Dinner early, the main event, then somewhere still open. Pick a neighborhood — each one is a complete three-stop night.
- Albany Park
Zaab-E-LEE Thai Street Food → Bokeh → Angelo's Wine Bar
- Andersonville
Lady Gregory's Irish Bar & Restaurant → Nobody's Darling → Little Bad Wolf
- Auburn Gresham
Glad You Asked → There Lounge → Lemelle's Luxury Lounge
- Austin
TNT Rooftop Restaurant → Distro Music Hall → One Lake Brewing
- Avondale
Picnic Digital Food Court - Avondale → The Beer Temple → Barra Ñ
- Belmont Cragin
Kim Long Chinese Restaurant → Pioneer Lounge → Escondite Vip
- Beverly
Franconello → Horse Thief Hollow Brewing Co. → Spoke and Vine
- Boystown
Lark Restaurant & Bar → Splash Chicago → Sidetrack
- Bridgeport
Changde Vermicelli 常德米粉 → Charis Listening Bar → The Duck Inn
- Brighton Park
Tio Luis Tacos and cafe → Michael's Sports Lounge → Co Co Club
- Bucktown
Lizzano Focacceria & Spritzeria → The Angry Cactus Lounge → The Charleston
- Chinatown
Dolo Restaurant and Bar → No.18 Karaoke bar → Sakura Karaoke Bar
- East Village
Alegrias Seafood → Loop Tavern & Liquors → Homestead On The Roof
- Edgewater
Zenwich Edgewater → Whiskey Girl Tavern → Burke's Public House
- Englewood
Peace of Mine Sweets and Spice → HOT CITY COCKTAIL LOUNGE → McGee's Juke Box Lounge
- Galewood
Il Vicolo Trattoria → Robert's Westside → Red Bottle Bar & Cocktail Lounge
- Gold Coast
Boutique → Tavern On Rush → LUXBAR
- Grand Crossing
Josephine's Southern Cooking → Fifty Yard Line → Lee's Unleaded Blues
- Humboldt Park
Kitchen 1217 (inside Cloud Kitchen) → Tiago’s Café → The Hi-Lo
- Hyde Park
Nella Pizza e Pasta → SOPHY - Hyde Park → Cantina Rosa
- Irving Park
Fresh Sushi Chicago → ERIS Brewery and Cider House → Lulu Lounge
- Lake View
Matisse Tavern & Grill → Murphy's Bleachers → Barcocina Lakeview
- Lincoln Park
Shore Club Chicago → The Broken Barrel Bar → Gaslight Bar
- Lincoln Square
Kimchi pop in Lincoln Square → Pueblito Viejo → Farm Bar Ravenswood
- Little Italy, UIC
Tuscany Taylor → The Embassy → Vintage Bar
- Little Village
Sora Temakeria → La Roka → Osito's Tap
- Logan Square
Logan 11 Bar & Kitchen → The Black Lion → The Whale
- Loop
ROLL UP BY OUI JAPANESE HAND ROLLS → Wagyu House Chicago → Brando's Speakeasy
- Lower West Side
Pilsen Yards → Simone's → The Giant Penny Whistle
- Magnificent Mile
The Cabin at Upstairs at the Gwen → THE CUBE Chicago → Michael Jordan's Steak House Chicago
- Near South Side
Chicago Waffles South Loop → THC by Chitiva South Loop → Fatpour McCormick: Ultimate Chicago Sports Bar
- North Center
Trattoria Vittoria → Feather & Tail → Bluelight
- Old Town
The VIG Old Town → Ranalli's Pizza Bar - Lincoln Park, Chicago → Spoko
- Portage Park
Magic Jug → Moonflower → Gracie O'Malley's Portage Park
- Printers Row
Chicago Curry House - Indian - Nepali Cuisine. → Printers Row Wine Bar and Shop → Vitalogy on Dearborn
- River North
Zombie Taco → Bar Goa → Arbella Cocktail Bar
- Rogers Park
Takibi → Rogers Park Social → Monday Blues Lounge
- Rush & Division
Maple & Ash → Hopsmith Chicago → Gold Coast Social
- Sheffield & DePaul
Dog Haus Biergarten - Lincoln Park → Prost! → Parlay Lincoln Park
- Streeterville
TE'AMO Boba & Desserts - Navy Pier → CURRENT → 360 CHICAGO
- Ukrainian Village
Los 3 Compadres de Guerrero → The Empty Bottle → HOLLOW LEG
- United Center
Golden Dragon → The Stanley Club → Goose Island Taproom
- Uptown
Lao Sze Chuan | Chinese • Sichuan → Meeting House Tavern → Chicago Eagle
- West Loop
The VIG West Loop → Elements Nightlife → The Publican
- West Ridge
Mr Farooj → Cali's Corner → My Hookah Cafe - Chicago Hookah Lounge
- West Town
Yuzu Sushi & Robata Grill → The Aberdeen Tap → Provare Chicago
- Wicker Park
Standard Bar and Grill → Big Mini Putt Club → Bourbon on Division
- Wrigleyville
Alma → Big Star Wrigleyville → Budweiser Brickhouse Tavern