Whether you’re heading to the downtown Loop or ultra hip Wicker Park, you won’t have any trouble deciding what to do in Chicago. After all, the city is home to a hotter-than-hot food scene, an artistic renaissance, and new hotels that are destinations in their own right.
Chicago has a seemingly endless parade of attractions. Think: comedy clubs, high-concept restaurants, dazzling architecture, and a sports scene that may beat out all others for its collective team spirit.
For the latter, you’re in luck no matter what time of year you’re traveling to Chicago. In spring, you can catch the Cubs or the Sox, in autumn, you can watch the Bears, and come winter, televisions are tuned to the Blackhawks and the Bulls. After all, Chicago is one of only four cities with a team for every major league sport.
Watching a show is one of many fun things to do in Chicago, whether you’re in the mood for comedy (head to Second City or the Laugh Factory) or an off-Broadway production. After all, there are more than 200 theaters, some of which are housed in storefronts.
When in Chicago, you can’t leave without sampling some of the best local beer from any one of the 68 breweries within city limits. Residents also love whiskey. Consider paying a visit to the Broken Share Lounge and ordering a Get Your Shine Box, made with vermouth (sweet and dry), Amaro Averna, orange bitters, and a grocery list of wintry spices.
Other must-see Chicago attractions include the Museum of Science and Industry (the only building left from the 1893 World’s Columbian Exposition) and art institutions such as the MCA and Art Institute.
And perhaps the most underrated Chicago sight of all? The beaches. Head to North Avenue Beach and watch a game of sand volleyball, or visit Ohio Street Beach, rent a lounge chair, and enjoy amazing skyline views as the sun sets. It’s the best way to end a perfect weekend in the Windy City.
For more panoramic vistas of Chicago, ascend Skydeck or 360 Chicago. You can also follow locals to any one of the city’s many downtown hotel rooftop lounges. The Chicago Athletic Association, for example, is crowned with a cool open-air terrace and restaurant.