I’m not from Chicago, but it has been my home for the past 22 years, so I think I qualify as at least an honorary local.
I have always taken pride in my being from South Dakota–I’m the first person most folks have ever met from that state! But more and more each year, I have grown to admire and love Chicago, this metropolis with world-class attractions and incalculably insolvable problems.
Murder capital of America? Check.
Most vacated county in the United States? That’s Cook County.
America’s most segregated city? Yes, according to CNN.
But it’s also the city of Carl Sandburg, Nelson Algren, and Saul Bellow. This city clawed and scratched its way to prominence in the 19th century, repeatedly reinventing itself through the decades, from the era of river traffic, railroads, and meatpacking through organized labor and bootlegging to interstate travel and flight. Al Capone ruled the roost in the 20s only to be brought down by Elliot Ness from his Printer’s Row office building in the 30s. Chicago somehow survived the collapse of Rust Belt manufacturing, managing to remain a city of international significance.
I’ve been thinking a lot about what I’ll mss most about this place as I make my move to San Francisco. Here are the top five things that get me a little misty-eyed when I think about leaving:
1. – Lake Michigan
A lake? Really? This would be a sea in any other part of the world. I’ve lived here for 22 years, and nearly all of them were spent within spitting distance of this great body of water. Though I’ve been living in the Midwest, but I probably spend more time walking on a beach than most coastal dwellers I know.
Chicago has more coastline than most American cities, stretching 25 miles north to south along the lake. I’ve explored every inch of it on foot and bike, traveling down from Evanston to the Loop and from Hyde Park both north and south. I’ve lived north, central, and south on the city’s lakefront and have found things to love about all three areas.
This city enters hardcore beach town mode in the summer—heck, they even plant palm trees on the beaches! The shore comes alive with runners, cyclists, hot dog vendors, volleyball, sunbathing, and tourists on Segways. Chicagoans know that the window for good weather is short, and pounce like rabid animals upon those precious few sunny, warm days.
Most Chicagoans have been known to shake their fist at the sky after another day of torrential rain or blustery snow, dreaming of being anywhere but this godforsaken swamp bog. When warm weather finally arrives they swarm outdoors in frantic droves, donning wrinkled shorts over pasty legs. They pound a cold one while getting sunburned at the harbor, watching the sailboats come and go while listening to Kanye West, Common, and Chance the Rapper.
Or maybe that’s just me.
2. – The Neighborhoods
Chicago truly is a city of neighborhoods. It’s like a collection of miniature small towns with distinctive flavors all their own, crammed up against one another, crammed together haphazardly in a mishmash of cultures, architectural styles, and ethnicities.
I was intimidated by this massive metropolis early on, venturing from my suburban safety bubble downtown on rare occasions. I was comfortable in a few familiar places like Lincoln Park, but most neighborhood names conjured up visions of carjackings and muggings.
I finally moved to the North Side during my graduate years and began exploring undiscovered areas. I fell in love early on with Montrose Point with its birds, birders, and naked men, making this place the destination for my daily run.
I started doing long city walks around this same time, typically following the lakefront trail through beaches and harbors to the Lincoln Park Zoo, then Oak Street Beach, and finally to dinner and a movie downtown before taking the El back north. Sometimes I would vary my path, following Clark Street past Wrigley Field and through the bustling center of Lincoln Park and into the Loop.
I’ve lived all over the city, from Rogers Park on the far North Side to Hyde Park on the South Side, with a few years living smack-dab in the middle of the Loop. I’ve also worked in Lincoln Park for years and lived in the uber-pleasant surroundings of North Evanston. My wife and I have wandered through pretty much every non-terrifying neighborhood (and even a few of those) in the city.
My Favorite Neighborhoods
Chicago has dozens and dozens of neighborhoods, but pressed to pick favorites I’d go with the following:
Lincoln Park – Saying you like Lincoln Park is kind of like saying you like ice cream. Of course you like ice cream—it’s ice cream. Nevertheless, I’ve had some outstanding times at the zoo, the Lincoln Park Conservatory (especially in the winter when I need a hit of nature), and wandering the incredibly beautiful brownstone-lined neighborhood streets. I just try to avoid all the bros wearing their backward baseball caps and open button down shirts. They travel through this neighborhood in large packs. Favorite hang: Local Option for sure. It’s the most non-Lincoln Park place in Lincoln Park.
Wicker Park – Though this neighborhood (especially Division Street) has kind of become Lincoln Park West, it is still full of relatively bro-free hangs. I’ve lost many an afternoon hitting up Antique Taco, Big Star, or Piece and then heading over the Emporium Arcade Bar. If I’m looking for a more clear-headed afternoon, I’ll head over to Wormhole Coffee with its 80’s nostalgia vibe (they even have a DeLorean in there!). Walking up to this neighborhood from our downtown pad was a regular weekend ritual.
South Loop – We lived for a couple of years in a townhouse smack-dab in the middle of the South Loop and loved it.. we even had a backyard! This neighborhood didn’t even exist when my wife and I were in college, but at this point, it’s like a whole new city got plopped on the lakefront. Modern blue glass skyscrapers form canyons around converted industrial buildings, with restaurants, parks, and other amenities nestled amongst them. This new neighborhood is full of people pushing baby strollers and walking dogs. We lived across from an elementary school in a particularly charming complex. It was kind of surreal to see this stereotypically suburban scene unfold in the shadow of the towering city skyline. Very cool urban living! Favorite hangs: Flo & Santos, the South Loop Gino’s East (we’re probably the only locals to go to this place on a weekly basis), and Vice District Brewing.
Pilsen – Oh man, do I love this neighborhood! It looks and feels totally unlike any other part of the city. Originally established by Czech immigrants in the mid-19th century, it became a largely Mexican neighborhood in the mid-20th century. It’s the Chicago version of San Francisco’s Mission District, complete with vibrant murals on every available surface. Pilsen has the largest stock of pre-Chicago Fire buildings in the city, making for a fascinating walking experience. Favorite hangs: Nuevo Leon (which was tragically gutted by a fire in 2015), Skylark, Simone’s, and La Casa Del Pueblo for some insanely cheap produce!
Evanston – I know that Evanston is its own sovereign city, but it warrants inclusion in this list anyway. I love Evanston. That comment makes some folks roll their eyes, but it’s true, and Evanston has finally started to pick up in terms of cool spots and nightlife. If I was feeling lazy, I’d wander down Central Street (where I lived for at least a decade) to Bluestone or Ten Mile House. Otherwise, I’d be found at some of the new breweries that have sprung up like the (ironically named) Temperance Beer Co., Smylie Brothers, Sketchbook, and Peckish Pig.
Logan Square and West Town – Logan Square has transformed from a sleepy West Side enclave to Chicago’s hipster capital. I spent at least part of every weekend there for seven years. Lots of cool and funky stuff to do. My favorites:
- Food and Beer (notice a trend?): Revolution Brewing, Boiler Room, Parts and Labor, Chicago Diner, Longman & Eagle
- Coffee: Star Lounge, Gaslight, Cafe Mustache, New Wave
- Outdoors: Humboldt Park, The 606 (Chicago’s version of the NYC High Line), Palmer Square, and the beautiful boulevards for which this neighborhood is famous
Longman & Eagle is an inn as well as a restaurant, and my wife and I did a couple of “staycations” in Logan Square over the years. It was great!
My Favorite Long Walks
I’ve explored this city on foot for years. When I think Chicago, I picture some of these long strolls:
- Hyde Park to downtown (lake shore) – easy and beautiful
- Hyde Park to downtown (city) – cool architecture, a little sketchy depending on the exact path
- Hyde Park to South Shore – architecturally first-class, but avoid “terror town” at all costs in South Shore
- Hyde Park to Bridgeport via Bronzeville – if you tie it together correctly, it can be a fascinating cross-section of neighborhoods
- Hyde Park to Evanston – beautiful but at over 20 miles can be quite strenuous
- Loop to Evanston (lakefront) – rocks
- Loop to Evanston (city) – rocks
- Loop to Logan Square – a cool walk and clocks in at only 5 miles
- Loop to Oak Park – I found two utterly terrifying ways to do this (I vowed to never either of these again – they were officially foolish) and one safe but incredibly long way where I circumnavigated the dangerous areas
- Evanston to Logan Square – a great and largely unknown walk that did this dozens of times via the North Shore channel
3. – Architecture
See that photo? That’s where I used to live! No, not in the Willis (Sears) Tower—the building with the funky modern white and black striping. That place was cool! My balcony overlooked the Chicago River and the Sears Tower. I spent hours on that balcony gazing at the city, watching life unfold in the bustling Loop on weekdays and watching helicopters hoist parts up to the antennae of the Willis Tower on weekends.
Chicago is an architectural dream. People flock to Chicago from all over the world to explore its abundance of cool structures from famous builders. From Daniel Burnham and Louis Sullivan through Mies van der Rohe and Helmut Jahn, if you’re into architecture, Chicago is the place to be.
My Favorite Architectural Destinations
I loved playing amateur tour guide when friends would visit me in Chicago. Here are some of the things I’d try to hit up:
- The Rookery – This place is wild. Built by Turnham and Root in 1888, it’s lobby was remodeled by Frank Lloyd Wright, architecturally vandalized (i.e. remodeled again) in the 30s, and restored again in the 90s. It’s one of the first places I take people because it encompasses so many famous architects (and it’s just a cool building!)
- Auditorium Building – This Adler and Sullivan creation was the United States’ largest and tallest structure when it was built in 1889. The Auditorium Theatre (located inside) is Sullivan architecture personified. It really is a remarkable structure.
- Fine Arts Building – This building is used extensively by musicians, and watching a bass section load into the pulley-operated elevators is always fun. It’s not a masterpiece in design, but it’s a slice of Chicago history and I like to take people by it.
- Oak Park – This nearby suburb was where Frank lloyd Wright spent the first 20 years of his career. It’s a smorgasbord of Wright architecture, from the Unity Temple in downtown Oak Park to his home and studio. Many streets in Oak Park are lined with Frank Lloyd Wright houses. It’s very cool! Hemingway also hails from Oak Park.
- Millennium Park – Though it took forever to build and went massively over budget, this park is now Chicago’s front yard. I never get tired of spending time here. My wife’s favorite thing to do here? Dip her feet in the stream and relax. My favorite? Wander the beautiful Lurie Garden.
- Willis Tower – the lines stink and there’s never really a good time to go, but it’s on everyone’s bucket list and it worth it
- John Hancock Center – I prefer this to the Willis—the view’s better and the line’s not as bad—hang out at the Signature Room for an overpriced cocktail with a first-class background
- Chicago Architecture Foundation – They’ve got a cool replica of downtown Chicago built to scale—I have gazed at this thing for hours
- Chicago Architecture Foundation River Cruise – Do this if you visit Chicago. It is the way to take in the architectural splendor of the city.
- Chicago Water Taxi – Take this bad boy down to Chinatown on the weekend!
- Garfield Park Conservatory – Garfield Park is a pretty rough neighborhood, but the conservatory is at must-see if you’re in Chicago. I’ve never been to a conservatory even remotely like it (sorry Lincoln Park Conservatory and Conservatory of Flowers, I still love you!)
- Lagunitas Chicago – Lagunitas Brewing took over a former steel distribution facility near Pilsen on the West Side and now distributes to half of the country through this location. It’s an awe-inspiring operation and one that I try to take visitors to if possible. It’s a totally cool experience!
4. – The South Side
See that view? I took that photo out of my living room window while living on the South Side. You could do worse in terms of scenery!
Chicago’s South Side has a pretty terrible reputation, and much of it is well-deserved, but there’s some incredibly cool stuff down there as well. Here’s my short list about why I loved living down there:
- Hyde Park – What a fascinating neighborhood this is. I lived on the top floor of a high-rise along the lakefront (you can see how close I was to the lake in that photo) and got a bird’s-eye perspective on the community. It was especially interesting at night to see the police lights zipping around! Despite being on the South Side, Hyde Park is actually quite safe, and the neighborhoods north of Hyde park have improved tremendously—check out the excellent book Black on the Block for more about the Oakland/North Kenwood gentrification process. It’s a great read.
- Off-the-Beaten-Path Neighborhoods – Most tourists don’t make it to Bridgeport, Back of the Yards, McKinley Park, Brighton Park, Heart of Chicago, Little Village, or Pilsen, but they’re all worth a visit. I doubt that I’d have visited any of them if I hadn’t been living on the South Side.
- The South lakefront – The lakefront path is so much quieter down on the South Side than up north. I got really spoiled being able to walk in solitude down there. Visiting the North Side lakefront actually became kind of annoying.
- Bookstores – Hyde Park is not a great place if you want to go out (a couple of places worth hanging are The Promontory and A10, but it’s slim pickings after that)
- University of Chicago – This place feels like Cambridge, or perhaps something out of Harry Potter. My wife went to medical school here, and I didn’t spend a ton of time on campus, but I always loved wandering the Midway Plaisance and the Neo-Gothic quad.
- Diversity – Hyde Park is the only place I’ve lived where I was in the minority. Grocery stores, restaurants, and even the elevator of my apartment building were way more diverse than anything I’d experienced before or after. It was a great experience living down there if only for that!
5. – My Friends
It’s all the great relationships I’ve made over these 20+ years that I’ll miss the most, of course! Looking back at my list of podcast guests makes me realize just how many great friendships have come about as a result of living in Chicago… and that’s just the bass-playing friends! I get choked up if I think about all the folks I know through playing gigs, my school jobs, and the friends that I still keep in touch with from college.
When I was starting out with the podcast and was relatively unknown, I would interview my bass buddies, so it made sense that these folks were Chicago-based. But the Chicago thread continued throughout my podcasting journey even as I started to branch out further. What has resulted is fascinating and quite public profile of the double bass scene in Chicago, and a collection of great moments from so many of my Chicago friends.
Here’s a chronological list of folks I’ve interviewed with some connection to Chicago:
- Andy Anderson – Lyric Opera of Chicago
- Phillip Serna – Chicago freelancer
- Bjorn Berkhout – used to teach composition at Loyola University
- Kate Nettleman – Minnesota Orchestra bassist who used to freelance in Chicago
- Greg Sarchet – Lyric Opera of Chicago
- Peter Lawson – former Chicago freelancer
- Eric Hochberg – Chicago-based jazz bassist (he and I play the podcast theme music together!)
- Weldon Anderson – Chicago freelancer
- Michael Hovnanian – Chicago Symphony (and my former teacher!)
- Rob Kassinger – Chicago Symphony (and my amazing colleague at DePaul)
- Peter Tambroni – Chicago-based teacher
- Brad Opland – Chicago Symphony
- Scott Rosenthal – former Chicago freelancer
- Mark Sonksen – Chicago-based jazz musician and luthier
- Hans Sturm – went to Northwestern University
- Steve Reinfranck – Chicago-based luthier
- Jerry Fuller – Chicago-based early music specialist, former Lyric Opera musician
- Ed Barker – former Chicago Symphony member
- Rufus Reid – attended Northwestern University
- DaXun Zhang – taught at Northwestern University
- Kells Nollenberger – former Chicago jazz musician
- Jeff Bradetich – taught at Northwestern University
- Dan Krekeler – played in Civic Orchestra of Chicago
- Michelle Fiore – former Chicago-based luthier
- Max Dimoff – attended Northwestern University
- David Cardon – former Chicago freelancer
- Matt Heller – attended Northwestern University
- Alan Steiner – Chicago freelancer
- James Knabe – former Chicago freelancer (trumpet)
- Doug Stuart – grew up in Chicago
- Alex Hanna – Chicago Symphony principal bass
- Larry Gray – Chicago-based jazz bassist
- Paul Ellison – attended Northwestern University
- Andrew Raciti – teaches at Northwestern University
- Ian Hallas – Lyric Opera of Chicago (and my former student!)
- Jeremy Attanaseo – Chicago freelancer
It’ll be interesting to see how the podcast changes as my focus shifts to the West Coast in coming months, but no amount of moving will ever knock the Chicago out of me–I’m hooked for life.