Chicago · for a first-time visitor
Just follow this.
Three ready-made food itineraries — one, three and five days — built only from places on the list, so you can eat well without doing the research. Every place links back to the guide.
Itinerary
One day
The Loop to Logan Square. A depression dog at noon, a Bib at eight, jazz in Capone's booth at eleven.
One day, on the L. Book one dinner. Book one thing: dinner at Galit (Resy) or Kasama's tasting menu (Tock).
The day
- 8:00Lou Mitchell's (West Loop)Since 1923, the free Milk Duds at the door, the omelet in the skillet. Walk-in; the line is the ritual.
- 9:30The LoopThe Art Institute or the architecture boat tour — the boat is the one to book. Garrett Popcorn's Chicago mix on the way.
- 12:00Gene & Jude's (River Grove) or Al's Beef (Little Italy)The depression dog (mustard, relish, onions, sport peppers, fries on top — no ketchup) is 25 minutes west; the dipped Italian beef is ten minutes south. Pick one. Cash is fastest at both.
- 2:00Pequod's (Lincoln Park)One pan, the caramelized cheese crust — the deep dish locals actually eat. Walk-in; order the moment you sit.
- 4:00The Violet Hour (Wicker Park)Behind the mural, no sign, the bar that started Chicago's cocktail revival. Walk-in; go early. Then Dorian's through the record shop next door.
- 6:00Cindy's (Chicago Athletic Association)One drink over Millennium Park at golden hour. Resy. If it's full, the Milk Room downstairs — eight seats, vintage spirits.
- 7:30Galit (Lincoln Park) ★ or Kasama (Ukrainian Village) ★★Galit for Zach Engel's Middle Eastern (Resy, 30 days); Kasama for the Filipino tasting menu that just earned its second star (Tock). Backup: Daisies (Logan Square, Bib + Green Star, Resy) or Lula Cafe (Resy).
- 10:30Green Mill (Uptown)Jazz since 1907, Capone's booth, a Malört if you dare. Cash at the door.
Itinerary
Three days
The Loop and Lincoln Park, then the West Side, then the South Side. One direction a day.
A long weekend. Day one is the one-day plan; day two is Fulton Market and Logan Square; day three goes south. Book three dinners the day reservations open: Galit or Kasama, Smyth or Oriole, and Virtue.
Day 1 · The Loop & Lincoln Park
- All dayFollow the one-day planLou Mitchell's, the Loop, a dog or a beef, Pequod's, the Violet Hour, Cindy's, Galit, the Green Mill.
Day 2 · West
- 9:00Kasama (Ukrainian Village)The morning bakery-café — ube pastries and the longganisa breakfast sandwich. Walk-in; the line moves.
- 11:00Fulton MarketPublican Quality Bread for a loaf to carry, Time Out Market for a look, Sawada's military latte in the West Loop.
- 1:00Au Cheval (West Loop)The burger. Walk-in, put your name down, expect an hour — or Monteverde for Sarah Grueneberg's pasta (Resy) if you can't wait.
- 3:30Logan SquareThe Bib row on foot: Lardon for a charcuterie plate, Cellar Door for a glass, Margie's Candies for a sundae if you've room.
- 5:30Best Intentions or Meadowlark (Logan Square)Both 50 Best; both walk-in early. Scofflaw for gin if you want a third.
- 7:30Smyth (West Loop) ★★★ or Oriole (West Loop) ★★Smyth for the only three stars in the city (Tock, weeks out); Oriole through the freight elevator (Tock). Backup: Elske ★ (West Loop; Resy) or Rose Mary (Fulton Market, Bib, Resy).
- 10:30Kumiko (West Loop)Julia Momosé's bar — 2024 James Beard Outstanding Bar. Resy; the counter takes walk-ins late.
Day 3 · South
- 9:30Manny's (South Loop)Corned beef on rye at the cafeteria line, since 1942. Walk-in.
- 11:00PilsenThe murals on 18th Street, then Carnitas Uruapan for a pound of carnitas by weight, since 1975. Cash.
- 1:00ChinatownMingHin for dim sum, Qing Xiang Yuan for dumplings, Chiu Quon for egg tarts on the way out. Walk-in.
- 3:00BridgeportMaria's Packaged Goods — a liquor store that's also the best bar on the South Side — and Kimski next door for Korean-Polish.
- 5:00Hyde ParkValois cafeteria for the atmosphere, the Robie House for the architecture, Plein Air for a coffee.
- 7:30Virtue (Hyde Park)Erick Williams' Southern room, a Bib and a James Beard Best Chef. Resy. Backup: Lem's Bar-B-Q rib tips in Chatham (walk-in, cash), then Calumet Fisheries for smoked shrimp if you have a car.
- 10:00Buddy Guy's Legends (South Loop)The blues, where it lives. Cover at the door.
Itinerary
Five days
The three-day plan, plus the North Side neighborhoods and a day for the counters and the lake.
Enough time to eat like a resident: Devon Avenue, Uptown's Asian blocks, a tasting counter, and the lakefront. Set alarms for Smyth, Alinea or Ever (Tock), Kasama, and Schwa's phone line.
Days 1–3
- AllFollow the three-day planThe Loop, the West Side, the South Side.
Day 4 · North
- 9:00Lost Larson (Andersonville)Cardamom buns and the Scandinavian case. Walk-in.
- 11:00Devon AvenueThe Indian-Pakistani strip: Sabri Nihari for the nihari, Uru-Swati for the vegetarian thali, the sweet shops between. Cash is fastest.
- 1:30UptownSun Wah for the Beijing duck ceremony (order it when you sit — it takes time), or Birrieria Zaragoza for the goat (Bib). Then the Green Mill by day for the room.
- 4:00Hopleaf (Andersonville)Belgian beer and the mussels; the back garden if it's warm. Walk-in.
- 6:30Cariño (Uptown) ★Norman Fenton's Latin tasting counter. Resy. Backup: Nadu (Lincoln Park; South Indian, Bib, Resy) or Boonie's (Filipino, Bib).
- 9:30Carol's Pub (Uptown)Honky-tonk, live country, cash. Or the Whistler in Logan Square for jazz in a tiny room.
Day 5 · The counters, and the lake
- 10:00Lula Cafe (Logan Square)The Sunday brunch that defined Chicago's neighborhood restaurant, since 1999. Resy, or a wait.
- 12:30The lakefrontRent a bike on the Lakefront Trail from North Avenue Beach to Montrose. Castaways or the Dock for a beer if it's summer.
- 3:30Offshore (Navy Pier)The largest rooftop bar in the world, for one drink and the skyline. Resy.
- 5:30Schwa (Wicker Park) ★ — the phoneCall. Keep calling. If Michael Carlson answers and has a seat, cancel everything else. Otherwise —
- 8:00Alinea ★★ or Ever ★★ or Next ★Alinea for Grant Achatz's theater (Tock; the Salon is the accessible seat); Ever for Curtis Duffy and the best service in the city (Tock); Next for whatever the menu is this season (Tock). All weeks out. Backup: Esmé ★ (Lincoln Park; Tock).
- 11:00Smartbar (Wrigleyville)Beneath Metro, since 1982, the best sound system in the city. Or the Milk Room if you'd rather end quietly.
Gotchas & reminders
Before you go.
The things New Yorkers know and visitors learn the expensive way.
Alinea's co-founder built Tock, so the tasting counters (Alinea, Smyth, Ever, Oriole, Next, Kasama, Schwa's neighbors) sell tickets in blocks, often prepaid and non-refundable. Set alerts. Resy runs the rest, 30 days out. Schwa takes reservations by phone only; the line is legendary.
Tourists eat deep dish (Lou Malnati's, Pequod's, Giordano's); Chicagoans eat tavern-style — thin, square-cut, from Vito & Nick's, Pat's, Marie's. Try both. Never call deep dish 'a pie' out loud.
The Chicago dog is mustard, relish, onion, tomato, pickle, sport peppers, celery salt on a poppy-seed bun. The depression dog (Gene & Jude's) skips the tomato and pickle and adds fries. Asking for ketchup will be noted.
Gene & Jude's, Jim's Original, Johnnie's Beef, Carnitas Uruapan, most of Devon and Maxwell Street Market, and the Green Mill's door are cash-first. Carry $60 on the neighborhoods days.
Chicago's restaurant tax is among the highest in the country — 10.75% citywide, 11.75% in the downtown zone. Menus exclude it. Some restaurants add a service charge; read the bill.
The Red and Blue lines run 24 hours; the others stop around 1am. Tap in with a contactless card (Ventra is optional). Late in Logan Square or Pilsen, the Blue and Pink lines get you home; the South Side after midnight is a car.
November to March the rooftops, the Riverwalk and the beach bars close; the Green Mill, the steakhouses and the tasting rooms don't. Summer is the season: Ravinia, the lakefront, Wrigley bleachers, Maxwell Street on Sunday.
Alinea, Smyth, Oriole, Ever, Kasama's tasting menu and most chef rooms close Sunday and Monday. The hot-dog stands, Chinatown and the taverns run seven days.
Platinum $100 per quarter, Gold $50 twice a year, at any Resy or Tock venue showing the 'Resy Credit eligible' badge. Tock's counters now count — a prepaid Alinea ticket is the easiest $100 you'll spend.
Chicago lost Berlin, Double Door, Lost Lake, Passerotto, Fat Rice and Xoco within a few years. A minute on Resy or Google before you take the L across town.
Jeppson's Malört is a wormwood liqueur that tastes like regret. A shot will be offered to you at some point as a test. Take it once.
O'Hare's Terminal 3 has a Tortas Frontera (Rick Bayless) that is the best airport food in America; Terminal 1 has Garrett's. Midway has a Harry Caray's and a Nuts on Clark.