HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$176+ 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 1/15. Fares are subject to change and may not be available on all flights or dates of travel.
GCM — CHI
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Cayman Islands to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap 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 December 18, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/15. 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.
Thu 12/252:40 pmGCM - ORD
1 stop10h 50mMultiple Airlines
Thu 1/16:00 amORD - GCM
2 stops28h 35mMultiple Airlines
Deal found 12/15$434
This United Airlines deal was found by Cheapflights users on 12/14. 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.
Thu 12/182:50 pmGCM - ORD
Nonstop4h 14mUnited Airlines
Sun 12/219:23 pmORD - GCM
1 stop17h 37mUnited Airlines
Deal found 12/14$438
This American Airlines deal was found by Cheapflights users on 12/15. 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.
Mon 12/223:35 pmGCM - ORD
Nonstop4h 10mAmerican Airlines
Mon 12/296:37 pmORD - GCM
1 stop16h 20mAmerican Airlines
Deal found 12/15$472
This United Airlines deal was found by Cheapflights users on 12/15. 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.
Mon 12/225:45 pmGCM - ORD
1 stop18h 17mUnited Airlines
Mon 12/296:20 pmORD - GCM
1 stop20h 40mUnited Airlines
Deal found 12/15$473
This United Airlines deal was found by Cheapflights users on 12/15. 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.
Thu 12/252:50 pmGCM - ORD
Nonstop4h 14mUnited Airlines
Thu 1/18:45 amORD - GCM
Nonstop4h 00mUnited Airlines
Deal found 12/15$508
This Kiwi.com deal was found by Cheapflights users on 12/16. 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.
Sat 12/205:56 pmGCM - ORD
1 stop7h 34mSpirit Airlines
Sat 12/277:57 pmORD - GCM
2 stops16h 48mSpirit Airlines
Deal found 12/16$590
This Kiwi.com deal was found by Cheapflights users on 12/14. 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.
Thu 12/182:40 pmGCM - ORD
1 stop10h 50mMultiple Airlines
Sun 12/217:57 pmORD - GCM
2 stops38h 38mMultiple Airlines
Deal found 12/14$642
This Kiwi.com deal was found by Cheapflights users on 12/15. 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.
Mon 12/224:45 pmGCM - ORD
1 stop25h 15mMultiple Airlines
Mon 12/296:00 amORD - GCM
2 stops33h 05mMultiple Airlines
Deal found 12/15$648

Find 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 December 18, 2025.

Round-trip from

$360
(Kiwi.com)

One-way from

$176
(Priceline)

Popular in

March

Cheapest in

January

Average price

$497

Good round-trip deal

$497 or less

Good one-way deal

$331 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. 35% potential increase in price ($347 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($37 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from Cayman Islands to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Cayman Islands to Chicago (CHI).
Search Deals

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 December 18, 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 1/30

4:45 pm-8:18 am

1 stop16h 33m

Chicago O'Hare Intl

Sat 2/14

12:06 pm-1:43 pm

1 stop24h 37m

$360

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Thu 1/22

1:30 pm-10:05 pm

1 stop9h 35m

Chicago O'Hare Intl

Mon 1/26

9:15 pm-12:25 pm

1 stop14h 10m

$361

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Thu 1/22

2:50 pm-6:04 pm

Nonstop4h 14m

Chicago O'Hare Intl

Mon 1/26

8:45 am-1:45 pm

Nonstop4h 00m

$438

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Fri 1/30

2:50 pm-6:04 pm

Nonstop4h 14m

Chicago O'Hare Intl

Sat 2/14

7:35 am-4:20 pm

1 stop7h 45m

$508

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Fri 1/30

1:50 pm-10:05 pm

2 stops9h 15m

Chicago Midway

Sat 2/14

6:05 pm-12:55 pm

2 stops17h 50m

$721

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Thu 1/15

2:49 pm-8:57 pm

1 stop7h 08m

$194

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Thu 2/19

2:49 pm-11:24 pm

1 stop9h 35m

$194

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Sat 1/17

2:34 pm-11:46 pm

1 stop10h 12m

$202

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Sun 1/11

2:49 pm-11:22 am

1 stop21h 33m

$202

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Sun 1/25

2:49 pm-9:03 pm

1 stop7h 14m

$218

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/15

Showing 1-10 of 25 results
1
2
3

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 December 18, 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.

Weekly flight availability from Cayman Islands to Chicago

Explore weekly flight availability from Cayman Islands to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated December 18, 2025.

The most flights from KY0 to CHI are scheduled on a Monday (2 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (1 on average).

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 December 18, 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
11,055 reviews

Overall

7.2

Boarding

7.5

Crew

8.0

Comfort

7.2

Food

6.5

Entertainment

6.9

Reviews

1 / 20
10.0
Excellent

Jeremy,Dec 2025

OKC - CLT

Was an okay flight. Had extra seat empty beside me so was able to stretch a bit
American Airlines
7.2
Good
11,055 reviews
American Airlines
7.2
Good
11,055 reviews

Overall

7.2

Boarding

7.5

Crew

8.0

Comfort

7.2

Food

6.5

Entertainment

6.9

Reviews

1 / 20
10.0
Excellent

Jeremy,Dec 2025

OKC - CLT

Was an okay flight. Had extra seat empty beside me so was able to stretch a bit

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 9h 15m. Air Canada provides one of the quickest options available for as low as $721. Airlines will cover a distance of 1598 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 $438 for a flight from Cayman Islands to Chicago. The cheapest flight overall is $193 while the most popular route, (George Town Owen Roberts Intl - Chicago O'Hare Intl) is currently priced at $438.

  • 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Cayman Islands to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Punta Cana to O'Hare Intl flights
Punta Cana to Midway flights
Luis Munoz Marin Intl to O'Hare Intl flights
Luis Munoz Marin Intl to Midway flights
Nassau to O'Hare Intl flights
Luis Munoz Marin Intl to St. Louis flights
Santo Domingo to O'Hare Intl flights
Oranjestad to O'Hare Intl flights
Saint Thomas Island to O'Hare Intl flights
Willemstad to O'Hare Intl flights
Santo Domingo to Midway flights
Kingston to O'Hare Intl flights
Nassau to Midway flights
Christiansted to O'Hare Intl flights
Simpson Bay to O'Hare Intl flights
Montego Bay to O'Hare Intl flights
Santiago de los Caballeros to O'Hare Intl flights
Port of Spain to O'Hare Intl flights
Saint Thomas Island to St. Louis flights
George Town to O'Hare Intl flights
Nassau to St. Louis flights
Port of Spain to St. Louis flights
Aguadilla to O'Hare Intl flights
Montego Bay to Midway flights
Road Town to O'Hare Intl flights
Bridgetown to O'Hare Intl flights
Oranjestad to St. Louis flights
Aguadilla to Midway flights
St. George's to St. Louis flights
Vieques to O'Hare Intl flights
Port Au Prince to Midway flights
Simpson Bay to Midway flights
St. John's to O'Hare Intl flights
Culebra to O'Hare Intl flights
Port Au Prince to O'Hare Intl flights
Roseau to O'Hare Intl flights

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.