Sunshine’s/Diablo’s Happy Space:
These are some of my favorite places in my beloved city by the lake, aka THE GREATEST PLACE ON EARTH (#GPOE!) They’re the spots that get my stomach rumbling and my heart aching whenever I’m away, and the first places I plan to go to when I land at O’Hare. The question is always how many I can hit in a single trip. It’s by no means an exhaustive list (that would be impossible – there’s just too much goodness!), but it does hit the highlights. I’ve tried to organize it by styles/foods so you can cater to your cravings and find something quick, and stuck the non-food/drink ideas at the end if for some reason you’re not hungry/thirsty (are you a robot?) Other than that, it should be relatively self-explanatory. I’m always adding to the list, so if you find something you think is worthy, just let me know – I’ll give it a spin next time I’m home!
–BS
Pizza – it’s the thing we’re best known for (and wrongly ridiculed for by idiot, arrogant New Yorkers), our warm and cozy deep dish. Yes, you eat it w/a knife and fork, and yes, it takes 30-40 min to order – but it’s absolutely delicious and totally worth the wait (and even better cold the following morning!) In my book there’s only two options — Gino’s East for deep dish sausage (it covers the entire bottom of the pie, like a second layer of crust), Giordano’s for stuffed spinach. Eat nowhere else…Unless you’re hunting something a little lighter — the other option we’re known for is the tavern-style thin crust (the one cut like a grid that also garners us ridicule by buffoons who have never enjoyed the delights of a crustless inner rectangle). There’s an endless array of places that serve solid tavern-style — Giordano’s has a solid option to go along with your stuffed spinach (any topping is good, but I like pepperoni and onions or sausage, green peppers, and olives – but straight cheese is delicious, too). John’s on Western is a great one (their Roma — sausage, onions, garlic, diced tomato, and basil — or the Italian beef pie — roast beef and giardiniera — are fantastic (they also do fried zucchini and fried mushrooms, which are killer classic apps to start the party)). Pizza Metro on Division is also solid. And then there’s a mid-level option with Pequod’s — they sorta do deep dish, only with a shorter Detroit-style crust that’s delicious. (They don’t hold up well in my morning after test — there’s just too much dough when eating cold — but you can pull a lot of it off to better balance things out and enjoy that crispy cheese crust.)
Beefs/dogs — there’s hundreds of solid neighborhood joints, but if you’re in town for a short time there’s only one place to go — Portillo’s. One of the places I hit each and every time I’m in town, without fail. Write this down and say it to the cashier – “I’ll have a beef dipped w/ sweet, a sausage w/ hot, and a regular dog w/ everything. And crinkle cut fries. And a chocolate malt.” Doesn’t matter if you understand what you’re saying – you will when the food shows up. Fu#$ing. AMAZING. It’s the holy trinity of sandwiches and a table full of happiness. Don’t skip it. If you happen to be out in the burbs, Carm’s and Johnnie’s are two other good options – Johnnie’s is an old shack from the 50s that hasn’t changed at all since. It always has a line, winter or not, and is always worth it. They do pepper and egg sandwiches on Friday, too, which further entices you to drive to Oak Park.
Latin — tons of options (Chicago IS the home to the third most Mexicans outside Mexico City and LA… #laraza), but Xoco is great for tortas (or caldos if it’s cold — the chocolate and churros are pretty great, regardless of the weather). Frontera/Topolobampo (same owner as Xoco) are great for bigger meals/dinner (and right around the corner). Antique Taco has some pretty tasty tacos (I dig the classic crunchy, the potato poblano, and the carnitas with bacon and avocado), as does Taqueria Chingon (their chorizo taco, with its pumpkin seeds and avocado salsa, or their duck carnitas one, with date puree, oranges, and chicharrones, are both great, but their breakfast sandwich — pastor sausage, serrano/pineapple jam, caramelized onions, and a sunnyside egg, all on a concha (?!?) — is absolutely fantastic.) Another Chicago standard is the jibarito — think delicious sandwich where the bread has been substituted for smashed, garlic covered tostones — and there are a bunch of places that do this one well, too. Jibaritos y Mas is one of my go tos (I like their lechon jibarito with avocado added — and don’t miss out on the “mas” part of their name. I always order a couple bacalaitos (CD-sized spiced salt cod fritters), alcapurrias (empanadas where the dough is plantains, but still stuffed with beef and raisins), and some carne frita (fried pork niblets, similar to masitas) and Nellie’s is great if you’re over in Humboldt (ground zero for Puerto Rican food). Get a parcha (passionfruit juice) and some arroz con gandules (rice and peas) to go with your pernil jibarito.
Irazu over in Bucktown/Wicker is great and the only time you’ll eat Costa Rican food when you’re not in that country — get the gallo pinto with skirt steak, some patacones, and a batido/horchata to wash it all down (I also love their pepitos, a pressed sandwich with caramelized onions, black beans, and Lizano sauce). Dove’s Luncheonette is great for brunch, as is Amaru (it’s more Latin than just Mexican, but super tasty – yuca hash browns w/ mojo, oxtail and grits, its version of a Cuban sandwich… YUM…) Also excellent are 90 Miles Cafe for Cuban (excellent Cuban/medianoche sandwich, super tasty lechon sandwich and/or masitas, really good ropa vieja, too) and Brasil Legal, a hole in the wall market that sells excellent Brazilian street food (I love the coxinhas with chicken — think softball-sized croquetas with meat and cheese — and the kibbeh) and lights out feijoada on the weekends. (This sh#$ is seriously legit — I get it pretty much every other weekend.) And if you’re wanting to walk with your food, look no further than Cafe Tola, which depending on the location you hit either has the best array of empanadas you’re ever likely to find (killer green pork, ropa vieja, chicken mole, rajas and cheese, or chorizo and potato options on the savory side, nutella and banana or guava and cheese on the sweet side (among many others) and/or banging breakfast tacos to go along with them (I love the machaca and egg, pork belly and beans, or chorizo and potato ones).
Swine – The city is traditionally known for its steakhouses (Gibson’s, Chop House, Gene & Georgetti’s), but we’re really a pig town at heart. (One of many reasons I sport one on my arm…) To that end Publican is great for beer and pig (think giant hall overflowing with both, along with oysters and other seafood – don’t miss the pork rinds to start and you skip the veggies at your own peril), Purple Pig is great for wine and pig (lots of tapas-style plates that’re all ridiculous – don’t miss the blade steak w/ ‘nduja and honey). I hit one of these almost every time I’m in town.
Bird — Budlong in Revival Food Hall is outstanding — the crunch on the bird is insane (it’s like a hot, spicy laquer that stays crispy no matter what), the biscuit and jam are delicious, and the greens are really tasty too. (Revival’s great writ large because you can hit several spots on this list at once — Furious and Antique, plus Aloha Poke and Mindy’s Hot Chocolate, which has some solid baked goods, and Fat Shallot, which has all kinds of tastiness.) Fry the Coop is another killer option in another killer food hall, this one in the new Wells St Market (which also has Piggie Smalls, a little Greek inspired place courtesy of Jimmy Bannos Jr of Purple Pig fame, and one of the best gyros I’ve ever had. Tempesta is also here, so you can hit a triple play and get something from each, taking a nap on the river just outside when you’re done.) Their Nashville chicken sandwich (get it hot) is outstanding, and their spicy butter fried chicken sandwich is pretty amazing too. (I actually like to get the former with a side of the honey butter from the latter – get the best of both worlds!) And then Parson’s Chicken and Fish is an old neighborhood stalwart with great versions of both titular proteins (I love the Nashville chicken sandwich and the basket of fried fish — and don’t sleep on the ridiculous green chile hush puppies or the frozen Negronis.) Roost is a newcomer, but has several fantastic chicken sammy’s on their housemade biscuits. I’m a big fan of their Carolina style one (hot honey and pimento cheese), as well as their more traditional house style (coleslaw, pickles, chipotle ranch). (Their version of breakfast poutine, the Good Morning bowl, is also excellent — fries, sunnyside eggs, sausage gravy, and chopped up tenders. Yeehaw…)
Sandwiches — Berghoff’s is great if you’re downtown — first place post-Prohibition to serve, it’s like a time warp back to the original waves of immigrants who built the city over a century ago. Get the corned beef and a pretzel (though the entire Old World German menu is pretty great – schnitzels, sausages, stroganoff…) while you work your way through their beer list, all brewed in house. (Their rauchbeer, among several others, was outstanding.) Helfeld’s Deli is another old school take (this time on a classic Jewish deli) that serves enormous sandwiches with house-cured meats — their corned beef and pastrami options are solid, overflowing beasts, but my favorite is the Kifer”baum,” which rocks salami, pastrami, coleslaw, and giardiniera on rye. It’s fantastic, as are their baseball-sized rugelach (both the chocolate and rotating berry options are delicious).
Robinson’s is great for ribs/rib sandwiches and Sultan’s Market has fantastic falafel sammies w/ all the fixin’s. (Get it spicy…) Tempesta is the new kid on the block and a can’t miss — the turkey sandwich is the best I think I’ve ever had (I thought about it for an entire year after I first ate it), the Potatonator is outstanding whether you’ve been drinking or not (hash brown patty, bacon, egg, cheese, and brioche), the muffaletta is a reinterpretation of the classic (pepper herb focaccia, pesto, fresh mozz, TONS of meat), the Italian is great (includes housemade ‘nduja) – pretty much everything here is excellent. Similarly, there’s Jerry’s, home of a million delicious sandwiches and twice as many beers. It’s scaled back to its original Lincoln Square location (and pared back its formerly beastly menu of 100-odd sandwiches at the same time), but it’s worth the trip if you’re nearby. Anything you get will be great – the Rocky B, Joey V, Fred R, William F, or any of their specials and burgers – it’s all on housemade bread and delicious. And then Graziano’s over in Fulton is another throwback classic — they’ve got multiple riffs on a traditional Italian sandwich (the Mr G is their kicked up killer and ordered every time I go), as well as a really good porchetta (using Tempesta meat!) and muffaletta (the sesame roll from D’amato’s is clutch). The staff are super nice, too…
Burgers — Kuma’s Corner has a ridiculously long list of metal-themed burgers and good beer (the Pantera w/ avocado is frigging bonkers) and then there’s White Castle for the mandatory late night sliders. (Laugh if you will, they’re delicious…) Au Cheval and Small Cheval are solid alternatives (I prefer the latter so I don’t have to wait in line and they’ve got a solid patio to boot…), while Gretel has one of the best (the garlic aioli just makes it scream) and Harry Caray’s has a pair of really solid ones too. (The Holy Cow sports smoked gouda, bacon, and steak sauce, while the Smokehouse has a smoked cheese fondue, tomato bacon jam, and balsamic onions — I alternate between the two, but both are excellent.)
Cajun/Southern — there’s one, and only one place to go here — Heaven on 7. Everything is delicious — the etoufees, jambalaya, po’boys, regular specials (grits, chops, etc) doused in red eye gravy… You can’t go wrong. Don’t forget the jalapeno corn muffins the size of grapefruit. Also, DO NOT miss the chocolate peanut butter pie. It’s quite customary (and appreciated) to lapse into a food coma and awaken at your table moaning in satisfied pain. Mmm… [Sadly this was one of the most painful casualties of COVID — I just can’t bring myself to move it to the memorial section yet. Maybe Jimmy will bring it back somehow…] A non-Cajun option is the excellent Green St. Smoked Meats, which has some positively lethal BBQ (their pork ribs and hot links were ridiculous, almost surpassing the solid standards of pulled pork and brisket, and their sides were good too — definitely get the beans to start) and if you find yourself on the south side (or in town for the Taste) then you have to hit BJ’s Market & Bakery, which has a slew of southern delights — must haves are the mustard-fried catfish and some dessert (I’m a fan of the cobbler or the sweet potato pie.)
Another non-Cajun option is Bang Bang Pie Shop, which has a range of killer scratch biscuit options — I usually get a sweet smothered (the classic with their homemade jams and cinnamon sugar butter), a savory (swaps the former duo for pimento cheese and pepper jelly spreads), the sausage and egg sandwich (ginger/sage sausage patty with white cheddar and peach habanero jam), and/or an order of biscuits and sausage gravy (topped with a runny sunnyside egg and a side of fantastic home fries). Their pot pies are also outstanding (both the traditional chicken and the surprisingly good vegetarian tomato option are worth a look for the flaky crust) and then don’t sleep on the endlessly rotating list of titular pie slices — I’ve tried a ton and never been disappointed (I’m a fan of the strawberry rhubarb and the S’mores pies when they’ve got em), so follow your stomach and grab a couple to share. (Also worth getting one of their gingersnap cookies, which are always perfectly soft and studded with raw sugar to add some crunch.)
Greek — there’s lots of good gyro shops if you’re looking for a lighter meal/snack (see Piggie Smalls above, for one), but Greek Islands is a great spot for more of the spectacle/broader menu (flaming cheese, spanakopita, lamb, lukaniko, etc, all while sitting in an area made out to feel like the streets of some small Greek town…) Quick cab back to the Loop. (10min)
Asian — Furious Spoon has great ramen w/a bangin’ hip hop soundtrack (and tall boys of Ninja vs Unicorn in the fridge), while Wow Bao has tasty little baos to snack on as you walk around. Thai Lagoon has a range of killer dishes (I love their housemade somen w roast pork and garlic, as well as their mussaman curry with chicken) and Ramen Wasabi has some solid bowls of noods, too (I prefer their spicy roasted garlic and pork ramen, which goes well with a nice hojicha-infused old fashioned from the bar.) And somewhat surprisingly, Gretel’s bowl is almost good enough to convince you not to get the burger — super rich and unctuous, it’s almost like gravy by the end. Super tasty…
Indian — The Spice Room has some of the best Indian food I’ve ever had, flat out — love their lamb roganjosh, their mango chicken, their palak/saag paneer, their mutter paneer, and their Kashmiri naan to sop it all up, but their dal tarka is a whole ‘nother level. Toasty, spicy, and delicious, this one is an absolute must have — total mind melter.
Bars — Bangers and Lace is great and has a huge beer list (and nice outside/open window seating in the summertime with solid small plates too), Map Room is also super cool w/an equally expansive beer list. (If you’re lucky the windows will be open and Drew will be slinging Ferraris for the bar — half Fernet, half Campari, and totally delicious shots to get you going…) Violet Hour is the long-time modern speakeasy in between w/ killer cocktails, while Rainbo Club is an actual former speakeasy up the street and delightful dive bar now. (Wicker/Bucktown area, easy to hit em all.) Cindy’s is really nice if you’re on the mile and want to cool your heels for a bit — it’s in the Chicago Athletic Association building (now a hotel) and lets you look out over Millennium Park, the Bean, Museum Campus, etc from its open air balcony right on Michigan. (The building itself has some beautiful halls, so wander around a bit before you leave. Rosebud on the opposite corner has a comparably solid patio and view if the wait at Cindy’s is too long — they make a solid cocktail, too.)
Getting a drink at the Drake is like a time warp back to the 50s and home to the best Manhattan you can buy in such a lovely setting (wifey says the martinis are legit too) — walk around the lobby afterward and admire an institution. And if you’re a Cubs fan going to Harry Caray’s is a must (sit at the bar for food – great burgers and sandwiches w/ housemade chips — and check out all the photos on the walls — don’t forget downstairs!), as is going north to catch a game (if it’s summer) or tour the field (if it’s offseason) and get a beer and a shot at Murphy’s just behind the park (all year).
If you’re in Old Town you have to hit the Ale House, “the premiere dive bar in the world,” according to its owner Bruce Elliott, who also happens to paint all the great items hanging on the bar’s walls. Grab a couple pints before/after catching a show at Second City down the street. If you’re hunting Belgian beers look no further than Monk’s, which has the best selection in town. And if you just want a quick and dirty can of Old Style or Hamm’s at one of the quintessential corner bars, look no further than MY corner bar — aptly named Corner Bar. (Rizzo loves going here and scratches at the door every time we walk by, which only slightly makes me look like a raging alcoholic to passersby…)
Quick bites — Garrett’s has crazy good caramel corn (don’t sleep on the caramel/cheese mix — it sounds odd but is amazing) and if you see anyone selling tamales out of their cooler at the bar you’re in, DEFINITELY buy some — they are cheap and always awesome, made by someone’s mom/grandma so you know they’re gonna be great. Artemio’s Bakery on Milwaukee also has tons of excellent Mexican pastries, so buy a bag to nosh on as you mosey — maybe on the way to Stan’s Donuts, which has a wild variety of fantastic sugar O’s, or to Mindy’s on the other side of the six-way, which boasts a ridiculous spread of French style pastries — outstanding bagels (I love the black Russian with cream cheese), the ham and gruyere croissant is bananas (give it 15 sec in the micro to make it sing), and their smorgasbord of sweets are worth a sampling. Just order with your eyes as they’ve always got a range of specials worthy of note. (The kouign-amann, bananas foster kolachy, and rugelach being several faves.)
Coffee — Intelligentsia is the big gun (get my namesake Diablo blend), but Metropolis, Dark Matter, and La Colombe are pretty good too. Buy some beans to bring home. Tape them to your chest if you can’t fit them all in your suitcase. No one will notice/bother you.
Beer — As noted before, Chicago is a pig and beer town. There’s too many can’t miss options of both to cover in one trip – but you shouldn’t let that stop you from trying. Hop Butcher, Goose Island, Three Floyds, Pipeworks, Half Acre, Revolution, Hopewell, Solemn Oath, Noon Whistle, Two Brothers — they’re all really good from top to bottom, so drink em wherever you find em. Then drink more.
RIP: similar to the awards shows, we should take a moment to remember those on this list that are no longer with us, to toast the good times (and meals) and remind ourselves to try and recreate both at home. Silver Cloud, with your guilty pleasure comfort food (Mom’s meatloaf, Frito pie, Sloppy Joe’s, etc), outstanding beers (Gumballhead used to regularly be on tap), and KILLER jukebox. Silver Palm, with your vaunted Three Little Pigs sandwich, which was a life-changer (or -ender, nearly) — bacon, fried egg, cheese, and a slice of ham on a breaded pork cutlet between two buns. Gooey, cheesy, piggy — amazing. Leghorn Chicken, with your legit spicy chicken sammie (years ahead of the hot chicken mania raging now), killer green chile hush puppies, and classic hardcore rap soundtrack. Picante, you were my late night (or hungover morning after) meal of choice for a solid decade — I will miss your delicious steak burritos and your white boy tacos. Heaven on Seven, you were THE Cajun place to eat if you weren’t down in New Orleans. (And the first place I ever bartended, in addition to working in the kitchen.) You will all be missed…
Now back to the gluttony and fun!
Things to do in between to earn your next meal: walk the mile, stopping in shops as need be and otherwise just aimlessly admiring the scenery. Depending on the time of year/your preference you can start at Millennium Park, check out the bean, Buckingham, and the other fun items there (maybe get a drink at Cindy’s if it’s warm), before wandering over to the river and eyeballing the Carbide and Carbon Building, Wrigley Building, and Tribune Tower (check out the lobby of the latter and the stones from landmarks around the globe in its exterior walls). If it’s summer you MUST do an architecture tour on the river (even as a lifer I learn something new every time I go and the views are amazing), and then can wander north towards the Water Tower and the Hancock (going to the top is a great view and totally worth doing), possibly stopping in Water Tower plaza to hit its assortment of shops (including the Chicago Sports Museum), and getting a drink at the Drake/wandering along the lakefront a little. Otherwise invert it and end up at Millennium/Grant park — either way is a solid circuit we’ve run many times over the years. If you’re wanting to explore the neighborhoods a little (or just have a little more structure to your Loop walking), check out the Chicago Architecture Center’s walking tours — they’ve got a slew that are reasonably priced and always interesting (they’re also behind the best of the aforementioned river tours).
Other options include any of the many museums — the Field Museum sports Sue and Maximo, the enormous dinosaur skeletons, as well as a bunch of other cool natural history exhibits. The Shedd Aquarium is an excellent option next door to probe the depths of the sea, while Adler next to that lets you turn your gaze skyward. The Art Institute has a world class collection worth wandering through, and the Cultural Center just across the street has beautiful Tiffany-domed ceilings and old European halls (it was built in 1897 and has played host to presidents and royals alike, so is worth a stop – it’s also free!) The Chicago Theater has a nice tour that lets you explore its incredibly beautiful interior, but Science and Industry is probably my overall favorite that’s worth the long cab ride if you’ve got time. It’s the last remaining building from the World’s Fair (one of the four red stars on the flag) and has a TON of cool exhibits – highlights include the coal mine, the U-boat, the whispering gallery, the chicks in the genetics area (baby birds, not ladies), the farm machinery/data, the full-sized Zephyr and miniature train set, the enormous fairy castle…etc etc etc. It hasn’t changed a ton since I was a kid and is still every bit as awesome.