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Chicago’s Commercial Real Estate Boom
November 23, 2022

Chicago’s Commercial Real Estate Boom

33 realty
Chicago’s Commercial Real Estate Boom
Chicago's Commercial Real Estate Boom

In his day, Frank Sinatra was America’s coolest crooner. This is what he had to say about Chicago: “…and each time I roam, Chicago is calling me home. Chicago is why I just grin like a clown — it’s my kind of town.” Today, Chicago remains a cool kind of town.

Chicago wasn’t always this way, though. For the past decade, Chicago commercial real estate has seen a boom like no other. Chicago commercial real estate investment is at a record high, and it’s due to a steady stream of corporate relocations, start-up businesses and trendy young professionals who are looking for authentic and unique spaces to work and live. Chicago offers them some of America’s coolest spaces.

Chicago commercial real estate investment is at a record high

Three main economic drivers are at work in Chicago. There’s been a huge growth in technology and other sectors as companies add to their workforce and expand their space. Suburban businesses are moving downtown or adding city satellite offices that are bringing demand for commercial lease space to an all-time high. Foreign investors also recognize Chicago’s commercial real estate values, and are pumping billions of dollars into the city. This is leading to a wave of other companies following the workforce and the talented workers who fill the spaces provided by cool new jobs.


There’s another boom going on in Chicago’s commercial real estate: flexibility and creativity in work and living spaces. Top trend-setting businesses realize the need for innovative spaces that fit corporate cultures, and aim to attract and retain a workforce of the Millennial generation. Young professionals who serve high-tech employers are looking for unique places and experiences. They’re looking to work, live, entertain and enjoy themselves in vibrant neighborhoods — cool spaces like loft apartments, restaurants with exquisite cuisine, cozy cafes, fashionable shops, professional sports venues, top theaters and ample access to public transportation.

Transportation-oriented development is a centerpiece of Chicago's growth plan

From private developers to city government officials and from restauranteurs to concert promoters, the programs and trends for a sustained real estate boom — and its critical Millennial component — are expanding. Transportation-oriented development is a centerpiece of Chicago’s growth plan, along with a dedication to community colleges designed to serve the demands of tech, logistic, healthcare and other growth industries. Chicago’s reputation as a “foodie” and entertainment mecca keeps up with the adventurous, evolving tastes of the Millennials. They’re demanding — and getting — authentic and cool spaces to live, work and play.

Chicago has responded. Chicagoans are thinking differently, rejecting what’s comfortable for what’s bold and what’s safe for what’s unexpected. And it’s paying off!

Today, Chicago has some of the coolest spaces that serve four cultural spheres: tech, cuisine, fashion and entertainment. It wasn’t always that way, so let’s look at a bit of Chicago’s history before seeing where the really cool places are in today’s Chicago.


Chicago wasn’t always the cool, trendy and desired American city it is today. As immigrants moved west, they saw Chicago as a swampy lowland that was unfit for building. It wasn’t until national trade recognized Chicago’s location as a transportation hub between eastern and western America that it came into its own. Railways and canals were built in the heart of Chicago and it became a powerhouse in retail and manufacturing. Chicago began to influence the American economy.

Great Chicago Fire impact on downtown

The Great Chicago Fire of 1871 was a blessing in disguise, as it leveled one-third of the city and allowed the downtown to start from scratch with an efficient design and layout that proves highly effective, even today. Chicago rivaled New York when it came to architecture, and its skyline of skyscrapers boast some of the tallest ever built. The Sears Tower is now the Willis Tower, but the neo-gothic Tribune Tower is still the Tribune Tower.

Some of the greatest American architecture still stands in Chicago — preserved spaces like the Chicago Avenue Pumping Station, The Chicago Merchandise Mart, Chicago’s Home Insurance Building, the John Hancock Building and the Buckingham Fountain.

What would Chicago be without Prohibition and the Speakeasies? Some of the best “green-door” buildings are being revived. They’re vibrantly serving patrons, and some of the spaces where Al Capone and the gangsters fought it out are trendy for foodies and hipsters. As it was in the Roaring ‘20s, Chicago is today’s perfect place for young entrepreneurs to break out.

From rail to road to air, Chicago’s location is ideally suited for sustained growth and connections. Its waterfront has unparalleled public access and the beaches and bike paths create spaces that simply can’t be found in other cities. Its sports teams are legendary and its entertainment unequaled. But what really ties old Chicago to the new and cool Chicago is the people.

Mix New York hustle with mid-western charm, generosity and hospitality, and you get Chicago. It’s the blue-collar past and the urban professionals that make new Chicago what it is. The people make the city, and the city makes the people. Now that’s cool!


Chicago has it all

As trendy spaces go, Chicago is one of the world’s best cities. Whether it’s work, food, arts, entertainment or great living places, Chicago has it all. Combine this with excellent transportation, the booming tech scene and an unmatched financial arena, and it’s a certainty that young professionals will continue flocking to Chicago.

Chicago is the third-largest city in America, yet there are plenty of spaces for people to call home. Many of Chicago’s older areas are reclaimed into the most unique places you can imagine. Here’s a look at the trendiest spaces Chicago has to offer.

  • Lincoln Park — LP is one of the largest areas of Chicago. It’s centrally located, with a 15-minute ride to the Loop and Downtown. Packed with restaurants, LP has great beach access and plenty of parks.
  • Wicker Park — West Chicago could be characterized as a hippy/trendy area, but more and more young professionals realize the value in Wicker Park. For downtown workers, it has excellent train connections and has the best bang for the buck when it comes to rent.
  • Gold Coast — This is the ritzy area of Chicago, and is right next to the “Magnificent Mile,” or Madison Avenue. It’s one of the flashiest, most affluent and most design-friendly streets in America, and is a shopper’s dream. Many new apartments are available here.
  • Old Town — The south side of Chicago is synonymous with organized crime and the mobsters. What used to be a run-down projects area is flourishing with million-dollar homes, streets filled with restaurants, bars and a coming mega-development.
  • Lakeview — “Wrigleyville” has everything young professionals could want. It has easy public transit and a great young bar scene, and is an affordable area of central Chicago.
  • River North — Here is the most expensive part of downtown Chicago, which is filled with well-paid professionals who work long hours and want to be right in the heart of the city. Not surprisingly, it has the best nightlife scene in town.

With so many trendy spaces to live in Chicago, it’s tough to make a decision. Usually, a cool living area goes with a cool workspace, and Chicago has some of the best trend-setting businesses currently out there.


The booming commercial real estate scene in Chicago has produced some amazingly creative workspaces. Innovation in “cool” ranges from several hundred thousand square feet down to several hundred, but size doesn’t necessarily win the prize for being cool. Here’s a look at some of the best office spaces in Chicago.

  • Gogo — Internet in-flight company Gogo took the old River Center building and transformed it into a fully shielded, mock airplane cabin with hallways named after local runways and vacation-worthy relaxation lounges. It’s got a roof deck with massive greenspace.
  • Agency EA — Take an old cookie factory and turn it into a three-floor mix of private and public spaces, add color, whimsy, special finishes and one-of-a-kind furnishings and you have the award-winning Agency EA. The designer needed to “see things from fresh angles.”
  • Sandbox Industries — A venture capital firm creating a flexible space based on the needs of its employees? Yep, that’s on trend. The first tenant in the big tech address, 1KFulton, has a collaboration room that serves as an informal classroom and a corporate roundtable for billionaire investor meetings.
  • Sterling Bay — One of the biggest developers in the Fulton Market boom designed its headquarters as a serene, spa-like setting with accents repurposed from unearthed Chicago job sites. Think of a steel-plated wall built from an old water tower, hung with antique tools.
  • Vivid Seats — These guys know a good time! They’re a fast-growing space for online concert, sports and theater tickets, and they’ve decorated their own space with recycled furniture from old stadiums. Individual workspaces play on the company’s love for entertainment.
  • Cards Against Humanity — 20 small companies do business in this co-space for artists, and its space is as clever as the game maker behind it. Playfully called “Some Office,” it features a 60-person black box theater, a recording studio and plenty of elbow room.
  • CMK — A real estate developer with a futuristic Shanghai Zen office. Bamboo stalks and leafy green foliage line the walls and corridors, while high windows and skylights reduce the need for artificial lighting. Asian art adds to the serenity.
  • BucketFeet — This West Loop shoe company connects people through local street art with painted murals over brick walls. Polaroid photos of visitors hang around couch-lined nooks, while displays of shoes sit like masterpieces.
  • Studio K Creative — What better way to crush workspace stress than with puppies, a stuffed peacock named Henri and an office swing? Find it at this chic and airy multidisciplinary creative studio in the West Loop.


Cool spaces to eat, drink and shop in Chicago are endless. Some are mainstays and have been serving Chicagoans for years, while some are new starts that are sure to compete.

The commercial real estate boom in Chicago has brought in thousands of young professionals who patronize cool places and generate the income to afford it. Touring around Chicago, these “it” spots stand out:

  • Au Cheval — Most people wouldn’t stand an hour in line at a burger joint, but they do at Au Cheval. Their cheeseburgers are blitzed with enthusiasm that most people have with a winning lottery ticket. Try their honey-fried chicken and griddled bratwurst. They’re worth the delayed gratification.
  • Saint Alfred — Of all the amazing shoe stores in Chicago, Saint Alfred’s has distinguished itself the most in the past five years. They’re linked with The Chi in exclusive distribution of the Vans Chukka and the Chicago-inspired Asics Gel-Lyte III. Sox and Cubs fans love them.
  • Billy Sunday — This prohibition-era haunt opened in 2013 to much ballyhoo. As far as high-concept cocktail bars go, this place is cool, casual and Capone. The hype hasn’t subsided, and it continues to be one of the best hang-outs in Chicago.
  • Leaders 1354 — Leaders is a pioneer in Chicago streetwear. You’ll find their own brand as well as prevailing labels like Jordan, Billionaire Boys Club and 10.Deep.
  • Scofflaw Chicago — A gin bar that looks like it’s staged with hand-me-down furniture from the Palace of Versailles? How cool, indeed! It’s uniquely perfect that way, but isn’t priced for royalty. Scofflaw’s has eight-dollar drinks across the board and comes with freshly baked cookies right from their own kitchen.
  • RSVP Gallery — This place hits like a neon light. It’s a “subterranean reminder of the shrinking chasm between streetwear and high fashion,” with clothing lines from Phillip Lim, A.P.C, Comme des Garcons and more. RSVP makes frequent appearances on Rihanna’s Instagram.
  • Revolution Brewing Company — This titanic brewpub’s IPA is tremendously popular with local Millennials. Besides the fire-grilled pizzas and regular bar grub, the in-house restaurant has a full menu of vegetarian options.
  • The Aviary — Located in the Fulton Market, The Aviary won the James Beard Foundation Award for “Outstanding Bar Program.”
  • Vertical Gallery — This shop features works by urban environmentalists with street art, graffiti and pieces influenced by pop culture. It’s less than a year old and has already gathered incredibly talented locals.
  • The Boarding House — Alpana Singh is the youngest woman to pass the master sommelier exam. She opened The Boarding House, which is a five-story space with a featured chandelier made of 9,000 wine glasses. The menu complements her passion for fermented grape juice.


Chicago is a showcase of cool

Theater, sports and event hosting help to make Chicago what it is. There are more on-trend spaces that cater to entertainment than you might imagine. With over 250 active theater groups in the cities and five major-league sports teams, Chicago has proven itself to be a showcase of cool.

Hotels, event facilities, arenas and theaters are spread throughout the city. They’re connected by a transportation system that smoothly serves thousands and thousands of young professionals who live in Chicago, as well as the multitude of yearly visitors. Let’s have a look at some of the coolest venues and entertainment spaces in Chicago.

  • Morgans on Fulton — This venue is to die for. It’s right in the heart of Fulton and breaks into four event spaces of nearly 12,000 square feet, including a rooftop penthouse with views over the Fulton Market. The building started in 1921 as a meatpacking warehouse.
  • Steppenwolf Theatre — No mention of coolness in Chicago would be complete without Steppenwolf. It’s grown to rival anything Broadway in New York puts on.
  • Lincoln Hall — Located across the street from the Biograph Theater where John Dillinger was gunned down, the Lincoln is a haunting reminder from the gangster era. It’s a bi-level theater with some of the best acoustics ever built.
  • Public Chicago — This is where Chicago’s beautiful people hang out, and the coolness of the space tells why. The Pump Room definitely needs checking out.
  • Ignite Glass Studios — This has to be the coolest space in Chicago. Ignite was founded in 2012 as a glass-blowing business that produced fine glassware and glass art. It has quickly evolved to become the most unique team-building venue where groups of young professionals flock. Guided by staff artists, teams of co-workers make unique glass pieces around 2,200 degree Fahrenheit furnaces. Getting out of the comfort zone teaches people about themselves and their co-workers. That transitions back to the workspace.
  • Symphony Center — This is an old Chicago concert hall that’s been renovated into a work of art. Symphony Center’s wow-factor extends through twelve event spaces, which accommodate meetings, conferences and the occasional orchestra.
  • City Winery — High-energy folks gravitate towards the music venue, while wine drinkers enjoy tastings in a quieter space. How City Winery blends the two just has to be seen. They pair wines with live music with performers like Rick Springfield and Sinead O’Connor.
  • Emil Bach House — Fans of Frank Lloyd Wright’s architecture will find the Emil Bach House familiar and enthralling. It’s a smaller space that holds up to 120 guests inside and 25 outside, but the magic of how light is distributed makes them work perfectly. Even the colors blend sunlight.
  • Elite Private Yachts — At 600 Grand Ave., there’s a converted yacht. It’s got three deck spaces for a capacity of 150 and caters to corporate parties, cocktail events and intimate formal events. The only thing guests can’t customize is the sailing route — it’s permanently fixed at the Navy Pier dock.

We’ve covered just a few of the cool theater and event spaces in Chicago. Now for the big stuff! The city of Chicago is home to five major league sports teams that, in total, boast one Super Bowl, five World Series, six Stanley Cups and six NBA Championships.

Cool spaces where these legends hone their craft include:

  • United Center — Home of the Chicago Bulls NBA basketball team and the NHL’s Chicago Blackhawks.
  • Wrigley Field — This name screams Major League Baseball and the Chicago Cubs.
  • Soldier Field — The Chicago Bears drag it out on the gridiron of the National Football League.
  • Guaranteed Rate Field — White Sox fans love to watch ball at GRF.


young professionals looking for cool places and unique experiences

Chicago’s commercial real estate boom has attracted corporations and startup business, and has produced some of the coolest spaces in all of America. The investment and management of corporate real estate has led to employment, housing, shopping, eating and entertainment destinations for thousands of trending young professionals who are looking for cool places and unique experiences.

But these young professionals bring more than talent and skills to the city. They also bring families, and no look at the cool spaces in Chicago would be complete without a peek at the spaces for kids. Here are some of the coolest:

  • Funtopia — This kids’ utopia is the newest addition to Chicago’s play scene. It’s got climbing walls, rope courses, caves, slides and a soft room for those under eight.
  • Little Beans Café — This is a slice of kiddie heaven. Little Beans resembles old town Chicago with a firehouse, car garage, grocery store and little houses. There are two locations to choose from.
  • Monkey Island — Monkey Island claims to be the largest kids’ playground, with 40,000 square feet of pure fun. Bounce houses, gigantic slides and a hurricane simulator are part of the action, and parents can watch from the side.
  • Lincoln Park Zoo’s Canopy Climbing Adventure — This is a cool stealth secret and is one of the best indoor play spaces in Chicago. There is a mass of ropes and bridges that keep kids entertained for hours. There’s also a pond with otters and beavers.
  • Go Bananas — What kid doesn’t love going bananas? They’re free to do so at this carnival-style play space. Bumper cars are a favorite, and parents ride for free.
  • Sod Room — Looking for an eco-friendly and healthy play environment for kids? This cool, indoor wonderland features drop-in and private events.
  • LEGOLAND Discover Center — Every LEGO lover must visit this building heaven — not just kids! The Kingdom Quest Laser Ride makes everyone young again.


After all that, who wouldn’t want to live in Chicago?

Home to nearly three million people and growing fast, Chicago has so much to offer young professionals and their families. At 33 Realty, we understand that and we’re proud of the city we call home. 33 Realty is one of Chicago’s leading commercial real estate investment and management companies, and we’re proud of that, too. Space in Chicago has never been so cool. Let us help you find yours!

33 Realty will help you find your Chicago home.
Written by:
Drew Millard
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