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Things to Do in Chicago This Weekend

December 4, 2019  |  by Taylor Randolph 

Chicago is quickly becoming one of my favorite cities in the US. The history, art, culture, and sports of the city are so enthralling. Not to mention the delicious food, which ranges from the legendary Chicago deep-dish pizza to Michelin-rated fine-dining restaurants. It’s hard to put together a list of things that would truly encompass everything about the Windy City, but I’ve tried to narrow it down to my top absolutely “can’t miss” attractions if you have a long weekend to spend in this iconic city.


Things to Do in Chicago - Millenium Park

Millennium Park

At Millennium Park, you will find the iconic symbol of Chicago – The Bean (or Cloud Gate). There are also plenty of other attractions including the Jay Pritzker Pavilion, the Crown Fountain, and the Lurie Garden. Millennium Park borders the Maggie Daley Park, which is an amazing lakefront recreation area. You will find a massive playground, a climbing wall, and a skating ribbon that is open for ice skating in the winter and roller-skating in the summer.


Things to Do in Chicago - Grant Park Buckingham Memorial Fountain

Grant Park

Known as “Chicago’s Front Yard,” Grant Park is a huge area that encompasses most of Chicago’s popular things to do. The centerpiece of Grant Park is the stunning Clarence Buckingham Memorial Fountain, which was built in 1927. Grant Park is also home to the Field Museum of Natural History, the Art Institute of Chicago, Shedd Aquarium, and the Adler Planetarium. Check out their event calendar, you will find famous events held here such as Lollapalooza, Chicago Marathon, the Grant Park Music Festival, and The Taste of Chicago, as well as many others. Make a stop by Grant Park at sunset when the fountain is lit up and the city skyline is glittering with its brilliant lights.


Things to Do in Chicago - Architecture Tour

Photo Credit: Chicago Detours

Admire Chicago’s Architecture

Chicago is famous for its bold architecture that has influenced the rest of American architectural design. There is so much of the city’s history and multicultural heritage displayed in each of the unique buildings. Some highlights are the sparkling Tiffany mosaics, the “Chicago Picasso” sculpture, Chicago’s underground Pedway system, and the Marshall Field’s department store. Marvel at the ingenuity and originality of Chicago’s architecture, learn about the city’s history, and soak in the culture of the Windy City on an awesome walking tour with Chicago Detours.


Things to Do in Chicago - Navy Pier

Navy Pier

Chicago’s Navy Pier has superb family-friendly entertainment coupled with a beautiful view over Lake Michigan. Kids and adults of all ages will enjoy the towering Ferris Wheel, the thrilling swing-set ride, and the 18-hole mini-golf course. Kids will love exploring the Chicago Children’s Museum with plenty of hands-on activities and adults will love relaxing in the Miller Lite Beer Garden.  In the summer, check out the frequent concerts and firework displays.


Things to Do in Chicago - River Walk


Chicago’s Riverwalk is a gorgeous 1.25-mile pedestrian walkway on the south bank of the Chicago River. From here, you can enjoy beautiful skyline views, walk through the public gardens, or grab a meal overlooking the river. Boat tours and kayak tours are also very common along the river and are a great way to learn more about the city. If you visit during St. Patrick’s weekend, don’t be surprised to find the entire river is dyed green!


Things to Do in Chicago - Willis Tower Skydeck

Willis Tower Skydeck

For the best views over Chicago, make your way up 103 floors to the Willis Tower Skydeck. The sweeping views from the top are so worth it! On a clear day, you can see into Indiana, Michigan, and Wisconsin. If you want an even more dizzying experience, step out onto The Ledge, a platform made entirely of glass. Look down and you will feel like you are hovering over the city. This attraction is popular, so plan to arrive early to avoid the crowds. The Skydeck is open daily March through September between 9 am and 10 pm and October through February from 10 am to 8 pm.


Things to Do in Chicago - Chicago Cubs at Wrigley Field

Wrigley Field

If you are looking for a true Chicago experience, there is nothing more genuine than catching a Cubs game at Wrigley Field. Even if you’re not a baseball fan, everyone will enjoy the energetic and lively atmosphere, as well as the legendary Chicago ballpark hotdogs! If your visit doesn’t coincide with a game, consider going on a tour of Wrigley Field. The stadium was built in 1914 and is the second-oldest MLB ballpark in the country. There are endless stories to be told about this ballpark. Tours happen on non-game days between mid-May through September.


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Check out other things to do in the USA:

Local's Guide to NYC
Top 10 Things to Do in Philadelphia
Lake Tahoe Travel Guide




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Hi there! 

We are Jacob and Taylor. Travel is our passion and we love sharing our experiences here at The Travelling Souk. Our hope is that you would be inspired by this little blog to try something new, embrace an adventure, and live life to the fullest. 

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