| Bocaditos Chicago |
| Restaurant | Mon–Thu, Sun | 4 PM – 6 PM | Beer, House Wine (Rosé, Prosecco, Chardonnay, Pinot Grigio, Sauvignon Blanc, Malbec, Cabernet, Pinot Noir, Red Blend) +12 | $$ |
| Black Barrel Tavern |
| Bar | Mon–Fri | 2 PM – 5 PM | — | $$ |
| Monteverde Restaurant & Pastificio |
| Restaurant | Tue–Fri | 2:30 PM – 4:30 PM | ABC, Aperitivo Spritz +18 | $$$ |
| Canal Street Eatery and Market |
| Restaurant | Mon–Fri | 3 PM – 6 PM | pizzas to share plus, spritz +3 | $$ |
| Jefferson Tap & Grille |
| Bar | Mon–Fri | 3 PM – 6 PM | Draft Beer, Appetizers | $$ |
| New Line Tavern |
| Restaurant | Mon–Fri | 3 PM – 6 PM | Jose Cuervo Devil's Reserve Shots, Teeling Shot +11 | $$ |
| Taste 222 |
| Restaurant | Mon–Fri | 3 PM – 6 PM | Year's N/A Beer, Stella Artois +4 | $$ |
| avec Restaurant |
| Restaurant | Mon–Fri | 3:30 PM – 5 PM | bartender's choice cocktail, wine by the carafina (sparkling, white, rosé or red) +3 | $$$ |
| 9 Muses Bar & Grill |
| Restaurant | Mon–Fri | 4 PM – 7 PM | — | $$ |
| Bunker |
| Bar | Tue–Fri | 4 PM – 6 PM | 1/2 Priced Appetizers, 1/2 Priced Cocktails +1 | $$ |
| Caché 310 |
| Cocktails | Mon–Thu | 4 PM – 6 PM | Signature libations, Beer & seltzer | $$ |
| CH Distillery | Jōtō Sushi |
| Restaurant | Tue–Sat | 4 PM – 6 PM | — | $$$ |
| La Josie |
| Bar | Mon–Wed | 4 PM – 6 PM | Humble Tepache #7, Tardita Guapita +22 | $ |
| Snorkelbox |
| Cocktails | Mon–Fri | 4 PM – 6 PM | HH Cocktail, HH Red +2 | $ |
| Spectrum Bar & Grill |
| Bar | Mon | 4 PM – 7 PM | Chicken Tenders, Onion Rings, Fried Zucchini, Halloumi Rolls | $$ |
| Carnivale Chicago |
| Restaurant | Tue–Fri | 4:30 PM – 6:30 PM | CAIPIRINHA, CLASSIC MARGARITA +27 | $ |
| Rye Deli + Drink |
| Restaurant | Mon–Fri | 4:30 PM – 6 PM | — | $$ |
| Stelios Bottles & Bites |
| Bar | Mon–Thu | 4:30 PM – 6:30 PM | — | $ |
| MONEYGUN |
| Bar | Tue–Fri | 5 PM – 7 PM | Tini | $$ |
| Asadito |
| Bar | Mon | Open to close | House Margarita | $ |
| Slightly Toasted |
| Bar | Wed | Open to close | Whiskey | $$ |