Maria Kowalski moved from Brooklyn to Chicago's Logan Square in 2011 for a job in urban planning. She never left. We sat down at her favorite coffee shop — Gaslight Coffee Roasters on Milwaukee Avenue — to get her unfiltered take on the city she's called home for 15 years.
Constantly. My family in Brooklyn still asks when I'm "coming home." But here's the thing — I bought a two-bedroom apartment in Logan Square for what a studio closet costs in Williamsburg. I have a 15-minute bike commute. I can see Lake Michigan, which is basically an ocean without the salt. And the food scene here rivals New York at half the price.
New York is great for visiting. Chicago is great for living. And honestly? It's also great for visiting. People just don't know it yet.
What's the first thing you'd tell a tourist arriving in Chicago?
Don't rent a car. I cannot stress this enough. The 'L' train covers everything you need — Blue Line from O'Hare to Downtown is $5 and takes 45 minutes. A Ventra day pass is $5. The Brown Line loop gives you a free architectural tour of the Loop's skyscrapers. You can walk from Millennium Park to Navy Pier in 20 minutes.
Parking downtown is $30-60 a day. Traffic is brutal. And you'll miss the best parts of the city if you're stuck behind a steering wheel.
Let's talk deep-dish pizza. What's the real deal?
Okay. I'm going to say something controversial, and every tourist blog will disagree with me.
Deep-dish is delicious. Eat it once. Go to Lou Malnati's on State Street, order The Malnati Chicago Classic ($20-25, feeds 2-3), wait the 40 minutes for it to bake, and enjoy it. It's a casserole. It's heavy. It's great.
But — and this is important — real Chicagoans eat tavern-style thin-crust pizza far more often. It's cut in squares, not wedges. The crust is thin and crackery. And it's what we actually order on a weeknight. Go to Pat's Pizza on Lincoln Ave. Get a sausage thin-crust. That's Chicago pizza.
And while you're at it — the Italian beef sandwich at Portillo's on Ontario ($8-10) might actually be the city's true signature food. Get it dipped with hot giardiniera. Your hands will be a mess. You won't care.
What neighborhood should tourists visit that they usually skip?
Wicker Park and Bucktown, absolutely. It's on the Blue Line (Damen stop) and it's where Chicago's creative energy lives. Vintage shops on Milwaukee Avenue — Kokorokoko has amazing pieces for $10-50. Coffee at Wormhole Coffee, which literally has a DeLorean inside the shop. Big Star on Damen Ave for pork belly tacos ($5) and whiskey on the patio in summer.
But the real answer? Pilsen. It's the Mexican-American heart of Chicago, on the Pink Line. National Museum of Mexican Art (free, and genuinely world-class). Murals covering entire buildings. Taquerias where you'll get the best tacos in the city for $3-4 each. And 18th Street has this energy — families, artists, small businesses — that feels more authentically Chicago than anywhere on Michigan Avenue.
What's the biggest tourist trap in Chicago?
The Navy Pier restaurants. Don't eat there. The Ferris wheel ($18) is fine for the view, and the free summer fireworks (Wednesday and Saturday) are worth seeing. But every restaurant on the pier is overpriced and mediocre.
Also, those double-decker bus tours ($45-55). The architecture river cruise from the Chicago Architecture Center ($49) is a far better use of your money — expert narration, beautiful boat ride, 90 minutes of actual learning about why Chicago's skyline matters. Book ahead at architecture.org because it sells out in summer.
You've survived 15 Chicago winters. How bad is it really?
It's bad. I won't lie. January and February are brutal. We're talking -10°C on a good day, with windchill off the lake making it feel like -25°C. The locals call the lake wind "The Hawk."
But here's what tourists don't know: the Pedway system. It's an underground tunnel network connecting 40 blocks of Downtown buildings. You can walk from the Art Institute to Millennium Park to the CTA stations without ever going outside. It's not glamorous — it looks like a hospital basement in places — but it's the reason people survive winter here.
And honestly? If you visit in winter, the city has a different beauty. The river freezes in parts. The skyline against a grey January sky has this stark, dramatic look. And every restaurant, bar, and museum is empty. You'll have the Art Institute practically to yourself.
Speaking of the Art Institute — is it worth the $35?
It's worth $100. That's not an exaggeration. Seurat's "A Sunday on La Grande Jatte," Grant Wood's "American Gothic," Hopper's "Nighthawks" — these paintings you've seen reproduced a thousand times, and standing in front of the originals is a completely different experience.
The Modern Wing has a free pedestrian bridge to Millennium Park, so you can combine them. Allow 3-4 hours minimum. And Illinois residents get free Thursday evenings — so if you happen to have a friend with an Illinois ID...
Best thing to do in Chicago that costs nothing?
Walk the lakefront trail. All 30 km if you're ambitious, or just the stretch from Oak Street Beach to Museum Campus — maybe 5 km. The skyline views from that trail are better than anything you'll see from an observation deck. Rent a Divvy bike ($3.30/ride or $16.50/day) if walking isn't your thing.
Millennium Park is free. The Bean (Cloud Gate) is free — get there at 8AM for photos without crowds. The Jay Pritzker Pavilion hosts free concerts all summer, Wednesday through Sunday evenings. Bring a blanket and a bottle of wine.
Lincoln Park Zoo is free. Always. One of the last free zoos in America, and it's genuinely good.
What do tourists get wrong about Chicago?
Three things.
First, they think it's dangerous. The tourist areas — the Loop, River North, Magnificent Mile, Lincoln Park, Wicker Park, the lakefront — are extremely safe. Chicago has a crime problem in specific neighborhoods that tourists will never visit. Don't let the cable news narrative scare you away from one of America's greatest cities.
Second, they only come in summer. Summer is amazing — festivals, beaches, outdoor dining, the Cubs at Wrigley. But fall is gorgeous (September-October, perfect weather, the trees along the lakefront turn gold), and even spring (April-May) has a raw energy when the city wakes up from winter.
Third, they skip the neighborhoods. Michigan Avenue is fine. But the soul of Chicago is in Logan Square, Pilsen, Humboldt Park, Bridgeport, and Hyde Park. Take the 'L' to a random stop and just walk. You'll find better food, better art, and more interesting conversations than anything on the tourist trail.
Your perfect day in Chicago?
Breakfast at Ann Sather in Lakeview — their cinnamon rolls (2 for $4, the size of your head) come with every meal. Then the lakefront trail by bike to Millennium Park. Art Institute until early afternoon. Walk to the West Loop. Randolph Street. Girl & The Goat if I can get in (book weeks ahead, $18-38 per dish).
Afternoon at the Riverwalk — grab a beer at Tiny Tapp ($7-9) on the water. Architecture cruise at 4PM. Dinner at a Pilsen taqueria. Then Green Mill for jazz at 9PM. Home by midnight on the Blue Line.
If you're comparing Midwest cities to visit, Toronto offers a similar multicultural food scene with a Canadian twist.
That's $150-200 for what I'd call a perfect day. Try doing that in New York.
Last question — are you ever moving back to Brooklyn?
Not a chance. Come visit and you'll understand why.
