- Chicago is one of the most artistic cities in America, evident by the impressive collection of museums. Head to The Art Institute of Chicago ($25 adults/$19 students), where you can view everything from Claude Monet’s waterlilies to 16th century Nigerian war remnants.
- The Museum of Contemporary Photography features incredible works in their permanent collection by Ansel Adams and Dorothea Lange, along with temporary exhibitions featuring up and coming photographers — all of which can be viewed for free.
The staircase at the Museum of Contemporary Photography in Chicago, which is, fittingly, often photographed for its unique design. // photo by Robyn White
- Take advantage of another one of the city’s best kept secrets — the Driehaus Gallery of Stained Glass at the Navy Pier. With no entrance fee, you can freely marvel at an incredible collection of stained glass, featuring the trademark style of Louis C. Tiffany (son of Tiffany & Co. founder), as well as breathtaking renditions of Alphonse Mucha’s The Seasons.
- In a city with such an impressive skyline, you can pay $18 to go to the top floor of the historic John Hancock Center for a 360° view, or you can get more bang for your buck by grabbing a drink on the 96th floor at Signature Lounge. The entire lounge offers jaw-dropping views of the city, even in the bathroom. The lounge is two floors above the observatory and has no entrance fee, although technically you’ll spend about the same, considering most drinks will set you back $15. Still, you’ll get to enjoy a sunset over Chicago with a drink in hand, inarguably more satisfactory than a few selfies at the observatory.
- Venture out to the suburb of Oak Park, about a half hour west from the center of Chicago on the green rail line. Oak Park is home to not only one of the most influential 19th/20th century architects and designers Frank Lloyd Wright, but also one of the most beloved 20th century writers Ernest Hemingway. Spend the day roaming the streets of this picturesque suburb with the audio version of the self-paced Historic Neighborhood Walking Tour (available at the Frank Lloyd Wright museum for $15 adults/$12 students).
- End the day at the Ernest Hemingway birthplace home (200 N. Oak Park Ave.), where the $15/$13 admission fee grants you access to a tour of the home, as well as to the Ernest Hemingway Museum (Closed M/Tu; open 1-5 p.m. W-Fri and Sun., 10 a.m.-5 p.m. Sat.), which provides an intimate look at the late writer’s work and life through private correspondence and other relics.
- Go deep with Chicago-style (deep dish) pizza. Deep dish pizza is not for the faint of heart, with its intimidating block of thick, dense dough, mound upon mound of mozzarella, and top layer of rich, thick tomato sauce, not to mention all the toppings. While the best place to try this uniquely Chicago treat might be highly contested (as both internet and extensive first-hand research have proved to be inconclusive), the good news is that there’s no shortage of places to help you check this must-eat off your list. Try a pie at one of the city’s traditional pizzerias, like Lou Malnati’s or Gino’s East, or try out one of the newer kids in town, such as The Art of Pizza. You can’t go wrong either way (but just to make sure, you might want to try them all).
- Check out a comedy show at Second City, which has essentially served as a pipeline for SNL for years. As the first ever ongoing improvisational theatre group in Chicago, this famous comedy club has been the breeding grounds for beloved comedians like Dan Aykroyd, Chris Farley, Tina Fey and Amy Poehler. Second City offers shows nightly, with most tickets starting at $15.
- As one of the greatest art cities in the U.S., it should come as no surprise that, in addition to great museums, the city also has numerous sculptures and public art installations all over town worth seeking out. While downtown, swing over to Millennium Park, home to the famous “Cloud Gate” sculpture (more commonly referred to as “The Bean”), as well as Crown Fountain, an interactive video installation known to occasionally, and not so dryly, interact with visitors (dress accordingly!).
Chicago’s “Cloud Gate” sculpture (commonly known as “The Bean”), located downtown in Millennium Park. // photo by Robyn White
- While there’s clearly no shortage of things to eat, see and do in Chicago, be sure to check out what festivals are happening when you’re in town. With the exception of the quieter winter months, you can rest assured that at least one festival will be underway during your visit. Here’s a sample of what’s going on just in November alone: https://www.timeout.com/chicago/events-calendar/november-events-calendar. The city also hosts one of the country’s best St. Patrick’s Day celebrations (where else does the city dye their river bright green?) and best musical festivals featuring over 130 musical acts (Lollapalooza), making a trip to the city worthwhile and fun-filled no matter when you visit.