Explore Chicago’s Literary Scene This Winter

Peruse these independent Chicago bookstores and find community, too.

Is there anything better than being curled up with a great book while the snow blankets the city? Chicago is a city of literary greats — Sinclair, Hemingway, Algren, Cisneros, Brooks — and a bubbling pot of new voices. Spend your winter exploring how the written word has shaped Chicago by visiting renowned independent bookstores, losing yourself in a library, and experiencing the community of literary events that bring culture and connection to the city. 


Chicago has plenty of cultural institutions to showcase the many sides of this multifaceted cosmopolitan city, and we are most proud of our literary backbone. Before you add to your Amazon cart, consider perusing your local independent bookstore, where you’ll find not only a book, but also a community and unparalleled service by some of the most expert and passionate booksellers. Lose an afternoon at any one of these bookish favorites:  

At Exile in Bookville (Mag Mile), the only thing to compete with the stunning Grant Park and lakefront views are the stacks and stacks of perfectly curated books… oh, and the author events within the iconic Fine Arts building. Swoon!

Women & Children First (Andersonville) is routinely touted on national lists of the best independent bookstores — with good reason. With a feminist focus, top-notch customer service, and eye for social justice, this neighborhood gem is a local legend.  

Semicolon (West Town) is a Black woman-owned independent bookstore that doubles as a gallery space and creative community hub.

Volumes Bookcafe (Wicker Park and Gold Coast) is eager to highlight local, emerging voices as well as notable bestsellers in their relocated store that also has a café and hosts a rotating calendar of events. 

Visit The Book Cellar (Lincoln Square) when you want to pair your book shopping with a delicious pastry or glass of wine—truly, the perfect afternoon.

A newer addition to the bookstore scene, Madison Street Books (West Loop) has all the latest bestsellers as well as a curated book subscription service (for kids and adults).

When people talk about “the smell of books,” it’s Myopic Books (Wicker Park) they are thinking of. A neighborhood staple, it’s the perfect amount of quirky and creaky, complete with towering bookcases to get lost in.

City Lit Books (Logan Square) is bright, airy, and brimming with top bestsellers and kids classics. 

The mom-and-pop shop Sandmeyers (South Loop) has been putting books in the hands of families and residents for 40 years.  

57th Street Books / Seminary Co-Op Bookstore (Hyde Park) are two neighborhood pillars, just one block apart and full of thoughtfully curated books — Seminary Co-Op hosts the largest selection of academic books in the world!

The Pilsen Community Books (Pilsen) is the only employee-owned and operated indie bookstore in Chicago, so you know the customer service and passion for books is stellar. 

Bookish Places to Read in the City 

Curled up on your couch is wonderful, but humans are social creatures and we need to get out, even — especially! — during the wintry months. These places offer communal solitude and comfortable seating so you can feed your introverted and extroverted self. 

  • The Chicago Athletic Association (Grant Park) lobby is all about drama. One part Hogwarts, one part Clue, and all the aesthetic of a classic library, the CAA lobby is a bookworm’s dream with ample velvet chairs, coffee and tea service, and a flickering fireplace. Plus, you can always grab a snack at the Shake Shack below or play a quick game of shuffleboard at the Game Room next door. Win-win!
  • Named for the Irish raconteur and author, Wilde Bar (Lakeview) leans heavily on firelit nooks and mahogany crannies, lined floor-to-ceiling with literary gems. Spend an evening with a pint and a hearty snack while your nose is deep in a good book.
  • Poetry Foundation Library (Loop) is the Midwest’s only library dedicated to poetry and it’s right in our backyard! Marvel at the 30,000 volumes (and audio of authors reading their work) in the airy space and be glad you live in a city like Chicago.
  • Over 100 years ago, the Chicago Cultural Center was the first library in Chicago and a Civil War memorial. Now it houses exhibits, a learning lab, workshop space for local makers, and a reading room — all under the impressive 38-foot-wide Tiffany Dome. 
  • Perched on the ninth floor of the Harold Washington library is the Winter Garden, a jewel of a space in which sunlight streams through the glass architectural ceiling — perfect for reading, writing, or just soaking in a beautiful day in the city. 
  • With chapters all over the world (!!!) the Silent Reading Club is all about being alone together. Every month, the Chicago chapter picks a place, usually a bar or restaurant, to gather for a specified time and just read in companionable silence. Ah…

Literary Events

Just like seeing live music or theater, attending a live literary event offers a new perspective, a communal experience, and often some good laughs. Chicago has limitless live lit happenings — there are several happening nearly every weekend. Grab some friends and check out these proven favorites:

  • The Frunchroom: Southsiders share their best stories at a beautiful theater. 
  • Funny Ha-Ha: A quarterly favorite where the only prerequisite is that the readings bring the laughs.
  • Write Club: Billing itself as a “literary deathmatch,” readers compete to win the audience’s approval. 
  • Do Not Submit: Based in Andersonville and North Center, this series invites anyone to join the open mic to tell their story.
  • The Moth: This international experience has a strong foothold in Chicago’s literary scene, with several shows at venues across the city. Find one tonight and be transformed! 
  • 2nd Story: Hosting events in venues across the city, 2nd Story works to build connection and empathy through shared experiences and story-telling. 
  • The Paper Machete: Every Saturday, the iconic speakeasy the Green Mill transforms into a modern salon with this raucous live magazine variety show. It’s always packed so get seats early and enjoy a cocktail.
  • Miss Spoken: After a long hiatus, this female-forward series is back and ready to roar. 

Whether you read the latest bestsellers or like to revisit old classics, Chicago is a booklover’s paradise. There is no shortage of ways to savor the written word in this city, so consider your TBR pile, pick a place to explore, and go enjoy the slower pace of a Chicago winter spent reading. Enjoy!

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