Chicago Best Restaurants
- RPM Seafood
- RPM Steak
- Ruby of Siam - Skokie
- Ruby's Fast Food
- Rudy's Bar & Grille
- RUK
- Russian Tea Time
- Ruth's Chris Steak House (Northbrook)
- Ruth's Chris Steak House - South Barrington
- Saba Italian Bar + Kitchen
- Sable Kitchen & Bar
- Sabor A Cafe
- Sabor Latino (Humboldt Park)
- Sabri Nehari - Chicago
- Saffron Street
- Sai Cafe
- Saigon Sisters
- Saint Lou's Assembly
- Sakura Teppanyaki & Sushi Bar
- Salam Bakery
- Salero
- Salsa 17
- Salvatore's, a Chicago Wedding Venue
- Sam and Harry's Public House
- Sam & Gertie's
- Sandwich Club
- San Soo Gab San - Chicago
- San Soo Gab San - Morton Grove
- Santullo's Eatery
- Sapori Trattoria