Chicago is a city of neighborhoods, each with their own distinct culture, nightlife, and colorful lamppost banners. But the names and borders of these mini-cities are a topic of hot debate. You might think your favorite bar is in Wicker Park, but as your pretentious upstairs neighbor will gladly inform you, it's actuallyin Bucktown if it's north of the 606. Your bad, bro. Do better next time.
The "Neighborhoods in Chicago" Wikipedia page alone lists more than 200 'hoods and so-called "community areas" which overlap more than the Marvel universe's storylines. This is a lot to take in if you're new to the city, so we're just gonna cover the basics.
A city-sanctioned gayborhood set up next to Belmont harbor, the typical evening out in Boystown is almost certain to end in pure debauchery. By day, you could be fooled into thinking this section of the city is just another upscale hipster enclave: cozy million dollar brownstones line the side streets, boozy brunch options abound, and hoards of beautiful men spend their afternoons walking adorable dogs past high-end, modern-concept coffee shops. But by night, the neighborhood is transformed into a square-mile rave. The shots flow freely, the dubstep remixes blast from every club on Halsted Street, and statuesque drag queens strut from bar to bar in gorgeous groups.
There's no such thing as "having a couple drinks" in Boystown. You will inevitably make some random besties at the bar and stay out until 4 AM dancing with your reflection in Berlin's mirrored walls. Please refrain from having sex in the one-stall women's bathroom at Roscoe's because the line is long enough as it is. We can see your feet, god dammit, you're not fooling anyone.
If it's summer festival season (think Pride and Market Days), going out in Boystown is usually a recipe for a 48-hour blackout binge. You've been warned.
Wicker gets a lot of hate for being the hipster center of Chicago, and while this area may be all but overrun with artisan donut shops, vegetarian restaurants, overpriced clothing chains, and skyrocketing rental prices, it's also home to some of the best bars, restaurants, and musical venues in the city. Go see a show at Double Door, and stay out late playing pool and smoking in the back at the dive-y Nick's Beer Garden.
Brunch options here are plentiful and delicious, and if your friends are in town, you can take them on a stroll past the fancy Victorian mansions situated around the park, or waste an afternoon getting lost in the organized chaos of Myopic Books. Sure, you might run into more than a few cynical 20-somethings wearing glasses they don't need and complaining about the gentrification they are an integral part of, but this is urban America in 2016. What do you expect?
River North is the worst. Like, the actual worst. OK, yeah, it's pretty with all its luxury high-rises, startup offices, and AVEDA salons, but let's be honest: River North is where you go when you want to get into hour-long arguments about the validity of global warming with a 45-year-old drunk finance bro who believes the environmental movement is a Marxist plot.
It's where you go when you want to be barred from entry to an overpriced lounge for not wearing a dress shirt or heels. It's where you go to see Brody-fucking-Jenner play a DJ set. And yet, it's also where you should go when your parents are in town and you want to drop a shit-ton of money on the best meal you've ever had at one of the million high-end restaurants in the neighborhood. The food is all so good and so expensive and as long as you keep your dealings in this area limited to parent-funded dinner consumption, you should be fine.
This South Side neighborhood is awash with colorful street art, superb vintage shopping, and the best damn Mexican food in the entire midwest. Pilsen is a beautiful melting pot of Mexican-American business owners, young students, and aspiring artists. Make no mistake, gentrification is coming and it's not cute, but for now rent is still relatively cheap and national chains are comparatively hard to come by. Grab a giant Mexican pastry at the self-serve Nuevo Leon Bakery and take a long walk around to do some mural peeping. Stop into Pinwheel, 18th Street's newest record store, for some retail therapy, check out the National Museum of Mexican Art for even more artsy goodness, and when you get thirsty, Skylark is a good (cash only) stop for craft beer, pierogies, and live music.
Uptown is a gritty and diverse mishmash of cultures, a place where a Target can exist on the same block as the head shop Smoke Dreams, which proclaims itself to have "Chicago's Largest & Finest Selection of Tobacco Accessories" (debatable). Uptown isn't the fanciest of neighborhoods, but what it lacks in bougie bullshit it more than makes up for in authentic Vietnamese cuisine, sprawling and cheap vintage apartments, former speakeasy jazz clubs, and close proximity to both the CTA Red Line and some of the city's best beaches.
Argyle Street is the place to go for pho, bahn mi, and all other delicious Vietnamese eats. The infamous Green Mill Cocktail Lounge, once owned by Al Capone's BFF, the casually nicknamed "Machine Gun" Jack McGurn, is still a hot spot for live jazz, poetry slams, and extra-strong drinks.
Wicker Park's chill stoner sister, Logan Square, is probably where your drug dealer lives and where that indie drummer you boned last weekend works as a bartender. The busy streets are filled to the brim with fixie bikers of all shapes and sizes, and locally-owned coffee shops, bars, and restaurants are a dime a dozen.
The wide, tree-lined boulevards are perfect for an early afternoon bowl-walk, and at night, Logan's music scene is grungy and loud. For cheap eats/drinks, try out the PB&J special at the Boiler Room to get drunk and full very quickly—$8.50 buys you a PBR tall boy, a shot of Jamo, and a slice of pizza. And while it's cash only, you'll get another free Jamo shot on the house if you show the bartender your ATM receipt.
Starve yourself for three days then go get some cheap-ass dim sum and revel in your happiness/impending obesity. Chicago's Chinatown is of course significantly smaller than its counterparts in NYC and SF, but it's still a fun day trip, and while you'll have to head over to nearby Bridgeport for a dive bar scene, karaoke options are plentiful even within the confines of Chinatown proper. This small subset of the city has something for everyone unless you're a psycho who hates Chinese food, adorable knick-knack stores, and the glory that is private room karaoke.