Chicago Insider Tips

Things to Do

Rory McHale: Go downtown to Millennium Park and see Anish Kapoor's reflective Cloud Gate sculpture better known as "The Bean." Go underneath it to see yourself reflected in the interactive mirror. Then, soak up the sun on Lake Michigan at the family-friendly Montrose Beach. It's Chicago's largest public beach and includes kayak and jet ski rentals.

Noel Abbott: Soak in Chicago's steeped architectural history by doing an architectural boat tour from the Chicago Architecture Center. Or try a walking tour of Chicago's architecture. The Metro, a 1,100-person music venue in Wrigleyville, is "a great venue for seeing up-and-coming bands. It's very intimate."

Sarah Schulte: Rent paddle boards at North Avenue Beach, but go early, before the crowds arrive. Then, eat on the beach at the Shore Club Chicago. Two favorite events: the annual Old Town Art Fair and the Chicago Marathon in October. "I live on the route of the Chicago Marathon. It's always a great neighborhood party. Everyone's out, and it's a morning of happiness."

Kate LeFurgy: Check out the A. Philip Randolph Pullman Porter Museum. It's an African-American Labor History Museum, the only one of its kind in the nation. For music, go to a concert at The Salt Shed, the former Morton Salt factory that's been transformed into an indoor and outdoor music venue with panoramic views of Chicago's skyline. Then go to the beach. "One of my favorite places is Reggies on 63rd Street Beach. It's a great outdoor bar-restaurant where you can sit on the beach."

Ahmed Hamed: During warmer months catch an outdoor concert at the Frank Gehry-designed Jay Pritzker Pavilion in Millennium Park, with its sprawling lawn perfect for picnics. "I just like hanging out with my friends, eating food, and drinking tea."

Dave Kovar: See Frank Llyod Wright's "Robie House," a 1910 Prairie-style masterpiece in the Hyde Park neighborhood boasting "amazing construction and design principles." And don't miss the Museum of Science and Industry, also near Hyde Park, and the Field Museum, known for "Sue," a 40-foot-long Tyrannosaurus rex skeleton, one of the largest ever discovered.

Christy George: Don't miss Chicago's beaches. Go to South Shore Beach, Rainbow Beach, or 31st Street Beach. "Those are classic."

Brian McConkey: Take a walk along the 1.25-mile Chicago Riverwalk, which meanders below street level from Lake Street to the lake front.

Mike McCluggage: Favorite music venues include Old Town School of Folk Music, Thalia Hall, City Winery Chicago, and the intimate concert venues of SPACE in suburban Evanston and FitzGerald's in Berwyn.

Places to Dine

Curtis Baddeley: For first-time visitors, go to Fulton Market. Try the Italian-Croatian cuisine at Rose Mary, the restaurant run by Joe Flamm. Nearby, in the West Loop, try Alla Vita, family style Italian-American, and Girl and the Goat, known for its innovative small plates by James Beard award-winning chef Stephanie Izard. For a good Chicago-style deep dish pizza, try Pequod's Pizza, a local favorite known for its caramelized crust.

Ran Wei: "I personally love Chinese hot pots. There's a new place that I really like, Qiao Lin Hotpot. SIFR for really nice Middle Eastern food. I also love RPM Seafood on the [Chicago] River, which has really good food and views, and Gibsons Italia [an Italian steakhouse] at the end of the river." Another favorite is Moody Tongue, a Michelin star restaurant that's coupled with a brewery. "We usually go there because they have the best fried whole fish." Go during the middle of the week to score a seat.

Rory McHale: Try the thin crust pizza at La Villa Restaurant, an Italian-American, family-run spot in the Old Irving neighborhood.

Ahmed Hamed: EuroAsia Restaurant in the Gold Coast neighborhood on the Near North Side. "It's an Eastern European, Central Asian restaurant with great portions and delicious food. It's a small, halal joint."

Noel Abbott: A favorite is the basic egg-and-pork-belly-bacontopped burger from the diner-style Au Cheval restaurant. "My wife jokes that I eat like a 12-year-old, but I really love hamburgers."

Sarah Schulte: Marge's Still, one of the oldest-run taverns in Chicago. "It's a total neighborhood place. It's like a Cheers." Another favorite in the Old Town neighborhood is Tuscaninfluenced Topo Gigio Ristorante. "You can't go wrong. I love the grilled calamari salad."

Kate LeFurgy: Calumet Fisheries, an old-school smokehouse that stokes its own fire. "I like the shrimp, but you can't go wrong with anything you get there." Then head to Ukrainian Village, a neighborhood on Chicago's near west side, to Black Dog Gelato. Try the goat cheese cashew caramel flavor. "I got married during the pandemic in August of 2020 in our front yard. We had Black Dog Gelato pull up and serve to our less than 10 people."

Christy George: When dating her now-husband, "We spent one whole year, every single weekend, we went to a different Latin American restaurant. Every type of food you could think of, we were eating it. There's such a large Latin American community in Chicago, it's a deep dive. And it's so good." Favorites include Sinhá, a Brazilian brunch-lunch spot near United Center, and Irazu, a Costa Rican restaurant in Logan Square.

Dave Kovar: Virtue, a James Beard and Bib Gourmand award winner known for its Southern food.

Brian McConkey: Head to Pilsen, a neighborhood known for great food, culture, and the National Mexican Museum of Art. "Go to Chocolat Uzma. It's on 18th Street, and I would highly recommend it for anybody who's a chocolate fan."