Traveling with Kids: a Chicago Adventure

photo by adam alexander photography, courtesy of choose chicago

Not even 15 minutes after we’d left our house in St. Paul en route to Chicago our 4-year-old asked, “Are we almost there?”

I looked over at my husband, Aaron, and raised my eyebrows. Were we crazy to drive? Should we have booked a flight instead?

We survived the marathon drive with a pile of books, movies, car games, frequent drive-time countdown (six hours until we’re there, five hours, four hours, three, still three, yep, I’m sure it’s still three, two, one…) and the occasional leg stretch/bathroom break. When we pulled up to our hotel and stepped out of the car, I felt a rush of excitement being among so many different cultures—and I hoped the boys sensed it, too. We were in a city that’s a global tourist destination. You get just a slight taste of that cosmopolitan feel in Minneapolis, but in Chicago it’s an all-out buffet.  

The Windy City might not be an obvious choice when planning a family vacation—like Wisconsin Dells or Disney World—but it should be on more parents’ radars. Family-friendly attractions include the Shedd Aquarium, Adler Planetarium, Field Museum, Lincoln Park Zoo, Chicago Children’s Museum, Navy Pier, Willis Tower, and massive Museum of Science and Industry. There was no way we’d see them all in one weekend, but we were going to cross off as many as we could. We wanted to give our boys, Ben, 4, and Adam, 7, the experience of seeing city life on a larger scale, and Chicago was the perfect place to do just that.

Bridge and flag courtesy of Somatuscani – Fotolia, Navy Pier and Skybox by adam alexander photography, courtesy of choose chicago, riverview by patrick l pyszka/city of chicago, courtesy of choose chicago

Our adventure began Saturday morning, when we got up early and caught a bus to  Navy Pier (, a 50-acre playground including a Ferris wheel, children’s museum, mini-golf course, restaurants, shops, movie theater, and seven-story Shakespeare theater. The popular attraction was relatively calm and quiet—like the calm before the storm.

An employee praised our early arrival: “You come any time after two and it’s crazy here.”

The pier offered views of the Chicago skyline with Lake Michigan out front, and up-close views of tall ships reminiscent of Pirates of the Caribbean. There were sightseeing double-decker cruise ships along the pier, too. On our next trip to Chicago, I’d love to see the sights from the water on an architectural boat tour ( Before we left, we rode the Ferris wheel because, you know, it’s the iconic Navy Pier Ferris wheel. Once our cart got to the top, Ben exclaimed, “You can see the WORLD from up here!”   

After our ride, we walked across the street to the plaza at Polk Bros Park, the entry point to Navy Pier (or, in our case, the exit point). Ben was intrigued by the square granite fountain, with water spraying from the top, flowing down the sides, and shooting up from the ground—designed by the same company that did the fountains at the Bellagio hotel in Vegas—water, water everywhere! Adam liked the colorful mosaic and life-size bronze sculpture of kids holding hands, running, and playing (coincidentally, the same sculpture Aaron and I had posed beside on our 2005 honeymoon).

Navy Pier Ferris wheel, photo courtesy of Choose Chicago

Outside the entrance to Navy Pier we purchased Explore Chicago Passes from Chicago Trolley & Double Decker Co. (, a vital decision for traveling with kids due to it being an easy, convenient way to see the city. The sightseeing tours follow a hop-on/hop-off format, so you can choose which attractions and neighborhoods you see, with buses circulating frequently at designated stops.

We chose the Signature Tour, covering downtown and the Loop. As we drove around the city, we learned why activist and social worker Jane Addams was so beloved (she founded Hull House, a settlement house providing childcare, education, and health care to poor European immigrants, worked to reform child-labor laws, and supported women’s suffrage), saw the longest freestanding bar in North America (the 160-foot-long bar at the Hyatt Regency), the Magnificent Mile shopping district (with luxury lifestyle shops, including Burberry, Chanel, Gucci, and Louis Vuitton, specialty shops Anne Fontaine and Tumi, and for the kids—the LEGO Store, Candyality, and American Girl Place), and learned that the neo-Gothic designed Tribune Tower was built with stones from world-famous landmarks, including chunks of the Great Wall of China, the Great Pyramid of Cheops, and the Berlin Wall—a tradition that began in 1914 when the Tribune’s editor was covering World War I and grabbed a piece of a French cathedral that had been bombed in a German air raid. There was a lot of information shared, but I never worried that the kids were bored because they were sitting on top of a bus—that, for them, was entertainment enough.

state street, photo by adam alexander photography, courtesy of choose chicago

My favorite site was the Aqua skyscraper, designed by Jeanne Gang with tinted glass and curved balconies that look like waves (I later found out that this building is now the Radisson Blu Aqua Hotel Chicago, complete with an indoor basketball court my kids would have loved). The boys perked up when we passed the distinctive Rock ‘n’ Roll McDonald’s, with two arches soaring into the sky. We learned that this McDonald’s is one of the busiest in the country, complete with a museum upstairs. Across the street are other kid-friendly dining options: Hard Rock and Rainforest Café. (“How’d they get that frog up there?” Ben asked of the statue above the sign. It was fun to see the city through the perspective of a preschooler.)

When you’re in Chicago, it’s kind of an unwritten rule to get deep-dish pizza at least once, so that’s the route we took for lunch. We debated between Lou Malnati’s, Unos, Pizano’s, Gino’s East, and Giordano’s, ultimately choosing Giordano’s (—mainly because they’re bringing the restaurant to Uptown Minneapolis and we were curious about the hype.   

Once we were seated, we were quoted a 45-minute wait, and passed the time by ordering an appetizer, doing puzzles on the kids’ menu, and watching part of a movie showing on a nearby TV. When our pie arrived, there was so much cheese on the pizza that the server had to cut the strings of mozzarella with a special little spatula in order to serve it to us. After I tried a bite, I made a mental note to put the Uptown opening date on my calendar.  

chicago waterfront courtesy of vichie81 – fotolia

After lunch, we took a bus over to Willis Tower (, formerly known as the Sears Tower, soaring above the other Chicago skyscrapers at 110 stories high.

Depending on the time of year you go (and time of day), the line to get up to the Willis Tower Skydeck (—where visitors can stand in a glass box and see the city 103 floors below—can be three-plus hours long, but thankfully our wait was only a little over an hour. Pre-purchasing tickets, as we did, eliminated one of the long lines; another option would have been the spendier $45 Fast Pass—an express line to the Skydeck elevators. The boys liked the ear-popping elevator ride (103 floors in 60 seconds!), and once we got to the 103rd floor, I was in awe of the view—looking out over Lake Michigan to Indiana, Michigan, and Wisconsin. We took a photo in the Skydeck glass box and didn’t feel as intimidated as I thought we would. Even the boys were OK with it. “This isn’t freaky,” Adam said. “It’s cool.”

After our Willis Tower experience, we rode another double decker over to Millennium Park (, a public park near Lake Michigan with four major attractions: the Jay Pritzker Pavilion, designed by renowned architect Frank Gehry (the Weisman Art Museum designer), “Cloud Gate” (better known to just about everyone as “the Bean,” a three-story sculpture reflecting the Chicago skyline), Crown Fountain, consisting of two 50-foot glass towers at each end of a shallow reflecting pool with faces projected on LED screens, and Lurie Garden, a four-season urban oasis. We brought a football, and the kids tossed that back and forth on the plaza near the Bean. We did our fair share of people-watching and taking goofy photos, too.

On Sunday, we expanded our circle of exploration when we took a trolley—a ride that left an impression on both boys—to the Museum of Science and Industry (, located in the Hyde Park neighborhood. Our tour guide brought us near President Obama’s house, shared fun facts with us (Buckingham Fountain was in the opening credits of Married…With Children), and told us that he had dated singer-songwriter Chaka Khan before she made it big (she now has a street named in her honor). That trolley tour was one of my favorites—I liked seeing the historic brownstones and hearing about real-life celebrities who lived and worked in blue-collar surroundings. A friend had told me before we left, “If you want to like Chicago, see downtown. If you want to love Chicago, see the neighborhoods.” I agree with that sentiment.

When we arrived at MSI, I was a little awe-struck. The sprawling exterior looks like a Roman palace, with rows of grand columns and ornamental sculptures. The museum is partly housed in the former Palace of Fine Arts, built in 1893 to display fine art collections during the World’s Fair. I loved that there’s so much history associated with the building itself.

Inside the museum, it’s so vast you need a map to find your way around. I was glad a friend had recommended we set aside half the afternoon to tour the museum, because anything less in the 400,000-square-foot space would have felt rushed. There are more than 800 exhibits and 2,000 interactive displays. (It’s the largest science museum in the western hemisphere.) We saw a model railroad with 20 trains running on 1,400 feet of track (perfect for any fan of Thomas & Friends), became part of an interactive exhibit about tornados, admired the Fairy Castle doll house, saw an actual World War II German submarine, stacked foam blocks and played with water cannons in the lower level 10-and-under area, and watched baby chicks being born in the hatchery—a highlight for all of us.  

howells & hood, photo courtesy of flik photography

That evening, we met up with extended family—who live in Chicago—on the patio of Howells & Hood ( The restaurant is a little upscale for kids, but the adults loved the fish tacos, New York strip steak, and variety of beer (114 unique craft beers on tap!). The location was great, too, at the base of the Tribune Tower, right in the heart of downtown.

After such a busy day, the kids were overstimulated and over-tired (the perfect recipe for a meltdown), so Aaron brought them back to the hotel while the rest of us walked below Michigan Avenue to the Billy Goat Tavern ( If the place sounds familiar, it was made famous by the 1970s-era “Cheezborger! Cheezborger! Cheezborger!” Saturday Night Live sketch featuring Dan Aykroyd and John Belushi. The restaurant is also known for the “Curse of the Billy Goat.” As the story goes, the tavern’s original owner, Cubs fan William Sianis, brought a goat to a 1945 World Series home game for good luck. He was ejected due to the goat’s odor, and was so upset, he allegedly put a curse on the team so they wouldn’t win a World Series. (And they haven’t since then, despite efforts to “reverse the curse.”)

From the foodies and craft-beer aficionados at the trendy Howells & Hood to the laidback salt-of-the-earth crowd at The Billy Goat, I felt like I experienced two different worlds my last night in town. At the Billy Goat, drinks were cheap (a tab of just $24 for six of us?!), the service surly, and the décor iconic. I especially liked the local journalism gods memorialized on the Wall of Fame. The experience was unforgettable.  

Back at the hotel, with the kids sleeping soundly—probably dreaming of a double-decker bus—I thought about our little getaway. I originally had worried that maybe the city would be too mature for our kids; maybe they were too young to appreciate it. I was wrong. They were having so much fun I knew they’d be disappointed in the morning to hear vacation was over. All we had left was packing up, checking out, and that long drive ahead of us.

Chicago definitely is for kids, and we’ll take them again. Only next time, maybe we’ll fly.