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Cheap flights from the Cayman Islands to Chicago from $212

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 12/6. 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.
United Airlines Logo
2:50 pm - 6:04 pmGCM-ORD
4h 14mnonstop
United Airlines Logo
8:45 am - 1:45 pmORD-GCM
4h 00mnonstop
$338United Airlines
Find Deal
Thu, Dec 18 - Thu, Dec 25
American Airlines Logo
4:09 pm - 7:19 pmGCM-ORD
4h 10mnonstop
American Airlines Logo
6:35 pm - 12:05 pmORD-GCM
16h 30m1 stop
$342American Airlines
Find Deal
Sat, Dec 6 - Tue, Dec 9
United Airlines Logo
5:45 pm - 9:16 pmGCM-ORD
28h 31m1 stop
United Airlines Logo
8:49 am - 4:30 pmORD-GCM
6h 41m1 stop
$343United Airlines
Find Deal
Tue, Dec 2 - Tue, Dec 9
Spirit Airlines Logo
5:56 pm - 12:09 amGCM-ORD
7h 13m1 stop
Spirit Airlines Logo
9:14 pm - 1:45 pmORD-GCM
39h 31m2 stops
$346Spirit Airlines
Find Deal
Sat, Dec 6 - Tue, Dec 9
American Airlines Logo
8:45 am - 12:37 amGCM-ORD
16h 52m1 stop
American Airlines Logo
6:35 pm - 12:05 pmORD-GCM
16h 30m1 stop
$352American Airlines
Find Deal
Sat, Dec 6 - Tue, Dec 9
American Airlines Logo
1:25 pm - 11:39 pmGCM-ORD
11h 14m2 stops
American Airlines Logo
5:00 am - 2:44 pmORD-GCM
8h 44m2 stops
$357American Airlines
Find Deal
Mon, Dec 8 - Fri, Dec 12
Multiple Airlines Logo
5:56 pm - 12:09 amGCM-ORD
7h 13m1 stop
Multiple Airlines Logo
7:10 am - 4:05 pmORD-GCM
31h 55m3 stops
$386Multiple Airlines
Find Deal
Sat, Dec 6 - Tue, Dec 9
American Airlines Logo
9:00 am - 5:52 pmGCM-ORD
9h 52m2 stops
American Airlines Logo
8:55 pm - 12:05 pmORD-GCM
14h 10m2 stops
$407American Airlines
Find Deal
Tue, Dec 2 - Tue, Dec 9
Multiple Airlines Logo
5:56 pm - 8:09 pmGCM-ORD
27h 13m3 stops
Multiple Airlines Logo
9:14 pm - 4:05 pmORD-GCM
17h 51m2 stops
$429Multiple Airlines
Find Deal
Sat, Dec 6 - Tue, Dec 9
Spirit Airlines Logo
2:40 pm - 7:02 pmGCM-ORD
29h 22m3 stops
Spirit Airlines Logo
7:30 am - 1:45 pmORD-GCM
5h 15m1 stop
$528Spirit Airlines
Find Deal
Thu, Dec 18 - Thu, Dec 25

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
Dec 18
GCM2:50 pmGeorge Town Owen Roberts Intl
4h 14m
ORD6:04 pmChicago O'Hare Intl
Dec 25
ORD8:45 amChicago O'Hare Intl
4h 00m
GCM1:45 pmGeorge Town Owen Roberts Intl
$338
Find similar
United Airlines
Dec 2
GCM5:45 pmGeorge Town Owen Roberts Intl
28h 31m
1 stop
ORD9:16 pmChicago O'Hare Intl
Dec 9
ORD8:49 amChicago O'Hare Intl
6h 41m
1 stop
GCM4:30 pmGeorge Town Owen Roberts Intl
$343
Find similar
United Airlines
Mar 10
GCM1:50 pmGeorge Town Owen Roberts Intl
4h 14m
ORD6:04 pmChicago O'Hare Intl
Mar 11
ORD9:05 pmChicago O'Hare Intl
18h 25m
1 stop
GCM3:30 pmGeorge Town Owen Roberts Intl
$661
Find similar

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
Dec 6
GCM4:09 pmGeorge Town Owen Roberts Intl
4h 10m
ORD7:19 pmChicago O'Hare Intl
Dec 9
ORD6:35 pmChicago O'Hare Intl
16h 30m
1 stop
GCM12:05 pmGeorge Town Owen Roberts Intl
$342
Find similar
American Airlines
Dec 6
GCM8:45 amGeorge Town Owen Roberts Intl
16h 52m
1 stop
ORD12:37 amChicago O'Hare Intl
Dec 9
ORD6:35 pmChicago O'Hare Intl
16h 30m
1 stop
GCM12:05 pmGeorge Town Owen Roberts Intl
$352
Find similar
American Airlines
Dec 8
GCM1:25 pmGeorge Town Owen Roberts Intl
11h 14m
2 stops
ORD11:39 pmChicago O'Hare Intl
Dec 12
ORD5:00 amChicago O'Hare Intl
8h 44m
2 stops
GCM2:44 pmGeorge Town Owen Roberts Intl
$357
Find similar

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 November 5, 2025.
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

Thu 12/18

2:50 pm-6:04 pm

Nonstop4h 14m

Chicago O'Hare Intl

Thu 12/25

8:45 am-1:45 pm

Nonstop4h 00m

$338

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Sat 12/6

4:09 pm-7:19 pm

Nonstop4h 10m

Chicago O'Hare Intl

Tue 12/9

6:35 pm-12:05 pm

1 stop16h 30m

$342

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Tue 12/2

5:45 pm-9:16 pm

1 stop28h 31m

Chicago O'Hare Intl

Tue 12/9

8:49 am-4:30 pm

1 stop6h 41m

$343

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Sat 12/6

5:56 pm-12:09 am

1 stop7h 13m

Chicago O'Hare Intl

Tue 12/9

9:14 pm-1:45 pm

2 stops39h 31m

$346

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Sat 12/6

8:45 am-12:37 am

1 stop16h 52m

Chicago O'Hare Intl

Tue 12/9

6:35 pm-12:05 pm

1 stop16h 30m

$352

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Mon 12/8

1:25 pm-11:39 pm

2 stops11h 14m

Chicago O'Hare Intl

Fri 12/12

5:00 am-2:44 pm

2 stops8h 44m

$357

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Sat 12/6

5:56 pm-12:09 am

1 stop7h 13m

Chicago O'Hare Intl

Tue 12/9

7:10 am-4:05 pm

3 stops31h 55m

$386

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Tue 12/2

9:00 am-5:52 pm

2 stops9h 52m

Chicago O'Hare Intl

Tue 12/9

8:55 pm-12:05 pm

2 stops14h 10m

$407

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Sat 12/6

5:56 pm-8:09 pm

3 stops27h 13m

Chicago O'Hare Intl

Tue 12/9

9:14 pm-4:05 pm

2 stops17h 51m

$429

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Thu 12/18

2:40 pm-7:02 pm

3 stops29h 22m

Chicago O'Hare Intl

Thu 12/25

7:30 am-1:45 pm

1 stop5h 15m

$528

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 $295. 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?

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

Best Price Found

$387

Fastest flight time

4h 10m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Cayman Islands in the past 72 hours is $387. The best round-trip flight deal from Cayman Islands to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $390.
The fastest flight from Cayman Islands to Chicago O'Hare Intl Airport takes 4h 10m
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
South Haven
Schaumburg
Rockford
Merrillville
Gurnee
Naperville
Rosemont
Kenosha
New Buffalo
Joliet
Oak Brook
Orland Park
Racine
Hammond
Tinley Park
Janesville
Aurora
Elgin
Benton Harbor

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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