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The Best Local Bookstores in Chicago

Cozy Chicago bookstores you must visit!

A used bookstore in Chicago

Is there anything more cozy and homelike than a bookstore? Anytime I travel I always carve out time to visit the local indie bookshops and used bookstores. It’s a unique look into the soul of a new city, seeing what kind of places they build to hold stories.

These are my favorites in Chicago. These five places are a perfect mixture of used bookshops and indie gems. They are truly Chicago's best bookstores.

a used bookstore in Chicago

Armadillo's Pillow

An icon of the Chicago used bookstore scene, Armadillo’s Pillow is the kind of cozy, overstuffed used bookstore that dreams are made of. It’s a well-organized space overflowing with books, with unique shelving and layouts that invite you to stay and relax.

They also sell odd trinkets and crafts from local artisans, and sometimes a guitar student from the music shop next door will set up and play for a while. It’s dreamy and cozy and everything you want in a bookstore.

staff picks at an indie bookstore in Chicago

Women and Children First

This is my favorite indie bookstore in the city. The kind of community-first, Amazon-bashing, social-justice-campaigning bookstore that you just can’t help but support. 

They’ve got a huge selection, incredibly knowledgeable and helpful staff, and robust sections of literature that feature queer, BIPOC, and disabled voices, among others. This is the kind of shop that goes out of the way to make sure that everyone feels not just accepted, but welcomed and valued.

Keep indie bookstores in business! Buy your new books from places like Women and Children.

a used bookstore in Chicago

Uncharted Books

Charming local used bookstore with a haunted painting and a resident bookshop dog.


Ok, here’s a little more info. Among the used bookstores around Chicago, Uncharted is definitely the smallest, but the selection is great and the vibes are immaculate. The space is well organized and beautifully decorated, and yes, one of the paintings at the back is allegedly haunted. And, depending on who’s working the desk on the day of your visit, you might get to meet Ramona! That’s the bookshop dog. Add this spot to your map immediately!

a drama bookstore in Chicago

The Understudy

Move over NYC! Chicago has a drama bookstore too!

The Understudy popped up in Andersonville post-pandemic, and it’s an artist’s dreamscape. It’s half bookstore, half cafe, and all amazing. It’s stacked with play scripts, books about art and theatre, and a few small sections of fiction and queer lit and social justice reads and… it’s everything you want in a creative hangout.

Heirloom Books

Heirloom is a newcomer to the Chicago bookstore scene, but after one visit it became -immediately and permanently- my favorite.

a used bookstore in Chicago

Picture two floors of used books in every possible variety, shelved beautifully and organized better than any used bookstore you’ve ever seen. Picture cozy furniture in every corner and classical music radio in the background.

Now imagine that this utopia is completely not-for-profit, staffed entirely by stupendously knowledgeable volunteers, and is determined to give you the cheapest possible price for every book in the place. Seriously, they don’t list their prices on their books. You bring your selections to the front counter, they do a quick internet search, and give you the lowest price they find.

It’s a gorgeous place founded on the love of books and reading and designed to be a welcoming community space that makes books as accessible as possible. Go check this place out posthaste. It’s probably what Jorge Louis Bourges meant when he said “I have always imagined Paradise will be a kind of library.”

These are Truly Chicago's Best Bookstores

I hope this list leads you to a new favorite bookstore!

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Love and Shenanigans,


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