From Architecture to Foodie Adventures: Top Things to Do in Chicago for Everyone

Chicago, the Windy City, is a hub of art, culture, and history. Whether you're an architect buff or a foodie adventurer, there's something for everyone in this vibrant city. From towering skyscrapers to mouth-watering deep-dish pizza - Chicago has it all! If you're planning a trip to this exciting metropolis but don't know where to start exploring, we've got you covered. In this blog post, we'll be taking you on a journey through some of the top things to do in Chicago that will appeal to every kind of traveler out there. So put on your walking shoes and get ready for an adventure!

top things to do in Chicago

Overview of Chicago

Anyone planning a trip to Chicago will find no shortage of activities to keep them busy. The city, considered as one of our top 10 places to visit in the summer in the US, is home to world-renowned museums, award-winning restaurants, and beautiful architecture. Here is an overview of some of the top things to do in Chicago for everyone.


The Art Institute of Chicago and Museum Campus are must-sees for art lovers. The former houses one of the largest collections of Impressionist paintings in the world, while the latter is home to three museums: The Field Museum, Shedd Aquarium, and Adler Planetarium. History buffs will enjoy exploring The Chicago History Museum and the Abraham Lincoln Presidential Library and Museum.


Chicago is known for its architecture, and there are several ways to take in the city's iconic skyline. A popular option is to take a river cruise down the Chicago River while learning about the city's history and architecture from a guide. For those who want a more hands-on experience, there are several companies that offer walking or biking tours of the downtown area.


Chicago is also known for its food scene, and there are plenty of places to sample the city's signature dishes. Deep dish pizza is a must-try, and there are several renowned spots like Giordano's and Lou Malnati's that serve up delicious slices. Another local favorite is the Italian beef sandwich, which can be found at many delis throughout the city. 

Architecture Tours

There are plenty of ways to explore Chicago's architecture, both old and new. For a taste of the city's history, take a walking tour of the Loop or visit one of the many museums dedicated to Chicago's architectural heritage. If you're looking for something more modern, take a tour of the Willis Tower or theJohn Hancock Center. And for something truly unique, check out the Frank Lloyd Wright-designed Unity Temple.

Shopping Spots

There's no shortage of shopping options in Chicago, ranging from luxury boutiques to vintage shops. The Magnificent Mile is home to some of the city's best shopping, with high-end stores like Neiman Marcus and Saks Fifth Avenue. For a more unique shopping experience, head to Wicker Park or Logan Square, where you'll find indie shops and one-of-a-kind finds. If you're looking for bargain deals, check out the outlets at North Avenue Beach or the Randolph Street Market.

Outdoor Activities

If you’re looking to soak up some rays, there are plenty of outdoor activities to take part in during your stay in Chicago. For starters, take a walk or bike ride along the scenic lakefront path. With 18 miles of lakefront trails, you’re sure to get your steps in while taking in stunning views of the city skyline and Lake Michigan.

If you’re feeling more adventurous, try your hand at stand-up paddleboarding or kayaking. Both can be rented from various locations along the lakefront. Or if you’d rather stay on solid ground, playing a game of beach volleyball is always a fun option.

Other outdoor activities in Chicago include exploring one of the many parks, such as Millennium Park or Grant Park, both of which offer free concerts and events throughout the year; going for a run or walk through one of the many forest Preserves; or attending a baseball game at Wrigley Field, home of the iconic Chicago Cubs.

Restaurants, Bars and Clubs

There's no shortage of things to do in Chicago, whether you're a fan of architecture, art, or good food. And while the Windy City is renowned for its deep dish pizza and hot dogs, there's much more to the culinary scene here than meets the eye. From Michelin-starred restaurants to hidden speakeasies, there's something for everyone when it comes to eats and drinks in Chicago.

If you're looking for a fine dining experience, make sure to check out Alinea, Grace, Smyth & The Loyalist. For something a little more casual, but no less delicious, try Au Cheval, Girl & the Goat, or Big Star. And if you want to really dive into Chicago's foodie culture, sign up for a food tour with context Touring!

When it comes time to raise a glass (or two), you'll find no shortage of options in Chicago. If you're looking for craft beer, head to Revolution Brewing Company or Half Acre Beer Company. Or if wine is more your style, stop by Prosecco or Enoteca Roma. And if cocktails are what you crave, don't miss The Violet Hour or The Aviary.

No matter what your taste buds are craving, you'll find it in abundance in Chicago. So come hungry and thirsty - and get ready to enjoy some of the best food and drink this city has to offer!

Museum Visits

There's no shortage of things to do in Chicago, but sometimes it can be tough to decide what to do next. If you're looking for some inspiration, check out our list of the top things to do in Chicago for everyone. From architecture buffs to foodies, there's something for everyone.

One of the most popular tourist attractions in Chicago is the Art Institute of Chicago. This world-renowned museum houses some of the most famous works of art in the world, including paintings by Van Gogh, Monet, and Leonardo da Vinci. If you're interested in learning more about the city's history, pay a visit to the Chicago History Museum. Here you can explore exhibits on topics like the Great Chicago Fire and see artifacts from the city's past.

If you're a fan of good food, you'll want to check out some of Chicago's best restaurants. Deep dish pizza is a must-try while you're in town, and there are plenty of great places to get it. For something a little different, head to Alinea for a truly unique dining experience. Or, if you're looking for a quick bite, stop by one of the many food trucks that line the streets downtown.

Free Things to Do in Chicago

Chicago is a city rich in culture and history, with something to offer everyone. If you're looking for free things to do in the Windy City, look no further! Here are some of our top picks:

  • 1. Take a stroll down Michigan Avenue and window shop along the Magnificent Mile.
  • 2. Visit one of Chicago's many iconic public art installations, like The Bean or Cloud Gate.
  • 3. People watch at one of the city's popular parks, like Millennium Park or Grant Park.
  • 4. Pay respects at one of Chicago's landmarks, such as the Willis Tower or Buckingham Fountain.
  • 5. Catch a free summer concert at Navy Pier or in Millennium Park.
  • 6. Walk along the riverfront and take in views of the skyline from different angles.
  • 7. Browse through the farmers markets located throughout the city on select days and seasons.
  • 8. Get lost in one of Chicago's many world-renowned museums, like The Art Institute of Chicago or The Field Museum (admission is free on Thursdays!).

From exploring the city’s famous architectural landmarks to trying out traditional Chicago-style food, there are plenty of things to do in Chicago for all different types of travelers. Whether you’re looking for an educational experience or a fun night on the town, this Windy City has something for everyone. With so many activities and sights to explore, you won’t be bored during your trip to Chicago!

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