The Run Down

Wine and book lovers, especially fans of the two combined, this one's for you. You'll venture to Printer’s Row, a neighborhood near the South Loop that makes walking through its charming tree-lined streets akin to a voyage back in time. As its name indicates, Printer’s Row boasts a history intertwined with literature. With old-world energy and activities to match, this guide includes quintessential stops at a pharmacy-turned-wine-bar, a mom-and-pop-owned bookstore and a jazz club that describes itself as being the place “where jazz lives in Chicago.”

1. Shop @ Sandmeyer's Bookstore

2. Wine @ Printer's Row Wine Shop

3. Live Show @ Jazz Showcase

1. Sandmeyer’s Bookstore

Begin with a walk along Dearborn Street in Printers Row. Historic brick buildings loom overheard. Their robust Romanesque revival designs, marked by rounded archways and bold lines, set the scene for what feels like Old World Chicago. For architecture buffs, this street is a destination itself.

A small park sits in its center, and as you take in the neighborhood from there, you half expect to see a kid standing on a soap box, dressed in a newsie outfit, shouting,  “Paper, paper, getcha paper.”

The first stop on your itinerary is Sandmeyer’s Bookstore, one of the oldest independent bookstores in Chicago. This cherished shop is the brainchild of husband and wife Ulrich and Ellen Sandmeyer. Both former librarians established this haven for book lovers in 1982 inside the Rowe Building, a former printing arts factory built nearly 150 years ago.

Ulrich passed away in 2018, leaving Ellen to navigate the world of literature alone. She continued to uphold their shared vision, preserving the bookstore’s unique charm, until her retirement in 2023. Long-time customers still stop by asking about Ellen. While she’s no longer behind the counter, she remains a vibrant part of the neighborhood.

The original wood floors creak as you step inside the shop.  The first shelves to greet you feature Chicago books like The Devil in the White City, Three Girls from Bronzeville, and other cornerstones of Chicago literature.

Beneath warm, homely lighting, you’ll discover new releases, timeless tales for adults and children, and a unique selection of employee-penned poetry.

Linger in the corner behind the register to uncover a trove of cute pins, stickers, mugs, and greeting cards – it’s your one-stop shop for gifts and mood-boosters.

2. Printer’s Row Wine Shop

Printers Row Wine Shop is across from the Sandmeyer’s; its cork-filled window displays, neon sign, and tree-covered patio invite you in.

Family-owned and a South Loop staple for nearly two decades, the wine shop replaced what was once a pharmacy. Today, it’s the place to go for natural wine, interesting beer varieties, and good conversation.

There’s no missing this bottle haven. If you didn’t notice the red “Wine Shop” sign hung above the entrance or the gold window lettering, you’d undoubtedly see the hundreds of wines peeking through the windows flanking the entrance. Once inside, you’ll either be met with a full house or a quiet room, depending on the evening, and both have their own appeal.

On one wall sits the register backed by shelves full of liquors and a craft beer sign (head to the back if you’re looking for brews). You’ll head to the opposite wall to peruse wines sorted by location and variety. If the nearby tables are packed, some maneuvering is required to scan the shelves up close, but it’s all part of the process.

After grabbing a seat at the bar, a table, or, if you’re lucky, the coveted window seat, it’s time to decide which wine to try first. Starting at $11, the wine selection ranges the scale to offer a little bit of everything. We recommend giving Gautier, a chenin blanc from France, and Domino, a red blend from Portugal.

Printers Row Wine Shop is the kind of place you might pop into on a whim if you’re walking through the neighborhood, but with an atmosphere as romantic and inviting as this one, you’ll want to pause time.

Things to note:

– The menu offers small bites to eat, including charcuterie, pretzel bites, and cashews

– Printer’s Row Wine Shop hosts occasional events, including live music and poetry readings.
The shop opens at noon every day of the week.


3. Jazz Showcase

After a glass — or four— of wine, walk a block into a nondescript business entrance with an enchanting and historic jazz club inside.

Jazz Showcase, a historical club, resides in Dearborn Station, a building just as historic. The Romanesque Revival structure, recognizable by its 12-story clock tower, used to be one of the six intercity train stations serving downtown in the late 1800s.

Now home to shopping and entertainment spaces — the train shed was demolished and tracks removed in the mid-1970s — Dearborn Station is one of the oldest railroad stations in the United States.

Joe Segal founded Jazz Showcase in 1947 and fought to showcase jazz in Chicago for 70 years. “No one did more for jazz in Chicago,” a Chicago Tribune columnist penned when the legend died in 2020.

A Chicago Sun-Times article cites saxophone great Donald Harrison as saying Segal “helped legends maintain a place to play in Chicago. And he made sure musicians who were coming up had a place to play.” His son, Wayne, went on to operate the club after his death.

Open seven days a week, the venue does what its name says: it highlights a balance of both international and Chicago homegrown musicians. Since its inception, it has hosted some of the most well-known names in jazz, including Charlie Parker, Roy Hargrove, and Richie Cole.

Inside, you’re transported to jazz’s golden age, surrounded by portraits of famous musicians, red velvet curtains, and a smartly arranged room that gives almost all seats a view of the stage (and a larger-than-life, black-and-white portrait of Parker) — the focus remains on the music and its composers.

Here are a few things to keep in mind before we end the guide:

– Artists are typically scheduled to perform multiple days at Jazz Showcase, giving guests ample opportunities to stop by and witness their art.

– Shows start at 8 p.m. and again at 10 p.m. most days. Sundays, performances begin at 4 p.m. and 8 p.m.