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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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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
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 - 12:05 am
GCM
-
MDW
11h 00m
1 stop
Southwest Logo
5:35 am - 12:10 pm
MDW
-
GCM
6h 35m
1 stop
$422Southwest
Thu, Apr 23 - Mon, Apr 27
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
12:25 pm - 10:18 am
GCM
-
ORD
21h 53m
2 stops
Air Canada Logo
8:20 pm - 11:25 am
ORD
-
GCM
15h 05m
1 stop
$426Air Canada
Mon, May 11 - Wed, May 27
Southwest Logo
1:05 pm - 11:30 pm
GCM
-
MDW
10h 25m
2 stops
Southwest Logo
5:35 am - 12:10 pm
MDW
-
GCM
6h 35m
1 stop
$427Southwest
Thu, Apr 23 - Mon, Apr 27
Multiple Airlines Logo
4:45 pm - 9:50 am
GCM
-
ORD
17h 05m
1 stop
Multiple Airlines Logo
4:15 pm - 11:10 am
ORD
-
GCM
18h 55m
1 stop
$440Multiple Airlines
Mon, Apr 13 - Mon, Apr 20
Multiple Airlines Logo
4:45 pm - 9:50 am
GCM
-
ORD
17h 05m
1 stop
Multiple Airlines Logo
3:45 pm - 11:10 am
ORD
-
GCM
19h 25m
2 stops
$444Multiple Airlines
Mon, Apr 13 - Mon, Apr 20
Air Canada Logo
12:25 pm - 9:05 am
GCM
-
ORD
20h 40m
1 stop
Air Canada Logo
8:20 pm - 11:25 am
ORD
-
GCM
15h 05m
1 stop
$448Air Canada
Mon, May 11 - Wed, May 27
Multiple Airlines Logo
8:00 am - 12:22 am
GCM
-
ORD
16h 22m
1 stop
Multiple Airlines Logo
5:05 am - 12:20 pm
ORD
-
GCM
7h 15m
1 stop
$451Multiple Airlines
Fri, Mar 27 - Sat, Apr 4

Air Canada flights from Cayman Islands to Chicago

Our best Air Canada deals on Cayman Islands to Chicago 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

Our best Spirit Airlines deals on Cayman Islands to Chicago 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 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 that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

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 - MDW

GCMMDW

George Town Owen Roberts Intl

Thu 4/23

1:05 pm-12:05 am

1 stop11h 00m

Chicago Midway

Mon 4/27

5:35 am-12:10 pm

1 stop6h 35m

$422

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

Mon 5/11

12:25 pm-10:18 am

2 stops21h 53m

Chicago O'Hare Intl

Wed 5/27

8:20 pm-11:25 am

1 stop15h 05m

$426

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Thu 4/23

1:05 pm-11:30 pm

2 stops10h 25m

Chicago Midway

Mon 4/27

5:35 am-12:10 pm

1 stop6h 35m

$427

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Mon 4/13

4:45 pm-9:50 am

1 stop17h 05m

Chicago O'Hare Intl

Mon 4/20

4:15 pm-11:10 am

1 stop18h 55m

$440

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Mon 4/13

4:45 pm-9:50 am

1 stop17h 05m

Chicago O'Hare Intl

Mon 4/20

3:45 pm-11:10 am

2 stops19h 25m

$444

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Mon 5/11

12:25 pm-9:05 am

1 stop20h 40m

Chicago O'Hare Intl

Wed 5/27

8:20 pm-11:25 am

1 stop15h 05m

$448

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Fri 3/27

8:00 am-12:22 am

1 stop16h 22m

Chicago O'Hare Intl

Sat 4/4

5:05 am-12:20 pm

1 stop7h 15m

$451

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

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?

The cheapest day to depart on your flight to Chicago 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. When flying out on a Tuesday, the most expensive travel day of the week, you can expect to see flight prices from Cayman Islands to Chicago for around $1,469.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is at noon. Flights from Cayman Islands to Chicago during this time can be as low as $497. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $707.

What is the cheapest Cayman Islands to Chicago flight route?

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

What cabin class options are available on Cayman Islands to Chicago flights?

There are 2 cabin classes available to choose from on Cayman Islands to Chicago 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 flights?

You could potentially save up to 44% on your flight if you consider stops on a Cayman Islands to Chicago flight.

Cheap Cayman Islands to Chicago flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Cayman Islands to Chicago

Best Price Found

$220

Fastest flight time

4h 23m

Direct flights

Every day

Airports in Chicago

3 airports
The best one-way flight to Chicago from Cayman Islands in the past 72 hours is $220. The best round-trip flight deal from Cayman Islands to Chicago found on momondo in the last 72 hours is $454.
The fastest flight from Cayman Islands to Chicago takes 4h 23m
Direct flights go from Cayman Islands to Chicago every day.
There are 3 airports in Chicago. From Cayman Islands there are direct flights to Chicago O'Hare Intl (ORD).
Search flight deals

  • When did momondo last update prices for flights from Cayman Islands to Chicago?

    Prices for flights from Cayman Islands to Chicago are refreshed on a daily basis.

  • How old do you have to be to fly from Cayman Islands to Chicago?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Cayman Islands to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The necessary travel and health documents for your Chicago 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?

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Valparaiso
Schererville
Munster
Crown Point
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

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

Finding the right flight to Chicago from Cayman Islands is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.

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 offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Cayman Islands to Chicago.

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

Yes. momondo can track prices for Cayman Islands to Chicago flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport