$$$$Coffee roaster
Intelligentsia Coffee in Chicago is the third-wave roaster founded 1995 by Doug Zell, with Black Cat espresso as its signature roast and a flagship cafe.
TipThe Direct Trade catalogue rotates by season; subscribe to the cupping-room newsletter for first access to new microlots.
$$$$Brewery
Half Acre Beer Co. in Chicago is the Bowmanville brewery on Balmoral since the 2021 consolidation, with the Daisy Cutter pale ale at its core.
TipDaisy Cutter cans are everywhere, but at the taproom you can order it on cask, which is the way the brewers themselves drink it.
$$$$Brewery
Marz Community Brewing in Chicago is the Bridgeport brewery on Iron Street, with experimental sours, lagers and a kitchen pairing from Maria's Packaged Goods.
TipThe Sunday afternoon brewery tour finishes with a flight; book online a week ahead. Kimski's kimchi-pierogi pairs with the Jungle Boogie pale.
$$$$Eastern European
Kasama in Chicago hides its bakery half: Tim Flores and Genie Kwon's Ukrainian Village kitchen on Winchester runs a Filipino-pastry counter.
TipDoors at 07:00; ube cruffins gone by 10:30. Get the longanisa breakfast plate and a cruffin to walk out.
$$$$Brunch
Kasama in Chicago is Tim Flores and Genie Kwon's Filipino bakery in Ukrainian Village, with longanisa breakfast plates, ube cruffins and a corner counter.
OrderLonganisa breakfast plate with garlic rice and an egg.
TipArrive at 07:15 to land the warm cruffins. The breakfast plate at the counter is a perfect 10:30 pause.
$$$$Coffee roaster
Metric Coffee in Chicago is the West Town roaster from Xavier Alexander and Darko Arandjelovic, operating from a former blacksmith shop on Fulton since 2013.
TipThe Fulton Street cuppings are open to the public Thursday 14:00; arrive 10 minutes early for a seat at the bar.
$$$$Brewery
Hopewell Brewing in Chicago is the Logan Square brewery on Milwaukee Avenue, with a lager-and-pilsner focus and a tap room full of natural-wood communal.
TipFirst Lager is the pilsner that put the brewery on the map; order a pint and a $5 hot pretzel for the back patio.
$$$$New American
Au Cheval in Chicago is the West Loop diner-bar on Randolph that runs the full menu until 02:00 nightly, with the country-famous single-with-egg cheeseburger.
OrderSingle cheeseburger with egg
TipSit at the bar past midnight; the queue clears at 23:30 and the kitchen runs the same menu without the dinner wait.
$$$$Cocktail bar
The Aviary in Chicago is the Achatz-Kokonas modernist cocktail bar on Fulton Market with a 21:30 late seating, edible-ice cocktails and the Office speakeasy.
OrderModernist cocktails
TipBook the 21:30 Wednesday or Thursday seating; the room is at half capacity, the cocktails come faster.
$$$$Brunch
Lula Cafe in Chicago hides its Monday Farm Dinner inside the Logan Square brunch menu: a single-farm five-course dinner since 1999 that set the farm-table.
TipReservations open four weeks ahead and book in a day. The farm dinner is $65 and includes wine pairings on certain weeks.
$$$$Taqueria
La Chaparrita in Chicago is the Loera-family taqueria off 26th Street in Little Village, a small storefront the downtown guide books overlook for noisier.
TipCash only. The salsas at the counter are unmarked; ask which is the hottest, start there.
$$$$New AmericanLogan Square
Lula Cafe in Chicago is Jason Hammel's 1999 Logan Square dining room and breakfast counter, anchored by a Monday farm-dinner menu the neighbourhood books out.
OrderMonday's farm dinner if you can book it; brown-butter pasta with sage on walk-in nights.
TipBrunch is walk-up only on weekends; aim for 09:30 to skip the worst of the queue.
$$$$ItalianLogan Square
Daisies in Chicago is Joe Frillman's Logan Square pasta-and-vegetable dining room on Milwaukee Avenue, with grain and produce sourced directly from Illinois.
OrderCavatelli with whatever ragu is current; the focaccia first, while you wait.
TipBrunch is the underrated meal here. The same pasta program with eggs and patio seating in summer.
$$$$PizzeriaLincoln Park
Pequod's Pizza in Chicago is the Lincoln Park pan-pizza institution on Clybourn since 1971, the caramelised cheese ring around the crust copied.
OrderMedium pan pizza, sausage and mushroom, with extra cheese around the rim.
TipWalk in at 16:30 to beat the queue; tables fill before the kitchen opens for dinner service.
$$$$Brewery
Off Color Brewing in Chicago runs the Mousetrap taproom on Kingsbury Street, with revival historical styles (gose, kottbusser, kvass) and mixed-fermentation.
TipThe Mousetrap sour-blend release schedule is monthly; check the website Monday for the Friday drop list of mixed-fermentation bottles.
$$$$Pakistani
Ghareeb Nawaz in Chicago is the West Ridge Pakistani halal counter on Devon, with $7 chicken biryani open until 02:00, the only Devon plate at that hour.
Order$7 chicken biryani special
TipCash only. Bring a container; the biryani plate feeds two with leftovers for the morning.
$$$$American BBQ
Calumet Fisheries in Chicago is the East Side smokehouse on the 95th Street bridge since 1948, smoked chub locals walk away with in butcher paper to eat.
TipCash only, no seating. Walk to the bridge with smoked chub in butcher paper, eat on the railing.
$$$$Brunch
Lula Cafe in Chicago is Jason Hammel's Logan Square brunch room on Kedzie since 1999, with farm-driven plates, vegetable hash and a Logan Boulevard patio.
OrderVegetable hash with poached egg and brown-butter sage.
TipArrive 09:30 on weekends. The queue is long by 10:30; the patio opens at 10:00 in summer.
$$$$Brunch
Daisies in Chicago is Joe Frillman's Logan Square Italian-influenced brunch on Milwaukee Avenue, with hand-cut pasta, a carbonara-and-egg plate and house.
OrderCarbonara with a sunny-side egg on top.
TipBook 14 days ahead on Resy. Patio seats in summer go first; the indoor banquettes are the second-best seat.
$$$$Brunch
The Publican in Chicago is Paul Kahan's Fulton Market Sunday brunch with oyster towers, ham plates and soft-scramble-and-biscuit at the communal mead-hall.
OrderOyster tower, country-ham plate, soft-scrambled eggs with bacon-cheddar biscuit.
TipBook at 10:00 for the lightest dining room. The oyster-shucker is at the bar; order a half-dozen there if you walk up.
$$$$Fried chickenAvondale
Honey Butter Fried Chicken in Chicago is the Avondale counter from Christine Cikowski and Joshua Kulp, with the honey-butter biscuit that named the place.
OrderTwo-piece dark plate with the honey butter biscuit and the corn salad.
TipOrder online from your phone before you walk in. The counter line is twice as long as the screen-pickup one most evenings.
$$$$American BarbecueIrving Park
Smoque BBQ in Chicago is the Irving Park no-frills counter on Pulaski Road since 2006, with brisket and St Louis ribs smoked over apple and hickory in-house.
OrderA sliced brisket plate with the St Louis ribs split. Half-rack rather than full.
TipClosed Mondays. Closes at 21:00 sharp and meat sells out from 19:30 on weekends.
$$$$Chicago Deep-dish PizzaLincoln Park
Lou Malnati's in Chicago is the Lincoln Park branch of the deep-dish chain founded 1971 by Lou (Rudy Malnati Sr.'s son), butter-crust pies with The Lou.
OrderThe Lou with sausage, plus a small Malnati Salad first, with sweet vinaigrette.
TipOrder the pizza when you sit; baking takes 45 minutes. Otherwise you wait twice.
$$$$BelgianAndersonville
Hopleaf in Chicago is the Andersonville Belgian beer bar on Clark since 1992, with moules frites, a 200-bottle Belgian list and the cashew-butter-and-fig.
OrderMoules frites with the Belgian-frites mayo. CB&J sandwich for the table.
TipThe back dining room takes walk-ups only. Aim for 17:00 on Sunday to land it for dinner without waiting.
$$$$Coffee roaster
Sparrow Coffee in Chicago is the Naperville-born roaster's flagship cafe in the Fulton Market on Green Street, with espresso flights and Saturday public.
TipSaturday cupping at 11:00 is the value play: two coffees, a 45-minute talk through origin, free with a cafe purchase.
$$$$Cocktail bar
Matchbox in Chicago is the four-foot-wide West Town cocktail bar on Milwaukee serving stiff classic cocktails until 02:00, a 30-seat triangle since 1995.
OrderOld Fashioned, Gimlet
TipCash and glass only. Order an Old Fashioned; the slim bartender pour is the house standard you do not modify.
$$$$Pizzeria
Vito & Nick's in Chicago is the Ashburn tavern at 8433 S Pulaski, the canonical Chicago tavern-cut thin pizza since 1949, far from the downtown tourist track.
TipCash only and the bar is the rhythm. Closes 22:00 sharp. Order a large party-cut sausage pie.
$$$$Brunch
Big Jones in Chicago is Paul Fehribach's Andersonville Southern brunch on Clark Street, with buttermilk biscuits, shrimp-and-grits and the Sunday-only brunch.
OrderButtermilk biscuit with sorghum butter and the shrimp-and-grits.
TipSunday tables go two weeks ahead. The bar takes walk-up if you arrive at 09:30 on the dot.
$$$$Southern AmericanAndersonville
Big Jones in Chicago is Paul Fehribach's Andersonville Southern kitchen on Clark Street, with shrimp-and-grits and buttermilk biscuits that anchor the brunch.
OrderButtermilk biscuit with sorghum butter, plus the shrimp and grits.
TipSunday brunch tables go on the books two weeks out. The bar takes walk-ups if you arrive at 11:00.
$$$$PizzeriaWest Loop
Bonci Chicago is Gabriele Bonci's West Loop pizza al taglio counter on Sangamon, the first US outpost of the Rome bakery, with rectangular pies cut by weight.
OrderMortadella and pistachio cream; potato and rosemary; whatever seasonal vegetable is current.
TipWalk up at 11:30 for the widest selection. By 14:00 the popular cuts are gone for the day.
$$$$TaqueriaWicker Park Bucktown
Big Star in Chicago is the One Off Hospitality taco room at Six Corners on Damen, with an outdoor patio, a frozen margarita machine and tacos al pastor.
OrderThree al pastor tacos, a frozen margarita, chips with the smoky tomato salsa.
TipThe patio queue is long in summer. The walk-up window pays out a perfectly good takeaway dinner in five minutes.
$$$$Brewery
Goose Island Beer Co. in Chicago is the 1988 John Hall brewery, with the Fulton Brewery taproom on West Fulton serving Bourbon County Stout from the source.
TipThe Bourbon County Stout Day in late November is the calendar event; otherwise the regular taproom has the year-round drafts the cans don't.
$$$$Seafood
The Fish Keg in Chicago is the Rogers Park no-frills fish-fry counter on Howard Street: deep-fried smelt by the cup, perch by the fillet, catfish on bread.
TipCash only and the wait is short Tuesday-Thursday. The smelt cup is the order; eat in the car.
$$$$Brunch
Bongo Room in Chicago is the Wicker Park brunch institution on Milwaukee Avenue, with three-pancake stacks the size of frisbees and a vegan jackfruit hash.
OrderPretzel-crusted French toast with white chocolate caramel.
TipOrder one savoury and one sweet to share. The pancake special is a quarterly-rotating menu posted on the front board.
$$$$Brunch
Ann Sather in Chicago is the 1945 Swedish-American breakfast room whose Broadway location carries the city's cinnamon roll after Belmont closes mid-2026.
OrderMaple-glazed cinnamon roll (free with every entree), Swedish pancakes with lingonberry.
TipThe cinnamon roll is included free with every entree; ask for it warm. The Broadway and Granville rooms continue after the Belmont site closes 28 June 2026.
$$$$PizzeriaThe Loop
Pizano's Pizza & Pasta in Chicago is the family-owned Loop deep-dish room founded in 1991 by Rudy Malnati Jr., son of Pizzeria Uno's original cook Rudy.
OrderThe cheese deep-dish, no toppings, the way Rudy Sr. baked it at Uno.
TipThe Madison location is the original; State Street is the bigger pre-theatre spot.
$$$$Tavern-cut Thin PizzaLincoln Park
Pat's Pizza in Chicago is the Lincoln Park tavern-cut thin room on Lincoln Avenue since 1950, with the cracker-crust pies locals send out-of-town visitors.
OrderMedium Pat's Special, party-cut; the meatball sandwich as a backup.
TipDelivery is the locals' move. The dining room is small, the carryout window quick.
$$$$Coffee roaster
Dark Matter Coffee's Star Lounge cafe on West Chicago Avenue serves the roaster's bold single-origin and signature blends in a long-running West Town space.
TipThe Star Lord blend is the everyday espresso; Unicorn is the seasonal showpiece. Buy both bags and decide at home.
$$$$Brewery
Maplewood Brewery & Distillery in Chicago is the Logan Square brewery-distillery on Maplewood, with IPAs, lagers and the Crooked Belgian-style ale under one.
TipThe distilled whiskey series is what separates this taproom from the others; the rye is the buy.
$$$$American diner
The Wieners Circle in Chicago is the Lincoln Park late-night hot dog counter on Clark, with char dogs, cheese fries and staff-customer banter past 02:00.
OrderChar dog with everything, cheese fries
TipChar dog with everything; the chocolate milkshake is the closing order for the walk back up Clark.