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Cheap flights from the Cayman Islands to Chicago from $161

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 2/7. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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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
12:25 pm - 9:00 am
GCM
-
ORD
20h 35m
1 stop
Air Canada Logo
8:20 pm - 11:30 am
ORD
-
GCM
15h 10m
1 stop
$321Air Canada
jue., jun. 11 - dom., jun. 14
Air Canada Logo
12:25 pm - 8:05 am
GCM
-
ORD
19h 40m
2 stops
Air Canada Logo
8:20 pm - 11:30 am
ORD
-
GCM
15h 10m
1 stop
$329Air Canada
jue., jun. 11 - dom., jun. 14
Multiple Airlines Logo
11:30 am - 8:18 am
GCM
-
ORD
21h 48m
1 stop
Multiple Airlines Logo
9:18 am - 4:05 pm
ORD
-
GCM
29h 47m
1 stop
$355Multiple Airlines
mar., feb. 10 - mar., feb. 17
Multiple Airlines Logo
11:30 am - 9:12 am
GCM
-
ORD
22h 42m
2 stops
Multiple Airlines Logo
9:18 am - 4:05 pm
ORD
-
GCM
29h 47m
1 stop
$383Multiple Airlines
mar., feb. 10 - mar., feb. 17
Air Canada Logo
1:30 pm - 6:55 pm
GCM
-
ORD
30h 25m
2 stops
Air Canada Logo
6:04 pm - 12:25 pm
ORD
-
GCM
41h 21m
2 stops
$405Air Canada
mar., feb. 10 - mar., feb. 17
Multiple Airlines Logo
8:50 am - 7:54 am
GCM
-
ORD
24h 04m
2 stops
Multiple Airlines Logo
8:16 pm - 1:43 pm
ORD
-
GCM
16h 27m
1 stop
$415Multiple Airlines
sáb., feb. 21 - mié., feb. 25
American Airlines Logo
8:50 am - 11:08 pm
GCM
-
ORD
15h 18m
1 stop
American Airlines Logo
9:36 am - 2:35 pm
ORD
-
GCM
3h 59mnonstop
$449American Airlines
mar., feb. 10 - mar., feb. 17
Air Canada Logo
12:25 pm - 8:05 am
GCM
-
ORD
19h 40m
2 stops
Air Canada Logo
3:40 pm - 11:30 am
ORD
-
GCM
19h 50m
2 stops
$451Air Canada
jue., jun. 11 - dom., jun. 14
Multiple Airlines Logo
11:25 am - 5:03 pm
GCM
-
ORD
6h 38m
1 stop
Multiple Airlines Logo
8:00 am - 12:25 pm
ORD
-
GCM
27h 25m
1 stop
$473Multiple Airlines
sáb., feb. 21 - mié., feb. 25
Multiple Airlines Logo
11:25 am - 7:54 am
GCM
-
ORD
21h 29m
3 stops
Multiple Airlines Logo
2:00 pm - 12:25 pm
ORD
-
GCM
21h 25m
1 stop
$522Multiple Airlines
sáb., feb. 21 - mié., feb. 25

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
Feb 10
GCM8:50 amGeorge Town Owen Roberts Intl
15h 18m
1 stop
ORD11:08 pmChicago O'Hare Intl
Feb 17
ORD9:36 amChicago O'Hare Intl
3h 59m
GCM2:35 pmGeorge Town Owen Roberts Intl
$449
American Airlines
Jan 22
GCM12:50 pmGeorge Town Owen Roberts Intl
7h 32m
1 stop
ORD7:22 pmChicago O'Hare Intl
Jan 26
ORD9:31 amChicago O'Hare Intl
4h 04m
GCM2:35 pmGeorge Town Owen Roberts Intl
$509
American Airlines
Feb 21
GCM4:00 pmGeorge Town Owen Roberts Intl
4h 20m
ORD7:20 pmChicago O'Hare Intl
Feb 25
ORD9:36 amChicago O'Hare Intl
3h 59m
GCM2:35 pmGeorge Town Owen Roberts Intl
$568

Air Canada flights from Cayman Islands to Chicago O'Hare Intl Airport

Our best Air Canada deals on Cayman Islands to Chicago O'Hare Intl Airport flight tickets
Air Canada
Jun 11
GCM12:25 pmGeorge Town Owen Roberts Intl
20h 35m
1 stop
ORD9:00 amChicago O'Hare Intl
Jun 14
ORD8:20 pmChicago O'Hare Intl
15h 10m
1 stop
GCM11:30 amGeorge Town Owen Roberts Intl
$321
Air Canada
Jun 11
GCM12:25 pmGeorge Town Owen Roberts Intl
19h 40m
2 stops
ORD8:05 amChicago O'Hare Intl
Jun 14
ORD8:20 pmChicago O'Hare Intl
15h 10m
1 stop
GCM11:30 amGeorge Town Owen Roberts Intl
$329
Air Canada
Feb 10
GCM1:30 pmGeorge Town Owen Roberts Intl
30h 25m
2 stops
ORD6:55 pmChicago O'Hare Intl
Feb 17
ORD6:04 pmChicago O'Hare Intl
41h 21m
2 stops
GCM12:25 pmGeorge Town Owen Roberts Intl
$405

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 enero 14, 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

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

jue. 6/11

12:25 pm-9:00 am

1 stop20h 35m

Chicago O'Hare Intl

dom. 6/14

8:20 pm-11:30 am

1 stop15h 10m

$321

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

jue. 6/11

12:25 pm-8:05 am

2 stops19h 40m

Chicago O'Hare Intl

dom. 6/14

8:20 pm-11:30 am

1 stop15h 10m

$329

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

mar. 2/10

11:30 am-8:18 am

1 stop21h 48m

Chicago O'Hare Intl

mar. 2/17

9:18 am-4:05 pm

1 stop29h 47m

$355

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

mar. 2/10

11:30 am-9:12 am

2 stops22h 42m

Chicago O'Hare Intl

mar. 2/17

9:18 am-4:05 pm

1 stop29h 47m

$383

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

mar. 2/10

1:30 pm-6:55 pm

2 stops30h 25m

Chicago O'Hare Intl

mar. 2/17

6:04 pm-12:25 pm

2 stops41h 21m

$405

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

sáb. 2/21

8:50 am-7:54 am

2 stops24h 04m

Chicago O'Hare Intl

mié. 2/25

8:16 pm-1:43 pm

1 stop16h 27m

$415

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

mar. 2/10

8:50 am-11:08 pm

1 stop15h 18m

Chicago O'Hare Intl

mar. 2/17

9:36 am-2:35 pm

Nonstop3h 59m

$449

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

jue. 6/11

12:25 pm-8:05 am

2 stops19h 40m

Chicago O'Hare Intl

dom. 6/14

3:40 pm-11:30 am

2 stops19h 50m

$451

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

sáb. 2/21

11:25 am-5:03 pm

1 stop6h 38m

Chicago O'Hare Intl

mié. 2/25

8:00 am-12:25 pm

1 stop27h 25m

$473

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

sáb. 2/21

11:25 am-7:54 am

3 stops21h 29m

Chicago O'Hare Intl

mié. 2/25

2:00 pm-12:25 pm

1 stop21h 25m

$522

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 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 $373. This is often the case because there is less demand to fly during this day of the week. On the other hand, Wednesday 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 $1,867.

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 flights?

There are 2 cabin classes available to choose from on Cayman Islands to Chicago O'Hare Intl 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?

You could potentially save up to 36% on your flight if you consider stops on a Cayman Islands to Chicago O'Hare Intl Airport flight.

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

4h 14m

Direct flights

Mon, Tue, Thu, Fri, Sat and Sun
The fastest flight from Cayman Islands to Chicago O'Hare Intl Airport takes 4h 14m
Direct flights go from Cayman Islands to Chicago O'Hare Intl Airport on Monday, Tuesday, Thursday, Friday, Saturday and Sunday. There are no airlines offering direct flights.
Search flight deals

  • 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 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?

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
Kenosha
New Buffalo
Joliet
Oak Brook
Orland Park
Racine
Hammond
Janesville
Tinley Park
Elgin
Aurora
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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