We’re starting at Hoosier Mama Pie, a small diner in West Town where you have your pick of sweet and savory pies. It has farmhouse wood paneling along the walls and splashes of soft pastels everywhere. It feels like an homage to the classic small-town 1950s diner.
It’s a casual order-at-the-counter spot, making it a bit easier to navigate with kids. They’ve got a variety of sweet and savory pies behind a glass display to help everyone choose.
Sit at one of the two cozy bay window booths that protrude out towards the sidewalk. It feels like dining in a small globe, immersing you in the energy of the surrounding streetscape.
For young children, it offers a constant new topic of conversation as buses, trucks, and people pass by. 
As far as food goes, everything here is made by hand. In fact, from where you sit, you can see the flour-covered workers tirelessly rolling out dough and loading batches of pies into the oven.
And out from the kitchen comes something like this. On the sweet side, they’ve got every classic pie you could want, like Apple and Banana Cream pies. But they also have a rotating mix of more non-conventional stuff like a Fruity Pebbles pie and Passion Fruit Meringue.
On the savory side, their Chicken Pot Pie is the epitome of comfort food. It’s got the right amount of flakiness to balance out a rich filling brimming with tender chunks of chicken, potatoes, and vegetables. It’s particularly great if you’ve been trying to sneak more veggies into your kid’s meal. 
If you know how to make a damn good pie, then you know how to make a damn good biscuit. Hoosier Mama makes an excellent buttery biscuit sandwich with thick bacon, a thick egg loaf, and gooey cheddar cheese.
Here’s one person’s in-depth review
The Chicago Public Library system deserves all the love in the world. It’s a godsend when looking for ways to keep your little ones busy and away from screens.
The West Town Branch is right across from Hoosier Mama Pie, where you’re headed next. It’s in the Goldblatt Building, which you can see from the booth inside Hoosier Mama.
As you enter, there’s a kid’s section with an entire open play area and things for kids to explore. It’s a solid hour of self-play entertainment.
While your kid is playing, here are some other free programming things to consider that are available to everyone.
– Once a month on Saturdays, the West Town Branch hosts Curious Kids Club, where kids partake in instructor-led projects like building a kaleidoscope or using Cubelets to build a robot.
– Each library has Kids Museum Passports available to check out. There are passports for nearly every museum in Chicago, and if you can snag one, it grants your household (two adults and at least one kid under 18) free entry to the museum designated on the pass.
Passes are first come, first served, so getting one can sometimes be tricky. You can ask a librarian which passes are available or search on the Chicago library website. Type in ‘Kids Museum Passport’ in the website search bar, and you’ll see various passes to different museums. Click on one, and it will list the available passes by branch.
