Thinking about a trip to downtown Chicago? Don’t just follow the crowds — follow the experiences that truly matter. From hidden architectural gems to riverside dining and a few overrated tourist traps, here’s everything we loved (and what we’d skip) from our recent adventure in the Windy City.

Must-See Experiences in Chicago

1. Take an Architecture Boat Tour

Even if architecture isn’t usually your thing, this is an absolute must. Cruising along the Chicago River gives you a wonderful perspective of the city’s history through its ever-changing skyline. We booked the Chicago’s First Lady cruise and could not recommend it enough. No matter where you sit, you’ll get stunning views, and our guide made Chicago’s story come alive with enthusiasm and detail.

Your ticket also includes discounted entry to the Chicago Architecture Center for $5. If you’re short on time, this is one you can skip, but it’s a nice add-on for those who want to dive deeper into the city’s architectural history.

2. Stroll Along the Riverwalk

The Riverwalk is one of the best ways to experience Chicago at your own pace. There are plenty of great spots to grab a bite to eat, have a drink, or pick up souvenirs from local vendors. I’d suggest combining this with a walk toward Navy Pier — it’s a scenic and relaxing route.

Now, about Navy Pier itself: for me, it was a bit of a disappointment. It’s a great destination if you’re traveling with kids during the summer when the rides and fireworks are in full swing, but otherwise, it’s skippable. The Ferris wheel offers nice views, but if you plan to visit the Willis Tower Skydeck or 360 Chicago, you’ll get far better panoramas there. The “Flyover Chicago” attraction also felt overpriced for what it offered — between the architecture tour and a roller coaster ride, you’ve already covered that experience. I’d save the money and pick up a few local souvenirs instead. Nearby Grant Park is a much better use of your time, especially if you enjoy open spaces, gardens, and views of the skyline.

3. Visit the Cloud Gate (“The Bean”)

Of course, no trip to Chicago is complete without stopping by Cloud Gate — better known as “The Bean.” If you want to avoid the crowds, arrive early in the morning. Bring a coffee and breakfast to enjoy while you walk around and take in the reflections of the city around you.

From there, head to the Chicago Cultural Center, home to two magnificent Tiffany glass domes. The intricate designs are breathtaking, and there are smaller exhibits worth exploring along the way.

A quick note: the restaurants directly across from The Bean tend to be overpriced. Walk just a few blocks further, and you’ll find much better food at more reasonable prices.

4. Explore the Art Institute of Chicago

A perfect pause amid the city’s energy is a visit to the Art Institute of Chicago — one of the best museums in the world. I was surprised by how much I enjoyed wandering through its extensive galleries. The museum is quite large, so if you’re short on time, pick a few exhibits that interest you most.

They offer free one-hour guided tours at 1 p.m. and 3 p.m. (check for updated times), which are a great way to see the highlights. The museum’s collection of Monets is exceptional — a must for fans of Impressionist art or anyone looking for a peaceful escape on a rainy day.

5. Skip the Walking Architecture Tour

While the boat tour is a must, the walking architecture tour is one I’d skip. Most of the sites covered are public spaces you can explore freely on your own schedule. The tour I joined included some questionable facts, and after two hours of walking and sore feet, I wished I’d spent that time wandering at my own pace instead.

6. Visit the Rookery Building

If you’re interested in architecture, don’t miss the Rookery Building. Its stunning interior, redesigned by Frank Lloyd Wright, showcases the best of Chicago’s architectural innovation. It’s a shorter, focused visit — and absolutely worth it.

Where to Eat in Chicago

For breakfast, I highly recommend Petee’s Coffee, tucked inside the Wrigley Building. The outdoor seating area is lovely, offering a quiet spot to enjoy your morning coffee while admiring the surrounding architecture.

Along the Riverwalk, Pinched is another great find. It serves delicious Mediterranean food — and surprisingly good soft serve — in a relaxed riverside setting. It’s a wonderful spot for dinner or a late afternoon meal while watching the city wind down.

If you have extra time, make a stop in Chinatown. I didn’t get the chance to visit, but it’s high on my list for next time. Locals rave about its authentic restaurants, bakeries, and shops — perfect for an afternoon of exploring.

Final Thoughts

Chicago offers a perfect mix of iconic attractions and hidden gems. While some tourist spots are better left for first-timers, the city’s architecture, food, and lakeside charm make it a destination that’s both inspiring and welcoming. Plan your days around what excites you most, and you’ll discover why Chicago continues to captivate visitors year after year.

The Traveling Dad