Chicago is second to no city. A Midwestern mecca of corruption and suspiciously clean downtown streets, this town rose to greatness from nothing—not once—but twice.
Let's not forget the time the entire city burned to the ground, then casually hosted the 1893 World's Fair two decades later. No big deal. Disaster doesn't faze Chicago. We'll just keep on building shit and embezzling money until the problem either goes away or gets so big that everyone's forced to accept it.
You like to drink legally and without fear of being poisoned? Thank Chicago and its dastardly team of 1930s gangsters, who fucked up the whole Prohibition situation to the point where the country just up and made liquor legal again.
New Yorkers think we're nice, Midwesterners think we're assholes. We're probably a little bit of both, depending on the weather and current CTA delays. But you're gonna love it here, because everyone does.
NEIGHBORHOODS WE LIKE
Chicago is a city of neighborhoods, each with its 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 actually in 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" that overlap more than the Marvel universe's storylines. This is a lot to take in if you're new to the city, so I'm 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.
WHERE TO EAT
This is the Midwest. Our food is fried and greasy and cheesy and horrible for you and that's the way we like it. This is also a big city, so yeah, we have a predictable number of uber-fancy, molecular gastronomy monstrosities that consistently top every "Best Restaurant in Chicago" list month after month. This is not one of those lists. This is a list of the fried and greasy and cheesy and horrible for you shit, because let's be honest, if you're reading this, you can't afford a meal at Alinea, let alone commit to a reservation six months in advance.
Deep dish is king in Chicago, and it's delicious, OK? Chicago locals rarely eat it unless we're entertaining curious guests, but we still like it because it's a fucking cheese-filled pie. Yes, one slice is enough to keep you full and farty for days, but it's still a cheese-filled pie. No one is complaining.
But not all deep dish is created equal. By far the best in town is at Pequods in Lincoln Park, where the added touch of caramelized cheese on the crust sets it far above the rest. We can already hear all the Lou Malnati's fanboys calling for our execution, but we stand by the assessment. Lou's is legit, though, as is the pizza pot pie at the Chicago Pizza and Oven Grinder Co. and the stuffed pizza at Art of Pizza. If you're still not down with deep dish, try the floppy thin crust at Jimmy's Pizza Cafe in Lincoln Square. The white pizza is the stuff of legend, and the garlic knots have been known to trigger orgasms. Oh and Piece Pizza in Wicker is pretty tasty too.
Now this sandwich is a Chicago staple we actually eat on the regular, and any place that sells one also cooks up a mean Chicago Dog. Portillo's has to be mentioned as an option, and it's a good one, although definitely not the cheapest. Then you've got Al's Beef, which has locations all around the city, Jay's Beef in Wicker Park (try the grilled chicken sammy for a change of pace), and the South Side classic Tony's Italian Beef. Here's a secret, though: It's hard to go wrong walking into any hole-in-the-wall with a Vienna Beef sign hanging out front. The greasier, the better.
Burgers are a national pastime and Chicago is no exception to this rule. Kuma's Corner in Logan is the metal bar/burger joint mashup of your fatass rocker dreams. Go early or expect to wait, but it's worth every impatient minute. DMK Burger Bar is heaven in your mouth and if you don't order a milkshake and the parmesan truffle fries, we're not friends anymore. Au Cheval is bougie and the line is long but oh my God. Just go, you'll see.
Then there's Big & Little's, which is so much more than a burger joint. You may have seen human sea anemone Guy Fieri snarfing down the foie gras fries (which are underwhelming and like $30) on TV, but you gotta get the porkbelly po'boy. Or the lamb gyro burrito. Or literally any of the tacos. They also deliver. You're welcome.
Look, this is a giant city. There is a lot of food. It doesn't all fit into neat little categories. Visit these places and your tastebuds will thank you. Your muffin top too.
Crisp sells out-fucking-standing Korean fried chicken and rice bowls. Get the Foodie's Choice sandwich and Seoul Sassy wings, and make sure you wait until after you pay to ask for extra Alison's Atomic sauce to go or they'll charge you $0.50 for each (which is bullshit because you can get it for free when you eat in, but whatever). You're gonna want extra. Trust us.
Tango Sur is an affordable and unreal BYOB Argentine steakhouse. Think giant piles of meat and actual serving platters filled with molten broiled cheese and peppers. Bring all the wine, order all the food. Then waddle home, go to bed, and eat leftover steak sandwiches for the next six days straight.
Honey Butter Fried Chicken literally serves fried chicken with a side of honey butter. It's glorious.
Carbon's steak tacos will change your life, the red pepper sauce will end it, and the crack chips and guac will raise you from the dead.
Yes Thai is incredible. When someone proclaims a particular Thai restaurant to be the best in the city, it's usually because it's across the street from that person's apartment. This is probably not across the street from yours, but you should take the trip up to Ravenswood for the ground pork crazy noodles anyway. The duck pad Thai is also amazing. So are all the curries.
Cafe Ba-Ba-Reeba! sells tapas and strong sangria. Take your mom here and have her buy you everything because it's all so good.
Leghorn is home to what is easily the best fried chicken sandwich in the world. You can customize it to your liking and get it on a warm flaky biscuit or a soft burger bun. Either way is delicious and the umami fries are nothing to sniff at either. Also: fried pork skins.
Irazu has inexpensive Costa Rican goodness and it's also BYOB. Like, you can bring your own liquor and they'll make drinks for you. If you think that's exciting, you should try the sandwiches.
Valois is a cash-only cafeteria-style Hyde Park staple. President Obama was a regular back in his HP days, and if you want to eat like the leader of the free world, there's a separate menu listing all his faves. Barry's into the steak and eggs and the Mediterranean omelette, but anyone who's eaten here will tell you all the food is up to presidential par.
The Duck Inn offers an upscale cocktail bar option in Bridgeport with a savory menu to boot, if you're into all things duck (think sticky duck wings in a sweet Asian glaze and a full rotisserie bird—BRB DROOLING) and drinks, you won't go home unhappy.
Yassa African Restaurant is a Bronzeville eatery that specializes in traditional Senegalese cuisine, a genre of food that's hard to come by in Chicago. The (mostly-meat based) food is packed with flavor, the waitstaff is friendly and it's BYOB so, like, why aren't you eating there right now?
But speaking of drinks...
WHERE TO DRINK
One thing we've always appreciated about the city of Chicago is how acceptable it is to be drunk in public at all hours of the day. Grocery store chains legitimately offer wine bars and outfit their carts with fucking glass holders so you can get wasted with ease while you buy cereal. This is Chicago and we have a God-given right to drink wherever and whenever we please.
Day drinking isn't just tolerated, it's downright encouraged—just remember the unspoken rules: No puking, no punching, no unsolicited ass grabs. Screaming incoherently is fine so long as it's about the weather, the Cubs, or Rahm Emanuel. But for the last time, no, we don't want a shot of Malort because we are human beings and not sentient trash disposals.
This prominent drinking culture means there are thousands of great places to get drunk in the city, so this is not an exhaustive list by any means. These bars are for the most part years-old Chicago staples that feature pool tables, jukeboxes, big booths, and occasionally craft cocktails. These are the bars to go to if you want to have one of those intense 2 AM heart-to-hearts with a stranger. If you want live music, keep scrolling.
Basically everyone can agree that "lesbian karaoke dive bar" is by far the most beautiful phrase in the English language. In addition to being the physical embodiment of these four words, the drinks at Spyner's are strong, the bartenders are sassy, the regulars are kooky, and the line for karaoke is never too long. The negative Yelp reviews are often straight, white dudes complaining about how lesbians get better service which, in our opinion, is always the mark of a good bar.
The Violet Hour
This place is classy as fuck. There's no sign, because of course there isn't, and the entrance is a hidden door on the ever-changing mural adorning the wooden building across from Big Star. Inside it's all velvet curtains, $13 craft cocktails that taste otherworldly, and delicious appetizers you can share with your table of fancy friends. The "house rules" card they present you with is just pretentious enough to make you feel superior to everyone in the line of shivering, well-dressed fools waiting to get in. You made it. You're here. It's happening.
Craft beer bar in the front, bump n' grind dance party in the back. The front bar's got a pool table, 16 different beers on tap, and a jukebox full of live-recorded rock songs, but the back bar is a world of its own. Expect steamy, sensual grinding to classic R&B hits, and plenty of sweaty singles to rub up against. We don't want to put too fine a point on it, but if it's been awhile since you got laid, this is gonna be a good place to remedy that situation.
A loud grungy metal bar with ample pool tables, video games, and wall-to-wall murals. It also features a photo booth and a 4 AM closing time, so things tend to get sloppy in the best way possible.
Maria's Packaged Goods & Community Bar
Part liquor store, part local tavern, this place is a perfect mixture of spooky (it features an unsettlingly large doll collection) and dive-y, and the bartenders know their shit. The beer selection is wide and varied and rotates in and out frequently. It's not huge—get ready to make some new friends while squished up against some strangers waiting for a drink—but there is a pretty sweet patio situation in the summer.
The Broken Shaker
Located inside the Freehand Chicago, this bar/lounge is basically a Wes Anderson movie set come to life. The cocktails are dangerously strong and tasty, the vibe is quirky chic, and the crowd is young and exceptionally chill given the River North location. Plus, if you drink too much, you can just book a cheap room upstairs and sleep it off.
Chicago is a Polish town, and this is a damn good Polish dive. It's got it all: the classic dive bar smell, dirt cheap drinks, a bumping 90s selection on the jukebox, pool, and the occasional free shot if you speak Polish. If not, try to keep up anyway and befriend the regulars, who tend to be a tough bunch of rowdy older Poles.
It is cash only and rarely packed, and it's a great place to take anyone you've just started dating to test his or her street cred. If he or she can't handle the vibe at Zakopane, how is he or she going to handle your naked body? Probably not well.
Think back to the person your childhood self imagined you would be as an adult. A person who actually has his or her shit together, who can taste the difference between various kinds of beer, who has a group of smart and interesting friends who meet up and smile knowing, adult smiles at each other at least once a week.
You are probably not that person, but hanging out at Hopleaf will make you feel like you are for a brief, shining moment. It's got high ceilings, lots of light, a wood cabin vibe, a vast international draft beer selection, a sweet summer patio, and fucking delicious food. Another major perk is that, although it is a top-notch eatery, absolutely no one under 21 is allowed, so no screeching babies or surly teens can salt your drinking game.
Town Hall Pub
This dive haven is smack dab in the middle of the Boystown club cluster and a godsend for anyone who needs a momentary break from the MDMA mayhem but doesn't want to stop drinking or doing drugs (the bathrooms are singles). Town Hall almost always features a drink special that's reminiscent of your college house party days—think jello shots, pudding shots, and vodka gummies. The jukebox is bumping, everyone sings along if you pick a banger, and the photobooth offers enough weird framing options to fit any occasion.
Big Chicks is brunch haven Tweet by day, and a gay dance party bonanza by night. When the sun is out, the food is heavenly, the bloodies are on point, and the coffee is strong AF. But the real fun begins when darkness falls: With Bear nights, monthly trans and genderqueer raves and queer musical events, this is always a great place for LITERALLY ANYONE to get his or her drank on.
Essentially three different bars for the price of one, Matilda is a good place to go if you've got a big group of friends with different drinking styles. The front bar's got a neighborhood restaurant vibe and great food, the side is dark and intimate, and down a set of dangerously steep steps is a party bar reminiscent of the classiest frat basement you can imagine. The DJ spins classic 80s/90s/00s hits all night, and the crowd (who are all over the age of 23 due to Matilda's entrance requirements) happily grind all night.
WHERE TO LISTEN TO MUSIC
Chicago is bursting at the seams with music, and it's hard to walk a mile without being subjected to an impromptu concert. There's music on the street, music on the El platform, music blasting from the phone speakers of the guy sitting next to you on the train who doesn't seem to realize that headphones are a thing. When it comes to venues, take your pick. Every neighborhood has one it's famous for, and whether the show of the night is an international dubstep DJ or a local indie band, you'll find plenty of space to "dance like nobody is watching."
Kingston Mines has been nurturing Chicago blues legends since it first opened in 1969, and with two stages, strong drinks, floor to ceiling murals, ample table space and lots of room to dance, this place is still bumping every night of the week. It's also a foreign tourist hotspot, which sounds like a bad thing until you're taking 3 AM shots with a 45-year-old Japanese homemaker, an Irish grad student, and the CEO of an Australian surf company.
The Vic has an old theater feel with a modern twist, ethereal lighting and plenty of space. On nights without shows it hosts a Brew & View featuring new movies. Admission is $5 and there's always plenty of beer.
This cash only, intimate venue has a bar in the back and a pool table/photo booth in the front. There's always an eclectic lineup—from big names to obscure local acts—and while the crowd depends entirely on who's headlining, there's dancing to be had seven nights a week.
A sophisticated space with big names, good beer, and great acoustics. The only downside is the proximity to DePaul which can occasionally bring out the messy college crowd, but they card hard so it's rarely an issue.
Schubas is under the same ownership as Lincoln Hall, which means the sound quality is top notch and the lineup doesn't disappoint. Other than that, they're two very different venues. Schubas gives off a grittier vibe than its Lincoln Park sibling, and is intimate without being claustrophobic. Lolla after parties here are honestly more fun than the festival itself and if you go during the day, the brunch menu is on point.
A great view of the stage no matter where you're situated, perfect sound, diverse crowd, and beautifully cheap drinks.
Less than a block away from Kingston Mines, this place plays the same old school blues in a much more intimate setting. It's usually packed to the brim on weekends but the music is well worth the squish, and the folksy decor is straight out of the 70s.
TOURISTY SHIT FOR THE NON-TOURIST
Conventional city wisdom will have you avoid all touristy areas at all times, and while there's something to be said for not paying $22 to wait in line for three hours at the Sears Tower, sometimes it's fun to play tourist whether you are one or not.
First of all, get drinks at the Signature Room—the Willis Skydeck is lame, but the Hancock Tower has a bar/restaurant at the top that you don't have to pay or wait in line to visit. The drinks are expensive and the bar food isn't great (brunch is another story), but the women's bathroom has the best, most Insta-friendly view in the city. Snap a shot and watch the likes roll in.
Then, pick a museum, any museum. If you think museums are boring, you are either six years old or in dire need of a cultural education. Guess what? You can find just that at the many museums around the city, most of which have free days. Joy to the world.
The Art Institute is great for a #meaningful date and the cafe is delicious. Take lunch outside into the courtyard on a sunny day and pretend you're vacationing in Europe. The Shedd Aquarium is fun if you're stoned or accompanied by little children (or both), and the Museum of Science and Industry is worth a trip down to Hyde Park because it has a giant mirror maze!
Hang out in Millennium Park. In the summer, there are free concerts, movie nights, and yoga pop-ups every day of the week. Bring a blanket and a cheese platter, or do some weird drugs and lie on the grass, lost in the splendor of outdoor music. In the winter there's a free ice rink in the shadow of the Bean, which is—incidentally—the best place in the city for a skinny selfie. Hello big head and seemingly-emaciated body, you're looking good.
Go to the beach! There are so many beaches. You should get well-acquainted with them all. North Avenue Beach is always a shit show of teenbros, illegal drinking, and impromptu volleyball. Montrose is a less-crowded party beach with a slightly older crowd. Oak Street is small but packed with coolers and both male and female Viagra Triangle regulars—lots of fake boobs and spray tans. Fullerton has a more laid back family/college vibe. 57th Street is peaceful, scenic, and clean. So is Foster. The list goes on. Find your favorite beach and throw down your beach blanket. Don't forget the sunscreen or the whiskey flask disguised as sunscreen.
Also, bike along LSD or the 606. Both are easy, scenic routes, and biking is good for you, dammit.
Crawl through some art. The Flatiron building in Wicker Park has an art crawl on the first Friday of every month, and a lot of the artists in the building give out free wine and beer to encourage drunken purchases, and while free alcohol is always cool, free art shows are even cooler. If you need a similar event for the second Friday of every month, check out the Second Fridays Gallery Night in Pilsen.
While Chicago's got all the obvious spots to help you stock up for your next haul video (think Michigan Avenue, Watertower Place, and State Street in the loop), designer chains only scratch the surface of the city's (often bizarre) shopping scene.
A vast and beautiful clusterfuck off Howard in Rogers Park that's part costume shop, part antique store, and part hoarding grandma's basement. Lost Eras is a terrifying labyrinth that starts out in a sunny, well-windowed room and continues on for what seems like miles through a maze of masks and puffy skirts, into a musty basement with five-foot ceilings. Costume rentals are available if you find something dope but expensive. Go with at least an hour to kill because this place can take you down some weird rabbit holes—like, actual rabbit holes. The corner of the basement made up of nothing but giant costume rabbit heads with buckteeth and dead eyes.
A geeky knick-knack shop with an art gallery in the back, this place is the answer to the question, "What should I get my nerdy boyfriend/girlfriend for his/her birthday?" You'll find something for him in the sea of pop culture collectibles and weird little toys.
A funky Wicker Park vintage shop so steeped in 90s nostalgia that it could legitimately be a forgotten Nickelodeon Studios gift shop. Advocates of the all-black-everything approach to dressing may be hard-pressed to find an outfit that suits them in this veritable explosion of color and neon pattern, but that's their loss. Rainbow is the new black, and this place is ON IT.
This amazing Pilsen vintage shop is straight out of a mid-century pinup dream, and the owners are the best. Let Carlos give you the once over and he'll come back with an arm full of retro shit that fits you like a glove. If you've ever watched Mad Men and thought, "Damn, I wish I could be Christina Hendricks," you can. All you need is a red wig, two water balloons, and a half-hour at Knee Deep.
The Brown Elephant consignment shop has the power to read your mind and make things you didn't even know you wanted appear in front of you. Looking for a solid wood dining room table and chair set? It's here for a cool $75. Have a vague idea about a Versailles-inspired end table for your bedroom? This place has three to pick from and they're all casually under $30. With two locations and a constantly rotating selection of clothes, furniture, and housewares to browse, this place is heaven on earth, especially if you just moved into a new place.
Reckless has been around forever. It has a great selection of vinyl, CDs, and DVDs, and three different locations around the city. They're famous for a reason. Go check them out.
We'll know you're a n00b if you ask "but which way is north??" after we give you directions. We talk in four directions here, and we always know which way we're facing. Get a compass or remember the lake is always east, because the streets are long, and the difference between 3030 N. Halsted and 3030 S. Halsted is about eight miles and two hours of hassle. Once you've got that down, the city is actually pretty easy to navigate.
We have a love/hate relationship with the Chicago Transit Authority, but we can't hate too hard on a system that gets us to work every day, even if we're always 15 minutes late. If you're waiting for a train during rush hour and one pulls up with an empty car, it's not your lucky day. Someone took a shit in there and it smells. If an old man or a pregnant woman gets on your bus and you're sitting in one of the handicap seats, get up and stand or be prepared to have six different people yell at you until you do.
No one asked for Ventra, but the new app is actually a godsend. It will tell you when your card balance is getting low and allow you to top it off at the bus stop. Also download the Transit Stop app, which gives you bus/train arrival times so you don't need to leave the warmth of your apartment until you absolutely have to.
This is the cheapest/healthiest of all your transportation options, and it's not a bad bet in the summer, spring, or fall. Chicago's a pretty city and is fun to traverse by foot as long as it's not icy or 900 below. Some caveats: Don't text and walk and expect not to die a violent death, because you will. Don't walk at a glacial pace on a crowded sidewalk because this will make people in your wake hate you with a passion that consumes their entire being. Don't assume that car is going to stop for you just because you're in the crosswalk. It's not going to stop.
These look really, really lame but are actually utilized on a daily basis by people who aren't tourists. Obviously if you're going to rent one please follow all the rules of the road and don't ride on the sidewalk or on the wrong side of the street unless you want to be hit by a car or shoved off your bike by a sassy old woman.
Get ready to hear an earful from your driver about how dangerous and illegal Uber is, and remember to give him a good tip because his business is legitimately being stolen by Uber drivers. You can catch a cab on the street downtown at all hours, but make sure you have a vague idea of where you're going because you may need to give directions.
It's probably going to be the death of the traditional taxi industry, but Uber's rate in Chicago is insanely low. Like, if a cab ride home would normally cost you $18, taking Uber X instead means you'll be paying $12. If you take Uber Pool, it will probably be somewhere around $8–9. For the same ride. It's really hard to justify taking a cab when Uber is this cheap and convenient.
Lyft is cool too, but it's a little more expensive and not as fast because there aren't as many drivers. That being said, if there's any kind of surge pricing, taking a cab is almost always going to be the cheaper option. You might think you can do math when you're drunk, but you can't, and that's why you paid $150 for your two-block Uber home on New Year's Eve.
Special thanks to Caroline Thompson for compiling all recommendations.