One Flight Wonder - Chicago, Illinois

One Flight Wonder - Chicago, Illinois : This spring, head to the Windy City for all-new performances, one-of-a-kind dining experiences, and modern architecture
Share this

Chicago, IL, is considered one of the world’s best cities, ranked among Beijing, Prague, and London. Alongside its infrastructure, Chicago has quite a few well-known attractions that put it on the map, like Chicago-style deep dish pizza and the Cloud Gate sculpture, better known as “The Bean.” But there’s lots more to explore, from historic architecture, food, and drink, to outdoor adventures, performing arts shows and beyond. 

Skyline Highs
Part of what makes Chicago such a global icon is the architecture that decorates the city. In 1871, a 24-hour blaze left the city decimated and hundreds dead. Nearly a third of the residents lost their homes. The loss prompted the Great Rebuilding, an era of construction that ushered in an urban renaissance of big business and architectural innovation. Greats like Frank Lloyd Wright, Daniel Burnham, Ludwig Mies van der Rohe, and more shaped the framework of Chicago.

When visiting, don’t miss the chance to observe the movement’s results by taking an architectural cruise down the Chicago River. Offered by the Chicago Architecture Center for more than 20 years, you’ll learn about more than 50 buildings from docent volunteers over the course of 90 minutes. Boating not your thing? The Center offers walking, train, and bus tours as well. 

Follow the River
There are many launch points for human-powered boats along the river—kayaks are one of the most popular methods of transportation, and many local companies like Urban Kayaks offer both tours and rental options for those looking to paddle. A favorite choice is their Happy Hour Tour. Led by an experienced guide, kayakers of all levels venture down the Chicago River and conclude the trip with a free drink from a local restaurant.

Along the river, you’ll find the Lakefront Trail and the Chicago Riverwalk, a 1.25 mile path that features a variety of businesses and eateries. One standout restaurant is Beat Kitchen, which offers up an eclectic blend of menu options from tacos and pizzas to salads and sandwiches. Grab a glass from City Winery, an expansive and upscale locale serving up Mediterranean food that begs to be paired with a glass of wine. Reservations are a must. 

After a bite, head to the Community Marketplace for some shopping. After its grand opening in 2019, the marketplace has created a space for women- and minority-owned businesses to peddle their wares. 
Curtain Call
The city of Chicago is often selected to host pre-Broadway premieres of upcoming performances; making its debut this spring at the Cadillac Palace Theater is Death Becomes Her, a musical comedy based on the 1992 film of the same name. Starring Megan Hilty, who’s best known for her performances as Glinda in Wicked and Doralee Rhodes in 9 to 5: The Musical, it’s sure to be an unforgettable performance, especially since nabbing a seat means you’d be one of the first to see the live show. Death Becomes Her runs from April 30 to June 2; be sure to buy your tickets early. 

Coming to the Windy City on May 18 is Wanda Sykes’s Please & Thank You tour at the landmark Chicago Theater. Sykes is an Emmy-winning comedian and actress, writer, and producer that has been in show business for more than 20 years, with pictures like Breaking News in Yuba County and Bad Moms on her résumé. 

Flight: American Airlines and United both offer flights to Chicago O’Hare International Airport (ORD) from Asheville Regional Airport (AVL). The trip lasts approximately 2 hours each way by plane.

Local Transport: The city is extremely pedestrian-friendly, and their railway system, the “L” train, is the second largest in the country. Ridesharing, biking, and water taxis are also viable methods of transportation. 
Chicago At a Glance
Population: 2,608,425
Average Spring Temp: 50°-70°
Resources: Choose Chicago is the city’s official destination marketing site. Visit choosechicago.com to learn more about upcoming events, popular destinations, and more.