Getaway to Chicago: The Paris of the Prairie

With the release of his poem “Chicago” in 1916, Carl Sandburg put Chicago squarely on the map. The poem celebrates the proud working class residents of Chicago and the impact the city had on the growth of this country. The poem also vaulted Sandburg to celebrity status in Chicago.

Chicago is commonly known as the “Windy City,” and most folks assume the nickname refers to the epic winds that blow off Lake Michigan and whistle through the cavernous skyscraper-lined city streets. But, in fact, the moniker was a result of the many brash and long-winded politicians of yesteryear. Chicago is also lesser-known as the “Paris of the Prairie,” as city planners, a century ago, had great plans to design the city similar to Paris. However, when the Great Depression hit, much of the plan was abandoned.   

Chicago itself is a study in contrasts—a metropolitan oasis nestled between the aquamarine beauty of Lake Michigan and the corn fields of the Midwestern plains. Chicago is an amazing city, truly a world unto itself. 


Chicago is designed for getaways, with multiple ways to get there. From Rochester, you can drive the 350 miles and arrive in about six hours, or you can fly or ride the train. 

American Airlines offers direct service to Chicago from Rochester, and with a flight time of just over an hour you can arrive fresh and ready to take in the sights. Depending on when you go to Chicago, roundtrip tickets typically cost approximately $275-$300 per person. 

Board the Amtrak train in Winona to view the countryside and small towns along the journey; however, switching and sharing tracks with freight trains may cause delays. The National Park Service Trails & Rails program provides passengers activities to connect with historic and natural resources seen between Winona and Chicago. You can bring food and beverages or purchase from the train cafe. 


Marcy Baker, owner of Adler’s Rochester Travel, offers some suggestions for sights to see and things to do in Chicago, depending on the type of getaway you want to plan. 

Girlfriends getaway: Go shopping on Magnificent Mile, view a comedy show, visit one of the many hotels that feature deluxe spa services or explore the city with a bicycle rental.

Romantic getaway: Visit a spa, enjoy the plethora of dining options, walk the lakefront trail along Lake Michigan, attend a free concert at Millennium Park or see a headliner at the iconic Chicago Theatre.

Family getaway: Visit “The Bean” at Millennium Park, watch a Cubs game at Wrigley Field, tour 360 Chicago (formerly the John Hancock Observatory), visit the Willis Tower SkyDeck or explore the Art Institute of Chicago, Field Museum and Shedd Aquarium.

Other popular attractions include Navy Pier, Museum of Science and Industry, Adler Planetarium and Grant Park, including a visit to Buckingham Fountain. Because Chicago is well-known for its daring and eclectic architecture, a walking tour is not to be missed.


Chicago is a very popular destination for vacations because so many of the attractions are near one another, and there’s truly something for everyone. Plus, Chicago is very visitor friendly.

Amy Brase, of Oronoco, says of her visit to Chicago last August, “Every family should visit Chicago at least once. From the towering skyscrapers of the city skyline to the clever sculptures at Millennium Park and the endless attractions under the night lights at Navy Pier, our kids were enamored with the Windy City. One of their favorite attractions was the Museum of Science and Industry. We also celebrated a birthday at the flagship American Girl store and were thrilled with our experience at the American Girl Cafe. Overall, the city was much more kid-friendly than we guessed it would be.” 

If you’re looking for a fun getaway this summer or fall, Chicago’s non-stop attractions and entertainment are for everyone. It’s perfect for a getaway with the family, girlfriends or that special someone.

Cindy Mennenga, owner of Straight-Talk Wellness, is a health coach and freelance writer based in Rochester.