The 10 best independent bookstores in Chicago

On one hand, embracing high-tech industry, architecture and urban design, Chicago’s true character may surprise you in all its quirky, analogue inclinations. Though not totally avoiding the hit from e-readers, chain stores and behemoth Amazon, Chicago’s bookstore scene is thankfully kept alive through the sheer obstinance of its bookish hipsters and literary Luddites. As well as flicking through fragrant pages at brick-and-mortar stores by day, Chicago offers lively literary nightlife by way of open mic nights and boozy literary events hosted at bars, cafés and bookstores throughout the city. To appeal to all the bibliophiles and city slickers out there, we bring you the 10 best independent bookstores Chicago has to offer.

Tailor Made Journey

Let Us Plan
Your Perfect Vacation

Mr Hudson designs unique and luxurious vacations for sophisticated travelers who prioritize beauty and style.

Book Your Luxury Vacation With Mr Hudson Book Your Luxury Vacation With Mr Hudson Book Your Luxury Vacation With Mr Hudson

Chicago | Photo: Pedro Lastra

Mr. Hudson highlight image

Unabridged Bookstore is a long-standing institution providing shoppers with top local authors and LGBTQ publications since the 1980s.

1. Unabridged Bookstore

Find the first of our Chicago best bookstores in Lakeside’s shopping district, a long-standing institution providing shoppers with top local authors and LGBTQ publications since the 1980s. This is Unabridged Bookstore, found on the ground floor of a red-brick tenement appealing to passers-by with its charming bay window façade framed by a pink fire escape. As well as being one of the oldest surviving bookstores in Chicago, Unabridged Bookstore is also one of its only gay bookstores, serving as a community outpost with knowledgeable staff and a purist attitude. Don’t expect to get a coffee on site but do expect a well-stocked selection of obscure queer literature beside more general titles adorned with handwritten yellow Post-It notes to signal staff approval.

2. Quimby's Bookstore

The centre of Chicago’s zine society, Quimby’s Bookstore is a globally recognised institution devoted to educating readers on anything from satanic sorcery to socialist systems for over 25 years. Whatever counterculture you’re looking to tap into, Quimby’s can offer an array of literature, independently-produced zines and graphic novels to fulfil your needs, all eclectically laid out within their low-key North Avenue store. Even if you don’t come intending to buy, the unique graphics and obscure titles will have your tote full in no time. Then, after buying out the store, commemorate your trip with a selfie session at the store’s own photobooth!

Photo: Cottonbro

Chicago | Photo: Jacob Blankenship

3. 57th Street Books

Just off of Hyde Park and hidden away down a sunken entryway, 57th Street Books is one to look twice for. What’s special about the store here is that it’s owned by customers, as part of Chicago’s Seminary Co-op, and therefore protected from the worst of the e-reader’s high street takeover. Anyone can join the co-op, and, in so doing, can become business partners with the likes of Susan Sontag and Barack Obama. Just one of two independent bookstores on the South Side (the other being the main branch of the Seminary Co-op), 57th Street Books provides a general interest focus in an otherwise academic-minded community, holding a huge range of indie titles spread throughout its warehouse-size store that’ll hold you engrossed for hours.

4. Armadillo's Pillow

The best-named bookstore in Chicago hands down is Armadillo’s Pillow in the Roger’s Park neighbourhood. More than its name however is its affordable collection of quirky titles and its boho vibe bought forth by burning incense and crystal jewellery concessions. Ask the helpful staff for recommendations or simply roam your eyes over the various titles and wild décor, losing yourself in the weird and wonderful world at the heart of Chicago’s second-hand literature scene.

5. Open Books

A sprawling West Loop store featuring a selection of over 50,000 works, Open Books is one of the biggest used bookstores in Chicago (with another location in Pilsen). As well as being the place for affordable reading, Open Books also wins us over with its non-profit business model and community mindedness. As well as reserving shelf space for 10,000 teen and children’s’ titles, the store also does educational outreach, pairing volunteers with schools throughout the city on its ‘reading buddy’ scheme and creative writing program, using book sales to fund their endeavours. As if you needed an ethical incentive to buy a book!

Photo: Phil Hearing

6. Sandmeyer's Bookstore

The heart-warming counterpart to Amazon’s cold economic model must be Sandmeyer’s Bookstore, a family-owned treasure at the historic centre of Printer’s Row, the city’s old publishing hub at its height in the early 1900s. Far from being outdated, Sandmeyer’s Bookstore brings working heritage to the area, in an original building formerly used as a printing press. Though most of the area’s printing companies are long gone, Sandmeyer’s Bookstore serves as a nod to the area’s past, operating since the 1980s. Though not much to look at from the outside, Sandmeyer’s outdoes itself with its fantastic collection and cosy atmosphere. Come in June for the Printer’s Row Lit Fest, the Midwest’s largest book fair which creates much cultural kudos in the area.

Mr. Hudson highlight image

Staying in Chicago for a while? See our Chicago travel guide for more attractions and things to do in The Windy City.

7. Uncharted Books

Bringing a classic feel to the bookstores of Chicago despite only being open since 2012, Uncharted books is exactly what it says; uncharted, off-the-map, and a total find! Located in Logan Square, Uncharted Books came to be thanks to a Kickstarter campaign which Chicagans rallied behind. Today the store thrives with locals (and their dogs!) looking for rare and unusual used books in rustic, unpretentious surrounds. As well as being a cool place to while away an afternoon, getting recommendations from Ramona the resident husky, Uncharted is also an evening affair, holding various events such as poetry slams and book readings.

Chicago | Photo: Benjamin Suter

Photo: Anna Nekrashevich

8. Volumes Bookcafe

If a cup of coffee with your literature is a must, Volumes Bookcafe is the one for you.  Owned by two book-loving sisters, Volumes Bookcafe is organised to perfection in a bright and cheery space on the edge of Wicker Park. Though not the only bookseller in the area, Volumes wins out for its well-stocked café serving up everything from craft beer to Dollop Pastries (and of course a mean espresso), alongside a large collection of literature spanning several niches. A fun space for international kids, thanks to its bilingual story time held twice weekly, Volumes also provides interest for adults with its open mic night, weekly trivia and Scrabble league.

9. The Book Cellar

A well-curated gem in Ravenswood tucked out of sight in an unassuming location off of Lincoln Square, is The Book Cellar. A bookstore, café and eatery, The Book Cellar is certainly more than meets the eye, independently run and staffed with smiling people who know what they’re talking about! Those wishing to get in on the literary discussion with the local community can come along to any of the book club events and reading parties, or simply come for a sandwich and glass of wine in the late afternoon, sticking around until the authors, slam poets or stand-up comedians show up (dependant on the schedule!).

10. Myopic Books

Lastly, don’t leave Chicago without a browse across the three-levels of Myopic Books, a huge (and hugely popular) bookstore in the centre of Wicker Park. Check your emails and pee before leaving home because Myopic has neither a bathroom nor WiFi. In fact, there’s a total no-cell-phone policy at Myopic books, making it a mecca for literary purists who come to search the impressive collection of general fiction, sci-fi and history titles without a Whatsapp alert in earshot. If in doubt, ask the staff for a recommendation, staying late on Monday night to sample the more experimental side of Chicago’s music and poetry scene.

Chicago | Photo: Max Bender

Want to simplify luxury travel planning?

Whether you want a resort vacation, wildlife safari, city break, luxury cruise, wellness retreat, honeymoon, once-in-a-lifetime adventure or weekend escape, the trip curation experts at Mr Hudson make travel planning a breeze. Find out how we can handle the finer details of vacationing in style.

Subscribe to our newsletter

You can unsubscribe at any time by clicking the link in the footer of our emails. We use Mailchimp as our marketing platform. By clicking below to subscribe, you acknowledge that your information will be transferred to Mailchimp for processing.

Sign up for exclusive insider promotions