The first time I visited Chicago was on a work trip in 2019. Even though I’ve only spent a few days there each time I’ve visited since, it’s not hard to absolutely fall in love with the city!

Chicago offers visitors so many activities to enjoy. From architectural masterpieces and world-class museums to award-winning restaurants and lively nightlife, the “Windy City” has something for everyone. Here are four not-to-miss activities when traveling to Chicago!

1) Visit the landmarks

When taking a trip to Chicago, you for sure have to visit all the city’s architectural landmarks! Chicago is home to some of the world’s most iconic skyscrapers, including the Willis Tower and the John Hancock Center. Take a tour of these and other notable buildings to get a sense of the city’s history and architecture, or you can hire a Twisted Road Motorcycle to sight see and make it even more fun!

For those interested in architecture, a must-see is the Frank Lloyd Wright Home and Studio in Oak Park. Visitors can take a guided tour of this national historic landmark, which was designed by one of America’s greatest architects.

If you’re looking for something different, check out the Museum of Contemporary Art or the art galleries at the Little Black Pearl & Design Center. The Little Black Pearl is a black-owned cultural center that provides opportunities in art, culture and entrepreneurship to youth, adults and families across Chicago.

Another great option is to take a stroll through Millennium Park. The park is especially beautiful in the summertime when its iconic Bean sculpture is surrounded by blooming flowers. There’s always tourists at the Bean so make sure to go early if you can!

2) Eat your way through the city

Chicago is known for its deep-dish pizza (tbh, not my fav), but there’s so much more to the city’s culinary scene. From world-class Michelin-star restaurants to local favorites, you’ll find something to suit every taste and budget!

For a truly unique experience, dine at Alinea. This three-Michelin-starred restaurant is one of only 13 in the United States and offers an unforgettable dining experience. Another high end restaurant to try is Pearl’s Place. This restaurant combines home-style foods with a fine-dining restaurant experience.

Or, if you’re on a budget, consider eating at One Off Hospitality Group’s The Publican. This popular spot serves up fresh seafood and farmhouse fare in a casual setting. But, if you’re vegan like me, some delicious restaurants to try are Chicago Diner, Handlebar, or Kuma’s Corner.

No matter where you decide to eat, be sure to save room for dessert! Chicago is home to some of the best bakeries in the country, including Bang Bang Pie Shop and Spinning J Bakery.

3) Shop ’til you drop

From high-end designer boutiques to local markets, Chicago is a shopper’s paradise. The Magnificent Mile is home to some of the best shopping in the city, with stores like Nordstrom, Neiman Marcus, and Saks Fifth Avenue.

For those looking for something more unique, head to Wicker Park or Logan Square. These hip neighborhoods are home to independent shops selling everything from vintage clothing to handmade jewelry. For example, The Silver Umbrella is a black-owned consignment service and boutique store located in Hyde Park.

You can also find great deals at the city’s many markets. The Randolph Street Market is held monthly and features vendors selling antiques, art, and collectibles. If you’re in town during the holidays, be sure to check out the Christkindlmarket Chicago too, which sells German gifts and food.

4) Enjoy the nightlife

Chicago is also known for its lively nightlife scene. There are countless bars and clubs to choose from, so you’re sure to find one that suits your taste. For a truly unique experience, head to The Aviary. This speakeasy-style bar serves up creative cocktails in an intimate setting.

On the other hand, if you’re looking for a more laid-back atmosphere, try The Violet Hour. This popular spot has a relaxed vibe and offers an extensive list of craft beers and wines.

You could also see a show at the Black Ensemble Theatre. This theater is recognized as one of the most diverse theaters in the country. Its mission is to eradicate racism and its damaging effects through theater arts. View show listings, and book tickets by clicking here!

No matter what your interests are, you’ll find plenty to keep you busy when traveling to Chicago. So be sure to add these four activities to your itinerary to make the most of your trip!

xoxo, Arielle