We visited Chicago while en route to a short summer trip to Wisconsin. Flying into O’Hare late on a Friday night, we had one full Saturday to squeeze in as much as possible before starting our road trip the next morning. Just thinking about it makes me a little tired, but I wouldn’t change a thing about the day. This itinerary captures how we spent our whirlwind day in Chicago with our 11- and 8-year-olds in July.

Practical Takeaways

• With just 24 hours to explore, we prioritized three must-do activities: Millennium Park, an Architectural Boat Tour, and the Griffin Museum of Science and Industry. We kept everything else flexible, which gave us structure without making the day feel stressful.
• We lucked out with gorgeous July weather. To beat the heat, we planned outdoor activities for the morning and evening, saving the hottest part of the day for an indoor museum.
• Living along the Northeast Corridor, we are accustomed to cities and bounce between Washington D.C. and New York often. What we aren’t used to are the clean urban lakefront beaches that Chicago offers. With more time, we would have enjoyed the access to Lake Michigan, a truly unique aspect to this American city. 
• I also wish we had time for a show at Second City, but I guess that just means we will need to go back.

Accommodations

We booked the Arlo Chicago on Michigan Avenue, right in the heart of downtown. For such a short stay, this location was perfect – we could walk to Millennium Park and other attractions with ease.

That said, being in the center of it all came with trade-offs: it was loud at night, and Michigan Avenue seemed to double as a drag racing strip. For a longer stay, I’d choose a quieter neighborhood, much like avoiding Times Square in New York or opting for residential areas as we did in London (more those cities here).

The hotel itself was clean, the staff friendly, and while the rooms were small with views into an alley, that’s what you’d expect from a central downtown hotel.

Our 1-Day in Chicago Itinerary

Millennium Park

As someone who has worked in urban parks for 20 years, Millennium Park was at the top of my list, and I can’t believe it took me this long to visit. I slipped out early in the morning to explore on my own, soaking in the lush landscapes, Frank Gehry’s sweeping pedestrian bridge, and the iconic Cloud Gate (aka “the Bean”), admiring the reflections from every angle.

Later, the kids joined me to splash at the Crown Fountain (“the Squirting Faces”) and enjoy the playgrounds. My son only wished he had a swimsuit! By 9 a.m., security began clearing the park for a festival scheduled later in the day. I recommend checking the park’s event calendar before your trip to make sure you can access everything you want to see.

Architectural Boat Tour

When we asked friends for recommendations, the Wendella Architectural Boat Tour came up every time. We booked a 45-minute tour leaving at 10 am, which turned out to be ideal with kids (if I were on my own, I’d have chosen the 90-minute option). The tour gave us a crash course in Chicago’s history and skyline, which I mostly only knew from watching Ferris Bueller’s Day Off.

Cruising along the Chicago River, we glided past more than 50 legendary landmarks—from the Wrigley Building and Tribune Tower to the Willis Tower (formerly known as the Sears Tower). The guide explained what makes each structure special. I particularly loved seeing the St. Regis Chicago, the tallest building in the world (101 stories) designed by a woman, Jeanne Gang.

Doing the tour in the morning helped orient us to the city and (mostly) spared us from the brutal midday sun on the upper deck.

Lou Malnati’s

After the tour, we walked to Lou Malnati’s for their famous deep-dish pizza. We arrived at 11:15 a.m. and were seated right away. By 11:30, the place was packed. Considered the oldest family name in Chicago pizza, Lou Malnati’s has been serving pies since the 1940s. (Tip: try the butter crust!). We also saw some pizza tours come through, which looked fun.

As a former New Yorker, I’m still not entirely sure about eating pizza with a fork and knife, but when in Chicago, this is a must-do.

Museum of Science and Industry

In the afternoon, we hopped on the #6 bus (an easy and fun ride through different neighborhoods) to the Griffin Museum of Science and Industry. It reminded us of Philadelphia’s Franklin Institute, especially the weather and body movement exhibits.

The highlight was the Coal Mine Exhibit (a small extra fee, but worth every penny). First opened in 1933, it remains one of the museum’s signature experiences. Guided by staff, we descended into a “working” mine, boarded a train, and explored how mining evolved through the decades. It was immersive, educational, and unlike anything we had experienced in a science museum.

Dinner at Sunda New Asian

After a bus ride back from the museum and a short rest at the hotel, we walked 20 minutes to Sunda New Asian in River North. The walk gave us a chance to explore less touristy neighborhoods.

I worried it might be too upscale for kids, but it was perfect. We enjoyed creative rolls (the Caterpillar roll with sweet potato and pear was a favorite), black cod, and even kid-sized bento boxes. No wonder a friend once told me she dined here three times in one trip. Also, the food was so good that I forgot to stop eating and take photos. All I have to show for this meal is a kids bento box that came out before my own order.

Helpful Hints

• Breakfast: On trips, we usually eat breakfast in the hotel room to save time. Luckily, Stan’s Donuts was right across the street. I grabbed treats both mornings at 6:30 am to bring back to the room. By the time we headed out around 8:00 am, the line was already out the door.

• Getting Around: Don’t be afraid of public transit. The bus was incredibly easy and gave us a glimpse of neighborhoods outside the tourist core.
  
• Beyond Chicago: From here, we rented a car and continued on to Milwaukee (including a Brewers game!) and Door County, Wisconsin, making this a full Midwest summer road trip. Along the way we also stopped to see the house from “Home Alone” because we just couldn’t get enough of John Hughes movie references.