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Chicago: A Weekend Itinerary

Updated: May 17

Cloud Gate in Millennium Park overlooking Downtown Chicago
Cloud Gate in Millenium Park

Chicago—have you bean there before? With its ample art displays, impressive architecture, and abundance of restaurant options, you will easily find yourself wanting to extend your stay in the "Windy City." Read along for a weekend itinerary!

Breakfast at Wildberry Pancakes and Cafe in Chicago
Breakfast at Wildberry Pancakes and Cafe

Where to stay in Chicago

There are a number of accommodation options in Chicago, including Airbnb and hotels. If you're looking to stay in a central location, I recommend looking for accommodation in or close to Downtown Chicago.

Getting around in Chicago

Chicago is a walkable city, and is also easily accessible by train, bus, or ride share apps. I recommend exploring the city on foot, so you're able to discover sights you might otherwise miss.


Day 1:

Wildberry Pancakes and Cafe: Start your morning off with breakfast at this popular spot serving big portions.

Millennium Park: You can easily spend an entire day at Millennium Park. This park is made up of expansive green spaces and interactive art displays. While you're there, stop by Cloud Gate (which you may know as The Bean). Check out the Crown Fountain, which boasts two glass towers projecting images of Chicago residents.

Magnificent Mile: Magnificent Mile is an upscale shopping street that stretches along Michigan Avenue.

Millennium Park overlooking Downtown Chicago
Millennium Park

Day 2:

Art Institute of Chicago: The Art Institute of Chicago is one of the most famous museums in the country, and for good reason—their collection is expansive.

Skydeck Chicago: For the best views in the city, check out the Skydeck at Willis Tower, which offers a glass viewing platform on the 103rd floor.

Lou Malnati's Pizzeria: A trip to Chicago isn't complete without trying deep dish pizza. Lou Malnati's is a classic that serves Chicago-style pizza.

Day 3:

Yolk: This is another popular spot for breakfast in the city. Yolk offers generous portions and a variety of dishes to choose from.

Lincoln Park Conservatory: Lincoln Park Conservatory is a hidden oasis away from the bustling city. The conservatory houses a variety of plants.

Chicago Riverwalk: Take a boat tour or walk along the Riverwalk—my friends and I did the latter. Walking along the river provides unhindered views of the city's skyscrapers.

Eataly: Finish your day with an Italian dinner at Eataly. If you've never visited an Eataly location, it offers numerous Italian eateries and a large marketplace.

Flowers and plants at Lincoln Park Conservatory in Chicago
Lincoln Park Conservatory


Visit in late spring or early fall: These are the best times to visit the city for more favorable weather and less crowds.

Purchase the Chicago CityPASS: If you're planning on visiting multiple attractions, purchase the CityPASS which will provide discounted access to the city's main attractions. Click here for more information.



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