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$277+ 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 5/10. Fares are subject to change and may not be available on all flights or dates of travel.
GCM — CHI
Apr 7 — Apr 141
Mon 4/7
Mon 4/14
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 2, 2025.

Round-trip from

$621
(American Airlines)

One-way from

$277
(Mytrip)

Popular in

March

Cheapest in

September

Average price

$908

Good round-trip deal

$428 or less

Good one-way deal

$412 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. 32% potential increase in price ($324 potential increase over avg. RT price).
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Cheapest flight prices on average. 7% potential price decrease ($45 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 2, 2025.

This Kiwi.com deal was found by Cheapflights users on 4/1. 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 4/811:30 amGCM - ORD
2 stops37h 07mMultiple Airlines
Tue 4/157:00 pmORD - GCM
1 stop21h 10mMultiple Airlines
Deal found 4/1$547
This American Airlines deal was found by Cheapflights users on 4/1. 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
1 stop22h 16mAmerican Airlines
Tue 5/205:00 amORD - GCM
1 stop8h 10mAmerican Airlines
Deal found 4/1$621
This United Airlines deal was found by Cheapflights users on 4/1. 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 8/91:45 pmGCM - ORD
Nonstop4h 22mUnited Airlines
Sat 8/169:00 pmORD - GCM
1 stop15h 30mUnited Airlines
Deal found 4/1$645
This Delta deal was found by Cheapflights users on 4/1. 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 4/2512:47 pmGCM - MDW
1 stop9h 35mDelta
Mon 4/286:04 amMDW - GCM
1 stop5h 18mDelta
Deal found 4/1$691
This Delta deal was found by Cheapflights users on 4/2. 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 4/2512:47 pmGCM - ORD
1 stop8h 03mDelta
Mon 4/285:30 amORD - GCM
1 stop5h 52mDelta
Deal found 4/2$691

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 2, 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

Fri 5/16

12:25 pm-10:41 am

1 stop22h 16m

Chicago O'Hare Intl

Tue 5/20

5:00 am-1:10 pm

1 stop8h 10m

$621

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Sat 8/9

1:45 pm-6:07 pm

Nonstop4h 22m

Chicago O'Hare Intl

Sat 8/16

9:00 pm-12:30 pm

1 stop15h 30m

$645

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Fri 4/25

12:47 pm-10:22 pm

1 stop9h 35m

Chicago Midway

Mon 4/28

6:04 am-11:22 am

1 stop5h 18m

$691

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Fri 4/25

12:47 pm-8:50 pm

1 stop8h 03m

Chicago O'Hare Intl

Mon 4/28

5:30 am-11:22 am

1 stop5h 52m

$691

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Sat 8/9

6:05 pm-3:14 pm

2 stops45h 09m

Chicago O'Hare Intl

Sat 8/16

6:15 pm-11:55 am

2 stops41h 40m

$936

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Sat 5/10

8:50 am-5:41 pm

1 stop8h 51m

$277

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Mon 8/4

12:50 pm-9:09 am

1 stop20h 19m

$330

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Fri 6/13

12:45 pm-9:25 am

2 stops20h 40m

$331

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Sat 5/10

1:10 pm-8:25 pm

1 stop7h 15m

$355

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Thu 8/7

12:50 pm-9:21 pm

1 stop8h 31m

$393

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/1

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.

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 2, 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 2, 2025.
Southwest
8.0
Very good
4,272 reviews

Comfort

8.0

Crew

8.6

Overall

8.0

Boarding

8.2

Entertainment

7.6

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.0
Very good
4,272 reviews
Southwest
8.0
Very good
4,272 reviews

Comfort

8.0

Crew

8.6

Overall

8.0

Boarding

8.2

Entertainment

7.6

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Delta
8.0
Very good
7,898 reviews
Southwest
8.0
Very good
4,272 reviews

Comfort

8.0

Crew

8.6

Overall

8.0

Boarding

8.2

Entertainment

7.6

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
United Airlines
7.4
Good
8,616 reviews
Southwest
8.0
Very good
4,272 reviews

Comfort

8.0

Crew

8.6

Overall

8.0

Boarding

8.2

Entertainment

7.6

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,272 reviews

Comfort

8.0

Crew

8.6

Overall

8.0

Boarding

8.2

Entertainment

7.6

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
WestJet
7.2
Good
2,789 reviews
Southwest
8.0
Very good
4,272 reviews

Comfort

8.0

Crew

8.6

Overall

8.0

Boarding

8.2

Entertainment

7.6

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

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 Air Canada ($330), Southwest ($331), and Delta ($393).

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

    On average you can expect to pay $646 for a flight from Cayman Islands to Chicago. The cheapest flight overall is $321 while the most popular route, (George Town Owen Roberts Intl - Chicago O'Hare Intl) is currently priced at $547.

  • 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
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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