This 5-Pound Donut Tastes Like Apple Pie
1. Full slab of St. Louis-style ribs
SmoqueAddress and Info
Chicago’s barbecue scene is surprisingly impressive, but other local ribs can’t touch the dry-rubbed, apple- and oak-smoked St. Louis-style racks at this North Side gem.
2. Cemita Atomica
Cemitas PueblaAddress and Info
West Loop, Fulton Market
Bad news: the original Humboldt Park restaurant has closed. Good news: the posh West Loop one serves just as great a version of this Mexican sandwich with three kinds of meat, cheese, avocado, the herb papalo, and smoky-hot chipotle.
3. Pan pizza
Pequod’s PizzaAddress and Info
Known as the deep-dish pizza locals actually eat, the pies at this Clybourn Avenue mainstay sport a hallmark caramelized cheese crust that’ll make you think twice about how you want to tackle each colossal slice: crust first, or save the best part for last?
Papa’s Cache SabrosoAddress and Info
West Town, Humboldt Park
This sandwich was invented here at La Borinquen to represent the whole Puerto Rican character in one bite -- meat, cheese, lettuce, tomato, and mayo on a garlicky “bun” of fried plantains. There are still La Borinquens around, though our favorite example today is at this rotisserie chicken place.
5. Arroz Gordo (Fat Rice)
Fat RiceAddress and Info
Having been a fixture in Chicago’s underground dining club scene for years, the Fat Rice chefs' blend of Chinese and Portuguese cuisine is embodied in their eponymous dish. Meant to be tackled by groups of four or more, feasting on the bountiful bowl is like digging for buried treasure in the form of prawns, sofrito, and Chinese sausage.
6. Bing bread
ParachuteAddress and Info
This upscale Korean restaurant from Top Chef alum Beverly Kim and her husband Johnny Clark has many good dishes, but one was an instant classic -- the warm, nourishing bread stuffed with bacon, potato, and onions, which seems to be Asian food by way of your Polish grandmother.
7. Seoul Sassy chicken wings
CrispAddress and Info
It’s hard to think of a food that wouldn’t benefit from a coating of the ginger-soy-garlic panacea known as Crisp’s Seoul Sassy sauce. Needless to say, we weren’t surprised the Korean chicken wing spot took top honors in our local wing ranking.
8. Boat noodles
Andy’s Thai KitchenAddress and Info
If you’re the sort of person for whom Thai food means pad Thai and nothing else, please, just this once, throw something else into the mix. In this case, that thing should be this impossibly flavorful assembly of brisket, pork rinds, and other goodness in all its sweet, spicy, meaty glory.
9. Churros and chocolate
XocoAddress and Info
River North, West Town
Rick Bayless’ casual sandwich place (and its very similar airport sibling Tortas Fronteras) is recommended for lunch. But a couple of freshly made churros (like unrolled donuts) and a pot of thick chocolate dipping sauce is a combo that works anytime.
10. 40-day ribeye
David Burke’s PrimehouseAddress and Info
Best steak in Chicago? Here it is: the 28-day aged-in-house ribeye at David Burke’s is very good for a better-than-standard steak. The 55-day aged ribeye is for the bold, who like a taste of blue cheese funk and iron bar in meat. The 40-day aged ribeye is stronger than the former, not as off-putting as the latter -- in short, it's just right.
11. French fries and ice cream
EL IdeasAddress and Info
Inspired by Chef Phillip Foss watching his daughters dip their fries in their ice cream, this dish has taken different avant-garde forms. But however it gives you potato to eat with your ice cream, it’s everything charming about Foss’ playful South Side fine-dining tasting menu spot in one bite.
12. Ma po tofu
Lao Sze ChuanAddress and Info
Chinatown, River North, Uptown
With its bobbing cubes of squishy tofu, this is a quintessential Chinese comfort food -- if your idea of comfort includes a bowl of bubbling volcanic ooze, like chili pepper-flavored lava. One of the city’s great vegetarian dishes, especially when you order it with pork.
13. Turtle sundae
Margie’s CandiesAddress and Info
If you’re looking for “artisanal” scoops and chic digs, you’ve come to the wrong place: Margie’s is a dingy yet charming relic from the past, and slings the best old-school sundae in town -- complete with nuts, whipped cream, caramel, hot fudge, a cherry on top, and a wafer cookie.
Kuma’s Corner/Kuma’s TooAddress and Info
Avondale, Lincoln Park
There’s nothing more metal than a burger that boldly defies burger convention. Case in point: Kuma’s Slayer, which involves a 10oz patty stacked atop a bed of fries, and smothered in chili, cherry peppers, caramelized onions, andouille sausage, shredded and melted Monterrey Jack, green onion, and a side of angel’s tears (not really).
15. Cake shake
Portillo’sAddress and Info
This legendary chain goes full-tilt dessert Inception with a dessert within a dessert known as a “cake shake,” into which an entire slice of diabolically rich chocolate cake is ground. Balance out all that sweet with a Chicago-style dog.
16. Mr. G
J.P. Graziano Grocery Co.Address and Info
Near West Side
The best sub in the city of Chicago features a spicy array of top-quality meats and cheeses from this old Italian wholesaler and grocer, all on a crusty coal-fired roll from the equally vintage D’Amato’s Bakery nearby.
17. Rainbow cone
Original Rainbow ConeAddress and Info
Remember concocting “suicides” at soda fountains as a kid? Well, this is kind of like that, but actually great -- as in, “some of the best ice cream in America” great. The cone comes stacked with a scoop each of chocolate, strawberry, Palmer House (NY vanilla with cherries and walnuts), pistachio, and orange sherbet.
18. Single burger
Au ChevalAddress and Info
Between a golden meat-to-bun ratio, house-made pickles, Dijonnaise, supremely thick and juicy bacon, and an oozy fried egg, Au Cheval’s single (which is confusingly actually a double) will leave you wanting for nothing.
19. Polish sausage
Jim’s OriginalAddress and Info
South Side cop? Trucker hauling a late-night load? U of I student trying to soak up some beers? They all come together all night long at this standup-only hot dog stand, famous for these plump, garlicky sausages served with mustard and grilled onions since 1939.
20. Pig face
Girl & the GoatAddress and Info
Say “hello” to your new favorite porcine delicacy (and yes, it really is worth the months-long reservation wait). The juicy meat has been wood oven roasted until tender, and is served with cilantro, tamarind, red wine-maple sauce, crispy potato sticks, and a perfectly runny sunny side egg.
21. Cinnamon roll
Ann SatherAddress and Info
Shopping mall cinnamon rolls can’t hold a candle to the pillowy, made-from-scratch buns at this time-tested diner that arrive at the table in pairs (!), come doused in a seemingly indelible pool of glaze, and are best washed down with a cup of coffee and shameless conviction.
22. Peking duck
Sun WahAddress and Info
Get a big group of friends, get your BYOB ammo ready, call ahead to reserve your birds, and get ready for the perfection that is a bite of succulent duck with crispy skin. Then take many more bites and find yourself pleasantly surprised by how cheap the bill is.
23. Glazed old-fashioned donut
Doughnut VaultAddress and Info
There are many great donuts in this city, but nothing is more iconic than a wonderfully moist old-fashioned donut lacquered in sugary glaze from Brendan Sodikoff’s seemingly always-sold-out donut emporium.
24. Depression Dog
Red Hot RanchAddress and Info
Logan Square, Lakeview
With the noticeable absence of Hot Doug’s in our lives, we’ve glommed onto a dog that’s much more simple but still every bit as traditional. The late-night hot dog stand offers steamed dogs simply dressed in mustard, relish, onion, sport peppers, and an overly generous mound of fresh-cut fries.
25. Peach Italian lemonade
Mario’s Italian LemonadeAddress and Info
Slushy Italian lemonade is different from hard Italian ice, and the place to go for it is this stand opposite Al’s on Taylor. It’s only open in the summer and the peach flavor is rarer than that, popping up for a few weeks every summer when peaches get cheap (and some years not at all).
The Tamale GuyAddress and Info
Roaming the dive bars of Chicago
Once you’ve had your hunger pangs -- built up over hours of drinking at some cash-only bar -- satisfied by the red cooler of Claudio Velez, brimming with hot tamales, your late-night drinking escapades will be lacking without them. Consider eating tamales from the Tamale Guy like taking communion directly from the patron saint of late-night munchies.
27. Mozzarella sticks
Roots Handmade PizzaAddress and Info
You’ll know that Chicago truly is the mecca of the Midwest when you look over a menu of ridiculously cheesy Quad Cities-style pizzas and think to yourself “I could use some jumbo mozzarella sticks too.” But your gut instinct is spot on here, because the mozzarella is made from scratch, coated in garlic breadcrumbs, and will inspire the envy of neighboring booths as you chew on a strand of cheese stretching to infinity.
Smak-TakAddress and Info
Mix and match the sauerkraut/mushroom and potato/cheese varieties of these phenomenally fluffy pierogi at one of Chicago’s Polish institutions.
29. Hot chocolate
Mindy’s Hot ChocolateAddress and Info
Ordering what the restaurant is named for is probably a pretty good rule of thumb. Especially at Mindy Segal’s Bucktown bistro, where dinner is what you eat to get to her cookies and amazingly thick and rich hot chocolate for dessert.
30. Italian beef
Al’s Italian BeefAddress and Info
What we like about Italian beef is that it’s a workingman’s lunch, but it’s not a gut-bomb -- it’s an artfully simple interplay of beef and Italian-spiced broth. It’s got class. We’ve argued the best many times here, but a good starting point is the original Al’s on Taylor Street. Get yours dipped, with sweet or hot peppers.
31. Chorizo-stuffed bacon-wrapped dates
AvecAddress and Info
Avec will see your run-of-the-mill bacon-wrapped dates and raise you medjool dates stuffed with spiced chorizo, wrapped in bacon, and drenched in piquillo pepper tomato sauce perfect for sopping up with bread.
La Sirena ClandestinaAddress and Info
The fillings in these little baked beauties change constantly, but the fact that you should always, always order them does not.
33. Fried chicken
Big JonesAddress and Info
Many places offer Southern food these days. Not all of them really “get” Southern food. This is not one of those places, and perhaps no dish makes that more plainly clear than the fried chicken.
KatsuAddress and Info
West Rogers Park
If you are a person who enjoys sushi and you’ve never had the full-on omakase experience, you’re doing yourself a disservice. If you decide to take your maiden omakase voyage at Katsu, you’ll understand why.
Baker MillerAddress and Info
You probably think you have had oatmeal before. After you eat this oatmeal, you will quickly realize you were wrong about that (unless it’s your second, third, or fortieth time eating it, which may come to pass once you’ve experienced a bowl of this hand-rolled, seasonally topped breakfast deliciousness).
36. Smoked shrimp
Calumet FisheriesAddress and Info
You shouldn’t necessarily limit yourself to the smoked shrimp (not that you’d leave unhappy if you did) -- but whatever manner of water-dwelling creature you go with -- smoked chubs, fried catfish -- you aren’t getting the full experience if you don’t eat it on the hood of your car.
37. Chicken Vesuvio
Harry Caray’sAddress and Info
Probably invented at a 1920s restaurant called The Vesuvio, this Chicago classic of roast chicken, garlic, and white wine has long been a socially acceptable alternative to red meat for manly dinners. Where better to eat it than inside of the namesake restaurant of legendary broadcaster and boozer Harry Caray.
38. Sausage pizza
Vito & Nick’sAddress and Info
The platonic ideal of Chicago-style thin crust. Best paired with a pitcher of Old Style.
39. Goat cheese cashew caramel gelato
Black DogAddress and Info
North Center, Ukrainian Village
This tangy, nutty bowl of perfection will make you wonder why more frozen desserts aren’t incorporating goat cheese.
40. Tagliolini nero
BalenaAddress and Info
Everything that is wonderful about impeccably executed handmade pasta and everything that is wonderful about harnessing the rich flavors of the sea in one beautifully executed dish.
41. Lamb vindaloo
Hema’s KitchenAddress and Info
West Rogers Park
There are many reasons Hema’s continues to stand out among a sea of excellent Indian restaurants on Devon Ave. One of them is unmistakably this marvelous melding of tender lamb, coconut, curry, and spice... if you’re the sort of person who can handle it, ask for extra heat.
42. Mussels and frites
HopleafAddress and Info
This highly regarded house of Belgian brews serves mussels steamed in wheat beer, served with beautifully crisped frites, garlic aioli, and bread for the mandatory task of soaking up any leftovers.
43. Garrett Mix
Garrett PopcornAddress and Info
You won’t understand the power of addiction until you sink your filthy paws into a bucket of Garrett’s cheese and caramel corn combo. What you hit bottom (of said bucket) 10 minutes later, it’ll suddenly all make sense.
Lem’s Bar-B-QAddress and Info
Greater Grand Crossing
The city’s oldest BBQ joint is home to the best rack of juicy, toothsome ribs in town, topped with the original spice-kicked BBQ sauce that Myles Lemons invented back in the 1940s.
45. Birria tatemada
Birrieria ZaragozaAddress and Info
This is a one-dish restaurant, which works when the dish is so good it could prompt serious thoughts of moving to the South Side. Spicy, comfy braised goat with chewy freshly made tortillas, served by the nicest family in town.
46. Breaded chicken sandwich
Johnny O’sAddress and Info
Now this is a gut-bomb -- a flat chicken filet deep-fried and covered in cheese, peppers, and tomato sauce. Mainly found in Bridgeport, some swear by the version at Ricobene’s, but this is our choice, not least for the friendly owner, a lifelong Sou’Sider.
47. Ouef Outhier
The BlanchardAddress and Info
The fanciest rendition of scrambled eggs you're likely to consume, delicately nestled inside an eggshell with the top removed with surgeon like precision. Joining the party with the impossibly creamy chicken embryos is vodka creme fraiche and osetra caviar (yep, more eggs), all mingling together in decadent harmony.
48. Sausage biscuit
Bang Bang Pie ShopAddress and Info
Bang Bang’s small-batch sour cream biscuits are topped with ginger-sage sausage, gravy, and a poached egg and come with a side of seasonal jam. Only sandwiches of this high a quality could make it a tough decision of whether to order a biscuit or a slice of pie (“both” is the correct answer).
49. Whole animal service
FrontierAddress and Info
You have yet to conquer Chicago’s carnivorous landscape until you’ve seen a cherry wood-smoked pig (or boar or goat) carved into it’s many usable and delicious parts.
50. Whole chicken & chamomile
RoisterAddress and Info
Though the Alinea Group’s casual concept is still in its relative infancy, its unique chicken preparation has already taken Chicago’s dining scene by storm. The coveted dish showcases impossibly moist deboned, buttermilk-brined, and deep-fried thighs, cast iron-seared breast meat, and legs that have been sous vide and tossed with sunchokes. Also available in sandwich form at lunch.
51. Prosciutto butter toast
MonteverdeAddress and Info
Though Sarah Grueneberg’s acclaimed restaurant may be best known for its hand-rolled and extruded pastas, it’s the savory prosciutto butter-laden toast that keeps diners coming back for more. Paper-thin radish slices, dill, and lemon provide just the right out freshness, texture, and acidity to cut through the richness of the toast.
BomboBarAddress and Info
In a city brimming with classic, American-to-the-core donuts, this hole-less, cream-filled Italian variety is a welcome change from the norm. Swing by the counter-service offshoot of Bar Siena for original (chocolate-filled), salted caramel, vanilla bean custard, a rotating selection of seasonal bomboloni, and more.
The Fat ShallotAddress and Info
Food Truck; Revival Food Hall
There are BLTs, and then there’s this BLT -- the veritable pinnacle of bacon-loaded sandwiches. Two hefty slices of truffle aioli-coated Texas toast contain enough bacon strips to induce a heart attack; peppery arugula, tomato, and avocado complete the masterpiece.
54. The OG
Honey Butter Fried ChickenAddress and Info
A lesson in superior sandwich construction, this fried chicken number is exactly what all other fried chicken sandwiches should strive for: a bun that’s sturdy enough to hold the sandwich ingredients, yet soft enough to sink your teeth into with ease, flaky-on-the-outside, tender-on-the-inside chicken strips, candied jalapeño mayo, and crunchy slaw. Pro tip: for an extra hit of brininess, request pickles as an add-on.
55. Breaded steak sandwich
Ricobene’sAddress and Info
The unassuming, blue collar breaded steak sandwich is the eating challenge that no one feels the need to brag about having accomplished. It's a simple pleasure: the beef fried and seasoned as if it were a chicken Parm, then layered with mozzarella cheese, sweet sauce, and hot giardiniera.
Johnny’s GrillAddress and Info
This old-school-diner-turned-hipster-diner has an Irish spin, but everybody turns out for the all-American double decker burger swimming in melty cheese.
57. Brisket frito pie
Green Street Smoked MeatsAddress and Info
Green Street accurately captures the honky-tonk feel of Texas BBQ, but this dish goes it one further to capture the true feeling of eating out of a gas station.
58. Black and white pizza
Nomad Food Co.Address and Info
Pizza places keep opening up, many of them great, but how often do you taste something really new on a crust? This pizza food truck (most often found at the Green City Market; the North Center home base is only for events) achieved that with this umami bomb pizza featuring black garlic tomato sauce, mozzarella, goat cheese, and chives.
Osteria LangheAddress and Info
“There’s not one table that doesn’t order plin,” says Aldo Zaninotto, owner of this Italian restaurant, of the little cheese-stuffed pillows of buttery pasta goodness.
60. Xiao long bao
CaiAddress and Info
Xiao long bao -- soup dumplings that pop in your mouth -- are coveted by dumpling fans, who line up for hours at world-famous places like Din Tai Fung in Asia. Cai’s aren’t on the same world-famous stage, but they’re the best example you’ll find in Chicago.
61. Mushroom and kale pie
Pleasant House BakeryAddress and Info
Any filling will do, the flaky butter crust on these British savory pies is so fine, but we’re especially partial to the locally grown simplicity of this vegetarian combination.
62. Pork belly pastrami sandwich
The Pork ShoppeAddress and Info
You’d be crazy to eat this lush, fatty-smoky-bacony sandwich as your meal. Better to share it with someone as an appetizer before your brisket comes.
63. Rotisserie duck
The Duck InnAddress and Info
A full feast for at least two, this crispy-skinned duck comes with duck fat potato salad, baby kale (so it’s healthy, see?), cherry duck sauce, and an immense feeling of satisfaction.
64. Chicken boti
Khan BBQAddress and Info
West Rogers Park
This Pakistani restaurant specializes in meats grilled fresh in a stone tandoor, and best of all is chicken coated in mind-bendingly bright yogurt-cilantro raita.
65. Crab legs
The Angry CrabAddress and Info
West Rogers Park, Wicker Park
Cajun-Vietnamese seafood took the city by storm in the last year, and it all started with lines out the door for bags of spicy crab legs, potatoes, and sausage at this northwest side storefront.