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Cheap flights from the Cayman Islands to Chicago from $222

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 6/1. 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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0 bags

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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.
Multiple Airlines Logo
11:30 am - 6:31 pm
GCM
-
ORD
7h 01m
1 stop
Multiple Airlines Logo
4:58 pm - 4:05 pm
ORD
-
GCM
23h 07m
1 stop
$405Multiple Airlines
Tue, Apr 14 - Mon, Apr 20
Air Canada Logo
11:25 am - 8:03 am
GCM
-
ORD
20h 38m
1 stop
Air Canada Logo
6:40 pm - 11:10 am
ORD
-
GCM
16h 30m
1 stop
$416Air Canada
Mon, Mar 30 - Mon, Apr 6
Air Canada Logo
11:25 am - 8:03 am
GCM
-
ORD
20h 38m
1 stop
Air Canada Logo
3:45 pm - 11:10 am
ORD
-
GCM
19h 25m
2 stops
$420Air Canada
Mon, Mar 30 - Mon, Apr 6
Southwest Logo
1:05 pm - 9:55 pm
GCM
-
ORD
8h 50m
1 stop
Southwest Logo
6:00 am - 12:10 pm
ORD
-
GCM
6h 10m
1 stop
$422Southwest
Thu, Apr 23 - Mon, Apr 27
Air Canada Logo
12:30 pm - 9:10 am
GCM
-
ORD
20h 40m
1 stop
Air Canada Logo
6:40 pm - 11:10 am
ORD
-
GCM
16h 30m
1 stop
$431Air Canada
Tue, Mar 31 - Mon, Apr 6
Multiple Airlines Logo
11:30 am - 10:02 am
GCM
-
ORD
22h 32m
2 stops
Multiple Airlines Logo
7:50 am - 9:15 pm
ORD
-
GCM
13h 25m
1 stop
$432Multiple Airlines
Tue, Apr 14 - Mon, Apr 20
Multiple Airlines Logo
11:30 am - 6:31 pm
GCM
-
ORD
7h 01m
1 stop
Multiple Airlines Logo
6:08 pm - 9:15 pm
ORD
-
GCM
27h 07m
2 stops
$434Multiple Airlines
Tue, Apr 14 - Wed, Apr 22
Air Canada Logo
12:30 pm - 9:10 am
GCM
-
ORD
20h 40m
1 stop
Air Canada Logo
3:45 pm - 11:10 am
ORD
-
GCM
19h 25m
2 stops
$435Air Canada
Tue, Mar 31 - Mon, Apr 6
Multiple Airlines Logo
11:30 am - 6:31 pm
GCM
-
ORD
7h 01m
1 stop
Multiple Airlines Logo
7:50 am - 9:35 pm
ORD
-
GCM
13h 45m
1 stop
$437Multiple Airlines
Tue, Apr 14 - Fri, Apr 24
Air Canada Logo
12:30 pm - 12:17 pm
GCM
-
ORD
23h 47m
2 stops
Air Canada Logo
3:45 pm - 11:10 am
ORD
-
GCM
19h 25m
2 stops
$440Air Canada
Tue, Mar 31 - Mon, Apr 6

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
Mar 30
GCM11:25 amGeorge Town Owen Roberts Intl
20h 38m
1 stop
ORD8:03 amChicago O'Hare Intl
Apr 6
ORD6:40 pmChicago O'Hare Intl
16h 30m
1 stop
GCM11:10 amGeorge Town Owen Roberts Intl
$416
Air Canada
Mar 30
GCM11:25 amGeorge Town Owen Roberts Intl
20h 38m
1 stop
ORD8:03 amChicago O'Hare Intl
Apr 6
ORD3:45 pmChicago O'Hare Intl
19h 25m
2 stops
GCM11:10 amGeorge Town Owen Roberts Intl
$420
Air Canada
Mar 31
GCM12:30 pmGeorge Town Owen Roberts Intl
20h 40m
1 stop
ORD9:10 amChicago O'Hare Intl
Apr 6
ORD6:40 pmChicago O'Hare Intl
16h 30m
1 stop
GCM11:10 amGeorge Town Owen Roberts Intl
$431

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

Our best Spirit Airlines deals on Cayman Islands to Chicago O'Hare Intl Airport flight tickets
Spirit Airlines
Mar 5
GCM2:49 pmGeorge Town Owen Roberts Intl
9h 58m
1 stop
ORD11:47 pmChicago O'Hare Intl
Mar 14
ORD6:10 pmChicago O'Hare Intl
18h 47m
1 stop
GCM12:57 pmGeorge Town Owen Roberts Intl
$368
Spirit Airlines
Mar 5
GCM2:49 pmGeorge Town Owen Roberts Intl
7h 24m
1 stop
ORD9:13 pmChicago O'Hare Intl
Mar 14
ORD6:10 pmChicago O'Hare Intl
18h 47m
1 stop
GCM12:57 pmGeorge Town Owen Roberts Intl
$396
Spirit Airlines
Mar 5
GCM2:49 pmGeorge Town Owen Roberts Intl
9h 58m
1 stop
ORD11:47 pmChicago O'Hare Intl
Mar 14
ORD7:31 pmChicago O'Hare Intl
17h 26m
2 stops
GCM12:57 pmGeorge Town Owen Roberts Intl
$423

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 March 4, 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

Tue 4/14

11:30 am-6:31 pm

1 stop7h 01m

Chicago O'Hare Intl

Mon 4/20

4:58 pm-4:05 pm

1 stop23h 07m

$405

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Mon 3/30

11:25 am-8:03 am

1 stop20h 38m

Chicago O'Hare Intl

Mon 4/6

6:40 pm-11:10 am

1 stop16h 30m

$416

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Mon 3/30

11:25 am-8:03 am

1 stop20h 38m

Chicago O'Hare Intl

Mon 4/6

3:45 pm-11:10 am

2 stops19h 25m

$420

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Thu 4/23

1:05 pm-9:55 pm

1 stop8h 50m

Chicago O'Hare Intl

Mon 4/27

6:00 am-12:10 pm

1 stop6h 10m

$422

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Tue 3/31

12:30 pm-9:10 am

1 stop20h 40m

Chicago O'Hare Intl

Mon 4/6

6:40 pm-11:10 am

1 stop16h 30m

$431

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Tue 4/14

11:30 am-10:02 am

2 stops22h 32m

Chicago O'Hare Intl

Mon 4/20

7:50 am-9:15 pm

1 stop13h 25m

$432

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Tue 4/14

11:30 am-6:31 pm

1 stop7h 01m

Chicago O'Hare Intl

Wed 4/22

6:08 pm-9:15 pm

2 stops27h 07m

$434

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Tue 3/31

12:30 pm-9:10 am

1 stop20h 40m

Chicago O'Hare Intl

Mon 4/6

3:45 pm-11:10 am

2 stops19h 25m

$435

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Tue 4/14

11:30 am-6:31 pm

1 stop7h 01m

Chicago O'Hare Intl

Fri 4/24

7:50 am-9:35 pm

1 stop13h 45m

$437

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Tue 3/31

12:30 pm-12:17 pm

2 stops23h 47m

Chicago O'Hare Intl

Mon 4/6

3:45 pm-11:10 am

2 stops19h 25m

$440

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, Tuesday 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 $1,469.

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 $497 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 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 44% 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

Best Price Found

$220

Fastest flight time

4h 23m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Cayman Islands in the past 72 hours is $220. The best round-trip flight deal from Cayman Islands to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $454.
The fastest flight from Cayman Islands to Chicago O'Hare Intl Airport takes 4h 23m
Direct flights go from Cayman Islands to Chicago O'Hare Intl Airport every day.
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
Naperville
Rosemont
New Buffalo
Orland Park
Kenosha
Oak Brook
Joliet
Racine
Janesville
Hammond
Aurora
Tinley Park
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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