Chicago has been counted out more times than an old deck of cards. But it still keeps a comeback up its sleeve. Right now the city—particularly its downtown—is aglow with new buildings, bountiful median planters, and the striking Millennium Park with its Frank Gehry–designed bandshell that puts on a show even when there’s no concert. Donald Trump is putting up one of the tallest buildings in North America here, and the city has erased nearly all of its bleak and notorious public housing high-rises and is replacing them with livable mixed-income neighborhoods.

So the bright new city beckons. But though his work has played a significant role in this revival, architect Brad Lynch, of the Chicago-based firm Brininstool + Lynch, doesn’t want to focus exclusively on that. “There is all kinds of good [architecture] going on,’’ Lynch says. “If you want to learn about the cool buildings, you can go to the Chicago Architecture Foundation and take a tour.”

That sounds dismissive, but it’s not. Lynch—who knows the terrain and navigates it with a “Yeah, the sign says ‘One Way’ but you can still go through” familiarity—recommends the foundation’s tours as a way to get a view of the city’s history and architecture. But for this architect, who’s not quite a local but has been here long enough to act like one, the true Chicago experience has to be rounded out by visiting places at the corners of downtown and off the beaten path, in neighborhoods and overlooked storefronts.
Our journey through the real Chicago begins—and ends—at the nondescript (from the outside, anyway) Club Lago, a bar at 331 West Superior in the fashionable River North neighborhood that Lynch has been coming to for 20 years. Club Lago is a remnant (though updated) from the area’s industrial era, when it was frequented by printers and packers. The 30-foot bar has a weathered linoleum top and when the original black rotary Western Electric Model 500 desk phone rings, it doesn’t beep, twitter, or play an anemic rendition of a top-40 hit—it rings.

Why are we here?

This is a Chicago bar. Although [the owner] doesn’t let me call it a bar because they want to be a restaurant about the Italian food—which is good fare. But there’s nothing fancy about it. They still have the old cash register; they’re not forcing the classic oak bar on you or hitting you over the head with how cute and fancy it is.

You say the Picasso sculpture in Daley Plaza is a must-see. Why?

It was 1967 and my parents put me in a car and drove down to see the sculpture. I was nine years old and they wanted me to see what the controversy was about. It was my first urban experience. Being in this plaza, surrounded by these buildings, was just a big moment in my life. It was like I knew someday I wanted to be in Chicago.

People often list Chicago’s tallest buildings as their favorite. But you’ve selected a relatively shorter building: the Inland Steel Building by Skidmore, Owings & Merrill.

Inland Steel—I think this is one of the greatest. Think of the time when it was built in the 1950s and what was happening in the city. A really big building hadn’t been built for 20 years and this was the first to go up in a long time. And it’s so thin and so pure. When I tell people when it was built, they go “Oh, my.” Because they thought it was built last year. I like it better than [Gordon Bunshaft–designed] Lever House. It’s on a much smaller lot than Lever House but it is just as big of a presence.

The South Side of Chicago has struggled for years with the stigma of being the wrong part of town. For a long time, tourist maps didn’t even include the South Side. It’s refreshing that it’s on your must-see list.

I had an intern in our office 15 or 16 years ago and I brought him to the South Side one day because he said, “Show me Chicago architecture.” I brought him down and said, “Look at all these streets. Look at all these buildings.” The South Side is such an incredible place in terms of history. Some of the better homes in the city are on the South Side: Frank Lloyd Wright’s Robie House, a Prairie School masterpiece at 58th and Woodlawn; stately turn-of-the-20th-century graystone mansions and apartment houses along Martin Luther King Drive between 35th and 47th. And Jackson Park has to be the best park in the city in terms of layout.

Jackson Park also has the Osaka Garden—a tranquil slice of Japan tucked behind the Museum of Science and Industry.

Just going down there and hanging out is great. It’s a special place to go walk and spend some time.

You don’t like baseball, but you have a fondness for Wrigley Field?

I just like sitting, having a drink, and looking at people. I miss half the game. And I used to be a Sox fan. I’m not a sports fan. I dislike sports. But the only professional baseball games I’ve been to in my life have been at Wrigley Field.

You recommend the Lake Shore Drive bike path at dawn. Other than avoiding manic bicyclists, what other benefits can be found in getting up that early? What will the riders see and hear?

I’m not sure there are any benefits to getting up that early, other than avoiding traffic and manic bicyclists—but that might be enough. There is something special about hearing the lake (and not the traffic) and watching the skyline emerge as you bike closer—without having to be as attentive to whether you are going to hit another biker or dog walker. If you start from the north at Foster Avenue, you are already in Lincoln Park and go by the expanse of soccer fields, the Sydney R. Marovitz golf course, a number of nicely designed park buildings, Montrose and Belmont harbors, and the Lincoln Park Zoo— which I usually cut through to get into River North—where you see the single scullers out early in the pond.

The city is filled with good places to eat. Where do you go?

Don Juan’s. It’s a traditional chips-and-salsa-and-guacamole restaurant. Then they have a fancy dining room called Patricio. The son [of the owner] went to work for Charlie Trotter, then came back. So he has this little room. But what you can do is sit in the front and mix and match orders [between the two restaurants].

You called the Music Box Theatre the last of the independents. What kind of movies do they show?

The Music Box is located in one of the last historic movie houses in Chicago, where it actually has been used as a movie theater since its original opening in 1929. It was designed by a local architect named Louis A. Simon and originally was an apartment house too. What makes it even more special is that there hasn’t been a Hollywood release shown there since 1977. And for approximately the last 15 years, it has consistently shown new releases of independent, foreign, and art films, as well as special film presentations. Over the summer, for instance, they showed Sketches of Frank Gehry, I Am a Sex Addict, and Russian Dolls.

Speaking of unique tastes, you suggest bypassing the grocery chains in favor of smaller, locally owned places. Such as?

Bari Foods is a small Italian grocery store at 1120 West Grand. They have a really good selection of Italian dry goods and staples, and a wonderful meat counter in the back with Italian sausages; hams, including Prosciutto di Parma; special cuts of meats; and where you can order the city’s best Italian sub directly from the butcher on duty. There is no PA system in this small, cramped store—someone shouts to the back room if they have a question. The current owners are the third generation of proprietors, and their grandfather started the business from a pushcart in Fulton Market. He, like most of the Italians that lived and had businesses in that neighborhood in the mid-20th century, is from the town of Bari in Italy.

You left Wisconsin for Chicago. Can you imagine leaving Chicago—giving up your seat here at Club Lago—for another city?

I get exasperated with a really bad month or really bad week and I say, “I’m going to move to Nova Scotia and open a Mexican restaurant.” Then I say, “Oh well—you can’t. Because you are embedded here now.” And I love that.