Strolling down the streets of downtown Chicago, you feel like the possibilities are endless. As the unofficial capital of the midwest, Chicago has everything you would expect from a major American city while retaining its midwestern charm and manners. With soaring skyscrapers, stunning landmarks, and plenty of green spaces, this city offers endless ways to dive into its rich history and unique local culture. If you’re looking for things to do in downtown Chicago, here’s a handy guide to get you started.
The Best Time of Year To Visit Downtown Chicago
Downtown Chicago, Illinois, has a buzz of excitement that runs through it no matter the season. If you’re considering a trip to the Windy City, you first need to consider the weather you would be most comfortable in, as downtown Chicago weather is famous for being a little crazy.
Winters can be pretty cold, with many days dipping below freezing temps. Summer, on the other hand, can be very hot and humid, depending on the year. However, spring and fall are usually relatively mild and perfect for spending long days outside enjoying the sights.
Beyond the weather, think about what you would like to see and do most while visiting Chicago. For example, summer in the city means festival season: outdoor concerts, the Taste of Chicago, and several music festivals, including Lollapalooza. Around the holiday season, there are parades, decorations galore, and an explosion of holiday cheer at the famous Christkindlmarket. Whichever season you prefer, the Chicago Loop has countless popular attractions to explore.
Key Area Attractions and Neighborhoods in Downtown Chicago
Strolling through downtown Chicago, you can feel the energy and see the rich history of this incredible city. From soaring skyscrapers to beautiful parks, downtown Chicago offers a perfect mix of city adventure and natural beauty. Here are the top attractions and neighborhoods you shouldn't miss on your trip to the Windy City.
The Field Museum of Natural History
Neighborhood: Museum Campus
Begin your downtown Chicago adventure at The Field Museum, one of the largest natural history museums in the world. Located on the picturesque Museum Campus, this museum takes you on a journey through time and around the globe. Walk with dinosaurs, explore ancient Egypt, and delve into the cultures of the Americas. The star attraction, Sue the T. Rex, provides an awe-inspiring glimpse into prehistoric life. In addition to Sue, the museum boasts a vast collection of fossils, gemstones, and taxidermy that will captivate visitors of all ages.
360 CHICAGO Observation Deck
Neighborhood: Magnificent Mile
Head to the iconic John Hancock Center on Michigan Avenue to experience the breathtaking views from the 360 CHICAGO Observation Deck. Positioned on the 94th floor, this deck offers panoramic vistas of downtown Chicago and beyond. Don't miss TILT, an exhilarating attraction that leans you out over the city for a thrilling perspective. Afterward, unwind with a drink at CloudBar, enjoying the sky-high views. For an even more memorable experience, visit during sunset or twilight to see the city transition from day to night, with the skyline sparkling under the stars.
The Art Institute of Chicago
Neighborhood: Grant Park
A visit to downtown Chicago isn't complete without exploring the Art Institute of Chicago. Situated next to Grant Park, this renowned museum houses an impressive collection of over 300,000 pieces of art spanning centuries and cultures. From ancient artifacts to modern masterpieces, there's something for every art lover here. The museum's extensive collection includes works by famous artists such as Vincent van Gogh, Claude Monet, and Pablo Picasso. Special exhibitions often showcase rare pieces from around the world, offering a deeper insight into various artistic movements and cultural histories.
Millennium Park and Cloud Gate
Neighborhood: Millennium Park
No trip to downtown Chicago is complete without a visit to Millennium Park, home to the famous Cloud Gate sculpture, affectionately known as "The Bean." This reflective stainless steel masterpiece offers fantastic photo opportunities with the city skyline mirrored on its surface. Millennium Park also features beautiful gardens, the Crown Fountain, and the Jay Pritzker Pavilion, where you can enjoy free concerts and movies in the summer.
Navy Pier and Centennial Wheel
Neighborhood: Near North Side
Navy Pier is a historic landmark offering various attractions, dining, and entertainment options. The Centennial Wheel provides stunning views of the city and Lake Michigan, especially when lit up at night. This pier is perfect for a family outing or a romantic evening. Beyond the Centennial Wheel, Navy Pier features an IMAX theater, the Chicago Children's Museum, and seasonal fireworks displays. You can also take a scenic cruise on Lake Michigan or enjoy live performances at the Chicago Shakespeare Theater.
Grant Park and Buckingham Fountain
Neighborhood: Grant Park
Grant Park, often referred to as "Chicago's front yard," is a sprawling green space in the heart of the city. It's home to the stunning Clarence F. Buckingham Memorial Fountain, one of the largest fountains in the world. The park also hosts numerous festivals and events throughout the year. Stroll through the park to enjoy its gardens, public art, and lakefront views. As a bonus, Shedd Aquarium is a five-minute walk from the southern end of Grant Park.
Lincoln Park Zoo
Neighborhood: Lincoln Park
For a family-friendly adventure, visit the Lincoln Park Zoo, one of the oldest zoos in the United States. This free zoo offers different animal exhibits, from big cats to primates, and provides educational programs for all ages. Nestled in the expansive Lincoln Park, it's a great spot to enjoy a day surrounded by nature while still being close to downtown Chicago. Note: Lincoln Park Zoo is free and open to the public every day. The zoo also features a charming Farm-in-the-Zoo, where children can interact with domestic animals and learn about farming. Seasonal events like ZooLights during the holidays add extra excitement to your visit.
Chicago Cultural Center
Neighborhood: The Loop
The Chicago Cultural Center is a must-see for architecture and art enthusiasts. This historic building features free art exhibits, performances, and the world's largest Tiffany-stained glass dome. It's a cultural hub where you can explore the city's artistic heritage and catch live music, dance, and theater performances. Make sure to take a guided tour to learn about its fascinating history and architecture.
Maggie Daley Park
Neighborhood: Millennium Park
Adjacent to Millennium Park, Maggie Daley Park offers a whimsical escape with its unique playgrounds, climbing walls, and skating ribbon. It's a perfect spot for families and outdoor enthusiasts. In the winter, the skating ribbon transforms into a magical ice skating experience with stunning views of the city skyline. The park's Play Garden, inspired by Alice in Wonderland and Charlie and the Chocolate Factory, features imaginative play structures that will delight children of all ages. Picnic groves and mini-golf add to the park's appeal, making it an ideal destination for a full day of fun.
Chicago Riverwalk
Neighborhood: The Loop
The Chicago Riverwalk is a beautiful pedestrian pathway along the Chicago River, offering stunning views of the city's architecture. It's lined with restaurants, bars, and public art installations — a great place to relax and enjoy the cityscape. Consider taking an architecture river cruise for a guided tour of Chicago's most iconic buildings from the water.
Skydeck Chicago at Willis Tower
Neighborhood: The Loop
A visit to the Skydeck at Willis Tower (formerly Sears Tower) is something to check off the list while in Chicago. Step out onto The Ledge, a glass box extending from the 103rd floor, for a thrilling view of the city from 1,353 feet above the ground. It's a must-visit for anyone wanting to see Chicago from one of the tallest buildings in the world.
Plan Your Downtown Chicago Adventure with CityPASS® Tickets
Downtown Chicago has many attractions and experiences that are waiting to be discovered. From world-class museums and iconic landmarks to beautiful parks and lively entertainment options, there's something for everyone in this city.
To make the most of your downtown Chicago visit, consider purchasing CityPASS® tickets. Chicago CityPASS® tickets offer a convenient and cost-effective way to see Chicago's top things to do.
Chicago Lodging
To get the most out of your stay in Chicago, we recommend finding lodging near Chicago's top attractions. Use this map to find the right lodging for you:
Booking.comHeader Image Courtesy of 360 CHICAGO