14 Things to Avoid in Chicago

Twenty years ago, Chicago’s hotel roster—particularly in the Loop—featured all the big brands, such as Marriott and Hilton, geared for conference goers, but thankfully there are now a slew of cool boutique hotels for leisure travelers. Newcomers within the last decade include Chicago Athletic Association across from Millennium Park (with an enclosed rooftop bar-restaurant, Cindy’s), The Robey (within a 1929 Art Deco building in Wicker Park), and Sophy Hotel (a Hyde Park beauty with incredible artwork and a cozy fireplace in the lobby). You might even want to eat dinner and order a drink at these hotels because they are that awesome and flaunt incredible designs. But if you must book a chain, choose only one: The Drake Hotel. While part of the Hilton brand, it’s also iconic to downtown Chicago and has been open since 1920 with afternoon tea and Italian-marble baths.

This revered art museum on South Michigan Avenue, flanked by two stone lions out front, gets all the credit for Chicago’s rise as an arts destination—but few shows feature local artists. To witness homegrown talent that’s more edgy and experimental, spread your wings a bit and check out the Museum of Contemporary Art Chicago near Water Tower Place just north of downtown Chicago or Chicago Cultural Center, a century-old former Chicago Public Library branch just four blocks north of the Art Institute along North Michigan Avenue and charging zero admission. Chicago is also home to art museums focused on artists of color, including South Side Community Art Center, tucked into Chicago’s Bronzeville neighborhood and the country’s oldest Black arts museum, open since 1940; and the National Museum of Mexican Art, in Chicago’s heavily Latino Pilsen neighborhood. Another little-known gem is Intuit: The Center for Intuitive and Outsider Art.

Like most Northern cities—from Amsterdam to Boston—the shoulder seasons of fall and spring are the best time to visit. You aren’t slipping and sliding on icy pavement and the wind chill is a non-issue. Traveling to Chicago during a warmer month means you can dip your toes in the sand at one of the 26 beaches dotting the Lake Michigan shoreline. Oak Street Beach at 1000 N. Lake Shore Drive is easy to get to from downtown and the Near North Side, while Shore Club at North Avenue Beach is worth the trip for its chic SoCal environment. And what better way to see Chicago’s world-class architecture than from a guided boat tour along the Chicago River? Locals love to jog and bicycle along Chicago’s lakefront, too, and so should you.

All the Broadway musicals and household-name shows (like Hamilton and Book of Mormon) perform in downtown Chicago’s Theater District at venues like Cadillac Palace Theatre and Goodman Theatre, and ticket prices tend to be steep. You can also probably see these shows in other cities. Support homegrown thespian talent at the Neo-Futurist Theater (think two- to three-minute plays in rapid succession, $15+) on the North Side or a comedy act at Second City (if you roar with laughter at Saturday Night Live, this is your place as many SNL alums started here, $39+). You just might meet the next SNL cast member (many started out here). Other alternatives to Broadway musicals in Chicago are at Steppenwolf Theatre and the David Schwimmer-founded Lookingglass Theatre Company.

Every city has its flagship beer, and for Chicago, that sudsy anchor is Goose Island Beer Company, only because it was among the first craft-beer success stories. But the problem is that you can find this beer easily outside of Chicago. Shift your palate to the local craft-beer scene instead, where there are around 160 breweries. Each taproom (and taps) has a unique personality, from Cultivate by Forbidden Root’s botanical-inspired beers (from Peach Wit to Strawberry Basil Hefeweizen) and Sunday brunch; to Metropolitan Brewing’s huge patio (and delicious tacos) along the Chicago River in Avondale.

Once you’ve got your Burberry trench coat or some new kicks at Nike, just two of the big retailers along North Michigan Avenue (affectionately dubbed “Mag Mile”), leave the area immediately. As a result of the pandemic, many retailers have pulled out. But eclectic boutique shopping still lies in neighborhoods like Old Town, including a quirky general-store-type concept from actress Joan Cusack called Judy Maxwell Home. In Lincoln Park, check out the art effect on Armitage for whimsical women’s clothes and gifts for anyone, and among Lincoln Square’s boutiques is Merz Apothecary dating back to 1875. Squasht is a retailer in Ukranian Village that support women-owned independent clothing designers.

While the Chicago Cubs winning the World Series in 2016 went down in the history books (the team’s first World Series win since 1908), don’t forget there are other sports teams. The Chicago Bulls are the city’s NBA team and play home games at the United Center, as do the Chicago Blackhawks, who have won six Stanley Cup titles since 1926. The Chicago Bears’ play at Soldier Field, as do the city’s other MLB team, the Chicago White Sox.

It’s imperative that you get schooled on Chicago’s amazing architecture because it’s home to what was at one time among the world’s tallest skyscrapers. However, waiting in line and plunking down $30+ to view the skyline from the top—via Willis Tower’s Skydeck, which features a cantilevered glass-floor ledge (The Ledge) on the 103^rd floor—is not the only way. Nor is it the best way. There is so much to see closer to the ground. Chicago Architecture Foundation offers 1.5-hour-long guided riverboat cruises on the Chicago River that sprinkle in facts and stats about the buildings seen along the way. Or take a walking tour, also hosted by the foundation’s docents. Do crane your neck up to see the Willis Tower, though. After, grab a drink at Kindling, the—pardon the pun—hot new wood-fired restaurant inside the tower, led by James Beard Award-winning chef Jonathan Sawyer. Among Chicago’s most celebrated living architects is Jeanne Gang, with two prominent buildings here: Aqua (the tallest woman-designed building when completed in 2009) and the 2020 St. Regis Chicago (welcoming the hotel in 2023 and surpassing Aqua’s earlier claim).

Seasoned travelers know to stray beyond any city’s center. But do you know which Chicago ’burbs to check out for dining, entertainment, attractions, and outdoor adventure? Charming downtowns are in Lombard, Lake Forest, and Naperville, for instance. If you’re an architecture buff, head to Oak Park, the birthplace of Frank Lloyd Wright and where he raised his own family. Learn more in an hour-long guided tour of the Frank Lloyd Wright Home & Studio, or simply stroll the largest collection of Wright-designed residential homes anywhere.

Highland Park’s Ravinia is the country’s first outdoor-music pavilion and the summer home for the Chicago Symphony Orchestra. In Evanston, you can easily find culture and art—including at Northwestern University’s Block Museum of Art—plus restaurants like The Barn Steakhouse, owned by Morton’s Steakhouses founder’s daughter Amy Morton and with a James Beard-winning chef in the kitchen. On the North Shore are the Baha’i House of Worship and the Illinois Holocaust Museum. Nearby is Chicago Botanic Garden, in Glencoe.

Hyde Park is one example of a South Side neighborhood rapidly evolving, yet the University of Chicago has long been here, and soon the Barack Obama Presidential Library opens in adjacent Jackson Park, also home to the Japanese-style Osaka Garden. You can also browse indie bookstores (a rare find these days) at 57^th Street Books, Powell’s Books Chicago (yep, a sibling to the West Coast bookstore), and Seminary Co-Op Bookstores. And one of Frank Lloyd Wright’s most well-known private residences—the Frederick C. Robie House—is open for tours. Sample Southern food at Virtue, whose chef-owner Erick Williams won Best Chef: Great Lakes in 2022.

Sometimes you have no choice—like late at night when arriving at the airport—to order a Lyft or Uber, but when in Chicago, you need to take the elevated train (the Chicago Transit Authority’s “L”) for a free tour of the city. Grab a window seat and watch from up high as it rumbles through the neighborhoods. Consider this the “back alley” tour of Chicago, and we mean this in a good way. Get a Ventra card (no cost, and easy to register, and there’s a companion app) at all “L” stations and load up on either cash value or unlimited trips, making travel around Chicago a breeze.

It’s called a Chicago-style hot dog for a reason: this is a recipe you don’t want to tinker with. The dog is stuffed into a poppy-seed bun before smothered with relish, yellow mustard, chopped onions and tomatoes, and a pickle spear. Looking for the best hot dog stands? While there are many, these tried-and-true legends, including The Weiners Circle, Superdawg Drive-In, and Wolfy’s, will satisfy you.

While there’s no shortage of deep-dish pizza—described as having a deep crust filled with cheese, tomato sauce, and whatever “toppings” you choose—in Chicago, you have choices. And now that Giordano’s, Lou Malnati’s, and Pizzeria Uno have locations outside of Chicago and around the U.S., stick with locally owned and operated options. Burt’s Place is in Chicago and the Northwest ‘burb of Morton Grove (since 1970). Slightly newer, as it debuted in 1991, Pizano’s has four Chicago locations. If you forget—as if!—to sample deep-dish pizza, you can always order from Reggio’s Pizza’s three locations at O’Hare. In 1998 the local pizzeria opened its first airport spot as a follow-up to its 1972 debut in Chicago.