by Jessica Howell
Great Lakes views. Big city bustle. Midwestern charm. Chicago is a destination city that’s perfect for families and kids of all ages (we’d know, because it was our first family trip as parents of a newborn!). If you’re looking for a weekend escape that’s truly got something for everyone, let’s chat about the Windy City.
There’s so much to see and do in Chicago and the surrounding area that it’s almost difficult to suggest it as a weekend getaway, but in truth, that’s the way we’ve always approached our stays with kids. Small doses of big cities seem to work best for us with little ones, with plenty of activity baked in, but also–a relaxed hotel that we can retreat to for naptime, snacks and maybe even a bit of pool play. (Because honestly, no matter where we go, that’s the kid’s favorite part.)
SIGHTSEEING
Millennium Park: Such a beautiful green space near the heart of the city. You’ll find the iconic Cloud Gate statue (better known as “The Bean”), fountains to splash in during the summer months, an ice rink at wintertime, and the legendary Maggie Daley playground with slides, bridges and climbing walls–the perfect picnic spot during a day out. (LINK)
Navy Pier: I’m fairly confident that you can’t visit Chicago without at least one child spotting the lit-up Ferris wheel perched on the pier. Here, you’ll find a variety of family-friendly attractions, a beer garden and also the launch place for many of the city’s boat tours, including architecture tours for older kids and the iconic Seadog speedboat tours that zip along the waterfront (kids must be at least 48″ tall). (LINK)
Riverwalk: Stroll the city without worrying about traffic–a family win–and score epic city views from the riverwalk. You’ll also find cafes, murals, and easy access to street shopping. (LINK)
ATTRACTIONS
Lincoln Park Zoo: Free to the public, Chicago’s Lincoln Park Zoo is such a fabulous resource. You’ll see loads of animals in the warmer months and in the winter, you can buy tickets for the impressive “zoo lights” evening events. Also nearby is the Lincoln Park Conservatory (definitely worth a stop!), and the shops and restaurants of this laid-back neighborhood, which moves at a slightly slower pace than downtown. (LINK)
Shedd Aquarium: Practically spilling into Lake Michigan, this saltwater and fresh water aquarium hosts a range of sea life, from penguins to beluga whales, sea lions to eels and octopi. It’s a showstopper for kids but notoriously busy, so you’ll want to buy tickets online in advance. (LINK)
Museum of Ice Cream: I can’t talk about Chicago without at least mentioning the candy-pink facade of the Museum of Ice Cream building, which makes for a fun afternoon. You’ll get plenty of ice cream (be warned, you’ll find some fanciful flavors!) and leave with loads of adorable photos. Did someone say sprinkle pool? All ages are welcome; note that the museum is closed on Tuesdays. (LINK)
SHOPPING
Harry Potter Shop: If you’ve got a little wizard, this store–located on the Magnificent Mile–is a must stop. Heck, it’s worth a stroll even if you don’t. You’ll be mesmerized by the magical decor (including flying books) and can grab a butterbeer at the store’s bar. Spin a gigantic wheel to see which jellybean flavor best suits your style. (LINK)
Starbucks Reserve Roastery: The largest Starbucks in the world, this five-story mecca is made for coffee addicts. We stopped in to appease dad, but the kids cooperated just long enough for us parents to enjoy an espresso martini on the fourth-floor cocktail bar. (There’s a rooftop terrace, too!) (LINK)
Water Tower Place: Not surprisingly, you’ll find this shopping area near the city’s historic water tower. It’s chock full of impressive shops, not the least of which are the dizzying American Girl Place with spa and luncheon reservations available, and a massive LEGO store. If the weather is sketchy, this spot should definitely be on your list. (LINK)
EATING
Grab coffee at the world’s largest Starbucks or hit Instagram-darling Ralph’s Coffee (in the chic Ralph Lauren store) as soon as it opens to avoid a line. Then head to Stan’s Donuts for some of the best that you’ll find. I vote Coconut Cake the clear winner!
Lunch at the Walnut Room inside of Macy’s (the first restaurant ever opened in a department store!) is a luxe splurge, and you’ll definitely want a reservation. The holiday decor is absolutely swoon worthy! Or, take an entirely different approach and head to Ed Debevic’s where you’ll find classic rock 60s decor, mohawked waiters and a hefty side of attitude with every entree.
We veered far outside of our comfort zone for an early dinner (hello, 3 p.m. reservation) at our longtime favorite, RPM Italian, for the first time with kids in tow. The vibe is relaxed-elegant and the restaurant easily accommodated our little ones, and the food, incredible, as always. This isn’t one I’d recommend to most families, but if you’re looking for a special meal, and can convince your kids to be chill, this is one that’s such a treat!
SLEEPING
HOLIDAY
There’s nothing like a big city during the Christmas season, and Chicago never disappoints. Gorgeous Christmas trees stand tall around every corner, it seems, and garland is strung about the city, with festive events by the dozen. We hit up the Christkindlmarket in Wrigleyville (recognized as a great option for kids) and enjoyed ice skating, riding the kiddie train, and–of course–some mulled wine.
Navy Pier also hosts a ticketed Winter Wonderfest with indoor ice skating, kids rides and gigantic decorations, while the Lincoln Park Zoo offers ticketed entry to their bright and festive ZooLights evening event.
