IMMERSIVE CHICAGO: Explore Windy City like a local   

TV’s The Bear shines renewed spotlight on Midwest city and its diverse neighbourhoods

Is The Bear a drama or a comedy?   

Some say the hit American TV show is the latter, others argue there’s no way that can be true. Trying to gain a consensus is akin to landing unanimously on the best deep-dish pizza spot in Chicago — if that even is the favoured style in town.   

What’s not up for debate is that the series that follows a young chef’s return home to run his family’s sandwich shop has shone a far-reaching spotlight on this popular Midwest city.    

If Chicago was already cooking — it attracts some 50 million visitors each year and was recently voted by Condé Nast Traveler readers as the best large city in the U.S. for the eighth straight year — now, it’s cooking with fire.    

Imaginations are being newly stirred thanks to The Bear, a love letter to Chitown. What’s more, ‘The Bear Effect’ has been steering visitors off the beaten path (in our opinion the best place to be in any big city, including Chicago). With more than 200 neighbourhoods to explore, the opportunities are as endless as a Michael Jordan highlight-reel package.   

Wrigleyville. The Loop. Lincoln Park. Fulton Market. The Riverwalk. Chicago’s neighbourhoods are as distinct as the architecture that forms the city’s iconic skyline. 

Of course, not everyone will have watched The Bear (quietly raises hand). Fret not. A tour based on the hit show only requires an appetite.  

Fans of the hit TV show The Bear will recognize Mr. Beef. The Italian sandwich shop is the inspiration for the show and is also highlighted on a food tour centred around the show. IAN SHANTZ/TORONTO SUN
Fans of the hit TV show The Bear will recognize Mr. Beef. The Italian sandwich shop is the inspiration for the show and is also highlighted on a food tour centred around the show. IAN SHANTZ/TORONTO SUN

YES, CHEF!

Start at Italian beef shop Mr. Beef, which served as the main influence for the show. As our tour guides, Casey and Teddy, explain it, the River North sandwich shop owner’s son is a friend of the show creator who years earlier proclaimed he was going to make a show based on Mr. Beef. He followed through, and the rest is history.   

Devour half an Italian beef (order it “hot, wet and sweet”), followed by dumplings, a New York-style slice at Pizza Lobo, a strawberry doughnut from the city’s oldest bakery, Roeser’s, and a hot fudge sundae at Chicago landmark Margie’s Candies, opened in 1921. Finish with an old-fashioned cocktail at the Green Door Tavern. It’s the city’s oldest tavern and a favourite of Bulls bad boy Dennis Rodman during his time in Chicago. 

The food tour aims to “feed your bellies, feed your minds and feed your soul.” It’s the perfect way to see a few Chicago neighbourhoods you might not otherwise experience — while being fed along the way.    

No walking calories off during this tour. Participants are transported around town in a comfy limo bus.    

Chicago’s skyscrapers as viewed from the Chicago Architecture Foundation Center River Cruise aboard Chicago’s First Lady. IAN SHANTZ/TORONTO SUN
Chicago’s skyscrapers as viewed from the Chicago Architecture Foundation Center River Cruise aboard Chicago’s First Lady. IAN SHANTZ/TORONTO SUN

A RIVER RUNS THROUGH IT

Chicago is the birthplace of the skyscraper and there is no better place to appreciate the city’s architecture than from a tour boat on the Chicago River, which winds through the downtown core and feeds into Lake Michigan.    

It really was a journey through time as we explored various architecture styles that arose from the 1871 Great Chicago Fire and, later, Chicago World’s Fair in 1893.    

If you haven’t heard about the infamous Dave Matthews Band Chicago River incident, for better or worse, you might learn about it on this tour.   

Chicago’s skyline, among the tallest in North America, really is a sight to behold, and an architecture tour should be mandatory for all visitors. 

Giordano’s is a popular choice among deep-dish pizza lovers in Chicago. giordanospizza/INSTAGRAM
Giordano’s is a popular choice among deep-dish pizza lovers in Chicago. giordanospizza/INSTAGRAM

DEEP THOUGHTS 

Not every local is head over heels for bulky Chicago deep-dish pizza (the antithesis of the thin-slice pies that dominate New York City), but it has its place.   

We tried another deep-dish spot for research purposes and can report that Giordano’s was our preferred pie. Many Chicagoans, meanwhile, will argue that the real Chicago-style pizza is “tavern style” — thin crust, cut into tiny squares.   

Chicago has plenty of pizza options, any way you slice it.   

Time Out Market is a food hall in the city’s Fulton Market District. IAN SHANTZ/TORONTO SUN
Time Out Market is a food hall in the city’s Fulton Market District. IAN SHANTZ/TORONTO SUN

MORE FOOD FOR THOUGHT   

Sushi, dumplings, German-style burgers, ramen and a shake bar are some of what’s available inside this 50,000-sq.-ft. facility in the Fulton Market District, a former meatpacking hub (we opted for Ethiopian injera rolls and didn’t regret it).   

Foodies will love Time Out Market, which follows in the footsteps of a concept first created by media company Time Out in Portugal in 2014. 

The Goose Island Brewery Salt Shed Pub has a solid beer roster. IAN SHANTZ/TORONTO SUN
The Goose Island Brewery Salt Shed Pub has a solid beer roster. IAN SHANTZ/TORONTO SUN

Choose from a full roster of tasty beers including our easy top pick, the seasonal Bourbon County bourbon barrel-aged stout. They do a mean smashburger and Bourbon County stout milkshake, too. Torontonians will recognize Goose Island, which operates a pub on The Esplanade.  

The Chicago Magic Lounge is home to Chicago-style magic. IAN SHANTZ/TORONTO SUN
The Chicago Magic Lounge is home to Chicago-style magic. IAN SHANTZ/TORONTO SUN

MAGIC IN THE AIR 

Hot dogs. Popcorn. Pizza. There’s a Chicago style for everything, including magic.    

Enter the intimate cabaret theatre through a hidden door in a “laundry room” (the venue is in a converted commercial laundry building) where a handful of magicians perform tableside tricks for guests and be astonished by unforgettable showcase magician performances on the main stage.   

We misplaced our entry ticket ahead of showtime and wondered if, based on this vanishing act, we, too, could be a magician.   

Food and drinks are available during each show. The Chicago Magic Lounge is open seven days a week and we hope it never disappears. 

Opened in 1914, Wrigley Field is the oldest ballpark in the National League. Public tours are offered. IAN SHANTZ/TORONTO SUN
Opened in 1914, Wrigley Field is the oldest ballpark in the National League. Public tours are offered. IAN SHANTZ/TORONTO SUN

SLUG THROUGH WRIGLEYVILLE 

Aside from being home to the second-oldest stadium in the big leagues, Wrigleyville scores with its all-star collection of classic bars and taverns. The Cubby Bear, Murphy’s Bleachers and HVAC Pub are always popular on game days.   

Not into baseball? Check out Chicago landmark-designated Alta Vista Terrace, which is lined with row housing constructed between 1900-1904. Every townhouse on one side is duplicated with only minor variations at the diagonally opposite end of the block.    

The main attraction, though, is always going to be Wrigley Field. Root for the beloved Cubs or hop on an official tour as we did. Opened in 1914 and eventually named for chewing gum magnate owner William Wrigley Jr., the ‘Friendly Confines’ is known for its ivy-covered brick outfield wall, unpredictable winds and famous red marquee. We learned that the folks who work inside the historic manual scoreboard do so without air conditioning or heat due to heritage protections. Canadian visitors can find the bronze statue of former Cubs great Fergie Jenkins on Statue Row at the north end of Gallagher Way.   

We’ll Fly the W for this terrific tour, just as the Cubs do after every home win.   

Wrigley Field will host the NHL Classic outdoor game on New Year’s Eve, pitting the Blackhawks against the St. Louis Blues, followed by a pair of college hockey doubleheaders in classic Ernie Banks fashion.    

Dovetail in Ravenswood has terrific German and Eastern European-style beers. IAN SHANTZ/TORONTO SUN
Dovetail in Ravenswood has terrific German and Eastern European-style beers. IAN SHANTZ/TORONTO SUN

SWIG THROUGH RAVENSWOOD 

At Begyle, sample a flight of beers on the patio, then head to Dovetail for German and Eastern European-style beers (the brewery has a rare brewing vessel called a coolship). Finish at KOVAL, which is not a brewery but it is Chicago’s first legal post-prohibition brewery. The women-owned distillery’s spirits are all organic and kosher and the grain-to-bottle approach means all ingredients are sourced from a 241-kilometre radius. The cranberry gin liqueur here is a beautiful thing. 

AIRE Ancient Baths Chicago offers traditional-style Roman, Greek and Ottoman baths in a restored factory from 1902. HANDOUT
AIRE Ancient Baths Chicago offers traditional-style Roman, Greek and Ottoman baths in a restored factory from 1902. HANDOUT

TAKE A BATH  

Fans of the John Wick movie franchise will recognize the AIRE New York bath and spa facility as being transformed into the scene of a shootout.   

Chicago’s AIRE is inside a restored paint factory from 1902 in the Fulton Market/River West/West Loop area. Original exposed brick, wooden beams and industrial columns set a unique scene to experience traditional-style Roman, Greek and Ottoman baths. There must have been a thousand or more candles glowing as we enjoyed the water treatments and steam rooms followed by a relaxing message.    

AIRE is the perfect escape in a part of town that will soon be home to a new Bally’s hotel and casino at the former site of the Chicago Tribune publishing centre.   

The Drawing Room Library inside the Chicago Athletic Association. HANDOUT
The Drawing Room Library inside the Chicago Athletic Association. HANDOUT

A HOTEL STAY THAT’S FUN AND GAMES   

It was the first of many pleasant, quirky surprises at what might be this writer’s new favourite hotel. From the incorporation of Edison lightbulbs to the association’s original C-shaped logo (later adopted for the Chicago Cubs by owner William Wrigley, one of the CAA’s founding members), the Venetian Gothic building that served as a members-only athletic club until 2009 is teeming with preserved history and mindful design.    

What was once an exclusive space is now inclusive. The Game Room and Drawing Room are popular gathering spots for hotel guests and non-guests alike.  

The Cherry Circle Room is a James Beard-award-winning establishment in the Chicago Athletic Association hotel. HANDOUT
The Cherry Circle Room is a James Beard-award-winning establishment in the Chicago Athletic Association hotel. HANDOUT

Other property highlights include the fourth-floor Stagg Court (the original basketball and fencing court flooring lives on in the elevators), eighth-floor Madison and White City Ballrooms and The Tank, a meeting space once used for swimming competitions.   

The Founders Room inside the Chicago Athletic Association. HANDOUT
The Founders Room inside the Chicago Athletic Association. HANDOUT

Also street level, there’s a Shake Shack and a coffee shop, Fairgrounds Coffee & Tea.   

Back to the pommel horse: No leg swings and dismounts were performed, but this 40-something with regular joint pain appreciated the sturdy build of the thing while putting on his shoes.   

The hotel is centrally located downtown on Michigan Ave., directly across from Millennium Park and the popular Cloud Gate sculpture (better known as the Bean), with views of the park and Lake Michigan from some of the 240 rooms.   

The Ben Paterson Organ Trio featuring Paterson on Hammond B-3 organ, Bobby Broom on guitar (pictured) and Greg Artry on drums perform at the Green Mill Cocktail Lounge, an institution for nightly live music in Chicago. IAN SHANTZ/TORONTO SUN
The Ben Paterson Organ Trio featuring Paterson on Hammond B-3 organ, Bobby Broom on guitar (pictured) and Greg Artry on drums perform at the Green Mill Cocktail Lounge, an institution for nightly live music in Chicago. IAN SHANTZ/TORONTO SUN

HERE AND THERE

HOW WE GOT THERE 

The Cloud Gate sculpture, commonly referred to as the “bean,” is a popular landmark in Chicago’s Millennium Park. IAN SHANTZ/TORONTO SUN
The Cloud Gate sculpture, commonly referred to as the “bean,” is a popular landmark in Chicago’s Millennium Park. IAN SHANTZ/TORONTO SUN

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