48 Hours in Chicago: Architecture, Deep Dish, and Hidden Gems

There’s a piece of the actual Moon embedded in a building on Michigan Avenue. Stone from the Great Wall of China, the Berlin Wall, the Taj Mahal, the Parthenon. All set into the base of a Gothic tower at street level, each with a small plaque. Most people walk right past it. We almost did too.

That building is Tribune Tower. Our friend was doing his MBA in Chicago, our local for the trip, and he’d been saving it for three days. “You’ll see it,” he kept saying when we asked. That’s all he’d give us.

That’s Chicago. The city doesn’t announce the good stuff. You have to get close.

Three of us drove nine hours from Toronto this spring for 48 hours in the city. We ate deep dish at Pequod’s, a twelve-dollar breakfast sandwich at a two-Michelin-star Filipino bakery, and a burger that had all of us go quiet for the first few bites. We did the architecture river cruise, the free zoo on the lakeshore, and a walk along the Northwestern shoreline where the Chicago skyline sits on the horizon like a postcard that somehow turned out to be real. Two days isn’t enough. We knew that by Saturday night.

Chicago skyline at sunset with the John Hancock Center silhouetted against an orange sky — First night in the city. The skyline doesn’t ease you in.

The Architecture Is the Main Event

If you’re going to Chicago and you’re not doing the architecture river cruise, you’re doing it wrong. I know it sounds touristy. It is touristy. Do it anyway. You spend an hour on the water while a guide walks you through building after building, what era it was from, who designed it, what problem they were solving. It reframes everything you see for the rest of the trip.

The one that got me was this green champagne-coloured building with a gold top. Our friend on the boat just pointed and smiled, wouldn’t say anything. We found out later it’s the Carbide and Carbon Building, built in 1929. The architects, two brothers, apparently designed it to look like a champagne bottle with gold foil on top. There’s a story that they each held a bottle of Moët while working on the design. That sounds exactly like something someone would make up, and it’s apparently true.

Tribune Tower on Michigan Avenue is Gothic and conspicuous, impressive the way a lot of buildings here are impressive. But what our friend had been holding back all trip was the base. Get close and you find it: stone from the Forbidden City, the Taj Mahal, the Great Pyramid of Giza, the Berlin Wall, the Parthenon, the Alamo, the Great Wall of China. A piece of the actual Moon from a NASA lunar sample. Each one in its own recess, each with a small plaque. You have to crouch to read them. Most people walking past never look down. Journalists and correspondents have been sending pieces back since the 1920s. It’s completely free and it’s one of the most interesting things I’ve seen on any trip.

The Magnificent Mile is worth the walk even if shopping isn’t your thing. There’s a Starbucks Reserve on the ground floor of one building that’s supposedly the largest in the world, a Harry Potter store, and above all of it, building after building that you’d stop and photograph in any other city but here you stop noticing after an hour because there are too many of them.

The Riverwalk

View straight down through iron bridge girders to the green Chicago River and buildings below — Straight down through the bridge ironwork. The river really is green year-round.

The Chicago Riverwalk runs along the banks of the river through the middle of downtown and it’s genuinely one of the best urban waterfront walks I’ve done. Restaurants, bars, kayak rentals, public art. The river gets dyed green every St. Patrick’s Day and holds a faint tint for the rest of the year. The bridges have eyelid arches built into their structure, protective arches designed to stop falling debris from hitting people on the riverwalk below. Standing on one and looking down through the ironwork at the green water with the towers rising on all sides is a view I wasn’t expecting to be as good as it was.

The Centennial Fountain and Arc is the riverwalk’s best party trick. It fires an 80-foot arc of water clean across the river, for five minutes at the top of every hour, May through September. We timed our walk to catch it. When it went off the people standing near us who didn’t know it was coming jumped. It’s that big.

The Neighbourhoods

We spent time in Wicker Park, Logan Square, Lincoln Square, and the West Loop. Wicker Park feels like the kind of neighbourhood that was cool before it was expensive and somehow stayed cool anyway. Independent coffee shops, vintage stores, street murals everywhere. Outside a Crumbl cookies there’s a full wall mural of CM Punk, the wrestler, in a Chicago flag shirt with the city’s red stars on either side of him. “Second City Saint” written across the top, his old nickname from before he blew up. It’s a great piece of work. We stood there for a few minutes just taking it in.

Second City Saint mural of CM Punk in a Chicago flag shirt on a brick building in Wicker Park — The Second City Saint mural on Milwaukee Ave. We stood here longer than planned.

Logan Square and Lincoln Square are quieter and more residential, good for walking with no particular plan. The West Loop and Fulton Market are where the restaurants are, which is where this post gets long.

The Food

I need to be upfront about something: we planned this trip partly around food. Not entirely, but partly. Chicago has a specific kind of food culture where every institution has a story and the new places are trying to earn their place next to the old ones. We ate a lot. We ate well. Here’s what I’d go back for.

Kasama is a two-Michelin-star Filipino bakery in Ukrainian Village. The breakfast sandwich is longanisa, a soufflé egg, American cheese, and Martin’s potato roll. Twelve dollars. We got there right when it opened and walked straight in. That sandwich is the best breakfast item I’ve had in North America. I’ve thought about it multiple times since getting home.

Au Cheval is in the West Loop and consistently shows up on “best burger in America” lists. Before you go, know that a “single” is actually two patties and a “double” is three. We ordered the single with a fried egg. English muffin bun, proper cheese melt, not just a slice of cold cheese dropped on top before serving. It tastes like someone thought very hard about what a burger should be and then just made that, no compromise. The line was about forty-five minutes. Worth it.

Au Cheval burger open-faced on a white plate: fried egg on one half, thick melted American cheese on the patty, cornichon alongside — Au Cheval. Forty-five minutes in line. Worth it.

Crying Tiger is Thai and nearly impossible to get a reservation at. Our friend had one. The food is excellent across the whole menu but everyone talks about the dessert, also called the Crying Tiger: a ring of sauce on a white plate with a vivid green ice cream in the centre. It looks like something from a fine dining tasting menu. We weren’t expecting it.

Crying Tiger dessert: dark green ice cream in the centre of a ring of brown sauce on a white fluted plate — The dessert at Crying Tiger. Nobody warned us this was coming.

Pequod’s is where you go for deep dish. The thing that sets it apart is the caramelized crust where the cheese has baked up the side of the pan and gone dark and slightly bitter at the edge. One slice is a full meal and I mean that literally.

Slice of Pequod's deep dish pizza on a red plate, with a heavily caramelized dark crust edge — Pequod’s deep dish. The dark edge is where the cheese caramelizes against the pan. One slice is a full meal.

We also hit Portillo’s for hot dogs and Italian beef (an institution), the original Billy Goat Tavern underground on Michigan Avenue (the “cheeseburger cheeseburger” place from SNL, and yes you order a cheezborger), Tilly Bagel Co. for a Chicago-style bagel with giardiniera cream cheese and smoked salmon which I can’t stop recommending to people, and Sawada Coffee in the West Loop run by the 2008 World Latte Art champion.

The McDonald’s global headquarters in Chicago has a café open to the public with a rotating international menu, items from other countries that you can’t get anywhere else. We stopped in mostly out of curiosity. It’s genuinely fun.

One honest note: Toronto is better for food from other cultures. The range and depth of what you can eat in Toronto across different cuisines is hard to match. Chicago’s food scene is incredible but it’s stronger in the classics. That’s not a criticism, it’s just a different city.

Lincoln Park and the Zoo

Flamingos at Lincoln Park Zoo walking along a wooden path with green trees behind them — Lincoln Park Zoo. Free admission. The flamingos were closer than expected.

Lincoln Park Zoo is free, which I keep telling people because nobody believes it. Free admission, proper size, well-maintained, right next to Lake Michigan. The flamingos were closer than I expected. We spent about an hour there before heading further up the lakeshore.

Navy Pier. The skyline view from the top is better than it has any right to be.

Navy Pier gets written off as a tourist trap but the Ferris wheel view of the skyline from the end of the pier is legitimately great. Buckingham Fountain in Grant Park is enormous and worth the walk, especially in the evening when they run the light show. The Bean in Millennium Park is exactly as good as advertised. I thought I was too cynical for it and I was wrong.

Northwestern and the Shore

We drove out to Northwestern’s campus in Evanston, about twenty minutes north of downtown. I wasn’t expecting much from this part of the day but it ended up being one of my favourite hours of the trip. The campus sits right on Lake Michigan and we walked down to the rocky shore and just sat there for a while watching the water, the wind coming off the lake, the Chicago skyline visible in the distance. No plan, no agenda. The kind of thing you don’t put in an itinerary but remember for a long time.

The City at Night

Marina City's circular towers lit up at night with their lights reflecting in the Chicago River below — Marina City from the riverwalk. The corn cobs. The river picks up every light.

Chicago at night hits differently. We ended up walking back along the river after dinner and the same buildings we’d seen during the day were completely transformed. Marina City, the two round towers everyone calls the corn cobs, looks best in the dark when the lit balconies stack up against the sky and reflect in the river below.

Chicago Board of Trade Building glowing gold at the end of a rain-wet LaSalle Street at night, L train tracks overhead — LaSalle Street on a rainy night. The Board of Trade is Wayne Tower in the Dark Knight. Standing here, it’s obvious why.

It rained while we were walking around that end of downtown. Standing at the base of the Board of Trade on LaSalle Street, L tracks overhead, the building lit up gold and the streets wet and throwing everything back at you, you immediately understand why Christopher Nolan picked it for Wayne Tower in the Dark Knight films. It looks like a city that takes itself seriously.

Would I Go Back

Yes, immediately. Two days is not enough. We said that out loud on the drive back and everyone agreed.

If you’re coming from Toronto, the cities rhyme more than you’d expect: similar density, similar neighbourhood feel, the lake, the mix of people. What Chicago has that Toronto doesn’t is that architectural confidence. The Tribune Tower, the Carbide and Carbon Building, the scale of the riverwalk. That stuff doesn’t happen overnight and Toronto isn’t there yet.

One practical note: free street parking in downtown Chicago is almost nonexistent. We wasted more time on this than I want to admit. Budget for paid parking or take the L.