There’s no shortage of things to do and see in Chicago — in fact, the seemingly endless list of sites, museums, restaurants and swank hotels can be quite daunting. Instead of wasting your time shuffling between so many, focus on these 10 Windy City attractions that won’t disappoint.
Go see some masterpieces
You’ve seen the iconic exterior of the Art Institute of Chicago in just about every movie filmed in the city, but it’s what’s on the inside that really captivates — more than 300,000 impressive works of art spanning the centuries. Take a spin through the newer Modern Wing to check out 20th- and 21st-century pieces, as well as the stellar design and architecture collection.
Stroll through the park
Once you’ve visited the Art Institute, swing by Millennium Park (a Windy City bucket-list must) via a futuristic pedestrian bridge. The 24.5-acre urban green space has public art installations (including the famed “Bean”), stunning landscape design, larger-than-life exhibits and, of course, the iconic Jay Pritzker Pavilion, a Frank Gehry-designed space that holds outdoor concerts.
If it’s summertime, grab a snack and sprawl out on the lawn to catch one of the many free outdoor shows.
Enjoy a majestic view
For incredible vistas (and equally stellar food) head to Sixteen, the Forbes Travel Guide Five-Star restaurant on the 16th floor of Trump International Hotel & Tower Chicago. From this vantage point, you’re high enough to see the city’s remarkable range of architecture, including an up-close view of the Wrigley Building’s clock tower. Linger over a bespoke cocktail on the Five-Star hotel’s glittery alfresco terrace and watch the sun set over the city.
Take a walk in the sky
The 606 is a formerly abandoned elevated rail line that now serves as a 2.7-mile recreational trail and park. The passageway cuts through the northwest side of town, running through Bucktown, Wicker Park, Humboldt Park and Logan Square. It’s a scenic, leisurely way to travel between the neighborhoods, especially when you stop for coffee (La Colombe) or cocktails (Scofflaw) at nearby spots just off the throughway.
When a respite from the breakneck speed of the city is needed, head straight up to the 20th floor of Five-Star The Peninsula Chicago for some R&R at the hotel’s indulgent Four-Star spa. While the top-notch, Asian-inspired treatments and warm service are quite lovely, the facilities are over the top — snag a lounger by the indoor, half-Olympic-length pool flanked by huge floor-to-ceiling windows to take it all in.
Dine in the Gold Coast
The tony Gold Coast neighborhood is filled with chic little boutiques and big-name brands as well as loads of buzzy eateries. For a posh, post-shopping meal that tastes as good as the restaurant (and patrons) looks, book a table at Nico Osteria inside the Forbes Travel Guide Recommended Thompson Chicago. Expect mouthwatering Italian dishes and a see-and-be-seen crowd.
Cheer on the Cubbies
Whether you’re a sports fan or not, you’ll agree that historic Wrigley Field is really something special. The legendary baseball stadium, home to the Chicago Cubs, has plenty for history lovers to enjoy (the manually operated scoreboard is a slice of old-time Americana), plus there’s a new plaza just outside where fans can gather and enjoy the lingering World Series champion atmosphere.
Check out local art
If you’re in town the second Friday of the month, don’t miss 2nd Fridays Gallery Night in Pilsen, a vibrant multicultural neighborhood close to downtown. It’s a chance to browse local works, and meet and mingle with the artists.
Afterward, grab a drink at Thalia Hall, an 1892 building that now houses a combo concert and event space as well as two hip spots for eats and drinks, Dusek’s and Punch House.
Indulge in haute cuisine
Foodies from all over the world flock to Five-Star Alinea, helmed by culinary genius Grant Achatz, but if an 18-course tasting menu of modernist cuisine doesn’t fit into your schedule, then head to one of Achatz’ other eateries (Next, Roister) in the Fulton Market district. Instead of making a reservation, you prepay for a ticket that guarantees your dining experience.
There are plenty of other options in the area, too. Swing by any number of hot Restaurant Row eateries and watering holes on Randolph Street. We’re partial to the French brasserie fare at Maude’s Liquor Bar and Green Street Smoked Meats for casual, cool Texas-style barbecue.
Sightsee on a boat
No matter how many times we take the Chicago Architecture Foundation River Cruise, we’re still stunned by the beauty of the city. On the tour, you’ll explore the riverfront with knowledgeable docents doling out interesting tidbits on the Windy City’s famous buildings.
Another way to experience the Chicago River is by taking a water taxi to Chinatown for some of the best Asian fare this side of Shanghai. Head to Phoenix for a traditional, authentic dining experience or to MingHin Cuisine for a sleek atmosphere and killer crispy pork belly.