3 Best Architecture Tours in Chicago (and What You Should Know Before You Go)
Visiting Chicago and wondering what activities to put on your list?
Even though I’ve lived in the city for more than a decade, I’ve done multiple architecture tours, and I keep going back. It’s my go-to recommendation for anyone visiting the city, whether it’s your first time or you’ve been before.
Chicago’s famous for its architecture, and for good reason. Skyscrapers that launched modern architecture, riverfront gems, hidden Art Deco details, and showstoppers by names like Frank Lloyd Wright and Jeanne Gang—you’ll find it all here. Sure, you can wander around solo and see the sights, but a great guide makes the buildings—and their stories—come alive.
Whether you’re a first-time visitor or a local looking to see your city in a new way, here are my picks for the best architecture tours in Chicago.
Frequently Asked Questions
Are architecture tours worth it?
Absolutely. Chicago’s skyline is basically an open-air museum, and these tours bring it to life. Whether you’re an architecture aficionado or just casually curious, you’ll see the city in a whole new way.
Do river cruises run year-round?
Mostly no. River architecture cruises usually run from late March or early April through November. Ice on the river shuts things down in winter. If you’re visiting in the colder months, opt for a walking or bus tour instead.
Are these tours good for kids?
Yes, especially the river cruises. Kids usually love being on a boat, and the views keep them entertained. Walking tours might be a bit long for younger kids unless they’re big architecture fans.
What should I wear?
Comfortable shoes are non-negotiable if you’re doing a walking tour. For river cruises, bring a light jacket even in summer, it can get breezy. If you’re doing a walking tour in colder months, definitely layer up.
Will I get seasick on the river cruise?
Very unlikely. The Chicago River is super calm. But if you’re prone to motion sickness, sit toward the middle of the boat and stay outside. As someone who suffers from motion sickness, I have never experienced any on a river cruise.
Do I need to book in advance?
Yes! Especially on weekends or in summer. The Chicago Architecture Center river cruises, in particular, sell out days ahead.
Details on Architecture Tours in Chicago
Chicago Architecture Center River Cruise – My Top Pick!
This is it.
I’ve lived here for years, and I’ve done this architecture cruise multiple times — and honestly, I’d go again tomorrow. It’s my favorite architecture tour in the city and the one I recommend to everyone who comes to visit because in my opinion, it’s #1 on the list of best architecture tours in Chicago.
Operated by the Chicago Architecture Center (CAC), this 90-minute tour dives deeper than any other. The docents are expert volunteers who know the architecture inside and out, sharing details about Chicago’s past, the evolution of its skyline, and why certain buildings look the way they do. It’s like getting a master class on architecture, but in a fun way in a great city.
Standout feature: The depth of storytelling and architectural insight. If you’re a design lover—or just curious about Chicago’s history—this tour will wow you.
Departs from: Chicago Riverwalk near Michigan Ave & Wacker Dr.
Length: 90 minutes
Season: Spring through fall
Frequency: Every hour on the hour, roughly 9 AM – 8 PM (varies by season)
If you’re only going to do one tour while you’re in Chicago, make it this one. There’s just something about being out on the water, hearing the city’s history while skyscrapers loom above you, that makes it feel special — even for a local like me.
Wendella Chicago River Architecture Tour
If you want a slightly shorter trip, Wendella’s 75-minute architecture cruise is a solid choice. The boat itself is classic and comfortable, with big windows for great views, and the narration strikes a nice balance between educational and conversational.
One thing I appreciate about Wendella is the little detour they take through the Chicago Lock, which briefly opens the river up to Lake Michigan — giving you that iconic skyline from a fresh angle, something most other tours don’t do.
The guides keep it approachable and friendly, so it’s perfect for families or anyone new to architecture.
Standout feature: Quick lake detour for unique skyline photos and that fresh-water breeze.
Frequency: Hourly departures from 10 AM to 6 PM
Departs from: Dock near the Wrigley Building (Michigan Ave & river)
Length: 75 minutes
Season: Spring through fall
Shoreline Sightseeing Architecture River Tour
Shoreline Sightseeing offers a lively 75-minute tour that hits all the main architectural highlights but does so with a bit more flair and humor. If you’re looking for a fun, energetic guide who makes the city’s buildings come alive with stories and jokes, this is a great pick.
They depart from both Navy Pier and the Riverwalk, which is handy if you’re already exploring the lakefront or headed to the pier for other attractions.
Since the boats are larger and more geared toward sightseeing, this is a good option for groups or families who want a comfortable ride with lots of space.
Standout feature: Energetic, entertaining narration that keeps the whole crew engaged.
- Departs from: Navy Pier or Riverwalk docks
- Length: 75 minutes
- Season: March through November
- Frequency: Every 30–45 minutes during peak times
Tips for the Best Architecture Tours in Chicago:
- Book in advance—especially in summer and on weekends. These tours are super popular, so snag your spot early to avoid disappointment and get your preferred time.
- Go early in the day or around golden hour for the best light (and fewer crowds). Morning light and sunset give you the best photos and a more peaceful vibe on the boat.
- Bring sunscreen and layers—it can get windy on the river. The weather can change fast on the water, so dress in layers and don’t forget sunscreen even on cloudy days.
- Don’t just stick to one tour. If you love architecture, try a walking tour for new perspectives.
- Keep an eye on the weather forecast. Chicago can surprise you, so check ahead and reschedule if needed to avoid rain or super windy days.
Best Architecture Tours in Chicago: Final Thoughts
Whether you’re a first-timer or a local looking for a fresh way to experience the city, these architecture tours are hands-down the best way to dive into Chicago’s incredible design story. I’ve lived here over a decade, and the Chicago Architecture Center river cruise remains my top pick, but it’s hard to go wrong with whatever tour you choose.
So, don’t just take my word for it. Book your tour now, grab a spot on the water (or on foot), and get ready to see Chicago’s skyline come alive with stories, history, and jaw-dropping views. Trust me — you’ll want to do it again.
Go ahead, make your Chicago trip unforgettable. Your perfect architecture tour is waiting.
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