Just 90 minutes outside Chicago’s city limits, this ever-evolving Wisconsin town is the perfect day trip or weekend getaway for families
If you live in Chicago, and you haven’t taken a trip up to Milwaukee, what are you even doing? In the time it would take you to get across town and back in rush-hour traffic, your family could be exploring one of the midwest’s hidden hubs for arts, culture, and family-friendly experiences. And although Wisconsin’s most populous city has been experiencing a major boom in tourism over the past few years, the close-to-home destination is still small enough that you can pack in the essential highlights for a quick day trip or check all the boxes on a two-day weekend getaway.
Where to Stay in Milwaukee
There are plenty of family-friendly hotels and AirBnBs throughout Milwaukee. Looking for a hotel with a rooftop swimming pool that boasts panoramic city views? The Pfister Hotel will keep your kiddos splish-splashing. Want your littles to feel like VIPs? Aloft Milwaukee Downtown boasts Camp Aloft, a children’s program that provides a welcome goodie-bag and plenty of kid-friendly, parent-approved snack options throughout your stay.
One hotel you might not expect to be kid-friendly but is actually a can’t miss stay for art connoisseurs of all ages? Saint Kate – The Arts Hotel. For a boutique hotel, it’s surprisingly comfortable and welcoming, from the glass of champagne given to adults upon checkin to the fast-casual Neapolitan pizzas being slung at Proof Pizza, which is connected to the lobby and makes for a perfect pit-stop for hungry travelers.
What sets this hotel apart, however, is not only the contemporary art around every corner, but the fact that there’s nothing strict or stuffy about the displays. No need to whisper or stand at arm’s length: they are meant to be seen up-close and explored from all angles.
Open to all visitors to the hotel, a main-floor gallery space features rotating exhibitions, and another nook houses an artist-in-residence. What’s perhaps most fun is stumbling on art where you least expect it. In the lobby, sculptures commingle with cozy couches (be sure to snap a pic with John, one half of artist Charity White’s “The Dinner Table” piece!). In the bathroom, striking photo galleries spark conversation among strangers.
But a true perk in staying at Saint Kate is being able to see all the art in the hotel’s guest-only floors, including outside elevators and blank-slate “canvas rooms,” where local artists create living, breathing pieces of art that guests can stay in.
Insider Tip: For a free activity, go on an artsy scavenger hunt! Be sure to page through your hotel room’s “art guide” booklet, which outlines the hidden gems throughout the hotel and within your own room, from the mural inside the closet to the not-your-average framed prints, all exclusively by Wisconsin artists. Consider ending the hunt on a true Saint Kate crowd-pleaser: the bar of soap in the bathroom that looks like a giant pink eraser. Designed by artist Niki Johnson and inspired by Andy Warhol and his Pop Art movement, it’s a literal hands-on “sculpture.”
Also perfect for families? Each room comes with its own ukulele, record player, and a selection of vinyl—a full collection is available at the front desk. Rooms also have a roll of butcher block paper and colored pencils, perfect for those inspired to create their own art.
What to Do in Milwaukee
No matter the weather—and, fair warning: in Milwaukee, there really can be any kind of weather!—the Mitchell Park Domes make for a memorable visit. The horticultural conservatory has more than 2,000 species of plants within its three themed domes—one is dedicated to flowers, another feels like a tropical rainforest, and the last is a living desert.
If you haven’t gotten your fill of art at Saint Kate, the Milwaukee Art Museum is another must-visit, even if you just go for the view of the museum, not what’s inside. That’s because atop the building’s vaulted, glass-enclosed ceiling are its signature “wings,” called the Burke Brise Soleil, that form a moveable sunscreen with a 217-foot wingspan.
Insider Tip: Time your viewing of the famous wings right: they open with the museum, closes and reopens at noon, and closes with the museum.
If your kids need a boost following the art museum, just next door is Discovery World, a science center that also happens to include a world-class aquarium.
If you prefer a go-at-your-own-pace walking tour of Milwaukee, be sure to snap a selfie with the Bronze Fonz, a tribute to the popular sitcom Happy Days, located on the city’s meandering RiverWalk. And don’t forget to look for ladybugs the size of 1960s-era Volkswagen Beatles crawling down the side of one of downtown’s office buildings (this one is appropriately nicknamed the Ladybug Building).
Where to Eat in Milwaukee
Although Milwaukee is perhaps most widely known for being home to the famous Miller Brewery, it’s also growing into an enviable food scene.
For breakfast, you can’t go wrong at Blue’s Egg or The Original Pancake House.
But for a dinner you won’t soon forget, you must check out Milwaukee’s best-kept secret, SafeHouse. It’s one of the only spy restaurants in the entire midwest, and getting in is half the fun. Just behind a nondescript door marked International Exports, Ltd., you’ll find Agent MoneyPenny guarding the entrance to ensure each spy knows the password.
Insider Tip: If you have time, make it a point to ask locals if they know SafeHouse’s password before you head over. But don’t worry: those without knowledge of the password can still get in. They’ll just be required to do a clearance test (it’s all in good fun, we promise!) to prove they’re no double agent.
Other family favorites include AJ Bombers—a fun spot for burgers and, ahem, aerial bombs of peanuts—and Tupelo Honey Southern Kitchen, which boasts an airy dining space and the city’s best house-made grits, served up all day.
If your family is having a hard time deciding what to eat (you know the drill: one kiddo only eats pizza while the other is demanding tacos, and all you want is a fresh vegan wrap), Milwaukee has a few food halls where everyone can win. Milwaukee Public Market is bursting with more than a dozen vendors serving up classic foods made from high-quality ingredients, ethnic spices, and artisanal treats. They even offer kid-friendly cooking classes. Third Street Market Hall is another great spot to sample some of the city’s best cuisine. The hall also features an arcade with both current and retro games, two custom-built shuffleboard courts, and a variety of other turf games, like giant : and bags. It’s even got a “selfie museum” perfect for snapping a family photo.
How to Get to Milwaukee
From Chicago, getting to Milwaukee is as easy as it gets. Depending on where in the city you are traveling from, the drive should take roughly 90 minutes. For a more relaxing trek up (that doesn’t eat up any additional travel time), the Amtrak Hiawatha train line offers seven roundtrips daily between the two midwestern cities. Plus, kicking off your trip at Chicago’s Union Station affords a rare opportunity to marvel at its exquisite architecture.
Insider Tip: As you’re boarding, ask the conductor where the dining car is located and make your way there to snag one of the four-top tables. It’s the perfect place to spread out, and gives little ones ample room to color or play card games.
