Downtown Chicago has something for everyone: shopping, restaurants, museums and more. Here’s why downtown Chicago is fun for kids and adults. Spend an entire vacation without leaving the neighborhood.
I’ve lived in Chicago for 14 years, but I still haven’t gotten tired of downtown Chicago. I make monthly treks here from the suburbs with my daughters, ages 7 and 10. We frequently take staycations just to experience the energy that makes up the Gold Coast, River North and Chicago Loop neighborhoods. And I’m ready to share my secrets!
Where to stay
On a recent staycation, we split our time between two hotels downtown: The Peninsula Chicago and the Fairmont Millenium Park.
The Peninsula is in the heart of downtown Chicago in the Gold Coast, and it screams, “luxury.” Our favorite part: the indoor pool, which has floor-to-ceiling windows and a clear view of the Water Tower. We spent half the day there, lounging in the pool and Jacuzzi, and sipping on organic herbal tea.
The Peninsula also has an infamous tea service every afternoon, and its new rooftop bar, Z Bar, sports some of the best drinks and hors d’oeuvres in town.
Fairmont Millenium Park
This hotel is steps from Maggie Daley park (the best part ever for kids ages 1-10), and that’s reason enough to stay there. But if you need any more convincing: It’s also a few streets away from the Maggie Daley Ice Skating Ribbon, the Bean (weird, but must-do tourist site), the Art Institute and the Chicago Symphony. Spring for a suite, and you’ll be treated to a room larger than most apartments – along with a gratis lounge where you can snack all day on everything from pecan pie to tuna tartare.
What to do
There’s plenty of shopping downtown, from the American Girl Store to the Apple store to the Disney store. But you didn’t come to Chicago just to shop, right?
For the views: 360Chicago is located on the top of the Hancock Building, and not only will you have the best views in all of Chicago, but for an extra $8, you can tilt. Translation: you can lean over glass and feel like you’re flying over Chicago. My 7-year-old was too scared to give it a shot, but my 10-year-old did it twice, and would have done it even more times if I hadn’t pried her away.
For the culture: The Chicago Symphony often offers children’s concerts for various age groups. They also have *very popular* movie nights (so if you’re planning on doing this, get your tickets ahead of time), where they’ll play music along to movies like Harry Potter or Star Wars while you can watch the films on a big screen. Or, older children can take in an adult concert.
The Art Institute is across the street from the Chicago Symphony. They even have a kids’ room complete with activities, crafts and more.
Prefer ballet? At the Auditorium Theatre Chicago, home to the Joffrey ballet, you can catch everything from The Nutcracker to Swan Lake to Cinderella. My kids have loved the Joffrey since they were toddlers, and it’s totally kid-friendly.
Just for fun There are two new ice rinks right in downtown Chicago that are open every winter. You can choose between Millennium Park McCormick Tribune Ice Rink, which is right on Michigan Avenue or the Maggie Daley Ice-Skating Ribbon, which is closer to Lake Michigan but still walking distance to downtown. The ribbon tends to be less crowded, but still demands a line at peak times. Both are great ways to experience Chicago, as you’re ice-skating with the backdrop of Chicago behind you.
Where to eat
There are so many places to choose from, but I’m going to share our favorites.
For light bites and the most amazing Sunday brunch, I always turn to the Peninsula’s ZBar. It’s got great views, fabulous drinks and a chef that cooks seasonal food that’s some of the best in Chicago.
If you want a true Chicago hot dog, turn to Downtown Dogs, where you can get the hot dog the way Chicagoans eat it: topped with a pickle, relish, tomato, mustard . . . and no ketchup.
Or, for a classic urban eatery that everyone can agree on (that’s not Cheesecake Factory), we head to Fig & Olive, which offers everything from burgers to risotto.
We can never resist Ghiradelli’s for a massive ice-cream sundae for dessert. Pro tip: When you walk into Ghiardelli’s, they always hand over a very large sample of their chocolate. Score!
Spending a weekend in Chicago? Here are some options: