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Greater Chicagoland

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Real Estate Agent with Jameson Sotheby's International Realty

I live in Evanston, which is the first suburb north of Chicago, IL, in an area known in our region as 'Greater Chicagoland'.  The entire area that surrounds Chicago (also known as the 'collar counties' that surround Chicago's "Cook County").

I don't know of any other community that speaks of itself in such terms.  We don't talk about New Yorkland, or San Franciscoland.  Houstonland, People who live in distant communities such as Naperville, which is over 30 miles from Chicago proper, calls itself a part of Chicagoland.  When traveling out of state, and people ask where we're from, we don't automatically say we're from Skokie, or Cicero... we say Chicago... with a modicum of pride.

According to TimeOut magazine, Chicago was voted as one of the top best cities in the world (#11).  I know, I know... you hear all the negative press from all the politicians... it's mostly bluster, and those of us who actually live here tend to just ignore it.

Chicago is a beautiful city. Property values continue to hold their own. Inventory is low and well-priced homes are still selling quickly with multiple offers and often over list price and show no signs of slowing down.  Greater Chicagoland is living up to the hype.

Comments(9)

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Liz and Bill Spear
Transaction Alliance 513.520.5305 www.WarrenCountyOhioRealEstate.com - Mason, OH
Transaction Alliance Cincinnati & Dayton suburbs

I've seen the term Chicagoland but never knew the details you've provided.  Considering how close I've been to Chicago for the last 30 years I should have taken a trip or two, but I've only passed through the airports and during my Navy days spent a chilly month at Great Lakes Naval Station for some specialty training.

Jun 03, 2025 06:21 AM
Alan May

I don't take advantage of my proximity to this great city, as much as I should.  I was actually "in town" last night for dinner, and it reminded me what a magnificent city it truly is.

Jun 03, 2025 06:27 AM
Nick Vandekar, 610-203-4543
Realty ONE Group Advocates 484-237-2055 - Downingtown, PA
Selling the Main Line & Chester County

I have been a couple of times to Chicago but never saw that park, it looks amazing. And I have never heard the term Chicagoland.

Jun 03, 2025 07:04 AM
Alan May

It's very much a regional nickname.  So I'm not surprised you haven't heard it.

Jun 04, 2025 12:23 PM
Michael Jacobs
Pasadena, CA
Pasadena And Southern California 818.516.4393

Hello Alan - while it's been years since visiting Chicagoland, my memories are favorable overall.  It does get cold - very cold as I first learned on my initial visit in January 1982.  Travelling there for business as well as for personal reasons showed me a vibrant city filled with lots of things to discover.  In the center of the city and beyond.  

Jun 03, 2025 07:12 AM
Alan May

Chicago is a great environment for business, and while we do get cold, we're not nearly one of the coldest.  New York gets a lot colder than we do.

Jun 04, 2025 12:24 PM
Ed Silva, 203-206-0754
203-206-0754 - Waterbury, CT
Retired Real Estate Broker

I have some great memories of traveling into Chicago on business back in the day 

not so much to view real estate as for the bi-annual trade shows downtow

Jun 03, 2025 08:03 AM
Alan May

We do have some great trade shows. McCormick Place has a monopoly on trade shows.

Jun 04, 2025 12:25 PM
Patricia Feager
Appraisal Review Board, Denton County, TX - Flower Mound, TX
Licensed to April 2027

Alan May - Ah! You're talking my language! For the first 25 years of my life, I was a true Chicago gal from Cook County. I was always a bus, subway, or El away from Grant Park, the three beaches, Michigan Avenue, Museums, downtown/Office Skyscrapers, or Lincoln Zoo. Then came the big move to Lake County where I worked at Abbott Laboratories and remained for an additional 20 years until I moved to TX. However, I had relatives and friends in all six counties on your map. All my life, there was a reason to go back to sweet home Chicago. 

Jun 03, 2025 10:01 AM
Alan May

You're preaching to the choir, Ms. Feager.

Jun 04, 2025 12:25 PM
Kathy Streib
Cypress, TX
Retired Home Stager/Redesign

HI Alan- I was in Chicago once for a trade show. It was held the Monday after Thanksgiving at McCormick Place. I stayed in a small hotel one block off the main street with all of the stores. When the plane landed, it had snowed, and I was like a kid in a candy store.  After the show, I dropped my stuff off in my hotel room and headed out to shop. I never worried about a thing being out there at night. (of course, this was about 15 years ago,)

BTW- not quite like Chicagoland but we live in Cypress TX , just northwest of Houston proper but when i'm asked, I'm from Houston. 

Jun 03, 2025 05:21 PM
Alan May

"right off the main street".. sounds like you're talking about Michigan Avenue.

Jun 04, 2025 12:26 PM
Dorie Dillard Austin TX
Coldwell Banker Realty ~ 512.750.6899 - Austin, TX
NW Austin ~ Canyon Creek and Spicewood/Balcones

Good evening Alan,

Wow I leaned a lot from your post and sense your pride (as it should be) and understand you are from Greater Chicagoland! Any city that can tout their property values continue to hold their own, inventory is low and well-priced homes are selling with multiple offers has a lot going for it!

Jun 03, 2025 06:15 PM
Alan May

I've called greater Chicagoland my home since the late 1960's.

Jun 04, 2025 12:27 PM
Lew Corcoran
Better Living Real Estate, LLC - East Bridgewater, MA
Expert guidance. Exceptional results.

Thanks so much for sharing this insightful peek into Greater Chicagoland, Alan May. I really appreciate your perspective and the pride you show for your community. It's contagious! 😊 Your post offers a fresh look at what makes the area special, and I'm grateful for the share.

Jun 04, 2025 08:00 AM
Alan May

I'm happy to share, Lew.

Jun 04, 2025 12:28 PM
Anna "Banana" Kruchten
Retired Broker/Owner - Phoenix, AZ
602-380-4886

Alan Chicago is a wonderful town!'ve been there many times with family meetups there for years.  My first ride in a jet when I was in grade school was to Chicago with my Dad on one of his business  trips.  We stayed at the Sir Francis Drake ( I think) and that was so cool, including the Door Man who was so good to me!  And I loved touring all the FLW homes and of course enjoying a few  steak houses too!

Jun 04, 2025 03:14 PM
Alan May

Well, we don't call it the Sir Francis... we just call it the Drake Hotel.  One of the most beautiful hotels on the Magnificent Mile in Downtown Chicago.  One of their great claims to fame is the bar in the hotel has Joe Demagio and Marilyn Monroe's initials carved into it from when they stayed their on their honeymoon.


It's a remarkable hotel.  I'm glad you enjoyed it.

Jun 15, 2025 05:34 AM