The 12 Best Things to Do in Chicago

Posted: 5/13/2024 | May 13th, 2024 Famously known as “the Second City” (meaning second in population to New York), I feel like Chicago is often overlooked by travelers. It sees a fraction of the visitors LA and NYC receive, which is a shame, as it’s one of my favorite cities in the world. Chicago is chock-full of world-class institutions, Michelin-starred restaurants, awe-inducing architecture, and verdant parks. There is a lot to do here and the city has a really rich history. I think more people should visit. Sure, the winters are brutal. But, come spring, Chicago blossoms into a dynamic urban landscape of street life, outdoor cafés, and sunny parks when locals take over the outdoors to enjoy the few months of nice weather. (I don’t think you can really beat Chicago in the summer.) To help you plan your visit, here’s my list of the best things to do in Chicago: Table of Contents   1. Take a Walking Tour One of the first things I do when I arrive in a city is take a walking tour. They’re a great way to see the main sights, get the lay of the land, and connect with an expert local guide who can answer all my questions. Free Chicago Walking Tours hosts regular free tours that can introduce you to the city. You’ll get to see many of the coolest buildings in the city while also learning about the history of Chicago. The tour lasts a few hours. Be sure 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 creepy past as you explore the Chicago Loop. The tour lasts two hours and really talks about 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 Located downtown, these gigantic parks provide a great place to hang out, have a picnic, or go for a run. People play chess here when the weather is nice and, during the summer, there are a lot of free concerts and events here. The larger Grant Park stretches along Chicago’s waterfront, while Millennium Park is the subsection where the famous “Chicago Bean” sculpture is located. This iconic work of public art is a must-see. And, starting at noon on the first and third Saturdays from April through November, the Chicago Cultural Center hosts walking tours focusing on the art of Millennium Park. It’s really interesting. I love strolling through the park or just chilling here with a good book on a nice day.  3. Take in some art at the Art Institute of Chicago Since 1879, the Art Institute of Chicago has been wowing visitors with its excellent collection of works from around the world. Located in Grant Park, the museum has a few immediately recognizable pieces, including “American Gothic” by Grant Wood, Edward Hopper’s “Nighthawks,” and “A Sunday Afternoon on the Island of Grande Jatte” by Georges Seurat. The vast 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 go to one museum in Chicago, this should be it. Expect to spend a few hours because the collection is so big. To beat the crowds, skip a weekend visit as the place gets packed. Instead, go on a Monday or Thursday evening (they’re open late on Thursdays). You’ll have the place virtually to yourself. 111 S Michigan Ave, (312) 443-3600, artic.edu. Open Thursday-Monday 11am-5pm (8pm on Thursdays). Admission is $32 USD ($40 USD for advance skip-the-line entry). Daily tours (included in the price of your ticket) are offered at 1pm and 3pm.  4. Admire amazing architecture on a river cruise Chicago is an architecture lover’s dream. The very best way to take in its famed buildings is via a river cruise. This way, you can sit back and cruise down the canals while an expert guide provides context for what you’re looking at. The guides will give you a detailed history of the architecture. Some of the buildings you’ll see on the boat ride include the Tribune Tower, 333 West Wacker, Navy Pier, the Willis Tower, the Wrigley Building, and Marina City, among others. All in all, there are about 50 structures to see on this fascinating tour, and I promise, it’s much more interesting than it sounds!  5. Stroll down the Magnificent Mile Often nicknamed “Mag Mile,” this stretch along Michigan Avenue from the Chicago River to Oak Street is known for its upscale designer boutiques. In fact, rent here is the third highest in the US (after Fifth Avenue in New York City and Rodeo Drive in Beverly Hills). Even if you don’t want to blow your budget shopping, it’s still an experience to stroll along the avenue and take in the sights and the people, and enjoy the view of the Chicago River. There are several landmarks and attractions along the way too, including the 360 Chicago Observation Deck for expansive views over the city (more on this below).  6. Visit the Shedd Aquarium If you’re visiti

The 12 Best Things to Do in Chicago