29 of the Best Things to do in Chicago
There are few cities more spectacular than Chicago. Nestled on the banks of Lake Michigan, Chicago has everything from sandy beaches and luxury shopping districts to vibrant cultural scenes and art galleries and there is something for everyone. The Windy City is a fabulous year-round destination for those who crave art, culture, adventure, world-class restaurants, and hotels. From fancy shops like Tiffany & Company on Michigan Avenue to quiet neighborhoods like Andersonville and Hyde Park, the city of Chicago offers an unequaled travel experience. With so much to see and do in Chicago, it’s hard to fit it all in one trip! Here are my favorite things to do in Chicago, including where to eat!
Best Things to Do in Chicago
Chicago is a very walkable city, especially in downtown areas like the Loop, River North, and along the Magnificent Mile. Chicago is bike-friendly, with many bike lanes and trails, especially along the Lakefront Trail. The city’s bike-sharing program, Divvy, offers an easy and affordable way to rent a bike for short trips. To get downtown from the airport, book a private airport transfer
Part One – Things to Do in Downtown / Waterfront
Looking for more information on Chicago? Read our article about the Best Places to Stay in Chicago.
1. The Bean – Millennium Park and the Cloud Gate
The Bean at Millennium Park is perhaps one of the most iconic sculptures in Chicago, or at least that’s how most visitors describe it. It’s actually named the “Cloud Gate”, created by the world-famous sculptor Anish Kapoor. Visit the beautiful Millennium Park to take advantage of a wonderful photo op with The Bean. Its gleaming mirrored finish makes a beautiful backdrop as it seems to distort the city’s skyline creatively. Other Things to Do at Millennium Park
Millennium Park isn’t just about seeing Cloud Gate, there are plenty of things to do to make it a day out. In winter, enjoy ice skating at the McCormick Tribune Ice Rink and in the warmer months, the rink is transformed into a rock-climbing wall. While at Millennium Park, you can’t miss the magnificent Crown Fountain and its two 50-foot glass towers bordering the reflecting pool. The Crown Fountain towers showcase video projections of Chicago faces and life. You’ll also find rotating public art installations in the park. Keep an eye out for two designs by architect Frank Gehry. Jay Pritzker Pavilion is a state-of-the-art outdoor concert venue hosts a variety of music events, including the Grant Park Music Festival, free concerts, and movie screenings in the summer. The BP Pedestrian Bridge is a winding bridge that provides a unique pedestrian route from Millennium Park to Maggie Daley Park and offers great views of the park and the city. Book this Segway tour – perfect for first-time visitors to Chicago, where you’ll visit Millennium Park, Grand Park, and the famous Buckingham Fountain.
2. Stroll the Chicago Riverwalk
Take a stroll along the Chicago River downtown on the Chicago Riverwalk. The Chicago Riverwalk is a 1.25-mile-long path that runs through downtown Chicago. There are shopping, dining, and museums along the path. Plus, it is easy to catch a boat tour from the Riverwalk to take in the sites in comfort. Start your day with this Yoga Riverwalk Tour. This Yoga-inspired walking tour combines sightseeing and wellness. Follow your guide along the Chicago River Walk while hearing about its history and famous architecture, all while stretching and doing meditative exercises.
3. Chicago Architecture River Cruises
One of the best things to do in Chicago is to tour the city on the Chicago River. The Chicago Architecture River Cruise, also included with the CityPASS, is one of the top attractions in the city. Chicago, known for its rich architectural history, is home to some of the world’s most iconic buildings and world-famous architects. You can book it in advance here.
4. Chicago River Boat Tour
If the architectural history of downtown Chicago isn’t your thing, you can book a shorter 45-minute boat tour of the Chicago River. This family-friendly boat tour with live commentary along the Chicago River is tailored to entertain the whole family and shorter to keep the kid’s attention. If you are looking for more things to do in Chicago with kids, the Chicago Children’s Museum is another fun to for the kids. A riverboat tour is a great way to take in the skyline and the city’s architecture while enjoying a pleasant trip through Chicago.
5. SkyDeck Chicago at Willis Tower
To get unparalleled views of the Chicago skyline, suburbs, and Lake Michigan, visit the Skydeck Chicago perched high atop the Willis Tower (formerly known as Sears Tower). If you’re feeling adventurous, hang over the city on the ledge, a glass enclosure with floor-to-ceiling windows and a transparent floor. You’ll feel like you’re floating 103 floors above it all. Visiting the iconic Willis Tower will teach you about Chicago’s history and architecture. Make sure to download the Willis Tower Skydeck Chicago Mobile App to show famous Chicago Landmarks. The Skydeck Pass gives you express entry to The Ledge, Free Wifi, and Theater presentation.
6. Art Institute of Chicago
In the center of Grant Park, on the famous Michigan Avenue, The Art Institute of Chicago is an architectural masterpiece is easily accessible with the Chicago CityPASS. Just walk between the two lion statues and step into a fantastic collection of art worldwide. The Art Institute of Chicago was voted the #1 Museum in the World by Trip Advisor, and it’s easy to see why when you gaze at masterpieces by Chagall, Matisse, and Georgia O’Keefe. Located in the Loop community of Chicago’s Central Business District, there are plenty of things to see in this area. Get your skip-the-line tickets for the Art Institute in advance, where you’ll enter 30 minutes before the museum opens to meet your guide and see iconic pieces by Picasso, Salvador Dali, and Andy Warhol. The Art Institute of Chicago has one of the world’s greatest collections of impressionist art. You can book with peace of mind for a full refund should you cancel within 24 hours of the activity. Best Money Saving Tip for Chicago On our last visit, we took advantage of CityPASS to get VIP access to some of the city’s most famous landmarks (and saved a lot of money)! The Chicago CityPASS bundles together Chicago’s top attractions with one purchase. The CityPASS is valid for nine consecutive days once activated. Save valuable time with skip-the-line tickets to your favorite attractions. The attractions include entrance to Skydeck Chicago, Shedd Aquarium, Field Museum, Art Institute of Chicago, Adler Planetarium, museums, 360 Chicago Observation Deck, and other top attractions in the Windy City. Click here for more information and to order your CityPASS today.
7. Take a Chicago Food Tour
A great way to explore Chicago by foot is to book a guided food tour. This guided tour takes you from the Chicago Theater to the Chicago Pedway, where local commuters move about the city’s underground tunnels. You’ll then walk from City Hall to the Chicago Riverwalk, where you’ll see famous landmarks such as the Marina Towers, the Britannica Building, and the Willis Tower. It’s then on to part two of the Chicago City tour with food tastings in the River North Neighborhood to sample Chicago staples like the Chicago hot dog, popcorn, and Chicago-style deep-dish pizza. Bring your appetite because there’s a lot of food on this tour. Check out more food tours here.
8. Enjoy The Crimes of Chicago Mob and Crime Bus Tour
Chicago has a colorful criminal past with some of the most notorious mob and crime bosses in history. This Chicago crime boss tour is one of the more unique things to do in Chicago. Ride through the Windy City by bus to see the areas frequented by the likes of Al Capone, John Dillinger, and the Terrible Tommy O’Connor. You’ll see mob staples like the Biograph Theatre, Holy Name Cathedral and the Site of the St. Valentine’s Day Massacres. This year-round attraction will take you to places like the criminal courthouse where the notorious criminals of Chicago were tried. You’ll recognize names like The Untouchables and Chicago Blackhawks and you’ll see notorious crime scenes from the Windy City like the Biograph Theatre, Holy Name Cathedral, Clark Street Bridge, and the St. Valentine’s Day Massacre
9. The Magnificent Mile
Read the full article