I feel like Chicago, known as “the second city” (which means the second largest city after New York), is often overlooked by travelers. It only gets a fraction of the visitor numbers of LA and NYC, which is a shame as it is one of my favorite cities in the world.
Chicago is packed with world-class institutions, Michelin-starred restaurants, stunning architecture and green parks. There is a lot to do here and the city has a really rich history. I think more people should visit.
Of course, the winters are brutal. But in the spring, Chicago blossoms into a dynamic urban landscape with street life, outdoor cafes and sunny parks as locals head outside to enjoy the few months of nice weather. (I don’t think Chicago can really be beat in the summer.)
To help you plan your visit, here’s my list of the best things to do in Chicago:
1. Take a walking tour
One of the first things I do when I arrive in a city is to take a walking tour. It’s a great way to see the main sights, get familiar with the area, and connect with an experienced local guide who can answer all of my questions. Free Chicago Walking Tours regularly offers free tours that will introduce you to the city. You’ll see many of the city’s coolest buildings while learning about Chicago’s history. The tour lasts a couple of hours. Don’t forget to tip the guide at the end!
For a more unique tour, try the Gangsters and Ghosts Tour. You’ll learn all about Chicago’s dark side and spooky past while exploring the Chicago Loop. The tour lasts two hours and really tells of one of the pivotal times in Chicago’s history. Even if you’re not a history buff like me, you’ll get a lot out of it.
2. Relax in Grant and Millennium Parks
These huge downtown parks are a great place to relax, picnic, or jog. When the weather’s nice, people play chess here, and in the summer, they host many free concerts and events. The larger Grant Park stretches along Chicago’s waterfront, while Millennium Park is the subsection that houses the famous “Chicago Bean” sculpture. This iconic piece of public art is a must-see. And starting at noon on the first and third Saturdays from April to November, the Chicago Cultural Center hosts walking tours that focus on the art of Millennium Park. It’s really interesting. I love strolling through the park or just relaxing here with a good book on a nice day.
3. Experience art at the Art Institute of Chicago
Since 1879, the Art Institute of Chicago has been wowing visitors with its outstanding collection of works from around the world. Located in Grant Park, the museum has some instantly recognizable pieces, including Grant Wood’s “American Gothic,” Edward Hopper’s “Nighthawks,” and Georges Seurat’s “A Sunday Afternoon on the Island of Grande Jatte.” The extensive collection also includes works by Picasso, Monet, Renoir, Van Gogh, Jasper Johns, and Jackson Pollock. There are also wings devoted to African, Asian, and American Indigenous art. If you’re going to visit one museum in Chicago, this should be it. Plan to spend a few hours, as the collection is so large.
To avoid the crowds, skip visiting on the weekend, as the museum is packed then. Instead, go on a Monday or Thursday night (they’re open late on Thursdays), and you’ll practically have the museum to yourself.
111 S Michigan Ave, (312) 443-3600, artic.edu. Open Thursday-Monday 11am-5pm (8pm on Thursdays). Admission is $32 ($40 for advance skip-the-line tickets). Daily tours (included in ticket price) are offered at 1pm and 3pm.
4. Admire impressive architecture on a river cruise
Chicago is an architecture lover’s dream. The best way to see its famous buildings is on a river cruise. This way, you can sit back and cruise down the canals while an expert guide explains the context of what you’re seeing. Guides will give you a detailed history of the architecture. Some of the buildings you’ll see on the cruise include the Tribune Tower, 333 West Wacker, Navy Pier, Willis Tower, Wrigley Building, and Marina City, among others. In total, there are about 50 structures to see on this fascinating tour, and I promise it’s plenty to see. l more interesting than it sounds!
5. Stroll the Magnificent Mile
Often called the “Mag Mile,” this stretch of Michigan Avenue from the Chicago River to Oak Street is known for its upscale designer boutiques. In fact, rents here are the third highest in the U.S. (after Fifth Avenue in New York City and Rodeo Drive in Beverly Hills). Even if you don’t want to break your budget while shopping, it’s still an experience to stroll down the avenue, taking in the sights and people, and enjoying the view of the Chicago River. There are also several sights and attractions along the way, including the 360 Chicago Observation Deck with sweeping views of the city