Eat and Drink Your Way Through 11 Chicago Neighborhoods for Less Than $100
Chicago is a city of neighborhoods. More than 200 of them, to be not exactly exact. (What can we say? There’s no definitive list.) And the beauty of visiting a city with literally countless neighborhoods is that there are plenty of great bars and restaurants off the beaten path(s).
So we’ve devised a game plan for eating and drinking your way through 11 different 'hoods over the course of a single weekend, all for less than $100. (Before tax. We’re not magicians.) For half the cost of one ticket to Alinea, ambitious visitors can sample some of the best cheap eats Chicago has to offer without eating up their entire travel budget. Be advised: there’s no deep dish, caramel corn, or Michelin stars on this list, but trust us, it’s still Chicago as heck.
Friday
Light(ish) lunch: Chiu Quon Bakery | Chinatown
The Chiu family has been holding down its Wentworth Avenue shop since 1986, making it the oldest Chinese bakery in the neighborhood. There’s a lot to drool over here—the Chius are known to fill their display cases with as many as 100 different types of treats—but it’s the BBQ pork buns you’re after. These steamy, saucer-sized savories are a gosh dang steal at $1 apiece.
World-class dinner: Ricobene’s | Armour Square
Despite the fact that there’s nothing more Chicago than frying meat, smothering it in cheese and giardiniera, then packing it into a hero roll as tightly as a puck caught in Corey Crawford’s glove, the breaded-steak sandwich ($7.49) at Ricobene’s remains somewhat of a city secret. One USA Today food writer even went so far as to anoint it the best sandwich in the world. It’s probably not, but you’re still curious to try it, aren’t ya?
Nightcap: Skylark | Pilsen
Chances are, you won’t have much room left in your tummy after conquering that meat mountain charading as a sandwich. But ending your first day of vacation without a nightcap is an absurdity akin to renaming the Sears Tower. Skylark is the perfect spot to wind down: the building’s been functioning as a bar for about 100 years, so it’s got that charming, sleepy thing down pat. Order a local brew—a Revolution Fist City ($4) is nice and light—then be sure to hit up the photobooth in the back for your first souvenir of the weekend.
Saturday
OK. You better put your game face on, because it’s about to get crazy. As in, pie-for-breakfast crazy.
Dessert for breakfast: Hoosier Mama Pie Company | Ukrainian Village
The $6 coffee-and-pie special Hoosier Mama has every morning is as good of an excuse as any to eat pie for breakfast. Not only does this adorably tiny shop serve what might be the city’s best pie, but the coffee is nothing to sneeze at, either—it’s compliments of Metropolis Coffee Company, an artisanal, award-winning roastery on Chicago’s North Side.
Afternoon snack: Podhalanka | West Town
Though you wouldn’t know it now, back in Nelson Algren’s day, the stretch of Division Street that runs from West Town through Humboldt Park was known as Polish Broadway. Get a taste of that at Podhalanka, a no-frills lunch spot that serves up homemade pierogis, potato pancakes, and blintzes. Tide yourself over until dinner with flaczki ($4.80), a beef-tripe stew that’s surprisingly hearty (and a godsend for hangovers).
Liquid lunch: Rhine Hall | West Loop
At this small-batch brandy distillery, the Solberg family handcrafts 100% fruit brandies—pear, mango, and plum among them—using recipes that dad Charlie learned while living in Austria. Sample one straight ($3), then try one mixed into a cocktail, such as a Bixby’s Double with apple brandy and cider ($8).
Sophisticated small plates: Ada Street | Noble Square
You might get confused trying to find this Bib Gourmand winner, as it’s on a quiet industrial street where the only (sorta) neighboring nightlife is the aptly named Hideout. But it’s there, and it’s great. Before settling in at the chic, candlelit bar, grab a couple of records from the collection in the hall—may we suggest Bill Withers?—to give the bartender for queueing up, as well as your order for pan-seared diver scallops ($15) and a glass of Spanish cava ($8).
After-dinner drink: The Matchbox | River West
At just 460 square feet, The Matchbox is smaller than most Chicago apartments. But people have been cramming into this historic building for upwards of 80 years, citing fondness for both the intimate digs and gimlets made with fresh lime juice. Order one of those ($9.50), and as you strike up a conversation with the friendly stranger on the next stool, be forgiving of everyone squeezing behind you to get to the micro-bathroom. (Seriously, it’s tiny.)
Game night: Logan Arcade | Logan Square
Barcades have sent Chicago into an 8-bit frenzy, but the scene is fairly chill at Logan Arcade. Even on weekend nights, you rarely have to wait for a cabinet to open up—there are dozens of pinball machines, and 40 multiplayer classics, such as Captain America and the Avengers. Of course, part of the reason it’s so easy to hop on a game is because everyone’s usually gathered around Killer Queen, an epic, 10-player competition that spectators can follow on a projection screen. It’s fun, but unless you have four pals to fill out a team, you’re better off sticking to PBR ($3.50 for a tallboy) and pinball ($1.50 for two games).
Sunday
Ah, Sunday. Also known in Chicago as Barbecueday. And don’t worry, we won’t make you choose between brats and burgers. You can have both.
A brat and a beer: Paulina Meat Market and Cody’s Public House | Lakeview
Chicago is known for meat, and that’s thanks in part to Sigmund Lekan. He opened Paulina Meat Market in 1949, and it remains one of the city’s most beloved butcher shops. Pick up a polish brat ($6.35)—smoked in house—then head down the street to Cody’s. This quintessential neighborhood bar boasts one of the city’s best beer gardens, complete with dart boards, bocce, bags, and grills you can cook on. Pair your brat with whatever draft beer is on special ($3.75).
Burger time: The Bad Apple | North Center
There’s going to be someone who swears you have to get a burger at Kuma’s or Au Cheval. A lot of someones, actually. And they’re not wrong. But if waiting for a table for upwards of 2.5 hours during peak dining times isn’t your thing (we’re not kidding), then try Bad Apple instead. Its burgers are perfectly great, and it has a better craft-beer selection than the two aforementioned spots combined. Balance the sweetness of a fig-and-goat-cheese burger ($11) with the tart finish of a sour ale, like Bockor’s Cuvee des Jacobins Rouge ($7).
Total spent: $99.89
Congratulations! You made it through 11 Chicago neighborhoods and still have 11 cents leftover. Time-travel to the 1960s and use it to buy a single packet of Alka Seltzer. That was a LOT of eatin’ and drinkin’.
