Know before you go: Want to visit the places recommended in this article? With local regulations changing frequently, it’s a good idea to check the web site of any attraction or business to make sure it’s open before you go.
It can be tempting to only spend a long weekend in Chicago, hitting major attractions and jam-packing your schedule with activities. But Chicago has a lot more to offer visitors with a few more days to spare. Extend your visit and really get to know one of the U.S.’s most interesting, diverse, and exciting cities.
Downtown Chicago: 1 day
Locals call downtown the “Loop,” and it is home to some of the city’s main attractions, such as Buckingham Fountain, the Bean, the iconic Chicago Theatre, and the Art Institute of Chicago (not to mention HI Chicago hostel). You’ll probably also want to head over to the Willis Tower for a view of the entire city at sunset from the 103rd floor!
Museum Campus in South Loop: 1 day
Just south of downtown is the South Loop neighborhood, which is home to some of the best museums in Chicago, including the Shedd Aquarium, the Adler Planetarium, and the Field Museum. Try exploring this area via bike and you’ll be able to enjoy the parks that surround the museums as well.
Lincoln Park neighborhood: 1 day
Lincoln Park is located on the near north side of Chicago and can be easily accessed via bus, ride share, or train. This neighborhood is one of the oldest in the city and offers a nice contrast to the concrete jungle of downtown or South Loop. You can find tree-lined streets and beautiful homes as you shop around Armitage Avenue, come face-to-face with animals at the Lincoln Park Zoo (which has free admission), and even catch a baseball game at the iconic Wrigley Field.
Hyde Park neighborhood: 1 day
Located on the far south side of Chicago, Hyde Park is one of the city’s most famous historically black neighborhoods. It has incredible architecture, beautiful historic homes, and a vibrant local culture. While you’re in the neighborhood, take of tour of the University of Chicago campus or learn some fun facts at the famed Science and Industry Museum. You’ll also find lots of locally owned shops and restaurants here, so support the local economy with a meal or shopping spree! This neighborhood is also the future home of the Barack Obama presidential library – a great reason to come back and visit again in a few years.
Magnificent Mile shopping: half day
Chicago’s most famous shopping district, the Mag Mile houses hundreds of shops and several malls where you can find just about anything you need or want to buy. You’re likely to catch some art here as well: this section of North Michigan Ave. hosts rotating installations throughout the year.
West Loop neighborhood: half day
West Loop is the kind of area where you go to experience the trendiest places in the city. The scene in West Loop is best experienced at night when all the restaurants and bars, and their patios, are open. Randolph Street is the heart of the activity, but don’t miss your chance to poke down some of the side streets too, where you can find hidden gems including tucked-away street art, speakeasy bars with fewer than 20 seats, and bespoke boutiques.
Wicker Park neighborhood: half day
Wicker Park is the perfect neighborhood for a relaxing afternoon wandering around, because it offers a little bit of everything. You can find delicious spots for a bite to eat, such as Big Star Taco or Jeni’s Splendid Ice Cream, shop for vintage treasures at the Vintage Underground, or look for famous murals along the neighborhood’s streets.
Logan Square neighborhood: half day
Historically home to large Mexican and Puerto Rican populations, today Logan Square is one of the fastest-changing neighborhoods in Chicago, but it’s still holding true to its roots. It has lately seen an explosion of newcomers bringing some of the best new restaurant and bar openings in the city, especially of the Latin variety (think amazing street tacos and mezcal cocktails). Head to the Logan Square blue line stop on the L train and make your way south along Milwaukee Avenue to find some of the best spots.