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$275+ 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 5/28. Fares are subject to change and may not be available on all flights or dates of travel.
GCM — CHI
May 5 — May 121
Mon 5/5
Mon 5/12
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 April 30, 2025.

Round-trip from

$559
(Mytrip)

One-way from

$275
(Kiwi.com)

Popular in

March

Cheapest in

September

Average price

$908

Good round-trip deal

$212 or less

Good one-way deal

$403 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. 31% potential increase in price ($297 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease ($39 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 30, 2025.

This Mytrip deal was found by Cheapflights users on 4/28. 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 6/124:45 pmGCM - ORD
1 stop29h 11mMultiple Airlines
Thu 6/191:43 pmORD - GCM
1 stop7h 37mMultiple Airlines
Deal found 4/28$559
This Delta deal was found by Cheapflights users on 4/28. 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 5/1612:35 pmGCM - ORD
1 stop8h 45mDelta
Tue 5/205:30 amORD - GCM
1 stop5h 50mDelta
Deal found 4/28$1,016
This United Airlines deal was found by Cheapflights users on 4/28. 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.
Wed 5/281:35 pmGCM - ORD
1 stop7h 55mUnited Airlines
Thu 5/299:40 pmORD - GCM
1 stop14h 50mUnited Airlines
Deal found 4/28$1,040
This American Airlines deal was found by Cheapflights users on 4/29. 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.
Fri 5/1612:25 pmGCM - ORD
2 stops11h 31mAmerican Airlines
Tue 5/205:00 amORD - GCM
2 stops8h 10mAmerican Airlines
Deal found 4/29$1,187

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 April 30, 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

Thu 6/12

4:45 pm-9:56 pm

1 stop29h 11m

Chicago O'Hare Intl

Thu 6/19

1:43 pm-9:20 pm

1 stop7h 37m

$559

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Fri 5/16

12:35 pm-9:20 pm

1 stop8h 45m

Chicago O'Hare Intl

Tue 5/20

5:30 am-11:20 am

1 stop5h 50m

$1,016

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Wed 5/28

1:35 pm-9:30 pm

1 stop7h 55m

Chicago O'Hare Intl

Thu 5/29

9:40 pm-12:30 pm

1 stop14h 50m

$1,040

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Fri 5/16

12:25 pm-11:56 pm

2 stops11h 31m

Chicago O'Hare Intl

Tue 5/20

5:00 am-1:10 pm

2 stops8h 10m

$1,187

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Wed 5/28

11:30 am-4:03 pm

1 stop28h 33m

$275

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Sat 8/23

1:10 pm-9:30 pm

1 stop8h 20m

$285

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Mon 6/2

12:50 pm-6:53 pm

2 stops30h 03m

$313

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Tue 6/3

12:45 pm-10:05 pm

1 stop9h 20m

$321

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Sun 6/29

12:40 pm-10:32 pm

1 stop9h 52m

$347

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Wed 6/4

12:35 pm-9:27 pm

1 stop8h 52m

$393

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/28

Showing 1-10 of 13 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 April 30, 2025.

One of the essential ways to save on airfare from Cayman Islands to Chicago is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the morning could potentially save you up to 4% on airfare.

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 April 30, 2025.
Southwest
8.0
Very good
4,295 reviews

Food

7.1

Boarding

8.2

Overall

8.0

Comfort

8.0

Crew

8.6

Entertainment

7.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Southwest
8.0
Very good
4,295 reviews
Southwest
8.0
Very good
4,295 reviews

Food

7.1

Boarding

8.2

Overall

8.0

Comfort

8.0

Crew

8.6

Entertainment

7.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Delta
8.0
Very good
7,936 reviews
Southwest
8.0
Very good
4,295 reviews

Food

7.1

Boarding

8.2

Overall

8.0

Comfort

8.0

Crew

8.6

Entertainment

7.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
United Airlines
7.4
Good
8,696 reviews
Southwest
8.0
Very good
4,295 reviews

Food

7.1

Boarding

8.2

Overall

8.0

Comfort

8.0

Crew

8.6

Entertainment

7.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,295 reviews

Food

7.1

Boarding

8.2

Overall

8.0

Comfort

8.0

Crew

8.6

Entertainment

7.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
WestJet
7.2
Good
2,826 reviews
Southwest
8.0
Very good
4,295 reviews

Food

7.1

Boarding

8.2

Overall

8.0

Comfort

8.0

Crew

8.6

Entertainment

7.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

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 ($285), Air Canada ($313), and Delta ($393).

  • What are the most reliable airlines from Cayman Islands to Chicago?

    Consider American Airlines (86%), United Airlines (72%) or Qatar Airways (67%) when booking your flight. These represent the most reliable airlines when flying from Cayman Islands to Chicago.

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

    On average you can expect to pay $449 for a flight from Cayman Islands to Chicago. The cheapest flight overall is $212 while the most popular route, (George Town Owen Roberts Intl - Chicago O'Hare Intl) is currently priced at $489.

  • 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
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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