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Downtown Chicago: Adventuring in the Windy City

March 6, 2023 By CityPASS

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.

Stops You Should Make When Touring Downtown Chicago

Of course, no trip to the Windy City is complete without stopping to see the city’s most famous attractions and iconic Chicago landmarks. Deciding what to see and do can be tricky if you’re strapped for time, but these are the things you really can’t miss if you want to see the best that Chicago has to offer.

The Field Museum of Natural History

Your first stop could be The Field Museum, one of the largest natural history museums in the world. It’s located on the shores of Lake Michigan, along with a few of the city’s other top-rated museums, collectively known as the Museum Campus. Once you step through the doors, you’re transported in both time and place as you walk with the dinosaurs, explore the world of ancient Egypt, and discover the cultures and civilizations native to the Americas.

The Field Museum’s top attraction is Sue, the most complete and one of the largest fossilized T. Rexes in the world. Both kids and adults get a kick out of coming face-to-face with the enormous creature from the past, giving us a glimpse of what life was like when dinosaurs roamed the earth. Sue is visible from both the upper levels and ground levels of the museum, letting you get an idea of how genuinely gigantic it is.

360 CHICAGO Observation Deck

To see Chicago like never before, make your way down Michigan Avenue to the famous John Hancock Center, one of the most recognizable pieces of architecture in the city’s skyline. While this building is worth seeing from the outside, the 360 CHICAGO Observation Deck on the 94th floor takes the cake. From here, you can take in unparalleled panoramic views of downtown Chicago and what lies beyond.

360 CHICAGO boasts large glass windows on four sides of the building, so you can see for miles in all four directions. Thrill seekers can experience TILT, windows you can lean against to incline over the city. If you’re thirsty, grab a cocktail with unforgettable views at CloudBar, the city’s bar in the sky.

The Art Institute of Chicago

For those seeking a little culture, a stroll through the vast collection of the Art Institute of Chicago is a must. This iconic museum is located alongside Grant Park on Michigan Avenue, right in the city's heart. This first-rate museum currently houses more than 300,000 pieces of art from around the globe, spanning centuries, styles, and movements.

The Art Institute of Chicago was founded in 1879 and continues to be the city’s premier museum for all things fine art. Since you could spend days in the museum and still not see everything, a little planning goes a long way here. The collection contains pieces from ancient through modern times, and there are countless rooms to explore. If you have the time, enjoy getting lost and let yourself wander and marvel.

The Bean in Millennium Park

Did you really visit downtown Chicago if you didn’t take a selfie at The Bean? Cloud Gate, known affectionately as The Bean, is the iconic stainless steel public sculpture that welcomes visitors to Millennium Park. It was installed in 2006 and reflects the city’s skyline on its shiny surface — as well as the faces of those who approach it.

Millennium Park is home to some of the city’s best gardens and green spaces, giving locals and tourists a much-needed green lung in the heart of the Chicago Loop. Stop by Millennium Park throughout the year for activities like ice skating, music in the park, and more.

Centennial Wheel at Navy Pier

Navy Pier is an important part of Chicago’s history, dating back to 1916. While there’s plenty to see here, one of the pier’s top attractions is Centennial Wheel, a Ferris wheel that stretches nearly 200 feet up into the sky. From the top, visitors can get a thrill from seeing the Windy City and Lake Michigan like never before. For a truly special experience, hop on Centennial Wheel after dark to see the sparkle of the city lights reflecting off of the lake.

Don't Miss Out on Any of Chicago's Biggest Attractions

To ensure you don’t miss out on any of downtown Chicago’s top attractions, buy CityPASS® tickets to save both time and money. The original CityPASS® ticket lets you save when you visit the city’s most popular attractions, many of which are on this list.

For a shorter visit to the Windy City, try Chicago C3® tickets and save up to on three top attractions. When you buy either one, you’re purchasing the ultimate ticket to exploring downtown Chicago!

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:

Header Image Courtesy of 360 CHICAGO

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