How to Spend the Weekend in Chicago- A Two Day Itinerary For Chicago

Chicago is constantly brimming with excitement and there is always something to see or do no matter the time of year. A weekend trip to Chicago is a great way to re-energize your soul while enjoying the many sights.

Visit a park, take a river cruise, explore a museum or two, or stroll along the Chicago River Walk. Our two day itinerary for Chicago will be jam-packed with activities, shopping, and eating. Bring your friends and your family for a memorable weekend in the Windy City!

While you are out and about exploring this fabulous destination, drop your extra gear at a luggage storage locker for safekeeping. Eat, shop, and dine hands-free without the burden of bags.

Millennium Park

Head over to Millennium Park for a few hours of fresh air while you enjoy some fantastic green space in the heart of Chicago. Originally built to celebrate the third millennium, the park is now home to the Civic Center and encompasses about 24 acres of Lake Michigan’s shoreline. 

The park is bordered by East Monroe Drive, Randolph Street, Columbus Drive, and Michigan Avenue, all featuring public art displays for people to enjoy. The park is considered to be the top tourist attraction in Chicago

While exploring Millennium Park during your weekend trip to Chicago you can enjoy the following: 

  • Boeing Galleries and Exhibition
  • Welcome Center
  • Chase Promenades
  • Crown Fountain
  • Great Lawn
  • Lurie Garden
  • BP Bridge
  • Jay Pritzker Pavilion 
  • McDonald’s Cycle Center
  • Wrigley Square

Skydeck Chicago

During your two day itinerary for Chicago, you must grab your camera and head to Skydeck Chicago! This exciting attraction is 1,353 feet above the city and offers breathtaking panoramic views of the city and Lake Michigan. Formerly the Sears Tower, Skydeck Chicago is the second tallest building in the western hemisphere

Get your tickets and head up to the 103rd floor to enjoy clear observation boxes and unhindered views that allow you to see miles around. You can even step outside the building on The Ledge, a 4-foot enclosed glass box.

The Ledge is the highest observation deck in the U.S. Snap a few photos to share with friends and family and see if they can name the four states that are in the pictures.

Chicago River Walk

bank of the main section of the Chicago River and is a cultural hub for the city. The walkway is 1.25 miles long and is lined with restaurants, art galleries, and shops. 

Many street performers gather on the River Walk to offer terrific impromptu performances. Stroll along and feel the vibrant hum of the city surround you. Become part of the excitement! Browse for fantastic souvenirs while you take your stroll.

The Chicago River Walk is divided into four districts: 

  • The Arcade
  • The Civic
  • The Confluence
  • The Esplanade

Adler Planetarium

You do not have to be an astrologer to fully appreciate the Adler Planetarium. The shows and exhibitions hosted in the galleries and theaters will turn you into an enthusiast and you will learn to pick out several constellations. 

Step inside the observatory for a more hands-on astronomy learning experience. Sign up for courses and lectures to expand your knowledge or just spend an hour or two taking in the exhibits.

Since you are only in town for the weekend, get your tickets in advance and skip long lines and wait times.

The Art Institute of Chicago

Head over to Grant Park and pay a visit to the Art Institute of Chicago, one of the biggest and oldest museums in the U.S. Founded in 1879, the museum sees about 1.5 million visitors each year. Grab your tickets online and avoid long lines.

The Art Institute is easily recognized by the large bronze lions that stand guard at the entrance. With over 300,000 works of art on display, plan to set aside a few hours to spend wandering through this magnificent museum.

The Wrigley Building

Make your way to North Michigan Avenue and visit the Wrigley Building. This iconic skyscraper was built to be the home of the Wrigley Company’s corporate headquarters. The building features two towers with a walkway connecting them. 

The building is just less than 500,000 square feet and was built during the 1920s. A fun fact about the Wrigley Building is that it was the first building in the city to install central air conditioning.

Wendella Tours and Cruises

Take a short but pleasurable cruise along the Chicago River. Or maybe a longer cruise on Lake Michigan can be worked into your weekend itinerary. Wendella Tours and Cruises has been offering expeditions since 1935 and runs boat tours from late April through early October. 

Pick your tour and order your tickets in advance to ensure you have a spot on the boat. Your guide will entertain you while detailing the history of the city and the different buildings you see while on the tour. It is a great experience when visiting Chicago.

Walking Tours

The ultimate way to get to know a new city is on foot. Many companies offer free walking tours with a knowledgeable guide such as Free Tours By Foot or Free Chicago Walking Tours. Remember to tip your tour guide when the tour is finished.

Inside Chicago Walking Tours is another great option. Although not free, they do offer comprehensive walking tours. You can join a small group tour or sign up for a private one-on-one tour and have the guide’s undivided attention.

Spending the weekend in the Windy City is a great way to experience new and exciting things and see some of the amazing and iconic landmarks that make Chicago so special. Pack your bags and plan your days carefully to experience the most during your time.

Chicago is a special city full of life and excitement! Remember to wear your comfiest shoes and sign up for a walking or boat tour to see more of this great city. Then hit some of the highlights on your own that were missed on the tours. You will not be disappointed spending the weekend in Chicago with our two days itinerary.

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