Chicago is one of those cities that you visit once for the tourist checklist and return to forever after for something harder to name. The Bean, the architecture tour, a deep-dish pizza — those get checked on trip one. After that, you keep coming back because the city delivers something different every time.
We’ve been five times in seven years. Here’s what I’ve learned.
The Architecture Is Actually Worth the Hype
I’m usually skeptical of tourism’s relationship with architecture — cities put their buildings on every brochure and the buildings are rarely as interesting as promised. Chicago is the exception.
The Chicago Architecture Center runs river boat tours that run 90 minutes and cover more than forty buildings with genuinely knowledgeable guides. Cost is around $47/person. I know people who’ve done it six times and still find it worthwhile.
But the thing that surprised me on our first trip and keeps impressing me on every subsequent one: you don’t need a tour. Walking the Loop, crossing bridges, looking up — Chicago rewards the observant walker in a way that doesn’t require context. The city is an open-air architecture museum that happens to also contain 2.7 million people going about their lives.
The Food Landscape Has No Ceiling
Chicago’s food scene operates at a level that the city’s Midwest-modest reputation consistently undersells. This is a serious food city.
Deep dish: Lou Malnati’s is the answer most locals give and it’s not wrong. Giordano’s is the tourist answer and it’s also not wrong. They’re different styles (stuffed vs. deep dish) and both are genuinely good. Get one on trip one, try the other on trip two.
Italian beef: Al’s Beef on Taylor Street, wet and hot. This is the correct order.
Smyth and The Loyalist in West Loop — two restaurants in one building by chef John Shields. Smyth upstairs is a tasting menu experience that ranks among the best meals we’ve had in America. The Loyalist downstairs does elevated pub food, best burger in the city by a significant margin, no reservation needed.
Avec — a Mediterranean small plates restaurant that has been exceptional for two decades, which in restaurant terms is geological time. Always busy. Worth the wait at the bar.
The Neighborhood Rotation
Every Chicago visit, we try to spend at least two hours in a neighborhood we haven’t done before.
- Wicker Park — vintage shops, coffee, a lived-in creative-class neighborhood that still has edges
- Pilsen — Mexican-American neighborhood with serious murals and taquerias
- Hyde Park — University of Chicago campus plus the Museum of Science and Industry
- Logan Square — cocktail bars and restaurants that punch above their surroundings
The L train connects most of these affordably — a 24-hour pass is $5.
What the City Feels Like
Chicago has a physical confidence that’s different from New York’s frenetic energy and LA’s sprawl. The lakefront is public by law — all of it. Miles of parks and beaches and running paths front the water with no private development blocking access. On a summer Sunday, the lakefront fills with every demographic in the city simultaneously.
That lakefront is why people who’ve never been to Chicago are consistently surprised by it. The city faces a lake that looks like an ocean, with a skyline reflected in it, with public beach access in every direction. It’s not what people expect from the Midwest.
The Honest Logistics
Best time: May–June and September–October. July and August get hot and humid. Winter is real and beautiful in a brutal way (architecture looks incredible in snow) but dress accordingly.
Cost: Chicago is not cheap but isn’t New York either. Budget hotels in decent neighborhoods run $120-180/night. Airbnb in Wicker Park or Logan Square offers more space for similar prices.
Getting around: The L plus walking handles most itineraries. Rent a car only if you’re leaving the city.
We’re already planning trip six. That says everything.
O’Hare is one of the most connected airports in the US — often a good deal to fly through when positioning for other destinations. Chicago is also excellent by Amtrak from several Midwest cities.