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$205+ 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 1/29. Fares are subject to change and may not be available on all flights or dates of travel.
GCM — CHI
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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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 October 30, 2025.

This Delta deal was found by Cheapflights users on 10/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/91:50 pmGCM - MDW
1 stop10h 50mDelta
Wed 11/126:00 amMDW - GCM
1 stop5h 35mDelta
Deal found 10/30$405
This Delta deal was found by Cheapflights users on 10/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/91:50 pmGCM - ORD
1 stop11h 11mDelta
Wed 11/125:23 amORD - GCM
1 stop6h 12mDelta
Deal found 10/30$405
This Mytrip deal was found by Cheapflights users on 10/28. 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.
Sat 11/158:50 amGCM - ORD
3 stops16h 37mMultiple Airlines
Sat 11/228:15 pmORD - GCM
1 stop15h 10mMultiple Airlines
Deal found 10/28$463
This American Airlines deal was found by Cheapflights users on 10/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/93:36 pmGCM - ORD
1 stop18h 29mAmerican Airlines
Wed 11/125:00 amORD - GCM
2 stops8h 46mAmerican Airlines
Deal found 10/30$478
This United Airlines deal was found by Cheapflights users on 10/28. 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.
Sat 11/152:50 pmGCM - ORD
Nonstop4h 14mUnited Airlines
Sat 11/228:45 amORD - GCM
Nonstop4h 00mUnited Airlines
Deal found 10/28$538
This Kiwi.com deal was found by Cheapflights users on 10/30. 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.
Sun 11/912:40 pmGCM - MDW
1 stop12h 50mMultiple Airlines
Wed 11/122:06 pmMDW - GCM
2 stops30h 09mMultiple Airlines
Deal found 10/30$594
This American Airlines deal was found by Cheapflights users on 10/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/1512:55 pmGCM - ORD
1 stop7h 55mAmerican Airlines
Sat 11/226:35 pmORD - GCM
1 stop16h 22mAmerican Airlines
Deal found 10/28$627
This Mytrip deal was found by Cheapflights users on 10/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/92:50 pmGCM - ORD
3 stops34h 37mMultiple Airlines
Wed 11/123:26 pmORD - GCM
2 stops21h 34mMultiple Airlines
Deal found 10/30$656
This Southwest deal was found by Cheapflights users on 10/30. 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.
Sun 11/91:30 pmGCM - MDW
2 stops11h 40mSouthwest
Wed 11/125:15 pmMDW - GCM
2 stops18h 20mSouthwest
Deal found 10/30$797
This Delta deal was found by Cheapflights users on 10/28. 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.
Thu 10/301:05 pmGCM - MDW
1 stop9h 09mDelta
Sun 11/25:00 amMDW - GCM
1 stop5h 44mDelta
Deal found 10/28$4,047

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 October 30, 2025.

Round-trip from

$405
(Delta)

One-way from

$205
(Expedia)

Popular in

March

Cheapest in

October

Average price

$503

Good one-way deal

$387 or less
From Cayman Islands to Chicago (CHI)
Search Deals
One-way flight from Cayman Islands to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 32% potential increase in price ($320 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($35 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
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Price to beat on a one-way flight from Cayman Islands to Chicago (CHI).
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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 October 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 - MDW

GCMMDW

George Town Owen Roberts Intl

Sun 11/9

1:50 pm-11:40 pm

1 stop10h 50m

Chicago Midway

Wed 11/12

6:00 am-12:35 pm

1 stop5h 35m

$405

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Sun 11/9

1:50 pm-12:01 am

1 stop11h 11m

Chicago O'Hare Intl

Wed 11/12

5:23 am-12:35 pm

1 stop6h 12m

$405

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Sat 11/15

8:50 am-12:27 am

3 stops16h 37m

Chicago O'Hare Intl

Sat 11/22

8:15 pm-12:25 pm

1 stop15h 10m

$463

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Sun 11/9

3:36 pm-9:05 am

1 stop18h 29m

Chicago O'Hare Intl

Wed 11/12

5:00 am-2:46 pm

2 stops8h 46m

$478

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Sat 11/15

2:50 pm-6:04 pm

Nonstop4h 14m

Chicago O'Hare Intl

Sat 11/22

8:45 am-1:45 pm

Nonstop4h 00m

$538

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Sun 11/9

12:40 pm-12:30 am

1 stop12h 50m

Chicago Midway

Wed 11/12

2:06 pm-9:15 pm

2 stops30h 09m

$594

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Tue 3/10

1:00 pm-5:10 pm

Nonstop4h 10m

Chicago O'Hare Intl

Wed 3/11

8:10 am-11:56 am

Nonstop3h 46m

$616

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Sat 11/15

12:55 pm-7:50 pm

1 stop7h 55m

Chicago O'Hare Intl

Sat 11/22

6:35 pm-11:57 am

1 stop16h 22m

$627

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Sun 11/9

1:30 pm-12:10 am

2 stops11h 40m

Chicago Midway

Wed 11/12

5:15 pm-12:35 pm

2 stops18h 20m

$797

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Sun 12/7

2:40 pm-11:13 am

1 stop21h 33m

$236

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/28

Showing 1-10 of 23 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
No data available for this route at this time. Please check back soon.

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 October 30, 2025.
Get a feel of what it's like to fly with 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.
American Airlines
7.2
Good
11,034 reviews

Comfort

7.2

Entertainment

6.9

Food

6.4

Overall

7.2

Crew

8.0

Boarding

7.5

Reviews

1 / 20
2.0
Mediocre

Nordia,Sep 2025

KIN - MIA

We were to land in Miami sometime after 3pm but couldn’t due to bad weather, we flew around for 2 hrs until we had to land in Forth Myers to refuel, we had to sit another 2 hrs at Forth Myers until given the clearance to refuel, we were hungry, thirsty and frustrated at that point. All the had on the flight to offer was a small plastic glass of water and a pack of biscoff, I requested a cup of tea and was told none was there. We were basically at another airport and not one of the staff could consider that the passengers might be hungry or thirsty being on a plane for around 8 hrs, which you weren’t prepared for, at least find some hot water on board.
American Airlines
7.2
Good
11,034 reviews
American Airlines
7.2
Good
11,034 reviews

Comfort

7.2

Entertainment

6.9

Food

6.4

Overall

7.2

Crew

8.0

Boarding

7.5

Reviews

1 / 20
2.0
Mediocre

Nordia,Sep 2025

KIN - MIA

We were to land in Miami sometime after 3pm but couldn’t due to bad weather, we flew around for 2 hrs until we had to land in Forth Myers to refuel, we had to sit another 2 hrs at Forth Myers until given the clearance to refuel, we were hungry, thirsty and frustrated at that point. All the had on the flight to offer was a small plastic glass of water and a pack of biscoff, I requested a cup of tea and was told none was there. We were basically at another airport and not one of the staff could consider that the passengers might be hungry or thirsty being on a plane for around 8 hrs, which you weren’t prepared for, at least find some hot water on board.

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.

  • How long is the flight from Cayman Islands to Chicago?

    A quick flight from Cayman Islands to Chicago can take about 4h 14m. Delta provides one of the quickest options available for as low as $538. Airlines will cover a distance of 1613 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    On average you can expect to pay $440 for a flight from Cayman Islands to Chicago. The cheapest flight overall is $312 while the most popular route, (George Town Owen Roberts Intl - Chicago O'Hare Intl) is currently priced at $343.

  • 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.

See more FAQs

Traveling to a place near Chicago?

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

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