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Cheap flights from Grand Cayman to Chicago from $227

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Grand Cayman 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.
1 adult
1 adult, Economy, 0 bags

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Cheap round-trip flights

Enter your travel dates to find the best prices.
Air Canada Logo
12:25 pm - 2:55 pm
GCM
-
ORD
26h 30m
1 stop
Air Canada Logo
8:40 pm - 11:25 am
ORD
-
GCM
14h 45m
1 stop
$345Air Canada
Mon, Jun 15 - Sun, Jun 21
Air Canada Logo
12:25 pm - 7:45 am
GCM
-
ORD
19h 20m
2 stops
Air Canada Logo
8:40 pm - 11:25 am
ORD
-
GCM
14h 45m
1 stop
$350Air Canada
Mon, Jun 15 - Sun, Jun 21
Air Canada Logo
12:25 pm - 12:11 pm
GCM
-
ORD
23h 46m
2 stops
Air Canada Logo
6:22 pm - 11:25 am
ORD
-
GCM
17h 03m
2 stops
$355Air Canada
Mon, Jun 15 - Sun, Jun 21
Air Canada Logo
12:25 pm - 9:00 am
GCM
-
ORD
20h 35m
1 stop
Air Canada Logo
8:40 pm - 9:45 am
ORD
-
GCM
13h 05m
1 stop
$373Air Canada
Thu, Jun 11 - Fri, Jun 26
Air Canada Logo
12:25 pm - 7:45 am
GCM
-
ORD
19h 20m
2 stops
Air Canada Logo
8:40 pm - 9:45 am
ORD
-
GCM
13h 05m
1 stop
$378Air Canada
Thu, Jun 11 - Fri, Jun 26
Air Canada Logo
11:10 am - 7:58 am
GCM
-
ORD
20h 48m
2 stops
Air Canada Logo
5:57 pm - 10:15 am
ORD
-
GCM
16h 18m
1 stop
$383Air Canada
Fri, Apr 17 - Sun, Apr 26
Southwest Logo
1:05 pm - 11:55 pm
GCM
-
MDW
10h 50m
2 stops
Southwest Logo
5:35 am - 12:10 pm
MDW
-
GCM
6h 35m
1 stop
$476Southwest
Thu, Apr 30 - Mon, May 4
Southwest Logo
1:05 pm - 8:40 pm
GCM
-
MDW
7h 35m
1 stop
Southwest Logo
5:35 am - 12:10 pm
MDW
-
GCM
6h 35m
1 stop
$492Southwest
Thu, Apr 30 - Mon, May 4
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
$506Southwest
Fri, May 1 - Mon, May 4
Delta Logo
1:25 pm - 10:28 pm
GCM
-
MDW
9h 03m
1 stop
Delta Logo
6:00 am - 12:00 pm
MDW
-
GCM
6h 00m
1 stop
$586Delta
Thu, Apr 23 - Wed, Apr 29

Air Canada flights from Grand Cayman to Chicago

Our best Air Canada deals on Grand Cayman to Chicago flight tickets
Air Canada
Jun 15
GCM12:25 pmGeorge Town Owen Roberts Intl
25h 00m
1 stop
ORD1:25 pmChicago O'Hare Intl
Jun 21
ORD8:40 pmChicago O'Hare Intl
14h 45m
1 stop
GCM11:25 amGeorge Town Owen Roberts Intl
$345
Air Canada
Jun 15
GCM12:25 pmGeorge Town Owen Roberts Intl
23h 46m
2 stops
ORD12:11 pmChicago O'Hare Intl
Jun 21
ORD8:40 pmChicago O'Hare Intl
14h 45m
1 stop
GCM11:25 amGeorge Town Owen Roberts Intl
$350
Air Canada
Jun 15
GCM12:25 pmGeorge Town Owen Roberts Intl
23h 46m
2 stops
ORD12:11 pmChicago O'Hare Intl
Jun 21
ORD6:22 pmChicago O'Hare Intl
17h 03m
2 stops
GCM11:25 amGeorge Town Owen Roberts Intl
$355

American Airlines flights from Grand Cayman to Chicago

Our best American Airlines deals on Grand Cayman to Chicago flight tickets
American Airlines
May 1
GCM2:10 pmGeorge Town Owen Roberts Intl
9h 44m
2 stops
ORD11:54 pmChicago O'Hare Intl
May 4
ORD8:46 pmChicago O'Hare Intl
14h 14m
2 stops
GCM11:00 amGeorge Town Owen Roberts Intl
$600
American Airlines
Apr 27
GCM2:10 pmGeorge Town Owen Roberts Intl
10h 15m
1 stop
ORD12:25 amChicago O'Hare Intl
Apr 29
ORD5:00 amChicago O'Hare Intl
8h 10m
2 stops
GCM1:10 pmGeorge Town Owen Roberts Intl
$630
American Airlines
Apr 27
GCM12:00 pmGeorge Town Owen Roberts Intl
11h 54m
2 stops
ORD11:54 pmChicago O'Hare Intl
Apr 29
ORD5:00 amChicago O'Hare Intl
8h 10m
2 stops
GCM1:10 pmGeorge Town Owen Roberts Intl
$650

momondo Fare Finder

 
Customize your flight search to find flights from Grand Cayman 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 April 1, 2026.
Use the filters below to find and compare flights from Grand Cayman to Chicago 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

Mon 6/15

12:25 pm-2:55 pm

1 stop26h 30m

Chicago O'Hare Intl

Sun 6/21

8:40 pm-11:25 am

1 stop14h 45m

$345

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Mon 6/15

12:25 pm-7:45 am

2 stops19h 20m

Chicago O'Hare Intl

Sun 6/21

8:40 pm-11:25 am

1 stop14h 45m

$350

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Mon 6/15

12:25 pm-12:11 pm

2 stops23h 46m

Chicago O'Hare Intl

Sun 6/21

6:22 pm-11:25 am

2 stops17h 03m

$355

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Thu 6/11

12:25 pm-9:00 am

1 stop20h 35m

Chicago O'Hare Intl

Fri 6/26

8:40 pm-9:45 am

1 stop13h 05m

$373

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Thu 6/11

12:25 pm-7:45 am

2 stops19h 20m

Chicago O'Hare Intl

Fri 6/26

8:40 pm-9:45 am

1 stop13h 05m

$378

George TownChicago

GCM - ORD

GCMORD

George Town Owen Roberts Intl

Fri 4/17

11:10 am-7:58 am

2 stops20h 48m

Chicago O'Hare Intl

Sun 4/26

5:57 pm-10:15 am

1 stop16h 18m

$383

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Thu 4/30

1:05 pm-11:55 pm

2 stops10h 50m

Chicago Midway

Mon 5/4

5:35 am-12:10 pm

1 stop6h 35m

$476
Quickest round-trip

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Thu 4/30

1:05 pm-8:40 pm

1 stop7h 35m

Chicago Midway

Mon 5/4

5:35 am-12:10 pm

1 stop6h 35m

$492

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Fri 5/1

1:05 pm-12:05 am

1 stop11h 00m

Chicago Midway

Mon 5/4

5:35 am-12:10 pm

1 stop6h 35m

$506

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Thu 4/23

1:25 pm-10:28 pm

1 stop9h 03m

Chicago Midway

Wed 4/29

6:00 am-12:00 pm

1 stop6h 00m

$586

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 Grand Cayman 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 $381. This is often the case because there is less demand to fly during this day of the week. When flying out on a Wednesday, the most expensive travel day of the week, you can expect to see flight prices from Grand Cayman to Chicago for around $2,042.

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 Grand Cayman to Chicago during this time can be as low as $513. 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 Grand Cayman to Chicago flight route?

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

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

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

No. A direct flight is the cheapest option for a flight between Grand Cayman to Chicago.

Cheap Grand Cayman to Chicago flight deals and tips

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

Fastest flight time

4h 23m

Direct flights

Tue, Thu, Fri, Sat and Sun

Airports in Chicago

3 airports
The fastest flight from Grand Cayman to Chicago takes 4h 23m
Direct flights go from Grand Cayman to Chicago on Tuesday, Thursday, Friday, Saturday and Sunday. There are no airlines offering direct flights.
There are 3 airports in Chicago. From Grand Cayman there are direct flights to Chicago O'Hare Intl (ORD).
Search flight deals

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

    Prices for flights from Grand Cayman to Chicago were last updated today.

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

    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 Grand Cayman 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 Grand Cayman 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
Saint Joseph
Benton Harbor
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 Grand Cayman to Chicago?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Grand Cayman to Chicago. Millions of users trust and use momondo every year so you are in good hands.

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

Flights from Grand Cayman 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 Grand Cayman 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 Grand Cayman to Chicago.

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

Yes. momondo can track prices for Grand Cayman 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