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I was feeling uncharacteristically hip. Somehow I managed to be in the right place at the right time — a skill that often eludes me. Specifically, I was sipping alfresco cocktails with friends on the IO Urban Roofscape at the Godfrey Hotel. I’m going to assume that IO is the new, urbane way to say “indoor-outdoor.” I’m always the last to find out about these things.

All around me were cute women in their 20s wearing short dresses and straightened hair. They were accompanied by sturdy, handsome men who I imagined to be hedge fund managers or up-and-coming vice presidents of something or other.


The Godfrey is a much ballyhooed posh hotel that opened earlier this year in the River North neighborhood. The Cubist exterior looks as if it could have been designed by painter Paul Klee, the sleek interiors could double as sets for a Smirnoff commercial.

Boston is getting a Godfrey of its own next year in Downtown Crossing. Fingers crossed we get our own IO. But as soon as I stepped out of this scene with a capital S and left the Godfrey, reality grabbed me by my spindly shoulders and shook me hard.

Just outside the Godfrey is a Hard Rock Cafe, a Rainforest
Cafe, and a mammoth McDonald’s. I have nothing against these establishments, with the exception of the Rainforest Cafe because I’m terrified of Tracy, the animatronic talking tree that inhabits the restaurant. My main complaint is that I can see these chains and others in nearly any municipality I visit.

Fortunately the Godfrey is also a quick walk to the Magnificent Mile (and a nearby burgeoning gallery scene). But I’ve spent plenty of time on the Magnificent Mile and in the city’s biggest tourist draws, so I was itchy to explore tucked-away neighborhoods beyond downtown. On a trip to Chicago more than a decade ago, I wandered around the then-emerging Wicker Park neighborhood. It’s now fully emerged and no longer gritty. Urban Outfitters, Aldo, G-Star, and American Apparel have all arrived.


Therefore my mission on this trip was to discover neighborhoods filled with dive bars, off-beat attractions, and locally-owned boutiques. Neighborhoods with names such as Pilsen and Logan Square meant little to me, so I spent a long weekend prowling these hamlets, all the while realizing I should have invested in shoes with better arch support.

Chicago gadabouts seem obsessed with trying to determine the city’s next hot neighborhood. The irony is that once a cool neighborhood becomes thoroughly gentrified, it’s no longer considered to be a hot spot (hello there, Wicker Park). This makes trendy neighborhoods a bit like geese: They’re cute until they grow up.

I questioned more people than a Gallup pollster to find hot spots on the verge. Relying on the kindness of strangers, I found myself in Pilsen, an arty neighborhood that has stood as the epicenter for the city’s Mexican community since the 1970s.

Lately, the Mexican restaurants have been joined by shops selling hip housewares, along with new bars and restaurants. I was wandering and starved when I found Dusek’s Beer & Board. The gastro pub is located inside a grand 1890s building called Thalia Hall. It’s modeled after the Prague Opera House. Dusek’s is the kind of place lorded over by bearded bartenders sporting skinny jeans and thick, tattooed arms. It also includes a bar in the basement that specializes in serving boozy punch, plus a concert venue on the top floor. The renovated space opened last year.


It joins the numerous taquerias and artist studios in the scruffy neighborhood. Pilsen is known for its murals. Grab a Divvy — a bike from Chicago’s bike sharing program — and ride the span of 16th Street to see some of them. I took a break from sidewalk prowling and biking at the National Museum of Mexican Art in Pilsen. The permanent collection ranges from fine art to folk art to ancient objects from the Mayan and Aztec empires. You can cover the museum in about an hour depending on your pace.

I spent more time poking around the stores than the museum (stop judging my philistine ways, please). There’s Chocolat, Revival A-GO-GO, Comet Vintage, and Modern Cooperative, a store that mixes mid-century vintage furniture with stationery and pillows. Modern Cooperative owner Mike Biersma, a man who sports what I believe to be the finest head of hair in Chicago, recommended I visit another neighborhood called Logan Square. If I’ve learned anything in life, it’s to trust people with good hair.

Logan Square mixes vintage with the new.
Logan Square mixes vintage with the new.city of chicago

Logan Square is a bit more polished than Pilsen. There are new shops and restaurants sprouting up between behemoth empty furniture stores. It’s become a haven for those priced out of neighboring Wicker Park and Bucktown. After a healthy walk from the main square I hit nerd pay dirt: the Logan Arcade. It’s filled with 25 vintage pinball machines and 40 retro arcade games. I played Ms. Pac-Man and Q*Bert, hit a row of old pinball machines, and ordered an adult beverage. It felt like the time I broke into my parents’ liquor cabinet and played Atari 2600 all night.


If you quiz enough people, or just explore, you’ll locate the gems in these areas. In Logan Square I found Wolfbait & B-girls, a store that sells all Chicago-made goods and fashions. When I complained that there were no men’s clothes, an employee pointed across the street to a newly-opened high-end men’s shop called Meyvn. Problem solved.

After a day walking under an unforgiving sun, I still didn’t have enough time to hit all of the burgeoning restaurants and record stores in Logan Square, although I did find the time to duck into a used bookstore to pick up “Kittens for Dummies.” Perhaps taking pity on a grown man buying this book, a friendly woman asked how my day was going (Midwest speak for “Are you normal, or should I fear you?”). I explained my quest to her, and she sent me back to Pilsen that night to check out the Skylark Lounge.

The Skylark was the dive bar of my dreams. There was even a photo booth. For the kids out there, a photo booth is a box your parents climbed into to take selfies and make out.


The burger I inhaled was divine. As I ate, I listened to two gents in their 20s talk about the discovery of a rare, unreleased Dolly Parton recording from 1977. The bartender snarled at them and turned up the cacophonous symphony of punk from his iPod.

On my third and last day, I had to start playing favorites. I still had a list of recommended neighborhoods to conquer: Ukrainian Village, Bridgeport, Andersonville, Noble Square, Humboldt Park, and Uptown. So I employed the most scientific method I could think of to make a decision. I wrote each name on a piece of paper, put them in a pillowcase, and drew a neighborhood. The winner: Andersonville.

Andersonville maintains its Swedish roots.
Andersonville maintains its Swedish roots. charles osgood/Getty Images

The Swedish-enclave of Andersonville, which still maintains its heritage, has become a haven for art galleries and antique shops. At one time there were more Swedes in Chicago than in any city outside of Stockholm. Therefore, as soon as I saw the Swedish diner Svea, I was sold. It’s such a homey space I felt as if I was sitting in my mother’s kitchen — that is if I had a mother who knew how to make killer Swedish pancakes rather than one with a penchant for burning waffles.

Andersonville’s answer to Pilsen’s National Museum of Mexican Art is the Swedish American Museum. It’s both an art museum and cultural center, although I was a bit disappointed by the under representation of Abba. Unlike Logan Square and Pilsen, Andersonville has the vibe of a leafy suburb. There are two dozen galleries and vintage shops. If you only have time for one, head directly to Brimfield, which has the look and charm of a Vermont ski lodge from the 1950s.

I’m ready to tour the remaining neighborhoods on the list for my next Chicago trip. The goal is to see them all before a jungle of Rainforest Cafes, and other corporate invasive species, start to overshadow the homegrown charm of these areas.

Christopher Muther can be reached at christopher.muther@globe.com. Follow him on Twitter @Chris_Muther.