Maria Kowalski moved from Brooklyn to Chicago's Logan Square in 2011 for a job in urban planning. She never left. Fifteen years in, here's her unfiltered take on the city she's called home — the kind of guidance that only comes from someone who chose Chicago and never looked back. Her morning ritual, for the record: Gaslight Coffee Roasters on Milwaukee Avenue.
Constantly. Family back in Brooklyn still asks when she's "coming home." But here's the thing — a two-bedroom apartment in Logan Square costs what a studio closet runs in Williamsburg. The commute is a 15-minute bike ride. Lake Michigan sits right there, basically an ocean without the salt. And the food scene 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.
The first thing every tourist arriving in Chicago should hear.
Don't rent a car. The point can't be overstated. The 'L' train covers everything you need — the Blue Line from O'Hare to Downtown is $5 and takes 45 minutes. A Ventra day pass is $5. The Brown Line loop hands you a free architectural tour of the Loop's skyscrapers. You can walk from Millennium Park to Navy Pier in 20 minutes.
Parking downtown runs $30-60 a day. Traffic is brutal. And you'll miss the best parts of the city stuck behind a steering wheel.
Deep-dish pizza — the real deal.
Here's the controversial take, the one every tourist blog will argue with.
Deep-dish is delicious. Eat it once. Head 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 matters — real Chicagoans eat tavern-style thin-crust pizza far more often. It's cut in squares, not wedges. The crust is thin and crackery. It's the weeknight order. 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.
The neighborhood tourists skip — and shouldn't.
Wicker Park and Bucktown, absolutely. It's on the Blue Line (Damen stop), where Chicago's creative energy lives. Vintage shops line Milwaukee Avenue — Kokorokoko has standout pieces for $10-50. Coffee at Wormhole Coffee, which literally parks 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 is Pilsen. The Mexican-American heart of Chicago, on the Pink Line. The National Museum of Mexican Art (free, and genuinely world-class). Murals covering entire buildings. Taquerias serving the best tacos in the city for $3-4 each. And 18th Street carries an energy — families, artists, small businesses — that feels more authentically Chicago than anywhere on Michigan Avenue.
The biggest tourist trap in Chicago.
The Navy Pier restaurants. Skip them. 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.
Same goes for 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, a beautiful boat ride, 90 minutes of actually learning why Chicago's skyline matters. Book ahead at architecture.org; it sells out in summer.
Surviving 15 Chicago winters.
It's bad. No sugarcoating January and February — they're brutal. Think -10°C on a good day, with windchill off the lake pushing it to -25°C. Locals call that lake wind "The Hawk."
But here's what tourists don't know: the Pedway. An underground tunnel network linking 40 blocks of Downtown buildings. You can walk from the Art Institute to Millennium Park to the CTA stations without ever stepping outside. It's not glamorous — parts of it look like a hospital basement — but it's how people get through winter here.
And winter has its own beauty. The river freezes in parts. The skyline against a grey January sky turns stark and dramatic. Every restaurant, bar, and museum sits empty. You'll have the Art Institute practically to yourself.
The Art Institute — worth the $35?
Worth $100, and that's not an exaggeration. Seurat's "A Sunday on La Grande Jatte," Grant Wood's "American Gothic," Hopper's "Nighthawks" — 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 the two pair perfectly. Allow 3-4 hours minimum. Illinois residents get free Thursday evenings — so if you happen to have a friend with an Illinois ID...
The best thing 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 — about 5 km. The skyline views from that trail beat 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 — arrive 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 genuinely good.
What 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's crime problem sits in specific neighborhoods tourists will never visit. Don't let the cable-news narrative scare you off 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 turning gold), and even spring (April-May) carries a raw energy as the city wakes from winter.
Third, they skip the neighborhoods. Michigan Avenue is fine. But the soul of Chicago lives 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.
A perfect day in Chicago.
Breakfast at Ann Sather in Lakeview — the cinnamon rolls (2 for $4, the size of your head) come with every meal. Then the lakefront trail by bike to Millennium Park. The Art Institute until early afternoon. Walk to the West Loop. Randolph Street. Girl & The Goat if you 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 counts as a perfect day. Try doing that in New York.
Ever moving back to Brooklyn?
Not a chance. Come visit and you'll understand why.
