My relationship with Chicago is probably my most forgiving relationship. If I could choose, I would live in a place where you could hike on the weekends, somewhere quieter and smaller where houses have yards, maybe down South where winters aren't as long (a city in North Carolina perhaps?). But Chicago is home, one that I both complain about and defend. It's a complicated, loving, real relationship.
At times, it's easy for me to find its allure. Things are happening in this city - not as much as in New York or LA - but the art scene is expansive, stimulating, and inclusive. Its tree lined streets, bungalows, and lakeshore add to its charm. Even though the land is flat and fairly unexciting, there are some nice Midwest hideaways like lakehouses in Michigan or farms in rural Illinois or Madison, Wisconsin. And the advantage of living in a big city means that no matter how long I live here, there are always pockets I stumble upon that I never knew existed before.
I've wanted to do a guide to my hometown in this space forever so here it finally goes...
The Lake - Lake Michigan is the largest piece of natural beauty in the city. Head to the lake shore for a run, a walk, or a bike ride. Sit on its concrete steps with a glass of wine or in the grassy areas and read. It is by far my favorite place in Chicago and a must-see if you come visit.
iO - The second best place in the city. Every night hosts multiple improv shows. I tend to go on Wednesday nights when the shows are free and the lineup hosts two of my favorite improv groups (Carl & the Passions and the Virgin Daiquiris). Bonus, the new location is right across the street from Chicago's largest Whole Foods, which is indulgent and obnoxious and really fun.
Millennium Park - The Art Institute, the Bean, the Pritzker Pavilion, and Maggie Daley Park all sit nestled together in the loop. Even if it is a debt-ladened endeavor, like most Chicago ventures, it is well done. The Bean never fails to amaze me, the Art Institute is my favorite place to spend an afternoon, and the Pritzker Pavilion (an outside concert venue) has movies in the park and live music during the summer. Everyone comes to gather in the pavilion after work and picnic on the grass with wine and cheese on warm days.
The Green Mill - The Green Mill is an iconic jazz bar that keeps its crowds small and always makes for an enjoyable night out. For other nightlife options, I've been meaning to check out Rosa's Lounge, a blues bar in my neighborhood. For dancing, I love Berlin, which (as yelp puts it) has "a diverse, no-attitude, all-orientations crowd on the dance floor." I recently discovered CumbiaSazo, a monthly dance party in Wicker Park that plays cumbia and other Latin music all night long, and Beauty Bar hosts nineties themed dance parties that are popular. Chicago has an endless amount of dive bars; for example, Delilah's, Rainbo Club, the California Clipper and Happy Village. I could really keep naming bars forever. Board games at Guthries Tavern in Lakeview is a favorite as well.
The Music Box - There are many movie theaters in Chicago that I love but for a visitor, the Music Box is the best. The theater plays Godard films, midnight showings of Jurassic Park, Sound of Music sing-a-longs, and other foreign films and cult classics. It touts itself as "the year round film festival", hosts a live organist at some showings, and is Roger Ebert's favorite.
Museum of Mexican Art - The Museum of Mexican Art in Pilsen is a nice contrast to the modern, white walls of the Art Institute. Though its a small neighborhood art museum, it hosts impressive exhibits. An added plus is that afterwards, you can wander down 18th Street for pupusas, cheap tacos, Mexican hot chocolate or take a walk through the neighborhood to look at the murals that line its side streets.
Devon St. - Devon Street is a ten block stretch of Indian, Pakistani, Iraqi (though mostly Indian) restaurants and shops. It's a wonderful example, as one of my professors said, of a non-gentrified, thriving commercial corridor. Its full of languages and aromas. For my birthday last year, I came here with friends for a dinner and bought a mortar and pestle that sits in my kitchen, beautiful and unused.
Chicago Neighborhoods - Chicago is broken up by neighborhoods, with each one deviating a little from the next. Head to Wicker Park for a strip full of record stores, book stores, and vintage clothes. Logan Square has amazing bars and restaurants (I recommend Lula Cafe for brunch and Longman and Eagle for dinner). Andersonville feels like a quaint Michigan town and Pilsen, noted before, has wonderful murals and Mexican restaurants and cafes. I spend most of my time in those four neighborhoods but Chicago is big and endless so there's a lot to explore.
Here's to hoping you do.