6

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.2

Food

7.1

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,287 reviews
Southwest
8.0
Very good
4,287 reviews

Entertainment

7.6

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.2

Food

7.1

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,950 reviews
Southwest
8.0
Very good
4,287 reviews

Entertainment

7.6

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.2

Food

7.1

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
United Airlines
7.4
Good
8,790 reviews
Southwest
8.0
Very good
4,287 reviews

Entertainment

7.6

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.2

Food

7.1

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,287 reviews

Entertainment

7.6

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.2

Food

7.1

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
WestJet
7.2
Good
2,868 reviews
Southwest
8.0
Very good
4,287 reviews

Entertainment

7.6

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.2

Food

7.1

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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 ($321), Air Canada ($383), and United Airlines ($438).

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

    On average you can expect to pay $470 for a flight from Cayman Islands to Chicago. The cheapest flight overall is $301 while the most popular route, (George Town Owen Roberts Intl - Chicago O'Hare Intl) is currently priced at $505.

  • 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, August is the cheapest month in which you can book a flight from Cayman Islands to Chicago (average of $245). Flying from Cayman Islands to Chicago in March is currently the most expensive (average of $321). 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

Traveling to a place near the Cayman Islands?

Book flights to the Cayman Islands if you plan to visit one of these locations
Merrillville
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
Chesterton

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