Chicago might be famous for its wind, but honestly, that’s the least interesting thing about this city. I’ve wandered through Chicago more times than I can count, and every visit reminds me why this place is a total paradise for anyone who loves towering buildings and seriously good pizza. You’re getting two amazing experiences for the price of one trip, and trust me, your Instagram feed will thank you later.
Whether you’re tilting your head back to stare at skyscrapers or debating which pizza joint deserves your loyalty, Chicago delivers. Let’s get into the best things you absolutely need to do here.
Take an Architecture River Cruise
Here’s the thing about Chicago architecture: you can’t really appreciate it from the ground. Sure, you’ll get a stiff neck looking up, but hopping on an architecture river cruise changes everything. You’ll glide along the Chicago River while expert guides explain why each building matters.
The docents know their stuff, pointing out everything from neo-Gothic towers to modern glass giants. You’ll see over 40 iconic buildings in about 90 minutes. IMO, this is the absolute best way to start your Chicago adventure because it gives you the lay of the land (or water, I guess?).
Most tours run from spring through fall, and honestly, a sunny afternoon on the river beats sitting in traffic any day. Book ahead though because these tours fill up fast.
Visit Willis Tower Skydeck
Want to feel like you’re floating above the city? The Willis Tower (yeah, some folks still call it Sears Tower) stands at 1,451 feet tall. It’s Chicago’s tallest building, and the Skydeck on the 103rd floor offers views that’ll make you forget about everything else.
But here’s where it gets wild: The Ledge. These glass balconies extend four feet outside the building, and when you step on them, you can see straight down. It’s terrifying and thrilling at the same time.
Pro tip: go during sunset if you can. The city lights start twinkling as the sun goes down, and it’s absolutely magical. Just maybe skip this one if you’re afraid of heights 🙂
Explore the Chicago Cultural Center
This gem used to be Chicago’s first public library, and now it’s a free cultural hub that’ll blow your mind. The Tiffany Dome inside is the largest in the world, and standing underneath it feels like stepping into a piece of art.
The building itself showcases stunning Beaux-Arts architecture with intricate mosaics and marble everywhere you look. You don’t need to pay a dime to wander around and take it all in. FYI, this is where I send friends who think Chicago is “just another city” because it proves them wrong immediately.
What You’ll See Inside
- The world’s largest Tiffany stained-glass dome
- Ornate marble staircases and columns
- Rotating art exhibitions and performances
- Beautiful Preston Bradley Hall
Gawk at Tribune Tower
The Tribune Tower is neo-Gothic architecture at its finest, designed by John Mead Howells and Raymond Hood. But here’s what makes it truly unique: the walls contain fragments from famous structures around the world. We’re talking pieces of the Taj Mahal, the Great Wall of China, and even the Berlin Wall.
Seriously, who thought of that? It’s like a scavenger hunt meets architecture. Walking around the base of the building, you can spot these embedded stones and read their plaques.
The tower’s intricate detailing and ornate facade make it a photographer’s dream. Even if you’re not an architecture nerd, you’ll appreciate the craftsmanship that went into this beauty.
Marvel at the Wrigley Building
The Wrigley Building literally glows. With its gleaming white facade and iconic clock tower, this Renaissance Revival-style structure lights up the Chicago River waterfront. At night, they illuminate it, and it becomes one of the most photographed buildings in the city.
Graham, Anderson, Probst & White designed this stunner, and the twin towers create this elegant symmetry that just works. It’s been a Chicago landmark since 1921, and honestly, it hasn’t aged a day.
Grab a spot along the river walk and just take it in. The architectural details are insane when you really look at them.
Check Out Millennium Park
Everyone knows about Cloud Gate (aka “The Bean”), but Millennium Park offers way more than just a shiny sculpture. This 24.5-acre park combines art, architecture, and green space right in the heart of downtown.
The Jay Pritzker Pavilion, designed by Frank Gehry, looks like something from the future with its swooping stainless steel ribbons. Free concerts happen here all summer long. Crown Fountain is another must-see, with its digital faces spitting water at delighted kids (and adults, let’s be real).
Park Highlights
- Cloud Gate sculpture (perfect for selfies)
- Jay Pritzker Pavilion concerts
- Crown Fountain interactive art
- Lurie Garden hidden oasis
- BP Bridge pedestrian walkway
Visit John Hancock Center
The John Hancock Center (now officially called 875 North Michigan Avenue, but nobody calls it that) features distinctive X-bracing on the outside. This isn’t just for show. That structural design actually makes the building stronger and more stable.
The 360 Chicago observation deck on the 94th floor gives you panoramic views of the city and Lake Michigan. They even have TILT, where the windows tilt outward so you’re leaning over the city. Yeah, it’s as crazy as it sounds.
The building represents a bold step in skyscraper engineering, and standing up there, you really feel the innovation that went into creating it.
Eat Deep Dish at Lou Malnati’s
Okay, let’s talk pizza. Lou Malnati’s has been serving Chicago’s favorite deep dish since 1971, and they’ve stayed true to the original recipe created by Lou Malnati himself. That flaky, buttery crust alone is worth the visit.
They layer fresh mozzarella directly on the crust, then add your toppings, and finish with chunky vine-ripened tomato sauce on top. It’s the reverse of regular pizza, and it works brilliantly. The cheese gets all melty and gooey, and that buttery crust? Chef’s kiss.
Lou Malnati’s has multiple locations around Chicago, so you won’t have trouble finding one. Just remember: deep dish takes about 30-45 minutes to bake, so order ahead or be patient. Good things take time.
Try Pequod’s Pizza for Something Different
If you want to start a debate among Chicago locals, just mention Pequod’s Pizza. Yelp ranked them as the #1 pizza in the country, and their secret weapon is the caramelized crust. They press the dough to the edges of the pan, and the cheese burns (in the best way possible) against the sides.
That burnt cheese crust creates this incredible texture that’s crispy, chewy, and ridiculously addictive. Bon Appetit called it “one of the finest versions of Chicago’s polarizing signature dish.” The sauce has a perfect spicy kick that balances everything out.
Why People Love Pequod’s
- Caramelized crust unlike anywhere else
- Perfectly spiced tomato sauce
- Generous cheese portions
- Cult following since 1971
- Worth the wait (and there will be a wait)
Walk Through the Loop
The Loop is Chicago’s downtown core, named after the elevated train tracks that circle it. Walking these streets feels like moving through an architecture museum. Every block reveals another masterpiece, from Art Deco gems to modern glass towers.
You’ll spot the Carbide and Carbon Building with its gold-topped Art Deco design, the historic Reliance Building, and dozens of other structures that shaped modern architecture. The energy here is electric, with street performers, food vendors, and that constant hum of city life.
Wear comfortable shoes because you’ll want to wander. Each turn reveals something new, and honestly, getting a little lost here is part of the fun.
Take an Inside Architecture Walking Tour
Most people photograph buildings from the outside, but Chicago’s interior architecture is equally stunning. Specialized walking tours take you inside iconic buildings to see lobbies, atriums, and spaces that regular tourists never access.
You’ll walk through Art Deco lobbies with original details, see soaring atriums filled with natural light, and learn how architects designed these spaces to inspire and impress. The marble, the metalwork, the attention to detail? It’s all incredible.
These tours showcase both famous buildings and hidden gems that you’d walk right past without knowing their secrets. It’s like getting VIP access to Chicago’s architectural soul.
Experience Multiple Pizza Styles
Here’s a hot take: you don’t have to choose just one pizza place. Chicago has thin-crust pizza too, and it’s seriously underrated. Lou Malnati’s makes an excellent tavern-style thin crust that’s crispy, cut into squares (Chicago-style), and loaded with flavor.
Deep dish is the star, sure, but trying different styles gives you a fuller picture of Chicago’s pizza culture. Some locals actually prefer thin crust for regular eating and save deep dish for special occasions. Can you blame them? Deep dish is basically a meal and a half.
Why not try both during your visit? Start with deep dish for lunch, then grab thin crust for a late-night snack. Your taste buds deserve the full experience.
Final Thoughts
Chicago delivers on both architecture and pizza in ways that other cities just can’t match. You’ll leave with a camera roll full of stunning buildings, a very happy stomach, and probably some strong opinions about which pizza place reigns supreme. The city rewards curiosity, so wander down random streets, ask locals for recommendations, and soak it all in.
Ever wondered why Chicago became such an architecture powerhouse? It’s because the 1871 Great Fire destroyed most of the city, and architects saw it as a blank canvas to innovate. That spirit of innovation still thrives today, making Chicago a living, breathing architectural timeline from the 1870s to now.
So pack your walking shoes, bring your appetite, and get ready to fall in love with a city that takes both its buildings and its pizza very, very seriously. You won’t regret it.
