Chicago
Sat. April 25- Sun. April 26 | 2026
The Chicago Books Weekend
Discover new books — and new corners of a great city — on a one-of-a-kind bookstore crawl though Hyde Park.
This weekend in Chicago:
Lose yourself in any of 80+ independent bookstores as part of a large-scale Chicago literary crawl
Stay in a bookshelf-bedecked hotel that’s just right for a weekend like this
Breakfast (or brunch if you’d rather) in a spot where the tables are covered in 60 years worth of scrawls and scribbles
As always, your stay, meal and local experience are all bookable in one click.
Get the full story for the weekend.
Where you’re going: into the heart of Chicago’s Hyde Park neighborhood as the city kicks off a one-of-kind literary crawl.
Why here?
Independent bookstores are in quite a renaissance these days, and this Saturday a celebration is in order: it’s Independent Bookstore Day in Chicago.
It used to be that smaller booksellers didn’t really need to qualify their independence at all; they were just, you know, bookstores. But that identifier means something. Mainly that an actual, warm-to-the-touch human being is at work curating those shelves, and jotting down the little staff-pick cards, and ginning up the reading nights and discussion groups and plucky small press imprints.
Read on or
photo by Payton Chung
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Seminary Co-Op Books
57th St. Books and its beckoning little step-down entrance
For many of these smaller shops, the late-twentieth century rise of big box retailers, and of the mom-and-pop-eating Amazon, was decimating.
Books could be had cheaper elsewhere. And as the internet and phones and social media began to do to us what it's done to us, the ongoing relevance of an inert printed page became a question.
But the small book business is doing something incredible right now: it’s coming back to life. The American Booksellers Association says membership doubled in the last five years.
And this weekend in Hyde Park, you can step right into that revival, on foot, moving between some of Chicago’s most storied independent shops. And you can step into the literary provenance of here in general.
Saul Bellow prowled the shelves in these parts as a professor at the University of Chicago, which sprawls placidly across the center of the neighborhood. Richard Wright’s Native Son has key scenes set nearby; Pulitzer-prize winning poet Gwendolyn Brooks spent formative years here.
We do our best not to be overly misty about these kinds of bookstores. Not everyone who loves books can afford to kick in the kind of I’m-making-a-point-here surcharge that others are happy to give.
But Chicago is a city that represents one of the most exciting fronts in the battling-back of the independent book business, and in Hyde Park you’ll have a chance to be unabashedly romantic about books, and about the people who continue to build their lives around bringing the written word — in its purest, dog-earable, inhalable form — to readers who wouldn’t have it any other way.
So join one of the best-coordinated literary crawls in the nation. Feel the old wood floors creak and half-threaten to give; smell the strange-familiar aromatics of paper and ink, and watch today’s independent bookstores fighting and winning.
Photo via Powell’s Books/Instagram
This weekend in Chicago, discover…
The stay.
Photo via The Study
The Study
Here’s the place for a weekend like this. The lobby holds a library curated by The Strand — the New York bookstore institution — and a rotating gallery of student art hangs alongside it.
More than 600 feet of new and used books, bought in bulk, line the guest rooms and function spaces.Every room has a reading chair and a writing desk. The hotel was designed around the theme of "reading, resting, and reflecting.”
You’re reserved and pre-paid for Saturday night. King Suite for two.
The day.
Cool crawl map via CHIBA
Chicagoland Bookstore Crawl
You’ll see the full roster of the participating bookstores in this map, and you absolutely should get to as many as you can.
But we also want to give single out a few in Hyde Park that are going to be walkable from your hotel, and are also some of the city’s most fantastic book stores
We’re thinking of it as a kind of mini-crawl within a crawl and we’re including three $25 credits, one for each store, to spend semi-wildly on books.
- Begin at Seminary Co-op, at 5751 S. Woodlawn. Founded in 1961 in the basement of the Chicago Theological Seminary, the Co-op is stocked with books from university presses and small publishers, prioritizing underrepresented voices, older works, lost volumes, and titles that rarely get shelf space elsewhere.
- Then, two blocks away, 57th Street Books — down a charming set of steps into a subterranean book nook. The Co-op's sister store since 1983, it carries a world-class children's department, deep backlist fiction, mysteries, cookbooks, and science fiction, on and on.
-Finish at Powell's, at 1501 E. 57th Street. The store holds nearly a quarter of a million books and is Chicago's largest dealer in quality used, rare, out-of-print, and scholarly titles.
The Chicagoland Independent Bookstore Alliance (CHIBA),which organizes the crawl, has its own cool thing going on ,which you should definitely do:
You grab a passport at any participating store, and collect a stamp at each subsequent stop, no purchase required. Ten stores earns 10% off at participating shops for a year. Fifteen stores gets you 15% off.
You’ll have three $25 gift credits to spend, one each at three walkable Hyde Park bookstores
The find.
Image via The Silver Room
The Silver Room
For the one non-book detour, make it The Silver Room, one of a number of thriving Black-owned businesses at the heart of Hyde Park.
It’s an art gallery and community hub where people gather for everything from tango lessons and DJ sets to language lessons and storytelling showcases. The wares here are an eclectic mix of locally and internationally sourced handmade jewelry, accessories, clothing, artwork, home goods, and a curated selection of music.
Not another bookshelf, but definitely another act of amazing curation.
The food.
Photo by fenstrbme
Medici
Your hotel checkout is at noon on Sunday. Before you drop your cards in the thing, take a Sunday morning stroll to Medici, which has been there since 1955 and has the tables to prove it: nearly every surface is scrawled over and scribbled on by decades of students and writers.
Medici started as a gallery and coffee house in the back of the Green Door Bookstore. They don’t take reservations, so try to get there when it opens (at 9am) so you have plenty of time to waltz back to your hotel and do some non-frenzied packing up.
Photo by Warren LeMay
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Just stop in. We’re including a food and drink credit of $100 .
The tucked away.
Photo by Richie Diesterheft
Osaka Garden
It began in 1893 as Japan's pavilion for the World's Columbian Exposition, and there’s a peaceful sort of haunt to it as it appears today, on an island flanked by twin lagoons in Jackson Park.
After the Second World Wa, the pavilion burned and the garden was left to go wild for decades, becoming a rest stop for migrating birds. This spot was eventually restored (beautifully) through Chicago's sister-city relationship with the Japanese city of Osaka.
The evening mood.
Photo via Bar David
BarDavid
A finish-the-night spot located in the David Rubenstein Forum on the University of Chicago campus. Worth going for the exterior architecture as much as the interior wine list. There’s food too, seasonal Mediterranean.
This is where you stack up your book purchases from earlier in the day, and if there’s something used, you can fan the pages and look for old, wedged-in bank slips or bus schedules or other artifacts.
Photo via the David Rubenstein Forum
Book it all in a click.
This Overnight includes:
Your stay at The Study. Reserved for Saturday, April 25, 2026. Two travelers, already paid for, ready to check in.
A small shopping spree at three of Chicago’s most interesting independent bookstores. All walkable from your hotel. $25 store credit in each shop.
Breakfast/brunch at Medici on Sunday. They don’t do reservations, but you have a $100 food and drink credit, ready to go.
Images in our stories may be sourced from publicly available materials, and are used to represent places as they exist. All rights remain with their respective owners.