Walk a Mile on 53rd Street

City Cast Chicago is the easiest way to stay updated on what's happening in Chicago. Their daily podcast and newsletter covers local news, gives the best life hacks, and curates recommended events. For more Chicago insider information visit chicago.citycast.fm.

I’ve spent half of my adult years living in Hyde Park. Whether performing, shopping, or hanging with friends, I have made lifelong memories exploring the neighborhood. Here's where I'd walk a mile.

How it Works

1. 1.
   We pick an area within city limits.
2. 2.
   We pick a mile to walk (along 53rd Street between Hyde Park Boulevard and Woodlawn Avenue).
3. 3.
   We recommend ~10 things to do in that mile.

How to Get There

• No. 6 bus to S. Hyde Park
• No. 28 bus to Lake Park
• Metra drop off at Lake Park
• Divvy at Lake Park and 53rd Street

What to Do

Harold Washington Park, tucked between DuSable Lake Shore Drive and Hyde Park Boulevard, is nice for a walk or watching the fellas play chess in the park.

Grab a drink from Sip & Savor. As a non-coffee drinker, I recommend the smoothies and refreshers! While I finish my strawberry dragon fruit refresher, I browse the racks at Designs by Anna J.

Heading west on 53rd Street, you can meet friends for short ribs and rum punch at 14 Parish or sip on a beer at Falcon Inn across the street. Fun fact: You can order a slice from Cholie’s next door from inside the Falcon Inn.

The Promontory always has great concerts and shows. I've hosted Karaoke Storytellers, Grown Folks Stories, and The Moth at the venue.

Miss me on stage? You can definitely find me spending bread on books, candles, paintings, Kangols, and more at The Silver Room.

At this point, the options for food are all around you. More than 50 restaurants are located within five blocks, and famed Chef Erick Williams will soon be responsible for three of them. I like to grab a berry smoothie from Bonne Sante and a butter cookie from Strugglebeard.

Harper Court is home to great concerts during the spring and summer, but the shops are buzzing all year long. I love checking out the great art at Recycled Modern, custom jewelry at Surri Design, and the gym shoes at Sneakerville.

Harper Theater was recently renovated and plays blockbusters and hosts film festivals throughout the year.

I love to look through the crates at Hyde Park Records. I left with two Teddy Pendergrass albums during this visit!

I finish out with a burger from Small Cheval and skip back up to Kilwins to grab a taffy apple for the Metra ride home!

Check out more Chicago insider information with City Cast Chicago. Their daily newsletter and podcast are the easiest way to stay up-to-date on Chicago. For life hacks, daily event recommendations, and local news visit chicago.citycast.fm.