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$264+ 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 1/14. Fares are subject to change and may not be available on all flights or dates of travel.
GCM — CHI
ago. 5 — ago. 121
mar. 8/5
mar. 8/12
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 julio 31, 2025.

Round-trip from

$410
(Southwest)

One-way from

$264
(Southwest)
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 julio 31, 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 7/31. 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
1 stop20h 23mAir Canada
dom. 10/193:35 pmORD - GCM
2 stops20h 20mAir Canada
Deal found 7/31$450
This Kiwi.com deal was found by Cheapflights users on 7/31. 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. 9/154:45 pmGCM - ORD
1 stop16h 33mMultiple Airlines
lun. 9/2210:27 amORD - GCM
1 stop10h 53mMultiple Airlines
Deal found 7/31$474
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 Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 11/142:02 pmGCM - MDW
1 stop8h 42mDelta
dom. 11/166:00 amMDW - GCM
1 stop5h 37mDelta
Deal found 7/30$511
This American Airlines deal was found by Cheapflights users on 7/31. 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.
mié. 9/312:10 pmGCM - ORD
2 stops19h 32mAmerican Airlines
sáb. 9/68:29 pmORD - GCM
2 stops14h 41mAmerican Airlines
Deal found 7/31$624
This Kiwi.com deal was found by Cheapflights users on 7/31. 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. 8/1412:40 pmGCM - MDW
1 stop9h 44mMultiple Airlines
dom. 8/173:58 pmMDW - GCM
1 stop25h 22mMultiple Airlines
Deal found 7/31$752
This United Airlines deal was found by Cheapflights users on 7/31. 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.
sáb. 8/161:45 pmGCM - ORD
Nonstop4h 22mUnited Airlines
lun. 8/186:00 amORD - GCM
1 stop6h 30mUnited Airlines
Deal found 7/31$899
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/1612:55 pmGCM - ORD
1 stop11h 02mDelta
dom. 10/195:20 amORD - GCM
1 stop6h 15mDelta
Deal found 7/30$2,211

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 julio 31, 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

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-9:13 am

1 stop20h 23m

Chicago O'Hare Intl

dom. 10/19

3:35 pm-11:55 am

2 stops20h 20m

$450

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

lun. 9/15

4:45 pm-9:18 am

1 stop16h 33m

Chicago O'Hare Intl

lun. 9/22

10:27 am-9:20 pm

1 stop10h 53m

$474

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

vie. 11/14

2:02 pm-9:44 pm

1 stop8h 42m

Chicago Midway

dom. 11/16

6:00 am-12:37 pm

1 stop5h 37m

$511

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

mié. 9/3

12:10 pm-7:42 am

2 stops19h 32m

Chicago O'Hare Intl

sáb. 9/6

8:29 pm-11:10 am

2 stops14h 41m

$624

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

jue. 8/14

12:40 pm-10:24 pm

1 stop9h 44m

Chicago Midway

dom. 8/17

3:58 pm-5:20 pm

1 stop25h 22m

$752

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

sáb. 8/16

1:45 pm-6:07 pm

Nonstop4h 22m

Chicago O'Hare Intl

lun. 8/18

6:00 am-12:30 pm

1 stop6h 30m

$899

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

jue. 10/16

12:55 pm-11:57 pm

1 stop11h 02m

Chicago O'Hare Intl

dom. 10/19

5:20 am-11:35 am

1 stop6h 15m

$2,211

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

mié. 1/14

1:50 pm-9:50 pm

1 stop9h 00m

$264

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

Showing 1-10 of 18 results
1
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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

What is the cheapest time of day to fly from LAW to CHI?

Find hourly flight availability from Grand Cayman 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 31, 2025.

When flying from Grand Cayman 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 31, 2025.
Read reviews from past customers who have flown Southwest, Delta, and United 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.
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,981 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
United Airlines
7.4
Good
8,900 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Air Canada
7.1
Good
9,851 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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.

  • 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 Southwest ($264), Air Canada ($275), and American Airlines ($387).

  • 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 $924, our data indicates the cheapest price to be $295. The most popular route (George Town Owen Roberts Intl - Chicago O'Hare Intl), is priced around $410.

  • 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
Valparaiso
Chesterton

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