Your first stop is off the Francisco Brown Line station. We’re at First Slice Cafe in Chicago’s Ravenswoond Manor neighborhood, a quiet residential district full of historic bungalows and homes with boat docks connected to the Chicago River.
When you exit the train, the first thing you might notice are the tracks are at street level. The Franciso Station sits along a one-mile stretch of the Brown Line, the only part of the “L,” that isn’t elevated.
First Slice Cafe awaits you around the corner. This is a coffee and pie shop with an assortment of quiches and pies. It’s got a super fan following in Chicago, and if you look up any of those “best pie in Chicago” lists, First Slice will most certainly be on it. They’ve also been doing this since 2005 and that means something to be on top of the pie game for so long.
One other thing to note about this place is that First Slice is actually a non-profit kitchen whose proceeds go towards addressing the immediate need of the hungry in Chicago. So if you’re eating that second or third slice of pie, that just goes to show how good of a person you are.
After First Slice, get on the train and go one stop over to the Rockwell Station. Once you’re here you’ll find yourself in a tiny business district in the middle of this residential neighborhood. With the train tracks passing through, it feels a bit like small town America.
Around the corner, you’ll find Rockwell Bottle Shop and Coffee. It’s a casual neighborhood hangout spot where you’ll find things things like drip coffee, tea, pastries…and rare sake and Japanese whisky.
Fridges on the right have an assortment of drink selections along with cheese and other beer snacks to pair with it.
Head towards the back and you’ll find what’s essentially a living room where you can hang out with your drinks and snacks.
This is the resident dog that’s here to make sure you have a good time.
Get back on the Brown Line and take it two more stops to the Montrose station. From there, you’ll walk a few blocks to a nondescript block that’s easy to overlook. Hidden in plain sight is Ravenswood Used Books, the type of bookstore that most book lovers dream of opening up one day. 
Right as you walk in you’ll be directed to a few different narrow passages filled with books stacked from floor to ceiling.
While there isn’t a lot of space in the store, the shelves create a meandering maze, and at certain points you’ll stumble upon these coves where you can post up for a bit.
There are category labels strewn throughout to help you navigate the used book selections. If you’re looking for something specific, the folks up front seem to have encyclopedic knowledge of their inventory and where things are shelved.
After you finish you here, the last two places are set up as choose-your-own-adventure options. The first is a dive bar/bowling alley and the second option is a movie at a 100+ year old theater.
Timber Lanes is right off the Irving Park Brown Line station — one stop from Ravenswood Used Books. If you’re looking for dive bar vibes, wood paneled walls, and paper-scored bowling, this this is your spot.
Here are a few things to keep in mind before you go.
– Cash Only
– Lanes are $$15/25 per hour or $2.50/3.00 per game
– Leagues take up big chunks of time so check their open bowling schedule before going
– BYOF
– They are open until 2am everyday and 3am on Saturday if you’re looking for some real late night bowling action.
Here’s a fun fact about Timber Lanes. There’s a hidden panel next to the lane furthest to the left. It leads to a tunnel that runs underneath the building and out to Wolcott avenue. While the actual entrance to the street has since been sealed, during prohibition, this was where booze was delivered to the building in the cover of night.
If bowling isn’t in the cards, the other option is to jump on the Brown Line and head towards the Western Station where you’ll catch a flick at Davis Theater.
This is a local institution that’s over 100 years old. It started out playing vaudeville and silent films in 1918, and during the 1950’s, they started playing German language films to serve the local German immigrant community.
Today, this small local movie theater is still going strong (after a massive remodel in 2016), and shows first-run movies in their small three theater venue. If you’re looking to avoid a massive AMC mega-complex, then this local theater works wonders and is affordable to boot. 