A Weekend in Chicago with Kids

Everyone passes through Chicago at some point. In fact almost everyone I know has been stuck just 14 miles from my house at O’Hare airport. But did you know that many families actually linger in Chicago on purpose?

It’s true. In fact, every friend who has visited us from California or the East Coast has told us that they didn’t expect to love Chicago as much as they did. Right now – May or June – is the best time of the year to visit, in my opinion, since the weather is much milder now than the brutality we experience in January or the sun-struck malaise of July. September and October are also lovely.

Here’s what I would do if I had one weekend to enjoy Chicago:

Millennium Park

Visiting Chicago with KidsYou have to take your kids to Millennium Park in the summer. Completed in 2004, this place will be new to you if you haven’t visited our city lately. Bring bathing suits – or just let them get their clothes wet – because every kid will want to wade in the fountain and let the giant projected face spit on them. Trust me, it’s more fun than it sounds.

Then there’s looking at your funhouse reflection in our most famous piece of public sculpture, the Bean. There are also organized summer activities like arts and crafts and song-and-dance sessions led by North Side institution the Old Town School of Folk Music.

Lake Michigan

Every kid should stand on the shores of a Great Lake and marvel at how much like an inland ocean Lake Michigan really is. If it’s hot, head to a beach with a lifeguard and swim. I like the beaches in Evanston, which are clean and less crowded, but really every Chicago lakefront neighborhood and nearby town has its own great beaches.

If it’s not between Memorial Day and Labor Day, get out on the lake by taking an architectural boat tour instead.  These usually run just over an our, short enough that the kids are still enjoying the novelty of being on the water through most of the outing, while you get to pick up a little information about the city. Another plus: They usually serve refreshments.

If you don’t have the time or don’t want to pay for the whole boat tour, the quickest and easiest way to get on the water in summer is to take the water taxi.

Visiting Chicago with KidsNavy Pier and The Children’s Museum

The kids will spot the Ferris Wheel from almost any point on Lake Shore Drive. Take them for a ride and treat them and yourself to a great view. Then enter the Chicago Children’s Museum on the Pier for some educational fun.

If it wasn’t warm enough for your kids to get wet outdoors with the last two stops, they can don raincoats and play indoors in the water play room. Mine can’t get enough of this – even the baby, who was nine months old when we last visited. Yes, I had to change his entire outfit afterwards, but seeing this grin was worth it.

The Lincoln Park Zoo and Notebaert Nature Museum

Visiting Chicago with KidsChicago’s free zoo north of downtown is a lovely place to take a stroll, and there’s a play farm where the kids can see cow’s milked. The Notebaert’s butterfly dome is one of my daughter’s all-time favorite city destinations.

Where to Eat

When it comes to downtown adventures, I’m a brown bag mom, because everything is so expensive. Or I treat the kids to that quintessential Chicago treat, a hot dog from any cart that happens to be handy.

But if you visit the Lincoln Park Zoo on a Wednesday or Saturday morning, you can buy your lunch fixings at the Green City Market, which runs indoors in winter and outdoors in summer.

Where to Stay

Our family recently enjoyed a stay at the Homewood Suites by Hilton, not far from Navy Pier. As you can read in my review, I found this property normally marketed toward business travelers to be the perfect haven for a family in the big city, with conveniences that make downtown Chicago much more manageable.

We also loved the elegant and fun Kimpton property, Hotel Monaco, which is also right downtown and accessible to the same attractions.

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  1. Erin says

    We live not too far from Chicago (about 2 hours), and get up there as often as we can! It’s such a great city, and I can’t second the suggestions of the Millennium Park Fountains and the Lincoln Park Zoo. On our week-long vacation last year, our son spent THREE days at the Face fountain, not wanting to do anything else! We stayed in the Omni Hotel off Michigan Ave – which features suites (we stayed for around $140/night at the time). It was a great location (downtown), and they were really nice and accommodating. Pre-kids I had a chance to do the architecture tour, and it’s an AWESOME and unique way to see and learn about the city. It never gets old!!


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