What are the fastest entry points into another neighborhood's culture in Chicago? Architecture, food, and street festivals, I suppose. Except that street festivals are too often jokes, staged by the same companies with the same food and bands. That leaves architecture and food, and for me there's no better weekend to combine the two than this coming one, when the Chicago Architecture Foundation's third annual Open House Chicago opens interesting architectural sites to the public on Saturday and Sunday.
Most of the traffic hits sites located downtown (including a number of architects' offices, not surprisingly), and there's nothing wrong with that except the occasional long line. But for me the real fascination is getting out to far-flung neighborhoods and discovering the secrets hidden in plain sight, from industrial buildings to old theaters to art deco swimming pools in apartment buildings that look like they walked out of a Fred Astaire and Ginger Rogers musical.
Food isn't officially part of the tour, but if you're in a neighborhood you don't normally visit, why wouldn't you go check out somewhere unique and reflective of the local culture to eat? Here are some recommendations of the sites I've enjoyed most, followed by a few dining suggestions for each, focusing on lesser-visited neighborhoods (I assume you know where to eat downtown or in Lincoln Park). The full list of sites is here, and note that some are Saturday or Sunday only, so plan accordingly—and I recommend printing out addresses, because the site has a tendency to bog down with heavy use during the event.
Bridgeport/Back of the Yards
With little remaining of the old stockyards, the lineup is mostly modern reuses of the area, including the Zhou B Art Center and the food business incubator the Plant, though you can evoke the neighborhood's Lithuanian past at Holy Cross Immaculate Heart of Mary Church. Have a royal pie at Pleasant House Bakery, classic Chicago joint food at Johnny O's, or upscale brunch at Nana.
Garfield Park/North Lawndale
The old Sears plant (including the original Tower and the power plant that's now a high school) are the main attractions, but also see Our Lady of Sorrows Basilica, a massive Italianate church which used to draw thousands every Friday night for a saying of the Rosary—which was broadcast on the radio. There's not a lot of food in the immediate area, but Ruby's Soul Food (the former Edna's) isn't far away, or Mary's BBQ for rib tips to go.
While others line up for the Robie house, you can see the wonderful Art Deco Powhatan Apartments, the KAM Isaiah Israel synagogue, and the freshly restored Hyde Park Bank. Matthias Merges hasn't opened his places yet, so your Hyde Park dining choices remain the likes of Cedars for Middle Eastern or the grocery/deli Zaleski & Horvath on 47th.
Pilsen has fewer destinations than you might think, mostly churches, though the freshly restored Thalia Hall/Dusek's is on the list. On the other hand, Pilsen has more dining choices than almost anywhere, mostly Mexican, of course (I like La Cebollita and Carnitas Uruapan), but also places like Take Me Out for chicken wings.
Old mansions, needless to say, plus the Gothic revival Second Presbyterian Church; for food try Panozzo's Italian Market or good south side pizza and pierogi at Flo & Santos. Chinatown, though not on the list this year, is close by.
New this year, Pullman opens up its Hotel Florence, the Greenstone Church (rare green limestone) and more. It has few food options, though, so make it a twofer with South Shore and then you can have soul food at Soul Vegetarian East and St. Rest No 2 Country Kitchen, or barbecue at Lem's.
Rogers Park/West Ridge
A fine Frank Lloyd Wright residence (the Emil Bach House), Catholic art deco at St. Scholastica, and another apartment-building swimming pool that will make you want to get on the waiting list immediately. All of Devon's Indian food is nearby, from grilled meats at Khan BBQ to vegetarian at Udupi Palace, or enjoy terrific coffee, good paninis and homey Ethiopian food at Royal Coffee.
See The Green Mill in daylight; the vault of the Bridgeview Bank; Essanay Studios, where Chaplin once worked; and the abandoned and decaying Agudas Achim North Shore synagogue. Get banh mi sandwiches at Ba Le, barbecued pork and duck at Sun Wah and bright Vietnamese soups and noodle dishes at Nha Hang, all on or near Argyle.