Good food, somewhere easy, home at a reasonable hour. Pick a neighborhood — each one is a complete three-stop night.
- Albany Park
First Slice Pie Cafe Manor → Restoried Bookshop → Perfect Brunch Bros
- Andersonville
A Taste of Heaven → Andersonville Galleria → defloured: A Gluten Free Bakery
- Auburn Gresham
Salaam Restaurant & Bakery. → Lemelle's Luxury Lounge → B & B's Ice Cream and Candy
- Avondale
Café Fénix → Skunk Cabbage Books → Sipping Turtle Cafe
- Belmont Cragin
Isla Tropical → Pioneer Lounge → The Fancy Scoop
- Beverly
The Original Rainbow Cone → Bookie's - New and Used Books → The Drip Bakery By Chef Ced
- Boystown
Wake N Bakery Lakeview → Jacqueline's → Stan's Donuts & Coffee
- Bridgeport
Te Cake → Tangible Books → NIA Drink & Dessert
- Bucktown
Allez Café → Lemmings On Damen → Boulevard Bistro
- Chatham
Baskin-Robbins → Licorice Lounge → Drop Inn Lounge
- Chicago
Ethio Beans Ethiopian Restaurant and Cafe → Classic Cinemas North Riverside XQ → Farmer's Best Market
- Chinatown
China Cafe 开饭 → Chinatown Branch, Chicago Public Library → Taian
- East Village
HEYDAY EATERY → Ola's Liquors → West Town Bakery
- Edgewater
Metropolis Coffee Company → Berger Park Cultural Center → Mella Café
- Englewood
Kusanya Cafe → HOT CITY COCKTAIL LOUNGE → McGee's Juke Box Lounge
- Galewood
The Brown Cow Ice Cream Parlor → Classic Cinemas Lake XQ → Red Bottle Bar & Cocktail Lounge
- Garfield Park
Destiny's Water Ice Company → Present Tense Bar → Lakeside Bar
- Garfield Ridge
Racine Bakery → Guide's Sports Bar → Weber's Bakery
- Gold Coast
The Original Pancake House → 3rd Coast Cafe → Gotham Bagels - Gold Coast
- Grand Boulevard
Sip & Savor → Juke Joynt → Pookie Crack Cakes
- Grand Crossing
Brown Sugar Bakery → The Woodshop Art Gallery → Baskin-Robbins
- Greektown
Stan's Donuts & Coffee → Greek Islands → Mariano's
- Hermosa
Los Pollitos (Cash Only) → Workshop 4200 → The Levee
- Humboldt Park
Chucherías Tropical Creations → Humboldt Park Branch, Chicago Public Library → Café Calidá
- Hyde Park
Cafe 53 → First Aid Comics → Sip & Savor | 53rd Street - Hyde Park
- Irving Park
Cascabel Taco Joint → Happy Day Tavern → Baskin-Robbins
- Kenwood
Carver 47 Food and Wellness Market → Call & Response Books → Almendro Cafe
- Lake View
Cielito Paradise → Chicago Comics → Queen B
- Lincoln Park
Blue Door Farm Stand → Barnes & Noble → Sweet Mandy B's Bakery
- Lincoln Square
Cafe Utjeha → Spiteful Brewing Tap Room → Ka Cafe
- Little Italy, UIC
Two Shades Cafe → UIC Bookstore → Stax Cafe
- Little Village
La Michoakana Golden Paleteria Y Nieveria → La Roka → Swirltruck
- Logan Square
MeLatte Coffee Shop → Logan Square Branch, Chicago Public Library → Miko's Italian Ice (Logan Square)
- Loop
Fannie May → Barbara's Bookstore → Cafecito
- Lower West Side
Nevería El Sabor de México → Inga Bookshop → Panaderia Nuevo Leon
- Magnificent Mile
Ghirardelli Ice Cream & Chocolate Shop → AMC 600 North Michigan 9 → TE'AMO Boba & Dessert - Northbridge Mall
- Mckinley Park
La Michoacana 1 → One City Tap → Kristoffer's Cakes
- Near South Side
Momentum Coffee - South Loop → The Staley → Mariano's
- New City
Amazcakes → Homer's → Baskin-Robbins
- North Center
First Slice Pie Cafe → Ravenswood Used Books → Au Levain Bakery & Cafe
- Old Town
Philz Coffee → Old Town Ale House → Kapéj Coffee Roasters
- Portage Park
Ciao Ciao Gelato & Cafe → Twilight Lounge → Gracie O'Malley's Portage Park
- Printers Row
Sofi Restaurant → Printers Row Wine Bar and Shop → Jazz Showcase
- River North
Schweet Original Homemade Chicago Cheesecake → after-words bookstore → ingrained
- Rogers Park
Paleteria Las Delicias de la Michoacána → Cunneen's → Mike's ice chicago
- Rush & Division
Tempo Cafe → Newberry Bookshop → Kilwins Ice Cream - Chocolate - Fudge
- Sauganash,Forest Glen
Sugar Rae’s → Fatpour Lincolnwood: The Ultimate Sports Bar → Chocolate Shoppe Ice Cream
- Sheffield & DePaul
The Bagelers Coffeehouse → The Red Lion Pub → Verzênay Chicago
- South Shore
Give Me Some Sugah → Da Book Joint → Jeffery Pub
- Streeterville
Dollop Coffee Co. → Barbara's Bookstore → TE'AMO Boba & Desserts - Water Tower Place
- Ukrainian Village
Chills Italian Ice → Stella's Tap → Shokolad Pastry & Cafe
- United Center
Cake Sweet Food Chicago → Corbett Vs Dempsey → The Stanley Club
- Uptown
HAIBAYÔ → Graham Crackers Comics of Andersonville → Straws n Bubbles
- Washington Heights
B&B Ice Cream And Candy → Wild Blossom Meadery and Winery → C & B Entertainment
- West Loop
Vietfive Coffee - Chicago → Open Books West Loop → Ground Up Coffee & Bites
- West Ridge
Dairy Star Ice Cream of Lincolnwood → Mark II Lounge → Rita's Italian Ice & Frozen Custard
- West Town
Blisspoint Bakery → Kinzie On The Rocks → Aglaïa Coffee & Tea Co.
- Wicker Park
Letizia's Natural Bakery → Easy Bar → Prequel Cafe – Wicker Park
- Woodlawn
Build Coffee and Books → Reva and David Logan Center for the Arts → Robust Coffee Lounge
- Wrigleyville
Artemio's Bakery → Alamo Drafthouse Cinema Wrigleyville → Bodega Sur