Jan 27, 2023 - Things to Do

Former WBEZ host Alison Cuddy's Best Day Ever in Chicago

Photo of a woman in a swim cap getting ready to swim in icy waters

Alison Cuddy gets ready for her morning swim. Photo: Courtesy of Alison Cuddy.

When former WBEZ host Alison Cuddy isn't finding joy in a frigid swim, she's out exploring Chicago.

  • So we asked her to curate her perfect day in the city.

🏊‍♀️ Morning activity: "Sunrise swim in Lake Michigan at the Point, of course." 🍳 Breakfast: "Plein Air for their omelet, which is so delicious, and they have these great side salads."

👗 Midday activity: "I will head to one of Chicago's many thrift stores [in various neighborhoods] and spend a happy hour there digging in the racks."

🌮 Lunch: "Tacos! I don't have a favorite place because the whole point — just like thrifting — is exploring, so I go to whatever taco place I noticed on the way there."

  • "There is one on Whipple and 25th in Little Village, La Chaparrita, that is so good. I get tacos al pastor, and you always have to try the house salsa."
  • "I go with a friend, and we are slowly eating our way through Chicago's amazing taco spots."

ğŸž Dinner: "To round out the day, I'd go to Truth Be Told Tavern in Hyde Park for smoked fish on toast."

  • Or the Strings Ramen in Hyde Park, where I always eat way, way too much!"

ğŸŽ¬ Evening activity: "A movie at Doc Films or the Siskel Film Center — they're both fantastic, especially in the winter."

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