Home Travel How to Spend a Weekend in Chicago?
Weekend in Chicago

How to Spend a Weekend in Chicago?

by Ruhia

A trip to Chicago is a must for any traveler. It’s no wonder the city draws in millions of tourists from around the world every year.

Chicago is filled with unique attractions. But with 77 different neighborhoods and more than 300 parks, seeing them all in just one visit is impossible. This is especially true if you’re only spending one weekend in Chicago.

In this guide, we’ll tell you how to maximize your time so you can get the most out of your trip to Chicago. Here are some ways to spend your weekend in the Windy City.

The Riverwalk

No trip to Chicago is complete without a stroll along the river. The Chicago River connected to Lake Michigan winds its way through the downtown area. 

Tourists who take the Riverwalk will gain access to a wide variety of attractions. It’s a great way to visit authentic Chicago restaurants and bars. 

While walking along the river, tourists will have the opportunity to view the city’s world-famous buildings. Chicago is now referred to as the “City of Architecture”, with breathtaking skyscrapers built by some of the world’s most celebrated architects.

Architect enthusiasts can take walking, biking, or kayak tours to hear more about the buildings.

The Willis Tower Skydeck

Visit Chicago from the highest observation deck in America, the Willis Tower Skydeck. 

Tourists pay a fee to ride the elevators to the 103rd floor where they will have incomparable views of the city skyline. But for an additional fee, you can visit the Ledge.

The Ledge is a glass enclosure that extends from the Willis Tower, making it feel as though you are standing 1,400 feet above the city in mid-air.

To save time while spending your weekend in Chicago, purchase tickets in advance.

Millenium Park 

You will find lots of things to do in Chicago tucked away in Millenium Park. The park is located at the end of the Riverwalk where the Chicago River meets Lake Michigan.

This is a spectacular place to view the Chicago skyline or spend an entire day exploring Chicago attractions. 

Crown Fountain

Among those attractions is Crown Fountain.

Crown Fountain displays the faces of everyday Chicago residents on two large LED screens. The mouths of the faces open every five minutes. At that time, water pours out like a fountain, forming a shallow reflective pool of water on the ground.

Crown Fountain is a great place to have some fun and cool down on a hot day. 

Cloud Gate

Millenium Park is also home to Cloud Gate—commonly referred to as ‘The Bean’. The kidney-shaped chrome art sculpture has become one of the most photographed locations in the city.

The structure stands 30 feet tall and is roughly 60 feet long.

Its chrome presents a reflective surface making it a great spot for Instagram photos. And while it typically draws a large crowd, there is plenty of room at the sculpture for everyone to enjoy it.

Maggie Daley Park

Maggie Daley Park is located at the edge of Millenium Park. If you visit Chicago with children, this is a must-see.

There are five playgrounds at the location. Each playground is built to accommodate different ages and abilities. 

The park also offers a rock climbing wall, large tube slides, a mini-golf course, and a splash pad to help cool little ones down.

And no trip to Maggie Daley Park is complete without ice cream. Treat yourself and your kids to an afternoon of fun in this gorgeous area.

Art Institute of Chicago

Before you depart Millenium Park, consider a visit to the Art Institute of Chicago. The museum is one of the largest in North America.

For that reason, this stop may require a bit of time. If you’re only visiting for the weekend, you may not have enough time to truly enjoy it. But if you’re an art enthusiast, it’s worth the trip!

The museum houses famous pieces from Van Gogh, Dali, Warhol, Seurat, and Picasso. 

If you do choose to visit here, make sure to buy the fast pass tickets to save time.

Midnight Cruise

If you’re spending your weekend with a group, avoid the crowds and view the night lights from the comfort of a private yacht. Adeline’s Sea Moose offers private yacht rentals and a truly unforgettable experience.

Watch the city lights reflect off the water with views of the illuminated Centennial (Ferris) Wheel and skyline on a luxurious midnight cruise.

This experience is perfect for those celebrating milestones like bachelorettes or bachelor parties. It also provides the perfect setting for a romantic proposal.

Magnificent Mile

Spend day two on the Magnificent Mile—13 blocks in Downtown Chicago that contain upscale shopping and popular Chicago restaurants. 

Here you will find several Chicago attractions, including the John Hancock Building. The 100-story skyscraper is home to Chicago’s famous 360 and TILT attractions.

The Magnificent Mile is also home to the Chicago Avenue Pumping Station and the Chicago Water Tower, two of the only structures that survived the Great Chicago Fire in 1871.

Although this walk can be completed quickly, it’s a great opportunity to try a Chicago hot dog or find a deep-dish pizza.

Wrigley Field

No trip to Chicago would be complete without a stop at Wrigley Field. This Major League Baseball park is the second-oldest ballpark in the country. 

Whether you’re able to watch the Chicago Cubs play, or just take a tour of the stadium, this is worth doing. 

And don’t forget to have a pint at Murphy’s Bleachers on your way out for the full Wrigley Field experience.

Make the Most of Your Weekend in Chicago

Chicago is a city packed full of attractions. Experts recommend visiting the area for three to five days to fully experience it. But if you prioritize your time, you can make the most out of a weekend in Chicago.

If you’re only spending two days in the Windy City, you’re probably wondering how to maximize your time. By visiting the Chicago attractions discussed in this guide, you will make your experience unforgettable!

Visit the travel section of our site for more tips like this.

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