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Cheap flights from the Cayman Islands to Chicago from $262

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from the Cayman Islands to Chicago departing on 9/12. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from the Cayman Islands to Chicago

Recent round-trip flight deals from the Cayman Islands to Chicago

Enter your travel dates to find the best prices.
Air Canada Logo
10:40 am - 1:22 pm
GCM
-
ORD
26h 42m
1 stop
Air Canada Logo
3:45 pm - 11:30 am
ORD
-
GCM
19h 45m
1 stop
$430Air Canada
Sat, Sep 5 - Wed, Sep 9
Air Canada Logo
10:40 am - 10:19 am
GCM
-
ORD
23h 39m
2 stops
Air Canada Logo
2:15 pm - 11:30 am
ORD
-
GCM
21h 15m
1 stop
$433Air Canada
Sat, Sep 5 - Wed, Sep 9
Air Canada Logo
10:40 am - 10:19 am
GCM
-
ORD
23h 39m
2 stops
Air Canada Logo
8:45 am - 11:30 am
ORD
-
GCM
26h 45m
2 stops
$436Air Canada
Sat, Sep 5 - Wed, Sep 9
Air Canada Logo
1:10 pm - 9:00 am
GCM
-
ORD
20h 50m
1 stop
Air Canada Logo
4:00 pm - 12:00 pm
ORD
-
GCM
19h 00m
1 stop
$457Air Canada
Sat, Nov 7 - Thu, Nov 12
Air Canada Logo
1:10 pm - 9:00 am
GCM
-
ORD
20h 50m
1 stop
Air Canada Logo
3:55 pm - 12:00 pm
ORD
-
GCM
19h 05m
2 stops
$460Air Canada
Sat, Nov 7 - Thu, Nov 12
Air Canada Logo
1:10 pm - 9:59 pm
GCM
-
ORD
9h 49m
1 stop
Air Canada Logo
8:00 am - 12:00 pm
ORD
-
GCM
27h 00m
1 stop
$590Air Canada
Tue, Dec 1 - Thu, Dec 31
United Airlines Logo
5:45 pm - 9:11 pm
GCM
-
ORD
28h 26m
1 stop
United Airlines Logo
2:15 pm - 4:30 pm
ORD
-
GCM
25h 15m
1 stop
$602United Airlines
Fri, Nov 6 - Mon, Nov 9
Multiple Airlines Logo
12:25 pm - 7:44 am
GCM
-
ORD
43h 19m
2 stops
Multiple Airlines Logo
8:40 pm - 10:25 am
ORD
-
GCM
37h 45m
2 stops
$608Multiple Airlines
Thu, Oct 8 - Mon, Oct 12
American Airlines Logo
12:40 pm - 9:26 pm
GCM
-
ORD
8h 46m
1 stop
American Airlines Logo
5:22 am - 11:00 am
ORD
-
GCM
5h 38m
1 stop
$611American Airlines
Thu, Oct 8 - Tue, Oct 13
United Airlines Logo
5:45 pm - 5:05 pm
GCM
-
ORD
24h 20m
1 stop
United Airlines Logo
8:45 am - 1:45 pm
ORD
-
GCM
4h 00mnonstop
$612United Airlines
Tue, Dec 15 - Tue, Dec 29

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United Airlines flights from Cayman Islands to Chicago O'Hare Intl Airport

Our best United Airlines deals on Cayman Islands to Chicago O'Hare Intl Airport flight tickets
United Airlines
Nov 6
GCM5:45 pmGeorge Town Owen Roberts Intl
28h 26m
1 stop
ORD9:11 pmChicago O'Hare Intl
Nov 9
ORD2:15 pmChicago O'Hare Intl
25h 15m
1 stop
GCM4:30 pmGeorge Town Owen Roberts Intl
$602
United Airlines
Dec 15
GCM5:45 pmGeorge Town Owen Roberts Intl
24h 20m
1 stop
ORD5:05 pmChicago O'Hare Intl
Dec 29
ORD8:45 amChicago O'Hare Intl
4h 00m
GCM1:45 pmGeorge Town Owen Roberts Intl
$612
United Airlines
Dec 1
GCM5:45 pmGeorge Town Owen Roberts Intl
15h 02m
1 stop
ORD7:47 amChicago O'Hare Intl
Dec 31
ORD8:45 amChicago O'Hare Intl
4h 00m
GCM1:45 pmGeorge Town Owen Roberts Intl
$652

American Airlines flights from Cayman Islands to Chicago O'Hare Intl Airport

Our best American Airlines deals on Cayman Islands to Chicago O'Hare Intl Airport flight tickets
American Airlines
Oct 8
GCM12:40 pmGeorge Town Owen Roberts Intl
8h 46m
1 stop
ORD9:26 pmChicago O'Hare Intl
Oct 13
ORD5:22 amChicago O'Hare Intl
5h 38m
1 stop
GCM11:00 amGeorge Town Owen Roberts Intl
$611
American Airlines
Oct 7
GCM1:25 pmGeorge Town Owen Roberts Intl
9h 56m
2 stops
ORD11:21 pmChicago O'Hare Intl
Oct 12
ORD5:22 amChicago O'Hare Intl
5h 38m
1 stop
GCM11:00 amGeorge Town Owen Roberts Intl
$616
American Airlines
Nov 6
GCM3:14 pmGeorge Town Owen Roberts Intl
8h 54m
1 stop
ORD11:08 pmChicago O'Hare Intl
Nov 9
ORD5:00 amChicago O'Hare Intl
14h 20m
1 stop
GCM8:20 pmGeorge Town Owen Roberts Intl
$646

momondo Fare Finder

 
Customize your flight search to find flights from Cayman Islands to Chicago O'Hare Intl Airport 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, momondo users made 832,500 searches. Data last updated June 20, 2026.
Use the filters below to find and compare flights from the Cayman Islands to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Sat 9/5

10:40 am-1:22 pm

1 stop26h 42m

Chicago O'Hare Intl

Wed 9/9

3:45 pm-11:30 am

1 stop19h 45m

$430

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Sat 9/5

10:40 am-10:19 am

2 stops23h 39m

Chicago O'Hare Intl

Wed 9/9

2:15 pm-11:30 am

1 stop21h 15m

$433

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Sat 9/5

10:40 am-10:19 am

2 stops23h 39m

Chicago O'Hare Intl

Wed 9/9

8:45 am-11:30 am

2 stops26h 45m

$436

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Sat 11/7

1:10 pm-9:00 am

1 stop20h 50m

Chicago O'Hare Intl

Thu 11/12

4:00 pm-12:00 pm

1 stop19h 00m

$457

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Sat 11/7

1:10 pm-9:00 am

1 stop20h 50m

Chicago O'Hare Intl

Thu 11/12

3:55 pm-12:00 pm

2 stops19h 05m

$460

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Tue 12/1

1:10 pm-9:59 pm

1 stop9h 49m

Chicago O'Hare Intl

Thu 12/31

8:00 am-12:00 pm

1 stop27h 00m

$590

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Fri 11/6

5:45 pm-9:11 pm

1 stop28h 26m

Chicago O'Hare Intl

Mon 11/9

2:15 pm-4:30 pm

1 stop25h 15m

$602

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Thu 10/8

12:25 pm-7:44 am

2 stops43h 19m

Chicago O'Hare Intl

Mon 10/12

8:40 pm-10:25 am

2 stops37h 45m

$608
Quickest round-trip

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Thu 10/8

12:40 pm-9:26 pm

1 stop8h 46m

Chicago O'Hare Intl

Tue 10/13

5:22 am-11:00 am

1 stop5h 38m

$611

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Tue 12/15

5:45 pm-5:05 pm

1 stop24h 20m

Chicago O'Hare Intl

Tue 12/29

8:45 am-1:45 pm

Nonstop4h 00m

$612

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Cayman Islands to Chicago O'Hare Intl Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Chicago O'Hare Intl Airport?

The month of May is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Cayman Islands averaging around $372.

What is the cheapest day to depart on your flight to Chicago O'Hare Intl Airport?

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Sunday when prices can be found for as low as $381. This is often the case because there is less demand to fly during this day of the week. On the other hand, Friday is the most expensive day to depart from Cayman Islands because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $2,559.

What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?

Flying to Chicago O'Hare Intl Airport from Cayman Islands at noon is the least expensive time of day to depart. momondo users have found prices as low as $513 when looking at flights departing at noon. Try not to purchase tickets in the afternoon because they tend to be around $707. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Cayman Islands to Chicago O'Hare Intl flight route?

Fly from George Town Owen Roberts Intl to Chicago O'Hare Intl for the best Cayman Islands - Chicago O'Hare Intl flight prices

What cabin class options are available on Cayman Islands to Chicago O'Hare Intl Airport flights?

There are 2 cabin classes available to choose from on Cayman Islands to Chicago O'Hare Intl Airport flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Cayman Islands to Chicago O'Hare Intl Airport flights?

No. A direct flight is the cheapest option for a flight between Cayman Islands to Chicago O'Hare Intl Airport.

Cheap Cayman Islands to Chicago O'Hare Intl Airport flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Cayman Islands to Chicago O'Hare Intl Airport

Fastest flight time

8h 20m

Direct flights

Sun
The fastest flight from Cayman Islands to Chicago O'Hare Intl Airport takes 8h 20m
Direct flights go from Cayman Islands to Chicago O'Hare Intl Airport on Sunday. There are no airlines offering direct flights.
Search flight deals

Frequently asked questions about flying from the Cayman Islands to Chicago O'Hare Intl Airport

  • When did momondo last update prices for flights from Cayman Islands to Chicago O'Hare Intl Airport?

    Prices for flights from Cayman Islands to Chicago O'Hare Intl Airport are updated daily.

  • How many operators does momondo search for flights from Cayman Islands to Chicago O'Hare Intl Airport?

  • How old do you have to be to fly from Cayman Islands to Chicago O'Hare Intl Airport?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Cayman Islands to Chicago O'Hare Intl Airport.

  • What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

    The necessary travel and health documents for your Chicago O'Hare Intl Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Cayman Islands to Chicago O'Hare Intl Airport?

Best airlines flying from Cayman Islands to Chicago O'Hare Intl Airport

Compare and see reviews for airlines that fly from Cayman Islands to Chicago O'Hare Intl Airport with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $389Free CancellationRating
7.1
11,715 reviews
Search American Airlines flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lake Geneva
Schaumburg
South Haven
Rockford
Merrillville
Gurnee
Rosemont
Naperville
Orland Park
Oak Brook
New Buffalo
Joliet
Kenosha
Aurora
Hammond
Racine
Janesville
Evanston
Elgin
South Holland

Why use momondo?

Why should I use momondo to find a flight deal from Cayman Islands to Chicago?

It is quick and easy to find Cayman Islands to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

Can I find flights from Cayman Islands to Chicago with flexible booking policies on momondo?

Flights from Cayman Islands to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Cayman Islands to Chicago?

momondo provides multiple filters to help you find the best flight to Chicago from Cayman Islands. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Cayman Islands to Chicago right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Chicago from Cayman Islands. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

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