If the tumultuous modern world has taught us anything it’s that life is as precious as it is unpredictable. Why not make the most of your time on this wild and wonderful planet by eating and drinking your way through some of its most appetizing cities? Get your appetite good and whetted by sampling these 25 must-tries from our kind of town, Chicago.
Pequod’s
Pequod’s
Deep-dish pizza
Multiple locations Is it actually pizza? Or is it tomato and cheese casserole? Regional squabbles aside, we can all agree that this unabashedly thick Chicago-born legend is damn delicious. And both locals and newcomers delight in the fact that no two pies are the same, from lauded chains like Giordano’s, Pizzeria Uno’s, Lou Malnati’s, and Geno’s East to smaller neighborhood operations like The Art of Pizza, Bartoli’s, and Lincoln Park’s beloved Pequod’s (this writer’s personal pick, for what it’s worth). Try to catch ‘em all. How to order: Contact your preferred shop directly for reservations, pick-up, or delivery or order online via GrubHub, Caviar, Uber Eats, DoorDash, and Postmates.
Photo by Jim Vondruska
Photo by Jim Vondruska
Rib tips
Multiple locations North Carolina bleeds pulled pork, Kansas City knows burnt ends, and Texas has brisket on lock, but when it comes to Chicago BBQ, it’s all about rib tips. Tried-and-true smokeshacks like Lem’s, Leon’s, Fat Willy’s Rib Shack, Uncle John’s, Earl’s, Robinson’s No. 1 Ribs, and Trice’s Original Slab usually cook up these chewy, saucy originals slow and low in massive aquarium smokers before dishing them out to hungry meat fiends the city over. Get in line, pronto-you’re going to want seconds. How to order: Contact your preferred shop directly for onsite dining, pick-up, and delivery or order online via GrubHub, Uber Eats, and DoorDash.
Uptown Make like modern day Scarface at this landmark cash-only jazz bar, known for incredible live music, stiff cocktails, and a deeply seedy history as Al Capone’s Prohibition-era headquarters. Rumor has it a network of tunnels still lies beneath the floorboards, connecting the watering hole to different former gangster hangouts all over the Northside. It’s touristy, sure, but the spooky-swanky atmosphere-not to mention the world-class nightly performances-is well worth waiting out the crowds. How to order: A brand new pandemic-fueled tented outdoor area keeps customers distanced and happy with drink service, concerts, and dancing most nights. The bar also streams select performances live online so you can stir yourself up a martini and enjoy the show from home. Keep an eye on the calendar for more info.
Fatso’s Last Stand
Fatso’s Last Stand
Chicago-style hot dogs
Multiple locations Leave it to a city steeped in meat packing to produce the world’s perfect hot dog: an all-beef frankfurter plopped into a steamed poppy seed bun and dragged through the garden, as they say, collecting a hoard of yellow mustard, neon relish, chopped white onions, tomato wedges, spicy sport peppers, a dill pickle spear, and a shake of celery salt in its wake. Get yours at a plethora of Chicagoland stands, quick-serve outposts, and even sit-down restaurants, each spot more colorful and charming than the last. Standouts include Fatso’s Last Stand, Superdawg Drive-in, Wolfy’s, Gene & Jude’s, Dog Haus Biergarten, Lulu’s, The Duck Inn, Satchell’s Beef, Portillo’s, Bangers & Lace, Byron’s, hipster favorite Hot G Dog, and the Wiener Circle, where the staff famously serves their char dogs with a side of expletive-streaked sass. How to order: Contact your preferred sausage slinger directly for onsite dining, pick-up, and delivery or order online via GrubHub, Uber Eats, Caviar, Postmates, and DoorDash.
Lakeview Pairs of satisfyingly chewy, oven-fresh, made-from-scratch cinnamon buns, intensely aromatic and drenched in a thick, creamy glaze, are the name of the game inside this long-revered breakfast hotspot. One whiff and you’ll never fall victim to a greasy mall kiosk bun-slinger again, we guarantee it. How to order: Contact your preferred location directly for onsite dining, pick-up, and delivery or order online via DoorDash, GrubHub, Postmates, and Uber Eats.
Greektown Who among us would refuse a block of fried white cheese glistening with oil and sizzling under the scorching blaze of an open flame? Another sneaky Chicago invention, Greektown stalwart Santorini’s flaming saganaki effortlessly evokes the exact kind of tableside whimsy we could all use right now. Not yet up to dining onsite? Feel free to try this one at home-just make sure to watch your eyebrows. How to order: Stop by Santorini’s website for information on onsite dining reservations and carry-out or order online via Uber Eats, Postmates, and GrubHub.
South Deering This humble Far South Side fish shack has been marinating and smoking their prime seafood over specially selected oak logs onsite since in 1948 and, unlike pretty much everything else in this crazy world, precious little about their award-winning process has changed. The menu runs deep, of course, but the shrimp, tender and bursting with briny, meaty succulence, remains an absolute no-brainer. How to order: Stop into the one and only E. 95th Street smokehouse for take-out or call your order into 773-933-9855
Multiple locations No Midwestern holiday photograph is complete without a family-sized tin of Garrett’s popcorn lurking in the background. The most popular option, a salty-sweet duo of Cheddar cheese and toffee-sticky caramel corn, tastes like a mix between Christmas morning bliss and childhood cavities. Ah, memories. How to order: Pick up in person at one of Garrett’s six storefront and kiosk locations, order delivery from Postmates, or have it shipped from straight from the source.
Fried chicken with mild sauce from Harold’s Chicken Shack
Multiple locations It might make up the bulk of the meal, but this storied regional chain’s beautifully scalded fried chicken takes a backseat to its prized mild sauce, a tomato-tinged, tartly sweet, smoky, and ever-so-slightly spicy potion that lurks quietly in the back of every Chicagoan’s childhood food memories. We’ll take ours with a side of wings and fries, please and thank you. How to order: Head any one of the chain’s Chicagoland locations for onsite dining and carry-out or order delivery online via DoorDash, GrubHub, Postmates, and Uber Eats.
West Loop When this West Loop pioneer opened back in 2003, the elegant yet approachable eatery quickly made a name for itself thanks to sleek communal tables, a forward-thinking wine list, and, most importantly, the juiciest medjool date dish the Midwest had ever encountered. Plump dates undergo the full hog treatment here, plied with spiced chorizo sausage before being wrapped in a thick slab of bacon, fired until crisp and crackling, and doused in a warm piquillo pepper tomato sauce that practically demands a hunk of good, freshly baked bread. Don’t think, just order. How to order: Head to Tock for onsite dining reservations and pick-up options or order delivery online via DoorDash and Postmates.
Buona
Buona
Italian beef
Multiple locations Any good Chicagoan knows our fair city is known far and wide for three specific belt-busting dishes: Chicago-style hot dogs, deep dish pizza, and, perhaps most significantly, Italian beef sandwiches. Why? Step inside one of the area’s many choice beef dealers, from familiar chains like Jay’s Beef, Portillo’s, Pop’s, Al’s, and Buona to mom and pop operations like the Original Chickies, the Original Mr. Beef, Roma’s, Johnnie’s, Luke’s, Freddy’s, Scatchell’s, and South Side giant Tony’s, and you’ll soon find out. That pile of broth-soaked shaved roast beef, dumped onto puffy Italian bread and smothered in sweet marinated peppers or spicy giardiniera, is well worth the inevitable belly ache. How to order: Contact your preferred location directly for onsite dining, pick-up, and delivery or order online via DoorDash, GrubHub, Postmates, and Uber Eats.
Uptown Gather up your pandemic pod and prepare to sink your collective teeth into this Uptown fixture’s not-so-secret signature dish: a gut busting, multicourse bonanza showcasing an entire duck, freshly roasted and sporting a layer of ultra succulent, crispy skin, carved tableside for your mouthwatering pleasure by the family-run spot’s expert staff. If you don’t know, now you know. How to order: Call 773-769-1254 to secure onsite dining reservations or place an order for curbside pick-up.
Ukrainian Village In the before times, local bar-goers would let out a cheer each time Claudio Velez, better known as the fabled Tamale Guy, ambled through the door toting his iconic red cooler packed full of hand-rolled tamales. And now that casual indoor bar hangs might be a thing of the past (sniff, sniff), Claudio and the team have thankfully set up shop inside the former Whisk space on Chicago Avenue so the tamale faithful can continue to get their expertly seasoned, endlessly tender chicken, pork, or cheese and pepper fix by the dozen, this time during daylight hours. How to order: Stop into the new Chicago Ave storefront for onsite dining and instore pick-up or check out the website for delivery and take-out.
Beverly Ah, the rainbow cone. Visually radiant and teeming with fruity, sugary goodness, it’s what every ice cream cone wants to be when it grows up. And no long, hot, unbearably sticky Chicago summer would be complete without at least once attempting to devour this handheld mountain of chocolate, strawberry, Palmer House (aka vanilla with cherries and walnuts), pistachio, and orange sherbet in full before it topples over and melts into technicolor sidewalk sludge. Godspeed. How to order: Grab a cone in-person at either location, track the ice cream truck schedule for pop-up appearances, or get it delivered via GrubHub, Postmates, and Uber Eats.
West Loop Fad foods come and go, but this West Loop haunt’s multi-award-winning cheeseburger-a scrumptiously sloppy pile of prime W.W. Johnson Farms beef griddled to greasy perfection, goopy American cheese, housemade pickles, a runny fried egg, thick-cut bacon, and a dollop of tangy Dijonnaise spread stuffed into a buttery double-toasted bun-is undoubtedly forever. Pair it with a frosty $3 tallboy and a Dr. Devon’s Pickleback shot for the full experience. How to order: Stop into the Randolph Street diner for onsite dining, nab carry-out on Toast, or head to Caviar and DoorDash for all your delivery needs.
The Chicago Handshake (aka a Malört boilermaker)
Multiple locations Malört, the gasoline-scented wormwood liqueur Chicagoans love to hate, is not so much an area tradition as it is a rite of passage. Or maybe a dare? Either way, no self-respecting boozehound can leave the Windy City without downing a shot or two of the amber-hued elixir. And those in the know opt for the Chicago Handshake, a dive bar classic that tempers the evil spirit with a chilly can of macro lager like Hamm’s or Old Style. How to order: Belly up to the bar in person (safely and politely, of course) or take the party home with delivery or take-out from Maria’s Packaged Goods, Haymarket Pub & Brewery, Revolution Brewing, Nisei Lounge, and CH Distillery.
Logan Square, Lincoln Park A Puerto Rican original born on the mean streets of Chicago, this Logan Square cult favorite’s flagship sandwich is a work of culinary genius. Replacing boring old bread with crunchy, juicy slabs of fried smashed plantains? Check. Cramming the whole thing full of richly seasoned roast pork, cheese, lettuce, tomato, onions, garlic, and a slather of tangy mayo? Double check. See you in line. How to order: Stop by the original Logan Square or newer Lincoln Park location for onsite dining, delivery, and carry-out, or order online via GrubHub, Postmates, and Uber Eats.
Multiple locations Not for the faint of heart, this chili pepper-flecked pool of bubbling hot broth littered with molten globs of silky tofu and slices of crisp, bright green onions is Chinese comfort food in its purest-and most delicious-form. It’s no wonder this dish helped put Lao Sze Chuan on the map, launching it from a homey Chinatown operation in 1998 to a mini-empire with celebrated outposts across the Midwest. How to order: Head to one of eight Chicagoland locations for onsite dining and carry-out or order delivery online via DoorDash, GrubHub, Postmates, and Uber Eats.
West Loop While the pandemic and its continued fallout have all but squashed traditional fine dining, Alinea Group mastermind chef Grant Achatz is keeping his penchant for executing feats of molecular gastronomy brilliance alive and well over at this long running West Loop cocktail bar-slash-innovation hub. Reserve your socially distanced seat for an intricate six-, five-, or three-course tour of top shelf tipples engineered to tickle the imagination alongside a host of creative bar bites. How to order: Hit up Tock for onsite dining reservations and curbside pick-up options.
Ashburn As much as we enjoy the occasional deep dish excursion, us urbanites know that real Chicago pizza means square cut, cracker thin tavern-style. And there’s no better place to rev your authentic pizza engine than Vito & Nick’s, a South Side institution that’s been perfecting the crunchy, fully-loaded style since 1923. The crust hits the spot, for sure, but it’s the toppings, a broad expanse of meats, veggies, and palate-scorching giardiniera stretching all the way to the flawlessly blackened edge, that slyly steal the show. How to order: Call 773-735-2050 or drop into the OG Pulaski pizzeria for onsite dining information and carry-out or order online via GrubHub.
West Town “New Orleans-style beignets in all their dreamy, doughnut-y goodness, but make it savory,” that was the original impetus behind this rustic-chic Western Ave chophouse’s boundary-defying appetizer. And savory it became, a blanket of puffy deep-fried dough wrapped tightly around a generous wad of short rib, seasoned, seared, and braised until fork-tender. Swap the requisite powdered sugar for a ladleful of haus jus and you’re in business. How to order: Order pick-up via Toast and keep an eye on the website for ongoing reopening updates.
Ukrainian Village Consistently awarded the best pierogi in Chicago by countless area publications, this bustling Ukrainian Village counterserve lives up to the hype with their rotating cast of masterfully doughy Eastern European dumplings. With each bite, the soft, toothsome exterior gives way to piping hot fillings like potato and bacon, cabbage and onion, beef goulash, sauerkraut and Polish sausage, mushroom with pesto and truffles as well as sweet options like fresh strawberries, plums, and wild blueberries. How to order: Check out the Chicago Avenue storefront for onsite dining and carry-out options or order online via Uber Eats and GrubHub.
River North Steakhouses are to Chicago as red sauce Italian joints are to New York and izakaya are to Tokyo-they’re simply embedded in the city’s dining DNA. See what all the meaty fuss is about in true go-big-or-go-home fashion with this hulking 24-ounce bone-in rib-eye from upmarket River North chophouse RPM, dry-aged for 28 days, peppered, salted, and expertly seared for a pleasantly smoky bite and velvety pink center. Life doesn’t get more *chef’s kiss emoji* than that. How to order: Make a reservation for onsite dining and schedule carry-out through Tock or order pick-up and delivery online via ChowNow, Uber Eats, Postmates, Caviar, DoorDash, and GrubHub.
Pilsen To claim that Don Pedro’s carnitas-knuckle-sized chunks of luscious pork, rife with crunchy chicharrón morsels, ambrosial caramelized fat, and pulpy shredded meat-stands as Chicago’s most coveted taco filling would be a grave understatement. Pick up a pound of the good stuff (alongside a stack of warm tortillas and a healthy sprinkling of chopped white onions, fresh cilantro, salsa, and lime, of course) on your way to the park and prepare to be the most popular guest at the socially-distanced picnic. How to order: Pop by the storefront, order online, or call 312-829-4757 for carry-out, or cop delivery via Uber Eats.
Bridgeport Seasoned beef, lovingly breaded and fried for the ultimate crispy outside-tender inside combo is an unparalleled delight for the senses. As if that weren’t enough, this revered South Side staple has been stuffing their perfected protein inside pillowy Turano French bread and layering the whole mess with gooey mozzarella and hot giardiniera since 1946. No wonder it’s been dubbed the best sandwich in the world by multiple publications. How to order: Call 312-225-5555 or place your order online straight from the source.Sign up here for our daily Chicago email and be the first to get all the food/drink/fun in town.
I was introduced to Robyn DaCultyre at an Untitled Queen show at C’mon Everybody in late January, and it was one of the most unique drag shows I’d seen in a while. Afterwards, I tracked down this self-described “drag creature” and video chatted about her drag origin story, the state of drag in her native Ohio, and the dual identities that make up her persona. Thrillist: I want to ask you about how Robyn DaCultyre came about and your point of view behind your performance.
Robyn DaCultyre: I’ve been travelling around the country from a young age in ministry and Christian studies. I moved to Chicago right after high school. Four years later, moved back to Columbus and decided I didn’t really want to do church anymore; that wasn’t where my heart was.
I had a really low point in my life and had a suicide attempt and then really found drag and started doing drag as a coping mechanism and way to let off steam. I started in July of 2019, and it was really a lot of punk and metal music. I created this drag creature of sorts and they were really out of this world and celestial and all of those fun alien type terms.
And then we went into a global pandemic and I had a lot of time to figure out who I wanted to be. Digitally I was still doing a lot of drag creature-esque numbers and all of that, but I had this moment where we’re on the front lines getting hit with pepper spray and rubber bullets and pepper spray-all of those lovely things. And I said, I have this platform and I need to start showcasing what’s happening.
Untitled [Queen] stepped in at the right time and messaged me and said, “I’m doing this show for Independence Day called Untitled in America with 52 different performers and I want you to be a part of it.” It was at that moment I was able to take the footage I had been recording on the front lines and incorporate it into digital content. I did a song called Black Like Me by Mickey Guyton that talks about white picket fences, but if you want to see how America is, then you should try being Black like me. The imagery of what’s literally happening in Columbus in that digital performance really spearheaded me into focusing on people who look like me.
Nina Simone is one of my biggest inspirations, and one of her quotes that resonates with me is that it’s the duty of the artist to resonate with the times. My art is politically charged. I like to entertain, but there will definitely be a time when you come to a show expecting to have your drink and be chill and that might not be the case.
How did the name Robyn DaCultyre come about?
I was smoking with Ursula Major, who was on season one of Dragula, and the first time I introduced myself to her I was Robyn Banks, which is my drag name originally. She said, “Well, do you just not want to be original at all?” [Laughs] And I sat with that for a couple of months, and I got really stoned one day and was listening to Janelle Monae, and she talks about doing it for the culture, and I said “I do it for the culture, too!” And the rest is history.
We started Melanated last February. I told the idea to my show director that there were no shows specifically run by Black people that only featured Black entertainers. I wanted to do this show for a night and she said, Why don’t we do it once a week for the whole month? The first show happens, and it’s a sold out crowd, and [my director] comes back and says we should do this every month. So I sucked it up and here we are a year later.
Melanated is the only fully Black show in all of the state. It’s a horrible marketing tool and not something I want to promote, but it is just a fact. It amazes me that we are the 13th largest city in America and there’s nothing here that’s fully focused on Black entertainers. The name also comes from Janelle Monae; she says she’s highly melanated and I said, that works.
Photos by Chay Creates LLC (left) and Bridget Caswell (right)
Photos by Chay Creates LLC (left) and Bridget Caswell (right)
You refer to yourself as a drag creature, as opposed to drag queen or king…
This is actually the first time I’m making this public. I am in this place where I want to separate the alternative creature from who this melanated goddess or whatever is. DaCultyre is definitely the person who runs Melanated and then Robyn is this drag creature that is out of this world and really loves punk and alternative music. And both intertwine to make Robyn DaCultyre.
You also do pageants. Tell me about that.
In 2020 I was appointed by Nina West, who is from Columbus, as the representative from Ohio for National Entertainer of the Year in Louisville, Kentucky. I placed ninth out of 13 contestants and I really fell in love with the system and fell in love with the pageantry and loved the idea of reigning and being different. I want to show that we as alternative performers, as bearded performers, you can come into these systems and shake things up.
Is there a uniquely “Ohio” style of drag?
No, and I think that’s one of the things that makes it so amazing is that everyone has their own unique style, and it’s all pretty much accepted. I started as a performer and a drag creature and there was space that was afforded to me and I transitioned to more glamor and pageantry and that’s afforded to me as well. I’ve been a bearded entertainer for a year now. The cool thing about Ohio is that there is literally a place for everyone.
I think I have everything I need. Is there anything else I didn’t ask you about that you want to bring up, or…
I don’t think so. Are there any generic questions you haven’t asked?
Generic questions…I think I asked all of them already [laughs]. I like to ask what you’d be doing if you weren’t doing drag?
It’s a great question. I have a day job that is very demanding so I need drag to get away. I’m also very creative and artistic. I used to do web design and all these other things to pull into my creativity. Drag is the longest thing I’ve stuck with in all parts of my life, so I don’t think it’s going anywhere anytime soon.
John deBary is a drinks expert and writer. His first cocktail book, Drink What You Want, is available now, and his next book, Saved by the Bellini, is expected in early 2023. He is also the co-founder and president of the Restaurant Workers’ Community Foundation, which is dedicated to improving the lives of hospitality industry professionals through advocacy, grant making, and impact investing.
