Billy Goat Tavern, 430 North Michigan Avenue » Few places embody Chicago—the tradition, the history, and the deep-seated love of greasy food and free-flowing beer—better than the legendary Billy Goat Tavern, a 75-year-old dive bar located on the subterranean level of North Michigan Avenue. Founded by Chicago legend William Sianis in 1934, the Billy Goat gained citywide notoriety through a series of publicity stunts: Most famously, Sianis refused to serve Republican patrons during the 1944 Republican National Convention in Chicago.
In 1945, Sianis tried to bring his pet goat to game four of the Cubs–Tigers World Series at Wrigley Field. (The Cubs refused to admit the goat and went on to lose the game and the series; diehard locals rue the “Curse of the Billy Goat” to this day.) Later, the tavern was immortalized on Saturday Night Live, when John Belushi furiously shouted the signature dish (“Cheezborger! Cheezborger! No fries, cheeps! No Pepsi, Coke!”) at unsuspecting patrons.
But no restaurant survives on publicity alone, and the Billy Goat still ranks among the best places in town to meet some friends, throw back a couple of Old Styles, mingle with disgruntled journalists who have escaped the nearby Tribune building, and catch the Cubs game. (312) 222-1525 (by Justin Sink)
Bongo Room, 1152 South Wabash Avenue » Right off the Red Line Roosevelt stop, this popular brunch spot serves breakfast foods so indulgent they’re practically the adult equivalent of Cocoa Puffs. And it’s an easy enough trip to the South Loop that, before the morning-after drunkenness turns into the morning-after hangover, you’ll have a cup of coffee and a glass of orange juice in your hands. So skip the Cocoa Puffs (don’t worry, we know you still eat them), and hit up the white-chocolate-and-caramel-covered pretzel pancakes.
If that sounds like slightly more sugar than you’ve consumed thus far in your life, and you would prefer to keep it that way, check out the chicken and pear club sandwich, with gorgonzola, tomato, and cranberry-pecan aioli. It’ll be enough food to keep you going for a full day of downtown adventures—or a Sunday afternoon in the Reg. (312) 291-0100 (Ella Christoph)
Cafecito, 26 East Congress Parkway » Cafecito is Spanish for a shot of espresso with a teaspoon of sugar; literally, it means “little coffee.” It’s a misleading title, not because Cafecito’s cafecito isn’t superb, but because it doesn’t even begin to get at the delicious depths of their solid offerings. It’s almost impossible to choose just one of their 19 pressed sandwiches—do you want to get the classic Cubans, with roasted pork, ham, swiss, pickles, and mustard, or feel like you’re skipping town for Cuba itself with the Ropa Vieja (slow roasted skirt steak, sweet plantains, black beans, tomato creole sauce)?
The most expensive sandwich on the menu at $5.99, it’s a deliriously cheap getaway. The budget and vegetarian-friendly Timba, with guava and swiss cheese, is just $3.59, making you wonder why anyone goes to Subway anymore. Even at lunchtime, when it’s packed to the brim, employees take your order in line and bring the food to you while you sit in one of their cozy chairs.
Despite their efficiency, Cafecito has the laid-back feel of Latin America, and you’ll be tempted to stay there as long as they’re open (7-9 Monday through Friday, and 10-6 on the weekends). Get started early — they stop serving the breakfast menu (huevos chimichurri, huevos chorizo, throw in a café con leche) at 11. (312) 922-2233 (Ella Christoph)
Captain's Hard Time Dining, 436 East 79th Street » Captain’s Hard Time Dining does not cater to those with hang-ups about food sanitation. The paper napkin is likely to be the one piece of your place setting not encrusted with food from previous diners, but if you’re willing to call such oversights “charming” rather than “health code violations,” there’s something special in store. While the offerings are mostly standard—eggs and sausage for breakfast, sandwiches for lunch, basic cuts of chicken and beef for dinner—Captain’s nonetheless operates at the outermost edge of the greasy spoon category, pressing the limits of what’s acceptable to fry, butter, or bread.
Sides of supposedly “fresh” broccoli and other greens invariably arrive sopping with butter and oil, so instead of beating around the bush, just order the “fried and battered vegetables.” Breads, whether biscuits, pancakes, or rolls, come so thoroughly pre-buttered you’ll want to wring them out. Fried meats aren’t simply fried: They’re “butter fried.”
In the Captain’s estimation, no dish is so refined that it wouldn’t benefit from a slice of bacon, a side of ranch, or a few onion rings—and mostly, he’s right. True, eat here regularly and you’ll follow up the freshman 15 with the sophomore coronary, but as an occasional treat, there’s no topping the delicious excess of Captain’s Hard Time Dining. (773) 487-2900 (Jordan Holliday
Earwax Café, 1561 North Milwaukee Avenue » This trendy, colorful diner is the perfect way to begin (or end) a day of shopping and general hipster-ing in Wicker Park. Make sure you arrive before you’re starving, though, because the wait is a killer if you’re already exhausted. But the food is worth it, with breakfast served all day and a menu of vegetarian and vegan options that won’t stifle carnivores.
Finding a restaurant even close to affordable is a challenge in this neighborhood, but Earwax manages to be inexpensive while still keeping portions large. Even meat-eaters will enjoy the vegetarian black bean burger served with cheddar, avocado, and salsa. Service is sporadic, with waiters who are as trendy (and fashionably late) as the customers, but also friendly and happy to chat. (773) 772-4019 (Ella Christoph)
Epic Burger, 517 South State Street » To say that the Epic Burger chose its eponymous adjective wisely would be an understatement. Its slogan, “A more mindful burger,” refers to the owner’s decision to use only ingredients that come with proper nouns and good eco-karma: Wisconsin aged cheddar and Kennebec potatoes, for example. The South Loop burger joint sits beneath a Columbia College dormitory on State and Harrison, which in U of C terms means it’s 63 feet from a #6 stop.
Ordering is a bit like playing 20 Questions—Onions? Grilled onions? Extra grilled onions? Fried egg? Bacon? Smoothie?—but as long as you get the fresh-cut fries, you should be fine. The prices make it hard to forget that every ingredient, including the milk in the smoothies, is organic (a burger, fries, and a smoothie will run you $11.99), but it’s worth it. Plus, good karma: Everything from the wrappers to the forks is biodegradable.
This restaurant should be of particular note to West Coasters jonesing for In-N-Out Burger: While Epic Burger doesn’t really compare—does anything?—it’s the best substitute the Windy City has to offer. (312) 913-1373 (Claire McNear)