| The Purple Pig Restaurant |
| Restaurant | Mon–Wed, Sun | 2 PM – 5 PM | — | $$$ |
| Siena Tavern |
| Restaurant | Mon–Sun | 3 PM – 6 PM | Arancini, Mini Wagyu Meatballs +13 | $$$ |
| Barrio |
| Restaurant | Mon–Sun | 4 PM – 6 PM | Margaritas, Margaritas - Grande +5 | $$ |
| River North Bistro |
| Restaurant | Mon–Tue, Thu, Sun | 4 PM – 6 PM | — | $$ |
| Storyville Chicago |
| Bar | Mon–Sun | 4 PM – 6 PM | House Cocktails, Old Fashioned +7 | $$ |
| Rebar |
| Bar | Mon–Sun | 5 PM – 7 PM | — | — |
| Redhead Piano Bar |
| Bar | Mon–Thu, Sun | 7 PM – 9 PM | Tullamore D.E.W. Manhattan | $$ |
| Five Iron Golf |
| Bar | Mon–Sun | 9 PM – close | Simulator Rentals, Boneless Wings +5 | $ |
| Gilt Bar |
| Bar | Mon–Sun | Until 5 PM | Sliders - American Cheeseburger, Sliders - Hot Fried Chicken +12 | $ |
| IO Godfrey Rooftop Lounge |
| Bar | Mon–Thu | 2 PM – 5 PM | Hummus, Wagyu Beef Sliders +14 | $$ |
| Avli River North |
| Restaurant | Mon–Fri | 3 PM – 6 PM | A-GOURI, KLIMA KLUB +17 | $$ |
| Jake Melnick's Corner Tap |
| Restaurant | Mon–Fri | 3 PM – 6 PM | Select Drafts, You Call It (Well Mixed Drinks) +6 | $$ |
| Lou Malnati's Pizzeria |
| Pizzeria | Mon–Thu | 3 PM – 5 PM | Drinks, Appetizers | $$ |
| Mercadito |
| Restaurant | Mon–Fri | 3 PM – 5:30 PM | — | $$ |
| Pippin’s Tavern |
| Gastropub | Mon–Fri | 3 PM – 6 PM | Burger, Draft Beer | $$ |
| Pops for Champagne |
| Wine Bar | Mon–Fri | 3 PM – 6 PM | Henry Varnay Blanc de, Charles LAFITTE Ros +2 | $$ |
| STK Steakhouse |
| Bar | Mon–Fri | 3 PM – 5:30 PM | Oyster on The Half Shell, Tater Tots +20 | $$$$ |
| The Smith |
| Restaurant | Mon–Fri | 3 PM – 6 PM | Martinis (assorted), The Raw Bar Special - Pickle Rick and three oysters +7 | $$ |
| XOCO |
| Restaurant | Tue–Fri | 3 PM – 6 PM | — | $$ |
| Yardbird |
| Restaurant | Mon–Fri | 3 PM – 6 PM | Chef's Sampler Platter, Deviled Eggs +13 | $$$ |
| avec River North |
| Restaurant | Mon–Fri | 3:30 PM – 5 PM | Bartender's choice cocktail, Wine by the carafina (sparkling, white, rosé or red) +3 | $$$ |
| Lil' Ba-Ba-Reeba! |
| Restaurant | Mon–Fri | 3:30 PM – 5:30 PM | Cava Sangria, Sangria del Día +12 | $$ |
| Arbella Cocktail Bar |
| Cocktails | Mon | 4 PM – 7 PM | House margaritas or mocktails | $$ |
| Broken Shaker at Freehand Chicago |
| Cocktails | Mon–Thu | 4 PM – 6 PM | — | $$ |
| Bub City |
| Restaurant | Mon–Fri | 4 PM – 6 PM | — | $$ |
| Centennial Crafted Beer & Eatery |
| Bar | Tue–Fri | 4 PM – 6 PM | All draft pours, Classic cocktails +4 | $$ |
| Ema |
| Restaurant | Mon–Thu | 4 PM – 6 PM | — | $$ |
| Gus' Sip & Dip |
| Bar | Mon–Fri | 4 PM – 5 PM | All Mixed Drinks, Rotating Cocktail of the Day | $$ |
| Hubbard Inn |
| Bar | Fri | 4 PM – 7 PM | Martinis | $ |
| Joy District |
| Club | Mon, Wed–Fri | 4 PM – 8 PM | — | — |
| La Grande Boucherie Chicago |
| Restaurant | Mon–Fri | 4 PM – 7 PM | Stella, House Wine (Sparkling, White, Red, Rosé) +15 | $$$ |
| Moe's Cantina - River North |
| Restaurant | Fri | 4 PM – 7 PM | — | $$ |
| River Roast |
| Restaurant | Mon–Fri | 4 PM – 5:45 PM | Specialty Cocktails, Wines by the glass +2 | $$ |
| Tanta Cocina Peruana |
| Restaurant | Mon–Fri | 4 PM – 6 PM | — | — |
| The Kerryman Irish Bar & Restaurant |
| Bar | Fri | 4 PM – 7 PM | Guinness, Teeling Shots +2 | $$ |
| Theory |
| Sports Bar | Tue–Fri | 4 PM – 7 PM | Domestic Bottles, Apps +1 | $$ |
| Tree House Chicago |
| Bar | Tue | 4 PM – 6 PM | — | — |
| Tzuco |
| Restaurant | Mon–Fri | 4 PM – 5:30 PM | Tzuco Margarita, Mexican Negroni +13 | $$$$ |
| Upstairs at The Gwen |
| Bar | Mon–Thu | 4 PM – 5:30 PM | — | $$ |
| Zombie Taco |
| Restaurant | Mon–Fri | 4 PM – 6 PM | Got Moxy Rum Punch, $2 off Draft Beers +3 | $ |
| Frontera Grill |
| Restaurant | Tue–Wed | 4:30 PM – 6 PM | Rick's Margarita, Oaxacan Old Fashioned +19 | $$ |
| No Vacancy |
| Bar | Mon–Fri | 4:30 PM – 6:30 PM | NV Valdo Brut Prosecco, 2021 Caposaldo Pinot Grigio +16 | $$ |
| Sophia Steak Chicago |
| Restaurant | Mon–Fri | 4:30 PM – 5:30 PM | House Wine, Classic Martini +8 | $$$$ |
| Charlie Martin's |
| Restaurant | Tue–Sat | 5 PM – 7 PM | Shrimp Cocktail, Oysters on the Half Shell +10 | $$$$ |
| Parlay River North |
| Bar | Mon, Wed–Fri | 5 PM – 8 PM | — | $$ |
| Stardust |
| Cocktails | Thu–Sat | 5 PM – 8 PM | — | $ |
| The Wellsey Tavern |
| Bar | Mon | 5 PM – 8 PM | Half off nacho, Domestic Beer +3 | $$ |
| Bar Sótano |
| Bar | Wed–Sat | Until 6 PM | Fire Fried Chicken, Dry Aged Beef Albondigas +9 | $$ |