| Le Bar Chicago |
| Hotel | Mon–Sun | 4 PM – 6 PM | — | $ |
| Maple & Ash |
| Restaurant | Mon–Thu, Sun | 5 PM – 6 PM | — | $$$$ |
| Eight Bar at Maple & Ash |
| Restaurant | Mon–Fri | 2 PM – 5 PM | — | — |
| Brass Tack |
| Restaurant | Mon–Thu | 3 PM – 6 PM | Lazy Old Fashioned, Manhattan +9 | $ |
| Somerset |
| Restaurant | Mon–Fri | 3 PM – 6 PM | wine | $$ |
| Adalina Italian |
| Restaurant | Mon–Fri | 4 PM – 7 PM | Classic Martini, Dolce Fresca +17 | $$$$ |
| Double Fun |
| Cocktails | Mon–Thu | 4 PM – 6 PM | — | $$ |
| La Storia, Italian Restaurant |
| Restaurant | Mon–Thu | 4 PM – 6 PM | — | $$ |
| The Lodge Tavern |
| Bar | Mon–Fri | 4 PM – 6 PM | Busch Light | $ |
| Hopsmith Chicago |
| Bar | Mon–Fri | 4:30 PM – 6:30 PM | You Call It Call Drinks, Mini Martinis +2 | $$ |
| Streeter's Tavern |
| Bar | Mon–Thu | 5 PM – 7 PM | Bud Light Drafts, Patron | $$ |