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$264+ 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
ago. 4 — ago. 111
lun. 8/4
lun. 8/11
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 julio 30, 2025.

Round-trip from

$447
(Air Canada)

One-way from

$274
(Delta)

Good round-trip deal

$660 or less

Good one-way deal

$380 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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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 julio 30, 2025.

This Southwest deal was found by Cheapflights users on 7/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 11/141:30 pmGCM - ORD
1 stop9h 20mSouthwest
dom. 11/166:05 amORD - GCM
1 stop5h 30mSouthwest
Deal found 7/30$410
This Air Canada deal was found by Cheapflights users on 7/29. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/1612:50 pmGCM - ORD
2 stops45h 01mAir Canada
sáb. 10/186:00 pmORD - GCM
2 stops41h 55mAir Canada
Deal found 7/29$447
This Delta deal was found by Cheapflights users on 7/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 9/1212:52 pmGCM - MDW
1 stop8h 44mDelta
vie. 9/196:00 amMDW - GCM
1 stop5h 36mDelta
Deal found 7/29$468
This Delta deal was found by Cheapflights users on 7/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 9/1212:52 pmGCM - ORD
1 stop11h 02mDelta
vie. 9/195:30 amORD - GCM
1 stop6h 06mDelta
Deal found 7/29$468
This American Airlines deal was found by Cheapflights users on 7/29. 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.
vie. 9/1212:25 pmGCM - ORD
2 stops11h 23mAmerican Airlines
vie. 9/198:30 pmORD - GCM
2 stops14h 40mAmerican Airlines
Deal found 7/29$481
This Kiwi.com deal was found by Cheapflights users on 7/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 8/184:45 pmGCM - ORD
1 stop16h 37mMultiple Airlines
jue. 8/2110:27 amORD - GCM
1 stop10h 53mMultiple Airlines
Deal found 7/29$482
This Southwest deal was found by Cheapflights users on 7/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 11/141:30 pmGCM - MDW
2 stops11h 00mSouthwest
dom. 11/166:05 pmMDW - GCM
2 stops17h 30mSouthwest
Deal found 7/30$500
This Kiwi.com deal was found by Cheapflights users on 7/30. 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.
jue. 7/3112:40 pmGCM - MDW
1 stop9h 44mMultiple Airlines
jue. 8/72:55 pmMDW - GCM
2 stops25h 05mMultiple Airlines
Deal found 7/30$1,052
This Mytrip deal was found by Cheapflights users on 7/28. 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.
mar. 8/121:45 pmGCM - MDW
2 stops23h 18mWestJet
vie. 8/151:43 pmMDW - GCM
2 stops23h 02mWestJet
Deal found 7/28$1,433

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 julio 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

vie. 11/14

1:30 pm-9:50 pm

1 stop9h 20m

Chicago O'Hare Intl

dom. 11/16

6:05 am-12:35 pm

1 stop5h 30m

$410

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

jue. 10/16

12:50 pm-9:51 am

2 stops45h 01m

Chicago O'Hare Intl

sáb. 10/18

6:00 pm-11:55 am

2 stops41h 55m

$447

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

vie. 9/12

12:52 pm-9:36 pm

1 stop8h 44m

Chicago Midway

vie. 9/19

6:00 am-11:36 am

1 stop5h 36m

$468

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

vie. 9/12

12:52 pm-11:54 pm

1 stop11h 02m

Chicago O'Hare Intl

vie. 9/19

5:30 am-11:36 am

1 stop6h 06m

$468

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

vie. 9/12

12:25 pm-11:48 pm

2 stops11h 23m

Chicago O'Hare Intl

vie. 9/19

8:30 pm-11:10 am

2 stops14h 40m

$481

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

lun. 8/18

4:45 pm-9:22 am

1 stop16h 37m

Chicago O'Hare Intl

jue. 8/21

10:27 am-9:20 pm

1 stop10h 53m

$482

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

vie. 11/14

1:30 pm-11:30 pm

2 stops11h 00m

Chicago Midway

dom. 11/16

6:05 pm-12:35 pm

2 stops17h 30m

$500

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

mar. 8/12

1:45 pm-1:03 pm

2 stops23h 18m

Chicago Midway

vie. 8/15

1:43 pm-12:45 pm

2 stops23h 02m

$1,433

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

mié. 1/14

1:50 pm-9:50 pm

1 stop9h 00m

$264

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

jue. 8/28

12:50 pm-10:37 pm

1 stop9h 47m

$274

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

Showing 1-10 of 18 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 julio 30, 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.

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 julio 30, 2025.
Get a feel of what it's like to fly with Delta, United Airlines, and American Airlines from the Cayman Islands to Chicago by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,980 reviews

Overall

8.0

Crew

8.5

Food

7.3

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Reviews

1 / 20
8.0
Excellent

Michael,Jul 2025

AMS - ATL

Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.
Delta
8.0
Very good
7,980 reviews
Delta
8.0
Very good
7,980 reviews

Overall

8.0

Crew

8.5

Food

7.3

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Reviews

1 / 20
8.0
Excellent

Michael,Jul 2025

AMS - ATL

Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.
United Airlines
7.4
Good
8,896 reviews
Delta
8.0
Very good
7,980 reviews

Overall

8.0

Crew

8.5

Food

7.3

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Reviews

1 / 20
8.0
Excellent

Michael,Jul 2025

AMS - ATL

Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,980 reviews

Overall

8.0

Crew

8.5

Food

7.3

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Reviews

1 / 20
8.0
Excellent

Michael,Jul 2025

AMS - ATL

Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.
WestJet
7.2
Good
2,975 reviews
Delta
8.0
Very good
7,980 reviews

Overall

8.0

Crew

8.5

Food

7.3

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Reviews

1 / 20
8.0
Excellent

Michael,Jul 2025

AMS - ATL

Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.
Air Canada
7.1
Good
9,837 reviews
Delta
8.0
Very good
7,980 reviews

Overall

8.0

Crew

8.5

Food

7.3

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Reviews

1 / 20
8.0
Excellent

Michael,Jul 2025

AMS - ATL

Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.

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 Delta ($274), Air Canada ($277), and American Airlines ($278).

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

    On average you can expect to pay $924 for a flight from Cayman Islands to Chicago. The cheapest flight overall is $295 while the most popular route, (George Town Owen Roberts Intl - Chicago Midway) is currently priced at $468.

  • 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 Chicago?

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

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