The Chirp Flock: Spotlight on Chicago

We’re talking with the Chirp team in six cities about what they think makes their city such a special place to live and work. Last but not least…Chicago, Illinois!

Millennium Park. Chicago was designed with 26 miles of uninterrupted lakefront biking and walking paths. Residents flock to the lakefront and city parks after a nasty winter, and Millennium Park is the Park District’s crown jewel. While most visitors know to go and snap selfies at the Cloud Gate, or “Bean,” Millennium Park offers so much more. The sprawling park right in the city’s center has architectural features like the massive metallic Pritzker Pavillion, a winding Serpentine Bridge, and family-friendly attractions like a climbing wall, skating ribbon, and the bigger-than-life Maggie Daley Park playground. 

Superdawg. Chicago is famous for its deep-dish pizza, but for a unique local experience, check out Superdawg, a historic 1940’s drive-in.  Order up their Superdawg or Supercheesie with a pickled green tomato and wash it down with a Supershake. Car hops deliver your food on trays that hang from your window Flintstone-style. The retro black and white facade is lit up in neon and topped with giant statues of founders Maurie and Flaurie as hotdogs. If you’re still hungry, our Chicago Chirpies recommend Delightful Pastries for paczkis, a Polish donut, or Bamba Bar for bombalinos, an Italian donut. 

Superdawg is a Chicago classic and a culinary time machine!”

Jane Deitrich, Director of Strategy and Innovation

Pop-Up Museums. Big city cultural pop-up experiences are everywhere right now, and Chicago is no exception. Instead of going to a major museum like The Art Institute or MCA, you can book tickets to unique art experiences that will only be in town for a few months like the Van Gogh experience, WNDR museum, and Womanish exhibit.

“Embrace it. The cold won’t kill you…probably.”

Winter. Every Chicagoan you meet will have some winter war stories. And while the Chicago winters may be brutal, they are part of a beloved four-season climate the warmer cities sometimes envy! While other cities shut down every time a few flakes fall, Chicago remains fully functional, even when inches of snow turn to feet.  

Transportation. Lots of Chicagoans choose to live vehicle-free, using the CTA trains and buses or simply walking or riding bikes, even in the cold winter months. And for travelling Chirpies, Chicago has two major airports and a central location that puts the whole country in reach for quick-turn projects. 

I can walk to three forms of transportation within 5-10 minutes from my doorstep.”

With new Chirpies hatching in cities nationwide, we might be firing up the Chirp spotlight again before you know it!