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$180+ 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 4/30. Fares are subject to change and may not be available on all flights or dates of travel.
GCM — CHI
Mar 7 — Mar 141
Sat 3/7
Sat 3/14
1 adult, Economy
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Cheap 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 February 5, 2026.

This Priceline deal was found by Cheapflights users on 2/2. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/191:52 pm
GCM
-
ORD
1 stop9h 25m
Spirit Airlines
Thu 3/265:05 am
ORD
-
GCM
1 stop7h 52m
Spirit Airlines
Deal found 2/2$363
This Kiwi.com deal was found by Cheapflights users on 2/4. 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.
Fri 3/65:05 pm
GCM
-
ORD
1 stop17h 48m
Multiple Airlines
Mon 3/99:05 pm
ORD
-
GCM
1 stop19h 00m
Multiple Airlines
Deal found 2/4$364
This Kiwi.com deal was found by Cheapflights users on 2/4. 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.
Fri 3/67:00 am
GCM
-
MDW
1 stop7h 41m
Multiple Airlines
Mon 3/96:00 am
MDW
-
GCM
1 stop15h 15m
Multiple Airlines
Deal found 2/4$367
This Air Canada deal was found by Cheapflights users on 2/2. 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.
Fri 4/1011:10 am
GCM
-
ORD
1 stop8h 15m
Air Canada
Sat 4/116:40 pm
ORD
-
GCM
1 stop16h 15m
Air Canada
Deal found 2/2$413
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 3/191:52 pm
GCM
-
ORD
1 stop9h 25m
Multiple Airlines
Thu 3/265:01 am
ORD
-
GCM
2 stops30h 34m
Multiple Airlines
Deal found 2/2$414
This Mytrip deal was found by Cheapflights users on 2/4. 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.
Mon 4/611:25 am
GCM
-
ORD
2 stops20h 36m
Multiple Airlines
Fri 4/103:21 pm
ORD
-
GCM
2 stops20h 59m
Multiple Airlines
Deal found 2/4$460
This Kiwi.com deal was found by Cheapflights users on 2/4. 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 4/21:52 pm
GCM
-
ORD
2 stops20h 58m
Multiple Airlines
Tue 4/74:51 pm
ORD
-
GCM
1 stop23h 14m
Multiple Airlines
Deal found 2/4$468
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 3/197:00 am
GCM
-
MDW
1 stop6h 41m
Multiple Airlines
Thu 3/2611:00 am
MDW
-
GCM
2 stops26h 00m
Multiple Airlines
Deal found 2/2$475
This Southwest deal was found by Cheapflights users on 2/1. 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.
Wed 4/112:20 pm
GCM
-
MDW
2 stops11h 35m
Southwest
Mon 4/66:25 pm
MDW
-
GCM
2 stops17h 45m
Southwest
Deal found 2/1$537
This Delta deal was found by Cheapflights users on 2/3. 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.
Fri 2/131:54 pm
GCM
-
MDW
1 stop9h 37m
Delta
Wed 2/186:00 am
MDW
-
GCM
1 stop5h 29m
Delta
Deal found 2/3$540
This Southwest deal was found by Cheapflights users on 2/2. 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.
Thu 3/1912:40 pm
GCM
-
MDW
1 stop6h 25m
Southwest
Thu 3/266:00 am
MDW
-
GCM
1 stop5h 45m
Southwest
Deal found 2/2$636
This Southwest deal was found by Cheapflights users on 2/4. 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.
Fri 3/61:40 pm
GCM
-
MDW
2 stops11h 25m
Southwest
Mon 3/95:40 pm
MDW
-
GCM
2 stops18h 05m
Southwest
Deal found 2/4$641

Find 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 February 5, 2026.

Round-trip from

$363
(Priceline)

One-way from

$180
(FlightHub)

Popular in

March

Cheapest in

February

Average price

$454
From Grand Cayman to Chicago (CHI)
Search Deals
One-way flight from Grand Cayman to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 21% potential increase in price ($172 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 February 2026
Search Deals

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 February 5, 2026.
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

Thu 3/19

1:52 pm-11:17 pm

1 stop9h 25m

Chicago O'Hare Intl

Thu 3/26

5:05 am-12:57 pm

1 stop7h 52m

$363

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Fri 3/6

7:00 am-1:41 pm

1 stop7h 41m

Chicago Midway

Mon 3/9

6:00 am-9:15 pm

1 stop15h 15m

$367

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Fri 4/10

11:10 am-7:25 pm

1 stop8h 15m

Chicago O'Hare Intl

Sat 4/11

6:40 pm-10:55 am

1 stop16h 15m

$413

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Fri 3/6

7:00 am-6:18 pm

1 stop12h 18m

Chicago O'Hare Intl

Mon 3/9

6:51 pm-4:05 pm

3 stops21h 14m

$415

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Mon 4/6

11:25 am-8:01 am

2 stops20h 36m

Chicago O'Hare Intl

Fri 4/10

3:21 pm-12:20 pm

2 stops20h 59m

$460

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Thu 4/2

1:52 pm-10:50 am

2 stops20h 58m

Chicago O'Hare Intl

Tue 4/7

4:51 pm-4:05 pm

1 stop23h 14m

$468

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Thu 3/19

7:00 am-1:41 pm

1 stop6h 41m

Chicago Midway

Thu 3/26

11:00 am-1:00 pm

2 stops26h 00m

$475

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Wed 4/1

12:20 pm-11:55 pm

2 stops11h 35m

Chicago Midway

Mon 4/6

6:25 pm-12:10 pm

2 stops17h 45m

$537

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Mon 4/6

7:00 am-10:19 pm

2 stops15h 19m

Chicago Midway

Fri 4/10

6:30 am-9:35 pm

1 stop15h 05m

$580

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Thu 3/19

12:40 pm-7:05 pm

1 stop6h 25m

Chicago Midway

Thu 3/26

6:00 am-11:45 am

1 stop5h 45m

$636

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/4

Showing 1-10 of 27 results
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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 February 5, 2026.

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 February 5, 2026.
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
11,237 reviews

Crew

8.0

Entertainment

6.9

Food

6.4

Overall

7.2

Boarding

7.5

Comfort

7.2

Reviews

1 / 20
2.0
Mediocre

Susie,Jan 2026

CLT - TPA

This flight was delayed 3 or 4 times. We had boarded the plane, sat on plane for a good 30 minutes, then we had to board the aircraft, walk to a different gate, wait and then board another aircraft. We arrived in Tampa 4 hours later than the original booking. I feel there should have been some sort of compensation especially for the advantage members.
American Airlines
7.2
Good
11,237 reviews
American Airlines
7.2
Good
11,237 reviews

Crew

8.0

Entertainment

6.9

Food

6.4

Overall

7.2

Boarding

7.5

Comfort

7.2

Reviews

1 / 20
2.0
Mediocre

Susie,Jan 2026

CLT - TPA

This flight was delayed 3 or 4 times. We had boarded the plane, sat on plane for a good 30 minutes, then we had to board the aircraft, walk to a different gate, wait and then board another aircraft. We arrived in Tampa 4 hours later than the original booking. I feel there should have been some sort of compensation especially for the advantage members.

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 8h 15m. 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 flights from Grand Cayman to Chicago?

    Looking for the cheapest flight from Grand Cayman to Chicago? While on average our users pay $512, our data indicates the cheapest price to be $218. The most popular route (George Town Owen Roberts Intl - Chicago O'Hare Intl), is priced around $364.

  • 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.

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

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