Journalist A.J. Liebling may have dubbed Chicago the “Second City” in 1949, but over the past 70 years, it's become second to none when it comes to culture, dining, and architecture. Bring comfortable shoes — and a warm hat if you’re traveling in winter — for a personalized walking tour. Be sure to allow time to indulge in Chicago's robust culinary scene, where a new generation of chefs are making their marks.
Chicago Detours: Founded by Amanda Scotese in 2010 after a decade in Italy as a guide for Rick Steves' Europe, Chicago Detours looks to the skyline to celebrate the city’s rich architectural history. None is more opulent than the Architecture of Money and Power Financial District Walking Tour. Highlights include the Chicago Board of Trade, The Rookery, Union League Club, the Federal Center, Field Building, and the Sky-Ride Cocktail Lounge — a famous watering hole for traders back in the day. $42 per person; minimum of nine guests and a maximum of 40 guests total with two guides.
Time Out Market Chicago: The food hall craze continues in the city's booming Fulton Market district, where this soaring 50,000-square-foot venue features 18 kitchens, three bars, and a rooftop lounge. Highlights include James Beard Award-winner Abe Conlon’s namesake spot, which serves up Portuguese-inspired fare. Be sure to stop by Lost Larson for decadent pastries like chocolate croissants, cinnamon rolls, and almond cakes. Then, head to the second floor to seek out the hidden Secret Sound, a tiki-themed speakeasy. Try to coordinate your visit with immersive programming such as pasta-making classes and twilight yoga.
Docent Tour at the Art Institute of Chicago: With more than 300,000 objects in its collection, a day at The Art Institute can feel like a race against time. Consider a private guided tour to learn more about areas of interests such as Impressionism, modern and contemporary art, or hidden histories. A recent tour revealed an often-overlooked visit to the serene Ando Gallery (designed by award-winning architect Tadao Ando), which features a rotating display of Japanese screens. ($250 for a one-hour tour; 30-person maximum.)
Yūgen: This modern Japanese restaurant is helmed by an all-female team and earned a 2020 Michelin star. Chef Mari Katsumura leads the way, with pastry chef Jeanine Lamadieu rounding out the extravagant menu, which ranges from eight to 11 courses. While the offerings change seasonally, we're hoping that Katsumara’s signature crab rice (served with tamari-cured egg yolk, salmon roe, and puffed grains dusted with fragrant furikake) remains. The eight-course Iwate menu costs $125 per person (plus $85 for beverage pairings), and the eleven-course Ibaraki menu costs $205 per person (plus $135 for beverage pairings).
The Hoxton: The British hotel brand arrived in Chicago last spring with a stunning property just steps away from Time Out Market Chicago. Original art adorns the walls, while each of the 182 rooms (sized “snug,” “cozy,” or “roomy”) burst with mid-century and industrial-inspired furnishings plus a curated collection of books. Locally made, limited-edition goods make for the ultimate souvenir, such as a handmade tote by 1733, a set of notebooks by Field Notes, or a vegan beauty travel set by Town & Anchor. Rates from $139 per night, depending on the season.