Chicago Best Restaurants
- Soupbox / Icebox - Lakeview
- Soupbox - River North
- South Branch
- South Coast Sushi Bar
- South Loop Club
- Southport Grocery & Cafe
- Southtown Sub
- Spacca Napoli
- Sparrow
- Spectrum Bar & Grill
- Spertus Institute for Jewish Studies - Kosher Catering
- Spice House - Chicago
- Spice House - Evanston
- SPiN
- Spinning J
- Spirit of Chicago Cruises
- Split-Rail
- Spoon Thai Restaurant
- Sportsman's Club
- Sprinkles Cupcakes
- Spunky Dunkers Donuts
- Spy Bar
- Stan's Donuts & Coffee
- Stan's Donuts & Coffee - Streeterville
- Starbucks - Clark & Belmont
- Starbucks - Pipers Alley
- Starfruit Cafe - Lincoln Park
- Starfruit Cafe - West Town
- Star of Siam
- State and Lake Chicago Tavern