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$193+ 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 5/7. Fares are subject to change and may not be available on all flights or dates of travel.
GCM — CHI
Mar 13 — Mar 201
Fri 3/13
Fri 3/20
1 adult, Economy
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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 February 11, 2026.

This Mytrip deal was found by Cheapflights users on 2/9. 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.
Thu 2/122:49 pm
GCM
-
ORD
1 stop9h 58m
Multiple Airlines
Mon 2/233:55 pm
ORD
-
GCM
1 stop19h 30m
Multiple Airlines
Deal found 2/9$301
This Kiwi.com deal was found by Cheapflights users on 2/10. 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 3/94:45 pm
GCM
-
ORD
1 stop16h 54m
Multiple Airlines
Wed 3/116:36 pm
ORD
-
GCM
1 stop18h 21m
Multiple Airlines
Deal found 2/10$331
This Kiwi.com deal was found by Cheapflights users on 2/10. 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 3/97:00 am
GCM
-
ORD
1 stop26h 39m
Multiple Airlines
Thu 3/125:05 am
ORD
-
GCM
1 stop7h 52m
Multiple Airlines
Deal found 2/10$354
This Travelocity deal was found by Cheapflights users on 2/7. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/281:40 pm
GCM
-
ORD
1 stop10h 01m
Multiple Airlines
Sun 5/316:23 pm
ORD
-
GCM
2 stops17h 07m
Multiple Airlines
Deal found 2/7$371
This Mytrip deal was found by Cheapflights users on 2/9. 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.
Thu 3/261:52 pm
GCM
-
ORD
1 stop9h 25m
Spirit Airlines
Thu 4/25:05 am
ORD
-
GCM
1 stop7h 52m
Spirit Airlines
Deal found 2/9$382
This Mytrip deal was found by Cheapflights users on 2/8. 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.
Tue 2/101:30 pm
GCM
-
ORD
2 stops19h 35m
Multiple Airlines
Thu 2/195:15 am
ORD
-
GCM
1 stop7h 28m
Multiple Airlines
Deal found 2/8$385
This Mytrip deal was found by Cheapflights users on 2/8. 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
1 stop25h 40m
Multiple Airlines
Fri 4/106:01 pm
ORD
-
GCM
2 stops18h 19m
Multiple Airlines
Deal found 2/8$393
This Booking.com deal was found by Cheapflights users on 2/8. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/91:30 pm
GCM
-
ORD
1 stop29h 18m
Air Canada
Thu 2/198:00 am
ORD
-
GCM
1 stop27h 25m
Air Canada
Deal found 2/8$396
This Kiwi.com deal was found by Cheapflights users on 2/9. 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 3/267:00 am
GCM
-
MDW
1 stop6h 41m
Multiple Airlines
Thu 4/25:11 pm
MDW
-
GCM
2 stops28h 24m
Multiple Airlines
Deal found 2/9$581
This Southwest deal was found by Cheapflights users on 2/10. 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 2/131:50 pm
GCM
-
MDW
1 stop8h 10m
Southwest
Wed 2/185:00 am
MDW
-
GCM
1 stop6h 55m
Southwest
Deal found 2/10$617
This Delta deal was found by Cheapflights users on 2/9. 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 2/9$618
This Southwest deal was found by Cheapflights users on 2/9. 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 3/2612:40 pm
GCM
-
MDW
1 stop7h 35m
Southwest
Thu 4/26:00 am
MDW
-
GCM
1 stop5h 25m
Southwest
Deal found 2/9$883

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 February 11, 2026.

Round-trip from

$331
(Kiwi.com)

One-way from

$193
(Kiwi.com)

Popular in

April

Cheapest in

November

Average price

$454

Good round-trip deal

$276 or less

Good one-way deal

$220 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. 28% potential increase in price ($231 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease ($43 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
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 February 11, 2026.
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

Mon 3/9

4:45 pm-9:39 am

1 stop16h 54m

Chicago O'Hare Intl

Wed 3/11

6:36 pm-12:57 pm

1 stop18h 21m

$331

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Thu 5/28

1:40 pm-11:41 pm

1 stop10h 01m

Chicago O'Hare Intl

Sun 5/31

6:23 pm-11:30 am

2 stops17h 07m

$371

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

$382

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Mon 3/9

7:00 am-8:23 am

2 stops25h 23m

Chicago O'Hare Intl

Thu 3/12

5:05 am-12:57 pm

1 stop7h 52m

$391

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Mon 4/6

11:25 am-1:05 pm

1 stop25h 40m

Chicago O'Hare Intl

Fri 4/10

6:01 pm-12:20 pm

2 stops18h 19m

$393

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Thu 3/26

1:52 pm-12:17 am

2 stops10h 25m

Chicago O'Hare Intl

Thu 4/2

6:40 am-9:15 pm

1 stop14h 35m

$396

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Mon 2/23

4:45 pm-4:52 pm

2 stops25h 07m

Chicago O'Hare Intl

Thu 2/26

5:15 am-1:43 pm

1 stop7h 28m

$418

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Thu 5/28

12:25 pm-7:35 am

2 stops19h 10m

Chicago O'Hare Intl

Sun 5/31

6:23 pm-11:30 am

2 stops17h 07m

$433

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Thu 3/26

12:30 pm-8:00 am

2 stops19h 30m

Chicago O'Hare Intl

Thu 4/2

3:45 pm-10:10 am

2 stops18h 25m

$456

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Thu 3/26

7:00 am-1:41 pm

1 stop6h 41m

Chicago Midway

Thu 4/2

5:11 pm-9:35 pm

2 stops28h 24m

$581

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/8

Showing 1-10 of 28 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

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 February 11, 2026.

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.

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 11, 2026.
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
11,262 reviews

Boarding

7.5

Comfort

7.2

Crew

8.0

Entertainment

6.9

Overall

7.2

Food

6.4

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
11,262 reviews
American Airlines
7.2
Good
11,262 reviews

Boarding

7.5

Comfort

7.2

Crew

8.0

Entertainment

6.9

Overall

7.2

Food

6.4

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 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 7h 35m. Air Canada provides one of the quickest options available for as low as $883. 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 $405 for a flight from Cayman Islands to Chicago. The cheapest flight overall is $212 while the most popular route, (George Town Owen Roberts Intl - Chicago O'Hare Intl) is currently priced at $301.

  • 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
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Hammond
Porter
Benton Harbor

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