Visiting Colleges in Chicago? Consider a Weekend in the Windy City

Chicago is my kind of town. From the breathtaking architecture, to the fabulous shopping on the Magnificent Mile, to their infamous Chicago pizza, the city offers visitors a plethora of activities for a weekend visit. If you’re visiting any of the colleges in the Chicago area, why pass up an opportunity to spend the weekend in the Windy City? Visit on Friday or Monday and spend the weekend exploring a city that Old Blue Eyes called, “my kind of town”!

The shopping

Chicago’s infamous Magnificent Mile offers the ultimate shopping experience. From upscale stores like Tiffany & Co. to iconic department and specialty shops, the mile of shops have something for everyone. You can spend an afternoon window shopping or even buy some Chicago souvenirs at any number of shops while browsing. My daughter has made it a goal to take her photo in front of every Tiffany & Co. jewelry store, inspired by the movie “Breakfast at Tiffanys”. Chicago offered an opportunity to do just that.

The architecture

Chicago’s architecture is second to none. The birthplace of the first skyscraper in 1885, it is the home to 1,264 high rises and the Willis Tower (formerly the Sears Tower), once the tallest building in the world. These buildings are best viewed on the Chicago Architecture River Tour where you can view over 40 buildings narrated by a guide while cruising down the river. There’s something about viewing the buildings on the 75 minute cruise from river level as they tower over you that is breathtakingly beautiful.

Make a visit to the Sears Tower, offering you a bird’s eye view of the city in a unique way. The observation deck at the top of the building gives spectators a view of the city and the surrounding area. To enhance the experience, visitors can take their turn standing on an entirely glass box hanging outside the building on the top level. You can even take your own photo or have one professionally taken while standing on the glass enclosure.

The Tribune Tower building has the unique distinction of housing 149 rocks from other famous feats of architecture around the world, such as: The Alamo, The World Trade Center, The Berlin Wall and Westminster Abbey to name a few.


Enjoying a meal at one of Chicago's restaurants along the Magnificent Mile.


A view of Chicago architecture during the river cruise.


Tiffany and Company on the Magnificent Mile.


A view of the city from the Chicago Navy Yard.


The famous Chicago Bean sculpture.


Standing on the glass enclosure of the Sears Tower.


Aerial view of Chicago from the Sears Tower.

The food

Who hasn’t heard of the famous Chicago pizza or the widely recognized Chicago hot dog? You can’t visit Chicago without trying both of these treats. Giordano’s stuffed deep dish pizza will leave you craving for more. The good news—you can order online and enjoy it anytime! For Chicago dogs, check out this list of the 10 Best Chicago Style Hot Dogs. From fine cuisine at restaurants owned and run by famous chefs to these favorites, Chicago offers some of the best food in the country.

The arts

Chicago is a mecca for outdoor artists. Sculptures line the Magnificent Mile along the park, the most famous one being the Chicago Bean. It’s a bean-shaped mirrored sculpture offering visitors an opportunity to take unique photographs of themselves with the city mirrored in the sculpture. It is a well trafficked photo spot for tourists. You should also spend a few hours in the Art Institute of Chicago viewing their collections of sculptures, paintings, photographs and more.

The history

Chicago has a colorful history. Visitors can learn about the Chicago fire and visit the many ethnic neighborhoods throughout the city. Take the big red bus tour that allows you to get off and on at your leisure. For an added treat, take some walking tours around the old neighborhoods and admire houses from the 19th century, some having survived the Chicago fire.

The outdoors

If you visit Chicago in the spring or summer, there are ample outdoor activities. Eat at a sidewalk café outdoors, take a walk or jog on the path along Lake Michigan, visit the Navy Yard and ride the Ferris wheel with views of the city, or have a picnic in any number of beautiful parks while enjoying the free outdoor entertainment.

Spending a weekend in Chicago will only whet your appetite for another visit. Chicago is a city of rich history, splendid architecture, cultural offerings and shopping and dining along the Magnificent Mile.

For more information about the many tourist attractions in Chicago, click here for the Fodors' Guide.


Author: Suzanne Shaffer

Suzanne Shaffer advises parents and students in the college admissions process and the importance of early college preparation at She is excited to share her knowledge with the readers of Smart College Visit.

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