You know how sometimes we don’t explore our own backyards? It occurred to me not long ago that I’ve written a number of literary explorations around the country and have NEVER highlighted Chicago. Despite the pandemic I rectified that and managed to visit a lot of bookstores, especially over the summer when things were a bit more cheerful.
Support the community and take your own tour of Chicago via books with my guide of the best independent and local bookstores below!
The Looking Glass – 823 S Oak Park Ave, Oak Park, IL
I love this little used bookstore. They have an eclectic mix of books and the shop is relatively small. But they have the BEST gifts! From blind books to journals to unique cards and knick-knacks – if you have a literary friend you are bound to find something cute for them here.
Roscoe Books – 2142 W. Roscoe Street, Chicago
You know those bookstores that just get you? They have the vibe, the beauty, and, even better, the inventory of books that makes you salivate? Roscoe Books is my happy place. They have so many great, new titles and lots of contemporary romance. Cute set up with the perfect mixture of lots of titles and room to stand. Win/win.
Volumes Bookcafe – 1474 N Milwaukee Ave, Chicago


SO cute. I unfortunately went during a pandemic so I didn’t get to try the café part of the book café, but I know I would love it. This place is set up so perfectly with a great little selection of stories and what looked like an excellent place to sit and relax with a hot beverage. I can’t wait to check it out in full force in the future.
Pro Tip – there is a sister location, Volumes Bookstore on Michigan Ave!
Bookends & Beginnings – 1712 Sherman Ave, Evanston


Oooh man – guys, this place is so worth the trek up to Evanston. You’re in the heart of Northwestern but you disappear somewhere else entirely for this store. It’s tucked away in an alley (SO adorable) and it’s so much bigger than it looks. Crazy good selection and has that tilty, old school book store feel. Love.
Myopic Books, 1564 N Milwaukee Ave, Chicago


Myopic is an establishment in Chicago. It’s your classic DGAF kind of used bookstore. Plenty of worn edges, musty corners, and books no one has touched in years. I also have a particular fondness for bookstores with stairs. This place has bizarre and wonderful half-levels that make you feel like an explorer.
Fun tip – it’s only a stones throw away from Volumes Bookcafe and Jeni’s Ice Cream… so you really never need to leave this block of the city. Ever. Just move in.
The Book Table – 1045 Lake Street, Oak Park
Back to my stomping grounds in Oak Park, this is a great new book store. It’s generously sized (they recently expanded!) so you know you can go in and get what you need. Tons of helpful staff and tips on what to choose next.
Madison Street Books, 1127 W Madison St, Chicago
This is such a lovely spot! This poor bookshop has a grand opening just two days before the pandemic March shelter-in-place hit so they could use some love – and do they deserve it! The staff is friendly and the kids section is adorable. I highly recommend!
Semicolon – 515 N. Halsted Street, Chicago
Black woman owned – so that right there makes it a winner. It’s not really open for in-store browsing because pandemic but they do lots of community support and it’s a fantastic stop. Definitely hit this one up!
The Armadillo’s Pillow – 6753 N Sheridan Rd, Chicago


Mad props for an amazing name. This place is soooo quirky. Used booked, piles everywhere, plenty of space to get lost. What more to do need? Oh, yeah, an entire afternoon to dawdle.
Unabridged Bookstore – 3251 N Broadway, Chicago
Love this place. It’s a great space and has some amazing travel and LGBTQ+ sections. Excellent selection (all new) with up to date trends. Plenty of room to linger.
Sandmeyer’s Bookstore – 714 S Dearborn St, Chicago
This is a lovely little spot to hit up if you are exploring downtown Chicago – just a few short blocks away from Willis Tower. With bright, wide shelves and all new books it’s a great spot to find some of the “top hits”. Add a star for the creakiest floors ever (and I mean that in the BEST way possible).
Open Books – 651 W. Lake Street, Chicago
(there are other locations in the city too!)


This book store is packed with books and yet the tall ceilings make it feel open (ha) and lovely. Great initiatives and events happen here too. It’s an easy place to get lost in.
Centuries & Sleuths – 7419 Madison St, Forest Park
Who doesn’t love a good themed bookstore?! Mysteries and histories are the game here and while the store itself doesn’t have a ton of browsing potential, they have a fun table of blind books and the staff will help you with anything you could desire. Madison Street in Forest Park is a delightful area to walk around (check out Twisted Cookie or The Brown Cow for some sweet treats)!
Book Bin – 1151 Church St Northbrook, IL
This is a fun little stop off! Great selection with some good gifts (I found a great puzzle of the Chicago skyline!) Super friendly and perfect for a visit if you’re in in those NW suburbs.
Barbara’s Books – 2651 Navy Boulevard, Glenview
Perhaps a little sterile (though that’s not a bad thing in a pandemic) this place has lots of room to breathe. Plenty of new hits and a nice getaway in this outdoor mall area. Other locations around the city.
I’m still working my way through Chicagoland and have lots to explore so check back for more! Let me know where I should go next!