Chicago Best Restaurants
- Richardson Adventure Farm
- Ricochet's Tavern
- Ridgeview Grill
- Ringo Sushi
- Rio's d'Sudamerica
- Ristorante Agostino
- Rite Liquors
- Rittergut Wine Bar & Social Club
- River Roast
- Rivers
- River Shannon
- R J Grunt's
- RL Restaurant
- RM Champagne Salon
- Roadhouse 66
- Robert et Fils
- Roberto's Ristorante & Pizzeria
- Robert's Pizza Company
- Robinson's No. 1 Ribs (Oak Park)
- Robust Coffee Lounge
- Rock Bottom Brewery
- Rock Bottom Brewery - Chicago
- Rock Bottom Brewery - Orland Park
- Rock Bottom Brewery - Yorktown
- Rocks Lakeview
- Rock Wrap & Roll
- Rocky's
- Roebuck
- Roeser's Bakery
- Rogers & Hollands Jewelers