The first stop of the night is Leavitt Street Inn. It’s located at the bend of an otherwise sleepy residential street that’s cut off by the highway. If you weren’t specifically looking for this place, you’d likely never come across it on your own.
But now that you’re here, what you’ll find on this corner lot is a big brick patio, laid back casual vibes, drinks, and bar food to start the night.
Started by husband and wife team, Teddy Harris and Sarah Brick, this bar is only here by sheer force of will.
Opened in 2020, it was six years of renovations and navigating Chicago’s licensing requirements before they opened their doors. Lucky for us they didn’t give up.
The reason we’re starting off here is to kick off the night with at least one good decision, and that’s to get some food in your system before embarking on this corner bar crawl. Afterwards, you can make as many bad decisions as you want.
Leavitt Street Inn is the only place you’re visiting tonight that has a full service kitchen. Think elevated bar food like a ricotta honey dip, fancy grilled cheese and burgers.
When the weather’s warm, their patio is a destination. During the day and early evening hours, you’ve got a mix of families with kids, young couples, and groups catching the latest sports ball game on TV.
With nothing but homes around and everybody hanging outside around picnic tables, it feels like a neighborhood block party.
If you’d rather pull up a seat inside, you’ll find this 75-seat space. 
The Charleston bar is up next and it’s less than a 10 minute walk to get there. Quite the opposite from Leavitt Street Inn, this is a small, dimly lit cocktail bar with no TVs and soft red lighting setting a more intimate mood.
If you squint hard enough, you can still see the space’s dive bar roots concealed behind some of the more polished up decor.
For a long time, this was a charming dive, but it went through a bit of a glow up in 2010 and fully embraced the cocktail bar theme while still keeping things casual. 
The last spot of the night is just a few blocks from Charleston. We’re at Gallery Cabaret which is more like refuge for artists and performers that also happens to have a dive bar thrown into the mix.
You can find a live performance every single night of the week.
Depending on the day, you might find a big brass band, a comedy open mic, or like we saw a few months ago, it was where the Logan Square UFO club met up to share stories of sightings and personal experiences.
In terms of the crowd, some nights can be pretty chill and other nights can be shoulder to shoulder at times.
What seems consistent, however, is the $2 can of Hams which seems to be the most inflation resistant product ever made. Can some economist please look into this? Do the people behind Hams have the solution to our economic woes? 