Milwaukee Day Trip: 12 Hours in Chicago

It may be called the Second City, but its culture, cuisine and scenery are all first-rate.

Chicago is large enough to sustain thousands of restaurants, hundreds of parks and dozens of museums. But only because it’s also large enough to sustain a population of 2.7 million people, spread out over more than 200 square miles. So if you’ve only got a day to spend in the city, choose depth over breadth. All of the destinations included in this art-inspired itinerary are within walking distance of the Blue Line – a 24-hour train line that passes through a few of the city’s hippest neighborhoods.

9:30 a.m.

Traffic is worse in Chicago, in terms of congestion, than it is in New York or Los Angeles. So leave your car at home and catch the 8:05 a.m. train into the city. From Union Station (225 S. Canal St.), you can walk to your first stop of the day.

10 a.m.

The wndr museum (1130 W. Monroe St.) began life as a pop-up exhibition, but was so staggeringly successful it’s now a permanent fixture of the West Loop. The standout work is a 2017 infinity room by nonagenarian pop artist Yayoi Kusama.

2017 infinity room by pop artist Yayoi Kusama. Photo courtesy of wndr museum.
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Fun Fact

Earlier this year, one of Yayoi Kusama’s paintings sold for a cool $7.96 million, the most money anyone has ever spent on a work by a living female artist. [/alert]


A five-minute walk from the museum, Monteverde (1020 W. Madison St.) is an elegantly understated Italian restaurant. Snag a seat near the restaurant’s open kitchen, and watch the chefs knead and roll out the dough for your pasta (you must order pasta) while sipping prosecco.

2 p.m.

Intuit. Photo by Cheri Eisenberg.

Board a Blue Line train and ride it to the Chicago stop. Intuit: The Center for Intuitive and Outsider Art (756 N. Milwaukee Ave.) is just a block away. One highlight is a re-creation of outsider artist Henry Darger’s colorful one-room apartment.

3:30 p.m.

Intuit is located near the southern border of Wicker Park. Stroll north along Milwaukee Avenue, where you’ll find Fat Tiger Workshop (836 N. Milwaukee Ave.), a streetwear boutique favored by Chance the Rapper, The Occult Bookstore (1164 N. Milwaukee Ave.) and plenty of other intriguing shops.

4:30 p.m.

Comfort Station. Photo courtesy of Getty Images.

Once you’ve reached the six-way intersection charmingly called The Crotch of Wicker Park, look for the Damen stop of the Blue Line. Three stops further north, you’ll find the Comfort Station (2579 N. Milwaukee Ave.), a quirky cultural center that mounts a new exhibition each month.

5:30 p.m.

The best cocktail bar in America – according to the New Orleans-based Tales of the Cocktail Foundation, anyway – is just a few blocks away from the Comfort Station. So of course you’re going to stop by for a drink. Each of the tiki-inspired concoctions at Lost Lake (3154 W. Diversey Ave.) looks like a work of art. And so does the flamboyantly decorated bar itself.

7 p.m.

Now that you’ve got a bit of a buzz, you’d better put something in your stomach, and it might as well be something delicious. So head back south along the Blue Line, to the newly opened Cabra Cevicheria. Perched atop the buzzy Hoxton Hotel (200 N. Green St.), this Peruvian restaurant enjoys panoramic views of the city and even better views of its chic clientele, who pack the place every night of the week.

Cabra is the latest venture by Stephanie Izard, who was the first female chef to win “Top Chef” in 2008. She’s gone on to win a James Beard award for best chef in the Midwest.

Photo courtesy of Cabra Cevicheria
You can’t go wrong with any of Cabra’s signature ceviche dishes (left). And its pisco sours (right) are a delight too. If you drink too many, you can always book a room at the Hoxton, and swim a few laps in its rooftop pool before returning home.
Photo courtesy of Cabra Cevicheria

8:45 p.m.

Give yourself some time to walk back to Union Station, so that you’re ready to board the 9:15 p.m. bus bound for Milwaukee. You can catch some Zs on your way home, or start planning your next day trip.

More to explore

GARFIELD PARK CONSERVATORY: One of the largest greenhouses in the United States, the Garfield Park Conservatory houses more than 2,000 species of plants spread out across eight indoor show houses and 10 acres of outdoor gardens. Admission is free, but donations are appreciated. 300 N. Central Park Ave.

Garfield Park Conservatory. Photo courtesy of Getty Images.
OAK STREET BEACH: This isn’t the largest beach in Chicago, but it may be the most popular. And it definitely boasts the best view – sometimes the glittering steel and glass skyscrapers that rise above Lake Shore Drive can even be seen refl ected in the surface of the water. 1000 N. Lake Shore Dr.
THE RIVERWALK: Stretching 1.25 miles along the Chicago River, The Riverwalk is the place to see and be seen – while sipping a glass of something bubbly from the City Winery (11 W. Riverwalk S.) patio – in the summer months. The Chicago Architecture Center’s perennially popular boat tours also depart from the area.
Chicago Riverwalk. Photo courtesy of Getty Images.



Lindsey Anderson covers culture for Milwaukee Magazine. Before joining the MilMag team she worked as an editor at the Museum of Contemporary Art Chicago and wrote freelance articles for ArtSlant and Eater.