When people think of Chicago, deep-dish pizza and Italian mobsters are some of the first things to come to mind. Indeed, Chicago is a city entrenched in history and tradition. Its downtown is filled with towering, Gothem-esque, hundred-year-old buildings, many decorated with intricately carved stone—the city famously served as the location for several Batman movies—and public art installations.
But over the past several years, the Windy City has transformed into a legitimate travel destination for dining, hospitality, and shopping, from adventurous dining options and luxury boutique hotels, to daring modern art exhibitions and innovative retail concepts.
The nearest major city from Minneapolis, Chicago is just a seven-hour drive (or hour-long plane ride) from the Twin Cities, making it a quick trip for a weekend getaway. Here’s my 48 hours in Chicago, moment by moment.
1. Check-in at The Gwen, 4 p.m.
The lobby at the Gwen with gwen lux’s original facade, Courtesy the gwen
the lobby at the gwen, image by brandon barre photography, Courtesy the gwen
the lobby at the gwen, image by brandon barre photography, Courtesy the gwen
the gwen lux suite at the gwen, Courtesy the gwen
the gwen lux suite at the gwen, Courtesy the gwen
Chicago is home to some of the most beautiful luxury hotels in the Midwest. One of the most artful is The Gwen, A Luxury Collection Hotel, a boutique hotel built on the former site of the McGraw-Hill Publishing Company. The original 1928-era, Art Deco building was designated a Chicago landmark in 1997 only to be demolished in 1998. However, its façade, created by iconic 1920s Chicago sculptress Gwen Lux, was saved and reinstalled two years later on the new building. After stints as the Le Méridien Chicago, and later the Conrad Chicago hotels, in 2015, the hotel was reimagined as The Gwen. The hotel’s interior design team, the Simeone Deary Design Group, smartly took inspiration from the site’s Art Deco origins. The style looks startlingly modern nearly a century later, and interiors include modernist tubular furniture (think rounded leather and brass chairs), decorative wallpaper, and geometric designs lining everything from the walls to the carpeting. It’s a luxury hotel for fans of Art Deco design and 1920s artwork alike (and for shoppers, there’s also a handy second-level walkway connecting it to Nordstrom). @ 521 N. Rush St., thegwenchicago.com
2. Cocktails on Cindy’s rooftop lounge, 5 p.m.
cindy’s rooftop patio at chicago athletic association, Courtesy cindy’s
Cindy’s, the 13th floor rooftop bar atop the historic, beautifully restored Chicago Athletic Association (a bar and hotel within a renovated 1890-era clubhouse in downtown Chicago), offers one of the best views of Millennium Park and Lake Michigan. The rotating cocktails are just as delectable: Try the Howl at the Jun ($15, gin, kombucha, grapefruit, and sparkling rosé) or the Grey Garden ($15, vodka, dolin blanc, crème de violette, jasmine pearl tea, and lemon). Cindy’s also serves lunch, dinner, and weekend brunch. Recently, the space debuted a new outdoor bar on its terrace, with boozy popsicles, ice cream pops, multiple rosé options, and a rotating cocktail menu. A word of warning: Getting onto the roof during peak times can be difficult, but the Game Room on the hotel’s second floor—complete with nostalgic, sports-inspired decor—is a great backup option. @ 12 S. Michigan Ave., cindysrooftop.com, chicagoathletichotel.com
3. Dinner at Tanta, 7 p.m.
a selection of dishes from tanta, Courtesy tanta
tanta’s rooftop lounge, Courtesy tanta
Chicago’s preeminent Peruvian restaurant, Tanta, serves authentic dishes and cocktails with a fresh, modern flair. The menu, conceived by famed chef and Peruvian food ambassador Gastón Acurio and curated by Tanta Chicago Executive Chef Jesus Delgado, showcases Peru’s diverse cuisine in a variety of shareable plates, from skewered grilled meat and fish to citrus-infused cebiche (ceviche), plus seasonal cocktails anchored by Peru’s national spirit, pisco. Try the flavorful, flaky empanadas ($5) and the lomo saltado ($32, beef tenderloin stir-fry with onions, tomatoes, potatoes, and rice in a garlic soy sauce). Afterward, head upstairs for a cocktail on the gorgeous rooftop. @ 118. W Grand Ave., tantachicago.com
4. After-dinner drinks at Arbella, 9 p.m.
Arbella lounge, Courtesy arbella
After dinner at Tanta, head next door to Arbella, a cozy, stylish little nook founded by the owners of Tanta in 2016. The 76-seat lounge and bar showcases globally inspired cocktails and upscale bar snacks, and leather booths and bar stools are mixed with raw brick walls, a giant mural, and high ceilings for a modern-industrial style. The bar’s mix of cocktail classics are augmented by “new-age progressive cocktails” from around the globe. Try the bar’s signature drink, the Pisco Sour ($13). On weekend nights, Arbella also hosts DJs playing old-school disco sets every weekend (aided by its top-notch sound system). @ 112 W. Grand Ave., arbellachicago.com
5. Lunch at Eight Bar and Patio, 12 p.m.
eight bar and patio’s patio, Courtesy eight bar and patio
eight bar and patio’s King crab, avocado & bibb salad, Courtesy eight bar and pato
Located downstairs from its brother restaurant, Maple & Ash steakhouse, the more casual Eight Bar and Patio is best known for its brunch and lunch. The sidewalk patio veranda is a must for the aesthetic alone, thanks to its lush greenery. Chef Danny Grant (also of Maple & Ash) has created a menu that upscales traditional fare with luxe ingredients and a refined presentation: King Crab, Avocado & Bibb salad with chile de arbol, radish, cucumber, mint, and basil ($26), the Spicy Meatball Fundido with chiles ($12), and the Shishito Peppers ($8)—all of which are packed with a spicy kick and lots of flavor, and the Slagel Farm Crispy Fried Chicken with hot sauce and pepper syrup ($18) rivaled the flavor and heat of that of Minneapolis favorite, Revival. I’m nuts about tequila and mezcal pairings, so I loved the Paloma Ahumada, which is topped with fresh grapefruit juice and soda ($12). @ 8 W. Maple St., eightbarchicago.com
6. Shopping at Wicker Park and Bucktown, 2 p.m.
moth, Courtesy moth’s facebook page
robin richman, Courtesy robin richman’s facebook page
purple llama coffee & records, Courtesy she she
The Wicker Park and Bucktown neighborhoods are like the North Loop of Chicago, littered with fair-trade coffee shops and cool indie boutiques. Gather Home + Lifestyle offers an Instagram-worthy selection of home decor, cards, apothecary, leather goods, accessories, jewelry, and books by small, independent makers. Moth has a unique, highly specific concept: It sells a mix of apparel and home goods that marry the simplicity and beauty of Nordic and Japanese design, crafted by brands and designers from Scandinavia and Japan. Robin Richman sells women’s and men’s apparel and accessories by high-end cult labels, including Rick Owens Drkshdw, A Detacher, Hache, and Henrik Vibskov, as well as a curated selection of home goods and fragrances. RSVP Gallery, which was co-conceived by Kanye West BFF Don C, sells a unique mix of elevated streetwear and menswear from high-end labels, including Acne Studios, Adidas, Common Projects, Public School, and Raf Simons, alongside artwork from Stephen Sprouse, Jeff Koons, and Takashi Murakami. And Purple Llama Coffee & Records—which features sweet, hand-painted wallpaper by Minneapolis design duo She She—lets you sip a latte while perusing its choice selection of vinyl. Gather Home + Lifestyle @ 2321 W. North Ave., gatherhomeandlifestyle.com; Moth @ 2008 N. Damen Ave., mothchicago.com; Robin Richman @ 2108 N. Damen Ave., robinrichman.com; RSVP Gallery @ 1753 N. Damen Ave., rsvpgallery.com; Purple Llama Coffee & Records @ 2140 W. Division St., purplellamachicago.com
7. Margaritas at Big Star, 4 p.m.
big star chicago, Courtesy big star’s facebook page
Big Star in Wicker Park is an essential destination when visiting Chicago. The Mexican restaurant is known for its huge patio (that’s always packed), its creative tacos, its whiskey selection, and its lowkey vibe. It also crafts a delicious margarita ($9 for the regular, $10 for a mezcal version), but the real deal is the pitchers ($36 regular, $40 mezcal). Fun fact: The margaritas are batched every morning using fresh lime. But be forewarned: There’s just about always a wait to get in, so plan accordingly. @ 1531 N. Damen Ave., bigstarchicago.com
8. Supper at Lawry’s The Prime Rib, 7 p.m.
lawry’s the prime rib chicago, Courtesy lawry’s
the brady and spinach at lawry’s the prime rib, Courtesy lawry’s
If you’re looking for an old-school steakhouse experience, you can’t get much better than Lawry’s The Prime Rib. Most people know the name Lawry’s for its Seasoned Salt. But in fact, the salt was created in 1938 to season prime rib served at the Lawry’s The Prime Rib restaurant in Beverly Hills, CA. The Chicago restaurant has been around since 1974, when it opened within the 1890s McCormick Mansion, which once housed a puppet theater, and it’s appropriately grand, with a winding staircase, dark wood, and cozy booths. But the service is what truly distinguishes the Lawry’s experience. The server tosses your salad right at your table, and slabs of prime rib are cut and served from a rolling cart. @ 100 E. Ontario St., lawrysonline.com
9. Cocktails at the Cabana Club at the Robey, 9 p.m.
the cabana club at the robey, Courtesy the robey
Want to feel above it all? It’s hard to beat the Cabana Club, a rooftop bar on the 6th floor of high-style hotel, the Robey, in Wicker Park that features 180-degree views of the city and a wading pool (intended only for guests of the hotel, natch). Lounge on nautical-striped couches with a cocktail, take in the view, and you just might think you’re in a tropical paradise. Despite the tropical vibe, the enclosed lounge features floor-to-ceiling windows, a wood-burning fireplace, and DJs to keep the party going during cooler days. @ 2018 W. North Ave., therobey.com
10. Korean BBQ at Seoul Taco, 12 p.m.
Nachos, the gogi bowl, burrito, and tacos at seoul taco, Courtesy seoul taco’s facebook page
Close out the weekend with lunch at Seoul Taco, a Korean-Mexican fusion restaurant that got its start as a food truck in St. Louis, Mo. by Korean-American David Choi in 2011. The sweet-and-savory flavors of Korean barbecue are reimagined as tacos ($2.50), quesadillas, nachos, and burritos ($8), the latter of which are filled with kimchi fried rice and choice of meat: bulgogi, chicken, spicy pork or tofu. For a brunchable option, there’s the Gogi Bowl, Seoul Taco’s take on the classic Korean Yum Yum Bowl, which combines rice (the delish kimchi fried rice is optional), fresh veggies, fried egg, carrots, green onion, sesame oil, and spicy Gochujang pepper sauce ($8). @ 738 N. Clark St., seoultaco.com
11. Pop Art at MCA Chicago, 1 p.m.
Courtesy mca chicago
Take in the Takashi Murakami retrospective at Museum of Contemporary Art Chicago. The almost 12,000-square-foot exhibition, The Octopus Eats Its Own Legs, features 50 works that span three decades of the iconic Japanese pop artist’s career, from his earliest works rooted in traditional Japanese painting to his better known, monumentally scaled, colorful paintings in his signature “superflat” style. The show also features a gallery of brand new, towering works created especially for the exhibition, several sculptures, and his album art for Chicago’s own Kanye West. Straddling high and low, eastern and western, and ancient and modern, the exhibition offers a more serious consideration of his commercial, pop art creations. Ends September 24 @ MCA Chicago, 220 E. Chicago Ave., mcachicago.org/murakami
12. Artful touristing at Millennium Park, 3 p.m.
jay pritzker pavilion, Courtesy City of Chicago
A trip to Chicago wouldn’t be complete without a visit to Millennium Park, the city’s most popular tourist attraction. Located within the larger Grant Park near the Lake Michigan riverside, it’s filled with a variety of public art, including the Jay Pritzker Pavilion, which was designed by architect Frank Gehry and serves as the home of the Grant Park Symphony Orchestra and Chorus. It features a large fixed seating area, a trellis network to support the sound system, and a signature Gehry stainless steel headdress. Millennium Park is also famous for Cloud Gate—better known as “The Bean”—a 110-ton elliptical structure made from a seamless series of stainless steel plates that reflect Chicago’s skyline and the clouds above by Indian-born British artist Anish Kapoor. @ 201 E. Randolph St., cityofchicago.org