Chicago Best Restaurants
- Roister
- Roka Akor
- Roka Akor Old Orchard
- Rollapalooza
- Romanian Kosher Sausage Co.
- Ronnoco Coffee Co
- ROOF on theWit
- ROOH
- Roots Handmade Pizza
- Rootstock Wine and Beer Bar
- Rosa's Lounge
- Roscoe's Tavern
- Rosded Too
- Rosebud Italian Country House and Pizzeria
- Rosebud Italian Specialties and Pizzeria - Naperville
- Rosebud Italian Specialties & Pizzeria
- Rosebud on Rush
- Rosebud Prime
- Rosebud Steakhouse
- Rose Mary
- Roti (Adams)
- Roti (Riverside Plaza)
- Rox City Grill
- Royal George Theatre
- Royal Grocer & Co.
- Royal Oak Farm Orchard
- Royal Thai
- Royal Victorian Manor
- RPM Italian
- RPM on the Water