City Cast

Get to Know the Loop

Sidney Madden
Sidney Madden
Posted on November 22, 2022   |   Updated on June 28
Bike riders riding along State Street at night

A bike ride down State Street in September 2021. (Jacoby Cochran / City Cast Chicago)

The Loop might not be what you think of as a typical Chicago neighborhood. Full of skyscrapers, museums, and shows, the city’s center can feel like a transient place where workers and tourists move in and out, especially this time of the year.

But an increasing number of residents call the Loop home. I did for most of my life.

Whether you’re headed to the Thanksgiving Parade or Christkindlmarket, here are some other spots to check out.

Something to eat
: Cafecito is one of the more affordable options in the area, serving sandwiches, platters, coffee, and cocktails. The Cuban cafe has breakfast and vegan menus! I’m partial to a jamon pressed sammie.

Something to see
: Harold Washington Library’s Winter Garden is a stunning atrium with greenery and natural light on the ninth floor of the building. It’s a great spot to work or study (hi free Wi-Fi) or have a little quiet from the business of downtown. While visiting, imagine the restaurant that once occupied the space or how much it’d cost to book a wedding there.

Something to do: Explore the Pedway, an underground network connecting 40 blocks of the city’s central business district — and a great way to get from point A to B during extreme weather.

Something on the bucket list
: Enter the Broadway in Chicago lottery to see “Wicked,” “The Lion King,” or “The Twenty-Sided Tavern” for $25. Persistence is key: I won the “Hamilton” lottery after entering every day for an entire summer.

Something for Insta
: Get stopped by What Was Breakfast, a popular photoblog account that asks Chicagoans what they had for breakfast.

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