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.
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.
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.
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.
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.
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.
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.