What to do in Milwaukee this Weekend

What to do in Milwaukee this Weekend
– Brady Street –

Welcome to Where Chicago Goes, a series offering itineraries for cities frequently visited by Chicagoans. These are not far away destinations. These are places many of us used to call home, cities where our parents have retired, and where we fly often for work and play. For our first installation, we headed to Milwaukee, just a 1.5 hour drive north of Chicago.

Harley Davidson
– Harley Davidson Museum –
Milwaukee Art Museum
– Milwaukee Art Museum –
- Cafe at the Plaza - Image: Cafe at the Plaza
– Cafe at the Plaza –
Image: Cafe at the Plaza

The way Chicago views Milwaukee can best be compared to how we as a nation view Canada. It’s extremely cold way, way up there. The people, who are refreshingly friendly, talk funny and smile too much. It’s basically the miniature version of us, right?

In reality, Milwaukee and Chicago are close to being twin sisters. Milwaukee, of course, is the smaller twin. Less than two miles north of the Loop is a big little town that boasts an amazing skyline along Lake Michigan, a nationally recognized art museum, and its share of James Beard Award winning chefs. Sound familiar? What Milwaukee has that Chicago doesn’t, however, is no traffic jams, affordable wedding venues, and dirt cheap parking – even during special events.

I grew up in Milwaukee but had the opportunity to see it with new eyes thanks to the city’s tourism bureau, Visit Milwaukee. Here are my top picks for what to do and see with one weekend in Brew City.

Day 1

How to Get There

Please consider taking the train. It’s clean, dependable, and super easy. Service is provided to Mitchell International Airport and downtown Milwaukee on Amtrak.

If driving, you may be pleasantly surprised by the city’s plentiful, free parking options.

Where to Stay

What to do in Milwaukee this Weekend
– Standard Room Stay –
Potawatomi Hotel
– Potawatomi Hotel’s Presidential Suite –

Less than a year old and Potawatomi Hotel is already cementing its place as one of the city’s most contemporary and accommodating places to stay. Rooms are clean and spacious with floor to ceiling windows, separate toilets, and standing showers. There is no need to cross through the casino on the way to your room and you can rest assured that smoking is not allowed in any guest rooms.

My only caveat? While communication with check-in assistance and the hotel’s dining service (speaking of both in-room service and hospitality at Locavore and Dream Dance Steak) was for the most part pleasant, valet service was decidedly less accommodating. No bag assistance is offered and they may not park your car unless it is stopped exactly where valet stands, even if that’s only steps away from where you mistakenly have stopped. I spoke with other guests who shared similar sentiments regarding the hotel’s valet. Still, for all I know, parking may be offered by a third-party which would explain its detachment from the overall culture of the hotel.

Potawatomi Hotel & Casino, 1721 W. Canal Street, 53233


If you love thoughtfully prepared dishes made with quality, locally sourced ingredients, Story Hill BKC is right up your alley! Equal parts restaurant, bar, and wine shop, this place has a cool vibe. European staples such as crepes and frittatas are reimagined by Midwest and Southern sensibilities. I love the Baked French Toast Bread Pudding which pairs well with the spicy Mexican coffee. Tip: The wait times at their sister restaurant, Maxie’s, can be quite long from what I hear. The menu is very different at Story Hill but it’s a good alternative if you don’t feel like waiting. Story Hill BKC, 5100 W. Bluemound Road, 53208 Maxie’s, 6732 W. Fairview, 53213

Do Something


Harley Davidson
– Tanks on Display –

I’ve never owned a motorcycle. I don’t think I’ve even ridden one more than twice in my life. For that reason, I was surprised at how submerged I found myself to be in the Harley-Davidson Museum.  Harley heritage is treated here with the utmost respect. A contagious air of pride and loyalty fills the large campus which houses the museum, restaurants, event space (perfect for weddings), storage, and restoration facilities. Take the audio tour for only $4 more and leave yourself enough time to convert to the museum’s infectious creed. For me, the process took about 4 hours. Get hungry? Take a break at Motor, the American bar and restaurant located inside.

Harley-Davidson Museum, 400 W. Canal Street, 53203

Summerfest 2
– Summerfest –

Summerfest is everything you love about Lollapalooza but cleaner, free, and with cheaper parking. Okay, so, it’s everything you want Lolla to be. The world’s largest music festival is held annually at Henry Maier Festival Park and boasts premium acts, rising artists, and local favorites. Technically, tickets are not free, per se, but you can get in free almost every day with a canned good or some sort of charitable donation.

Before and after the Big Gig are numerous cultural festivals known collectively as Milwaukee World Festivals, also held at Henry Maier Festival Park. Of these, the most notable and worth attending through the end of this year are Festa Italiana, German Fest, and Mexican Fiesta.

Summerfest and the Milwaukee World Festivals, 200 N. Harbor Drive, 53202


Pizza Man is to Milwaukee what so many deep dish joints are to Chicago: a point of pride for an almost cult like following. Make no mistake, the pizza here is good. What makes Pizza Man stand out, however, is their devotion to culinary ingenuity. They put cream cheese on pizza here, okay? By the way, it’s amazing. Why isn’t everyone putting cream cheese on their pizza?! Not to mention the pasta. So, is Pizza Man’s pie better than Chicago’s deep dish? Um… Let’s move on.

Pizza Man, 2597 N. Downer Avenue, 53211

Day 2


Café Benelux in Milwaukee’s historic third ward is a big plate café inspired heavily by the lowlands of Europe, specifically Belgium, the Netherlands, and Luxembourg. Brunch here covers a wide range of tastes with beignets, buttermilk fried chicken waffles, omelets, BLTs, and much, much, much more. Enjoy your meal on the patio or their beautiful rooftop. Can’t get enough? Visit their market and take a few flavors home with you.

Café Benelux, 346 N. Broadway, 53202

Do Something

Milwaukee Art Museum

Milwaukee Art Museum

The jewel of the city is the Milwaukee Art Museum and the sparkle of that jewel is its newest addition designed by Spanish architect and sculptor Santiago Calatrava. Prior to the add-on, the museum sat on the lake relatively hidden from view by the street. Today, chances are, even if you’ve never been to Milwaukee, you’ve seen this breathtaking bird like, boat like building. It has starred in everything from Victoria’s Secret commercials to blockbuster movies.

To better complement Calatrava’s masterpiece, the rest of the museum is currently undergoing renovations. Expect an unveiling this year, possibly near November. In the meantime, I highly recommend Van Gogh to Pollock: Modern Rebels, a collection of mold breaking paintings, sculptures, and installations held in the open wing.

Milwaukee Art Museum, 700 N. Art Museum Drive, 53202

Lakefront Brewery
– Lakefront Brewery –

The Milwaukee area is full of breweries but Lakefront Brewery offers one of the most fun, boozy tours you’ll find. For just $8, receive a souvenir pint glass, four 6 oz pours, and a tour guided by one of the brewery’s hilarious, super-knowledgeable beer enthusiasts. If you’re serious about brewing at home, purchase a ticket to the technical tour for $30.

Lakefront Brewery, Inc., 1872 N. Commerce Street, 53212

What started as a small idea among inebriated friends, is now a solid craft distillery producing fine whiskey, gin, and vodka. I’m not a vodka person, but Central Standard Craft Distillery has some of the best vodka I’ve ever tried. It goes down smooth with a surprisingly fruity end. The distillery is set to celebrate its first full year this month. (July 24, 2015)

Central Distillery
– Central Distillery –

Central Standard Craft Distillery, 613 S. 2nd Street, Suite 609, 53204

In the center of much of the action is the Milwaukee River and there’s no better way to see it all than on a kayak from the Milwaukee Kayak Company. Select from unguided tours, guided routes, and even night tours. A great date option!

Milwaukee Kayak Company, 318 S. Water Street, 53204


Highly ranked, La Merenda is a small plate restaurant inspired by cuisines from around the world. Linger here over rich cheese plates and filling meat presentations. Ingredients are sourced locally for farm to table authenticity.

La Merenda, 125 East National Avenue, 53204

More Things to do and See…

Milwaukee Public Market
– Milwaukee Public Market –
Purple Door
– Whiskey Old Fashioned Ice Cream from Purple Door –

Something like Seattle’s, minus the flying fish. Milwaukee Public Market (400 N. Water Street, 53202)

Come here for a casual brunch in their intimate garden. Try the breakfast poutine, Bloody Mary, and delicious muffins, all of which are thoughtfully prepared by Chef Kady.  Café at the Plaza (1007 N Cass Street, 53202)

Ice cream made with real whiskey, brandy, and anything else you can think of. Purple Door Ice Cream (205 S 2nd Street, 53204)

An incredible agricultural collection and an affordable wedding option. Mitchell Park Conservatory (The Domes) (524 S. Layton Boulevard, 53215)

Grab a chair, blanket, and head to the lawn for a movie screening and fish fry. Note: All movies are not kid friendly. Use your discretion. Fish Fry & a Flick (at Discovery World, 500 N Harbor Drive, 53202)

A strip of pubs, cafes, bars, restaurants, and mom and pop shops. Also plays host to the city’s best neighborhood festival. Brady Street (1224 E. Brady Street, 53202)

All photos are taken by Kari of Chicagoings.com unless otherwise noted. Be sure to contact each company before your visit for current information and prices. A big thanks to Visit Milwaukee for facilitating meals and excursions. All opinions expressed here are those of Kari Herrera and are not indicative of those held by Visit Milwaukee or any other entity.