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$208+ Cheap flights from Grand Cayman 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 12/14. Fares are subject to change and may not be available on all flights or dates of travel.
GCM — CHI
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
1 adult, Economy
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Cheap flight deals from Grand Cayman to Chicago

Keep the following information in mind while searching for Grand Cayman to Chicago flight deals. Data was last updated September 17, 2025.

Round-trip from

$471
(American Airlines)

One-way from

$208
(Priceline)
From Grand Cayman to Chicago (CHI)
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One-way flight from Grand Cayman to Chicago (CHI)
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Find flight deals from Grand Cayman to Chicago

Cheapest flights from Grand Cayman to Chicago
Explore the most affordable flight options available from Grand Cayman to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 17, 2025.

This American Airlines deal was found by Cheapflights users on 9/15. 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.
Sat 10/412:25 pmGCM - ORD
1 stop8h 02mAmerican Airlines
Sat 10/117:05 pmORD - GCM
1 stop16h 05mAmerican Airlines
Deal found 9/15$471
This American Airlines deal was found by Cheapflights users on 9/17. 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 11/18:25 amGCM - ORD
1 stop15h 33mAmerican Airlines
Sat 11/87:07 pmORD - GCM
1 stop16h 06mAmerican Airlines
Deal found 9/17$477
This Delta deal was found by Cheapflights users on 9/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/412:52 pmGCM - ORD
2 stops19h 13mDelta
Sat 10/115:20 amORD - GCM
1 stop6h 15mDelta
Deal found 9/15$487
This United Airlines deal was found by Cheapflights users on 9/17. 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 11/11:50 pmGCM - ORD
Nonstop4h 14mUnited Airlines
Sat 11/88:48 amORD - GCM
1 stop6h 47mUnited Airlines
Deal found 9/17$492
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 11/18:50 amGCM - MDW
1 stop12h 32mMultiple Airlines
Sat 11/82:05 pmMDW - GCM
1 stop20h 30mMultiple Airlines
Deal found 9/17$524
This Mytrip deal was found by Cheapflights users on 9/15. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/48:50 amGCM - ORD
2 stops23h 34mMultiple Airlines
Sat 10/117:43 pmORD - GCM
2 stops21h 37mMultiple Airlines
Deal found 9/15$598
This KAYAK deal was found by Cheapflights users on 9/16. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/2412:25 pmGCM - ORD
1 stop8h 02mAmerican Airlines
Sat 9/278:47 pmORD - GCM
1 stop14h 35mAmerican Airlines
Deal found 9/16$618
This Mytrip deal was found by Cheapflights users on 9/17. 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 11/18:50 amGCM - ORD
3 stops16h 13mMultiple Airlines
Sat 11/88:50 pmORD - GCM
2 stops23h 25mMultiple Airlines
Deal found 9/17$673

Cheapflights Fare Finder

 
Customize your flight search to find flights from Grand Cayman 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 September 17, 2025.
Use the filters below to find and compare flights from Grand Cayman to Chicago that are best for you.

Fly from

Grand Cayman

Fly to

Chicago

Route

Depart

Return

Price

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Sat 11/1

8:25 am-11:58 pm

1 stop15h 33m

Chicago O'Hare Intl

Sat 11/8

7:07 pm-12:13 pm

1 stop16h 06m

$477

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Sat 10/4

12:52 pm-8:05 am

2 stops19h 13m

Chicago O'Hare Intl

Sat 10/11

5:20 am-11:35 am

1 stop6h 15m

$487

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Sat 11/1

1:50 pm-6:04 pm

Nonstop4h 14m

Chicago O'Hare Intl

Sat 11/8

8:45 am-1:45 pm

Nonstop4h 00m

$487

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Sat 11/1

8:50 am-9:22 pm

1 stop12h 32m

Chicago Midway

Sat 11/8

2:05 pm-11:35 am

1 stop20h 30m

$524

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Tue 3/10

1:50 pm-6:04 pm

Nonstop4h 14m

Chicago O'Hare Intl

Wed 3/11

9:35 pm-3:30 pm

1 stop17h 55m

$578

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Sat 10/4

8:50 am-8:24 am

2 stops23h 34m

Chicago O'Hare Intl

Sat 10/11

7:43 pm-5:20 pm

2 stops21h 37m

$598

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

$615

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Sun 12/14

11:55 am-7:21 pm

1 stop8h 26m

$238

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Sat 12/13

11:55 am-9:00 pm

1 stop10h 05m

$238

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Thu 12/18

11:55 am-9:00 pm

1 stop10h 05m

$238

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/17

Showing 1-10 of 20 results
1
2

Best time to book a flight from Grand Cayman to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Grand Cayman 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 Grand Cayman 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 September 17, 2025.
Read reviews from past customers who have flown American Airlines from Grand Cayman to Chicago. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
10,000 reviews

Overall

7.2

Comfort

7.2

Crew

8.0

Food

6.4

Boarding

7.5

Entertainment

6.9

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
10,000 reviews
American Airlines
7.2
Good
10,000 reviews

Overall

7.2

Comfort

7.2

Crew

8.0

Food

6.4

Boarding

7.5

Entertainment

6.9

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 Grand Cayman 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 Grand Cayman to Chicago?

    Departing from Grand Cayman to Chicago will take you 4h 14m. There are 1613 mi between Grand Cayman and Chicago. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines to fly from Grand Cayman to Chicago one-way?

    The cheapest airlines for a one-way flight from Grand Cayman to Chicago are Spirit Airlines ($238), Southwest ($375), and Delta ($523).

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

    Looking for the cheapest flight from Grand Cayman to Chicago? While on average our users pay $387, our data indicates the cheapest price to be $326. The most popular route (George Town Owen Roberts Intl - Chicago Midway), is priced around $468.

  • Can I find deals for flights from Grand Cayman to Chicago that include hotel bookings?

    Yes. In addition to deals on Grand Cayman to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Grand Cayman to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Grand Cayman to Chicago.

  • Can I find deals for business class flights from Grand Cayman to Chicago?

    Yes. Cheapflights offers flight deals from Grand Cayman 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 Grand Cayman to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Grand Cayman to Chicago (average of $245). Flying from Grand Cayman 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
Chesterton

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Alternative routes for Grand Cayman to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
George Town to O'Hare Intl flights

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