We’re midway through August. School is starting next week (!), and maybe you feel like summertime Chi is winding down. But not so fast — on today’s podcast, we’re describing our perfect Chicago Summer Day.
Emmi’s Perfect Chicago Day
How do you start your morning?
Wake up late, throw on some cowboy boots — I’ll be on my feet all day — and walk East down Armitage Avenue. Stop at Katherine Anne Confections for coffee and keep walking till Red Hot Ranch.
What’s for lunch?
At Red Hot Ranch, I go for the Chicago-style cheeseburger with depression dog toppings.
What are you doing in the afternoon?
I’ll get some shopping done in Wicker Park — many feature on our Chicago vintage shopping guide! There’s also a new place, Vintage House, where I just scored a Diesel cap. After that, I’ll take the Armitage bus to the zoo real quick — just to say hi to the gorillas.
What’s for dinner?
Wieners Circle, naturally. Since I did the burger at Red Hot, I’ll have a char dog here.
How are you spending your evening?
After dinner, I’ll head to Bobby and Chunghwa’s place. You don’t know Bobby and Chunghwa, but rest assured, their place is THE SPOT to pregame. Also, congrats on your engagement, guys!
Any late-night shenanigans?
Smart Bar is a solid option. I’ll usually dance or gossip in the hazy corner till someone agrees to walk to Belmont Harbor with me.
Belmont Harbor is my favorite place to watch the sun rise and to float. I recently did that with my old college roommate, staying up until we inevitably Googled, “What time does Red Hot Ranch open?”
Jacoby’s Perfect Chicago Day
How do you start your morning?
Divvy e-bike to Kenwood. Take the scenic route past Chinatown square and Bronzeville Arts District to Carver 47 to get a breakfast sammie and a smoothie before playing pickleball at Gwendolyn Brooks Park. Divvy back up the lake past Oakwood and 31st Street beaches.
What are you doing in the afternoon?
Walking Milwaukee from Division to California — friends probably have a pop-up around here. Maybe hit Una Mae, Round Two, Myopic Books, Mindy's Bakery, or Saint Alfred.
What’s for lunch?
Tacotlan’s shrimp and birria tacos or the burger and wings at Mott St.
How are you spending your evening?
Promontory Point kickback.
What’s for dinner?
Monteverde in West Loop.
Any late-night shenanigans?
Expat — get there before 10:45 p.m. Gino and Marty's for cocktails. Chi Cafe or Harold’s for late-night grub.
📍 Wanna see these spots on a map? Check out our list on Overlook.
