The South Loop in Chicago is one of those neighborhoods that has changed dramatically in recent decades.
In the late 1980s I used to venture down to a house music record shop near Printers Row for hard-to-find 12” gems and around the same time I helped a friend move into a newly renovated loft apartment on Polk Street.
The place had a frontier vibe to it, surrounded by parking lots and train tracks.
Nowadays, for a variety of reasons I’ve been spending more time there than in almost any other Windy City neighborhood and I’m always amazed by how much has changed.
All those parking lots and other sites have been covered with glassy apartment towers and vacant storefronts are filled with bars, restaurants and shops.
Thanks to Columbia College, which has space in buildings all around the neighborhood, the South Loop is wallpapered with colorful murals.
And, South Loop benefits from really incredible architecture.
Like the boom in West Loop/Fulton Market, it’s an intriguing turnaround. (Although it's not the neighborhood's first makeover. In the 19th century, the four blocks of the notorious Levee red light district were between Clark and Dearborn, Harrison and Polk.)
Reading the late Lois Wille’s excellent 1997 book, “At Home in the Loop: How Clout and Community Built Chicago’s Dearborn Park,” has further sparked my interest the area.
It’s definitely a worthy One Tank Getaway destination (and a perfect zero-tank getaway if you take the Amtrak Hiawatha).
I should note, that while the boundaries of the South Loop depend a bit on who you ask – with some suggesting it has, thanks to development in recent years, reached all the way down to the Stevenson Expressway if not Chinatown.
“The South Loop is a neighborhood where everyone agrees on three of the boundaries, and argues about the southern boundary,” notes Chicago Velo. “Without question, the northern boundary is Congress, the western boundary is the Chicago River and the eastern boundary is Lake Michigan.
“As to the southern edge of the South Loop, some will tell you it goes as far south as Roosevelt. Others argue it ends at 15th Street. The more logical end would be at 18th Street others argue, or Cermak, say a different contingent. From Roosevelt to Cermak marks a total difference of a mile.”
For this post I’m sticking to the older and tighter definition of Ida B. Wells Drive to the north, Roosevelt Road to the south, the Chicago River to the west and Lake Michigan to the east. It’s not only more manageable for this story and for a weekend jaunt, but it also leaves me with the opportunity for a south-of-Roosevelt follow-up!
Where to Stay
The neighborhood has many hotel options, ranging from a Hostling International hostel on Ida B. Wells Drive to the boutiques Hotel Blake on Printers Row and Le Meridien Essex Inn across from Grant Park to the hulking historic Hilton and Congress Plaza Hotels on Michigan Avenue.
But I’m a big fan of The Blackstone, which occupies a stunning building designed by Marshall & Fox, who also designed the legendary Drake Hotel (and Milwaukee’s Northwestern Mutual Building on Wisconsin Avenue).
I’ve written a whole story about the incredible history of this hotel, which has a stunning ballroom and lobby, great views over Grant Park and Lake Michigan, a fabulous Catalan-inspired restaurant called Mercat in the lobby, an art gallery floor and more.
As I’ve written, the history of The Blackstone involves every president from Woodrow Wilson to Jimmy Carter; political conventions at which presidential candidates were nominated; a famous mob convention attended by Al Capone and Lucky Luciano; an owner with ties to The Beatles; appearances in well-known films; and guests ranging from Rudy Valentino, Nat “King” Cole and Lena Horne, to Astors, Vanderbilts and Rockefellers, to the Duke and Duchess of Windsor.
Plus, it was home to Joe Segal’s legendary Jazz Showcase for a while and I was blessed with seeing some great shows there, by the likes of Kenny Burrell, Milt Jackson, Dirty Dozen Brass Band and others.
The hotel also keeps bees on the roof and makes its own honey, which figures into some of the special packages they offer, which in addition to amenities like early check-in and late check-out also include in-room cocktail kits, cookies and more that include that honey. Pretty sweet.
Where to Eat
Like most anywhere in and around downtown Chicago, South Loop has copious dining options, from homegrown favorites like Harold’s Chicken Shack (celebrating 75 years!) and Lou Malnati’s to chains and more.
For your morning coffee, consider the evocative Cafe Deko on Dearborn in the heart of Printers Row with its tiled floor and ornate chandeliers transporting you to Europe, or opt instead for the Cuban flavor of Cafecito, which also serves breakfast and lunch food, including pressed Cuban-style sandwiches. For a more contemporary vibe, grab a seat and a cup at Necessary & Sufficient Coffee, also on Dearborn, near Deko.
For breakfast, you can’t beat Eleven City Diner, but that just might be the Brooklyn in me talking. This New York-style diner has all the breakfast (and lunch and dinner) classics, but also serves Brooklyn’s beloved chocolate egg creams. Much of the decor in this classic diner atmosphere is Big Apple themed.
For lunch, following the clocktower to Dearborn Station and right across the street is Roots Pizza, which opened five years ago in the depths of the pandemic, serving Quad City-style pizza on two floors with a lively atmosphere that’s family friendly.
Upstairs, in the specially-constructed building is a retractable glass roof strung with colorful lights, which makes it especially fun on a nice summer’s day (or evening). That roof helped make Roots a destination when folks were still concerned about indoor dining during the pandemic.
What, you ask, is Quad City-style pizza?
First, it has brewers malt in the dough, which creates a sweet crust. Second, the toppings are typically hiding mostly under the cheese and, third, it’s cut into strips rather than pie-cut triangles or tavern-cut squares.
The pizzas here are doughy and packed with toppings and in addition to classics like crumbled sausage, pepperoni and margherita, you can also get things like butter chicken, and you can do halves, too, such as half margherita and half butter chicken, if that’s your vibe.
For dinner, stay nearby and hit Umai, a great Japanese restaurant on the corner of Clark and Polk. The restaurant does carry-out but dine-in for the full bar. Then, order from a menu that offers a range of udon and ramen, sushi, maki rolls, Japanese barbecue and more.
If you prefer your waitstaff to be at least partially robotic, head south on Clark Street to the Roosevelt Collection where you’ll find Wagyu House, a sleek hot pot restaurant that has human staff, but also robots that deliver food to the table. This one is a bit of a splurge, but the food is good and the experience is fun.
Where to drink
Two of the best options for a quaff are right near each other on Dearborn Street on Printer’s Row.
Kasey’s Tavern occupies a space on Printer’s Row that has been a tavern for well over a century. In fact, it claims to be the second oldest bar in Chicago, though the Kasey’s era dates to 1974.
Good tavern-style pizza, great craft beer list, outdoor seating and a classic Chicago tavern vibe inside, Kasey’s is a South Loop landmark.
Just down the street is the Printer’s Row Wine Shop and Bar, which has wines from around the world, local craft beer and more. You can in the shop to-go or you can grab a seat and enjoy the wine bar selections on site.
It’s a great date-night spot or a place to just hang out and meet the locals.
Half Sour is a brunch spot, across from Umai, that is known for its cocktails. Located in the old Blackie’s, which was South Loop’s longest-running family owned bar, you can get shaken and stirred cocktails, beer on draft and in cans, THC and CBD beverages and N/A drinks, too.
Don’t kill me because Industry Ales Brewpub, on Wabash, is not technically in South Loop but since there are no breweries in the area we’re discussing (which seems hard to believe), Industry is the closest and it’s a great spot just a block out of the zone.
Only just a little over a year old, Industry serves tasty upscale chef-driven plates and really good beer made on-site. There’s table seating in the stylish brewpub, but I prefer to belly up to the bar where the bartenders can tell you everything you want to know about the beer.
What to do
There’s a lot of fun to be had in the South Loop.
Do not, under any circumstances, miss the tours of Adler & Sullivan’s incredible, landmark Auditorium Theater, if you are a fan of history and/or architecture. A feat of engineering, for which Dankmar Adler revolutionized foundation construction, a stunning building designed by Louis Sullivan (with help from his young sidekick Frank Lloyd Wright) and an important building in helping to catapult Chicago toward its status as a world architecture capital, the Auditorium still has shows today and sounds incredible, thanks to Adler’s skill in sound engineering.
Tours take you through the lobby and the auditorium as well as backstage, which is super fun. Because the office and (former) hotel sections are now part of Roosevelt University, you won’t visit those.
For more art, check out the free Museum of Contemporary Photography, a great photo-focused gallery that is part of Columbia College Chicago. There are always interesting shows on in this multi-level space and, for better or worse, it feels like a secret and you just may have the entire place to yourself.
If you love books, check out Sandmeyer’s, the last remaining bookstore on Printers Row. It’s not a huge store but it’s an extremely well-curated one, with especially great selections in its Chicago, art, architecture and travel sections.
While you’re on Printers Row, don’t forget to look up and check out the amazing architecture (Chicago Architecture Foundation offers tours, too).
The New Franklin Building has stunning terra cotta tiles around its entrance and the underside of the oriels on the Manhattan Building are creepy and fun. Lakeside Press’ former building looks like a vintage public high school, and Dearborn Station, with its soaring clocktower, is the last of the 19th century train stations in the city.
Located now in the old station is the Jazz Showcase, which had previously been in The Blackstone (among many other locations in its 78-year history), which still has shows pretty much nightly.
If blues is more you bag, Buddy Guy’s Legends is just a few block away on Wabash with live music most nights and the allure of knowing that Guy himself could show up.
Take a stroll, too, through Dearborn Park, the leafy, almost suburban-style neighborhood within South Loop that helped jump start the area when it was built in the late ‘1970s and early ‘80s atop land that had been home to the tracks that brought trains in and out of Dearborn Station.
For more walking (and running and biking) fun, Grant Park lies just across Michigan Avenue. To the east of that is the lakefront with its waterfront paths that lead north to the Buckingham Fountain, the Art Institute (which has a great Frida Kahlo show on at the moment) and Millennium Park, and south the Museum Campus, with the Field Museum, the Shedd Aquarium and the Adler Planetarium.
There’s more great stuff across Roosevelt Road, too, like the Chess Studio tour, a coffee shop in the old Vee-Jay Records headquarters, a steakhouse in an old firehouse (that was used as a set in “Chicago Fire”) and more.
But that’s a whole ‘nother story.
Born in Brooklyn, N.Y., where he lived until he was 17, Bobby received his BA-Mass Communications from UWM in 1989 and has lived in Walker's Point, Bay View, Enderis Park, South Milwaukee and on the East Side.
He has published three non-fiction books in Italy – including one about an event in Milwaukee history, which was published in the U.S. in autumn 2010. Four more books, all about Milwaukee, have been published by The History Press.
With his most recent band, The Yell Leaders, Bobby released four LPs and had a songs featured in episodes of TV's "Party of Five" and "Dawson's Creek," and films in Japan, South America and the U.S. The Yell Leaders were named the best unsigned band in their region by VH-1 as part of its Rock Across America 1998 Tour. Most recently, the band contributed tracks to a UK vinyl/CD tribute to the Redskins and collaborated on a track with Italian novelist Enrico Remmert.
He's produced three installments of the "OMCD" series of local music compilations for OnMilwaukee.com and in 2007 produced a CD of Italian music and poetry.
In 2005, he was awarded the City of Asti's (Italy) Journalism Prize for his work focusing on that area. He has also won awards from the Milwaukee Press Club.
He has be heard on 88Nine Radio Milwaukee talking about his "Urban Spelunking" series of stories, in that station's most popular podcast.
