Chicago Itinerary: Top things to do in the city

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Following New York and Los Angeles, Chicago is one of America’s most populous cities. Known for its cultural diversity, cold winters and deep dish pizza; the city is a beautiful place with plenty to do, see, eat and explore. 

In this blog post, I’ll be recapping my recent trip and sharing recommendations for places you should visit and add to your Chicago itinerary.

Things to do in Chicago

The Windy City has a lot of beautiful views to take in and one of the best ways to do it would be through booking an architecture river cruise

During the guided tour, you will get a front row seat to take in the views and hear live commentary about the history and architectural makeup of Chicago.

The tour is family-friendly and highlights landmarks such as the Chicago Riverwalk, Michigan Avenue Bridge, Wrigley Building, Willis Tower and more. 

I recommend arriving early so you’re able to sit on the open-air top deck. Otherwise you will be seated on the sheltered bottom of the deck. You will not be able to see the full view.

Explore Millenium Park

In the heart of Chicago is Millenium Park where you can take a leisurely stroll and visit the famous Cloud Gate. The sculpture is more popularly known as the bean for its shape and was unveiled in 2005. 

The shiny surface of the structure allows you to see yourself and the city skyline making it perfect for snagging a cool picture. 

Also in Millenium Park is the Crown Fountain which includes two 50ft towers that are also an interactive video sculpture with images of Chicagoans. 

In the summers, the structure spouts water so many people take advantage of that and have a fun time splashing around. 

During the winter months, the park transforms into a winter wonderland with an ice skating rink.

Visit the Navy Pier

The Navy Pier is an iconic lakefront destination. There are dozens of shops, eateries and attractions like the Centennial Wheel here so you can easily spend hours at the pier.

Shop along the Magnificent Mile

The Magnificent Mile is a popular shopping district full of retailers fit for any budget. If you can think of it, chances are you can find it here. 

From luxury and designer stores to pet boutiques there is literally something for everyone. Even if you’re not looking to buy anything, the area is littered with restaurants.
It’s also home to the world’s largest Starbucks. The Starbucks Reserve Roastery is a selection of the rarest, most extraordinary coffees Starbucks has to offer, and as a coffee lover this was really cool to experience.

Additional places to add to your Chicago Itinerary

  • The Art Institute of Chicago
  • Willis Tower
  • Chicago Riverwalk
  • Garfield Park Conservatory

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