| Le Sud Mediterranean Kitchen |
| Restaurant | Tue–Sun | 4 PM – 6 PM | House Wine of the Day, Brut Prosecco +16 | $$ |
| Kitsch'n on Roscoe |
| Restaurant | Mon–Fri | 9 AM – 11 AM | — | $$ |
| Ekiben Japanese Kitchen |
| Restaurant | Mon–Fri | 3 PM – 6 PM | Beer, Wine +1 | $$ |
| Lou Malnati's Pizzeria |
| Pizzeria | Mon–Thu | 3 PM – 5 PM | Draft Beer, 6oz. Glasses of Wine (LaMarca Prosecco, Ecco Domani Pinot Grigio, Seven Daughters Moscato, Josh Cabernet Sauvignon, La Crema Pinot Noir) +6 | $$ |
| Mrs. Murphy & Sons Irish Bistro |
| Pub | Fri | 3 PM – 6 PM | — | $$ |
| The Ravenswood Tavern |
| Bar | Mon–Fri | 3 PM – 6 PM | Fireball, Miller Lite pints +1 | $$ |
| Lush Wine & Spirits - Roscoe Village |
| Wine Bar | Mon–Thu | 3:30 PM – 6 PM | — | $$ |
| Cobblestone Cafe & Bistro |
| Restaurant | Tue–Fri | 4 PM – 6 PM | Old Fashioned, Daiquiri +13 | $$ |
| Grace & Leavitt |
| Bar | Mon–Thu | 4 PM – 6 PM | — | $$ |
| Heineken 2nd Star Tavern |
| Bar | Mon–Fri | 4 PM – 7 PM | Drafts, Well Cocktails +1 | $$ |
| The Globe Pub |
| Bar | Mon–Thu | 4 PM – 6 PM | — | $$ |
| The Western Bar & Kitchen |
| Bar | Mon–Fri | 4 PM – 6 PM | Buffalo Wings, Queso + Chips +11 | $$ |
| Volo Restaurant Wine Bar |
| Wine Bar | Tue–Sat | 4 PM – 6 PM | Oysters, Limoncello Fizz Shots +6 | $$ |
| Feather & Tail |
| Bar | Tue–Thu | 5 PM – 7 PM | New to the Villa, Champagne Problems +7 | $$ |
| Reclaimed Bar & Restaurant - Chicago | Southern |
| Restaurant | Mon–Thu | Until 6:30 PM | Draft Beer, House White +4 | $$ |