| Brass Tack |
| Restaurant | Rush & Division | Mon–Thu | 3 PM – 6 PM | Lazy Old Fashioned, Manhattan +9 | $ |
| Carmine's Italian Rosemont |
| Restaurant | North Side | Mon–Fri | 3 PM – 5 PM | Glass of House Selected Wine, Cocktail of the Week +16 | $$$ |
| Leña Brava |
| Bar | Fulton Market | Mon–Fri | 3 PM – 5 PM | MEZCALITA, MARGARITA +19 | $$$ |
| Michael Jordan's Steak House Chicago |
| Bar | Streeterville | Mon–Fri | 3 PM – 5 PM | BBQ Chicken or Tomato Flatbread, Mixed Drinks +10 | $$$$ |
| Monarch & Lion, A British Restaurant |
| Pub | Streeterville | Mon–Sun | 3 PM – 5 PM | Blue Point Oysters, 1000 Layer Potatoes +11 | $$ |
| Pippin’s Tavern |
| Gastropub | River North | Mon–Fri | 3 PM – 6 PM | Burger, Draft Beer | $$ |
| STK Steakhouse |
| Bar | River North | Mon–Fri | 3 PM – 5:30 PM | Oyster on The Half Shell, Tater Tots +20 | $$$$ |
| Taureaux Tavern |
| Restaurant | The Loop | Mon–Fri | 3 PM – 6 PM | Buffalo Wings, Sliders +13 | $$ |
| Tavern On Rush |
| Bar | Gold Coast | Mon–Thu, Sun | 3 PM – 6 PM | Caesar Salad, Feta Hummus +11 | $$$ |
| The Grillroom Chophouse & Wine Bar |
| Wine Bar | The Loop | Mon–Fri | 3 PM – 6 PM | Select Featured Wines, House Margarita +7 | $$$ |
| The Smith |
| Restaurant | River North | Mon–Fri | 3 PM – 6 PM | Martinis (assorted), The Raw Bar Special - Pickle Rick and three oysters +7 | $$ |
| Adalina Italian |
| Restaurant | Rush & Division | Mon–Fri | 4 PM – 7 PM | Classic Martini, Dolce Fresca +17 | $$$$ |
| Bocaditos Chicago |
| Restaurant | West Loop | Mon–Thu, Sun | 4 PM – 6 PM | Beer, House Wine (Rosé, Prosecco, Chardonnay, Pinot Grigio, Sauvignon Blanc, Malbec, Cabernet, Pinot Noir, Red Blend) +12 | $$ |
| Half Shell |
| Bar | Lakeview East | Mon–Fri | 4 PM – 6 PM | White Wine, Red Wine +5 | $$$ |
| HIDE+SEEK |
| Restaurant | Fulton Market | Mon–Thu, Sun | 4 PM – 6 PM | French Fries, Grilled Oysters +13 | $$ |
| Kindling | Downtown Cookout & Cocktails |
| Restaurant | The Loop | Mon–Fri | 4 PM – 6 PM | The OKC Onion Smashburger, Raw Oysters +7 | $$$ |
| La Grande Boucherie Chicago |
| Restaurant | River North | Mon–Fri | 4 PM – 7 PM | Stella, House Wine (Sparkling, White, Red, Rosé) +15 | $$$ |
| Ostras |
| Bar | North Side | Mon–Fri | 4 PM – 7 PM | Cosmopolitan, Espresso Martini +9 | $$ |
| PERILLA korean fare |
| Restaurant | West Town | Mon–Sun | 4 PM – 6 PM | Raw oyster, Whole shrimp +30 | $$$ |
| Southern Chicago |
| Restaurant | Near South Side | Mon–Fri | 4 PM – 6 PM | House White, House Red +13 | $$$$ |
| The Chicago Firehouse Restaurant |
| Restaurant | Near South Side | Mon–Thu | 4 PM – 5 PM | Oysters on the Half Shell, Beef Empanada +6 | $$$ |
| The Publican |
| Restaurant | Fulton Market | Mon–Fri | 4 PM – 6 PM | Pimento Cheese, Caesar Frites +14 | $ |
| Trivoli Tavern |
| Restaurant | Fulton Market | Mon–Fri | 4 PM – 5 PM | Oysters on the Half Shell, Pigs in a Blanket +8 | $ |
| Truluck's Ocean's Finest Seafood and Crab |
| Restaurant | North Side | Mon–Sun | 4 PM – 6 PM | Handcrafted cocktails, Premium spirits +2 | $$$$ |
| Kayao Restaurant |
| Restaurant | Near North Side | Mon–Fri | 4:30 PM – 7 PM | Pisco Sour, House Wines +11 | $$$ |
| S.K.Y. |
| Restaurant | Lincoln Park | Mon–Thu | 4:30 PM – 6:30 PM | Chilled Oyster, Marinated Japanese Cucumbers +9 | $ |
| Swift Tavern - Wrigleyville |
| Bar | Lakeview East | Mon–Fri | 4:30 PM – 6:30 PM | Oysters, Tavern Burger +3 | $$ |
| LÝRA |
| Restaurant | Fulton Market | Mon–Sat | 5 PM – 6:30 PM | House Red or White, Classic Martini +12 | $$$$ |
| Mariscos San Pedro |
| Restaurant | Pilsen | Mon–Sun | 5 PM – 6 PM | Margarita Pitcher, Cocktail of the day +3 | $$ |
| The Wellsey Tavern |
| Bar | River North | Mon | 5 PM – 8 PM | Half off nacho, Domestic Beer +3 | $$ |
| Bar Parisette |
| Wine Bar | Logan Square | Mon | Open to close | champagne, cava +19 | $ |
| Bistro Monadnock |
| Restaurant | The Loop | Tue–Sat | 2:30 PM – 5:30 PM | Gimlet, Sazerac +8 | $$ |
| Tierra y Fuego Mexican Steakhouse |
| Restaurant | Irving Park | Tue–Sun | 3 PM – 6 PM | Mini Flauta Rolls, Guac & Chips +4 | $$$ |
| Bar Pendry Chicago |
| Cocktails | The Loop | Tue | 4 PM – 9 PM | Chef's Choice Oysters | $$ |
| Dearly Beloved |
| Cocktails | Near North Side | Wed–Sun | 4 PM – 7 PM | Oysters, Wine by the Glass +2 | $$$ |
| La Licor Panamericana |
| Bar | Logan Square | Wed–Sun | 4 PM – 6:30 PM | 4AM Burger, Veggie Empanadas (2) +15 | $$ |
| Nafsi South Shore Beach |
| Restaurant | South Shore | Tue–Thu | 4 PM – 7 PM | Garlic Truffle Fries, Nafsi Wings +14 | $$ |
| Volo Restaurant Wine Bar |
| Wine Bar | North Center | Tue–Sat | 4 PM – 6 PM | Oysters, Limoncello Fizz Shots +6 | $$ |
| Brasero |
| Restaurant | West Town | Tue–Sat | 5 PM – 7 PM | Pork Sammy, Yellowfin Tuna Crudo +13 | $$$$ |
| Cantina Rosa |
| Cocktails | Hyde Park | Wed–Thu | 5 PM – 7 PM | Guava Colada, Margarita Clarita +6 | $$$ |
| Charlie Martin's |
| Restaurant | River North | Tue–Sat | 5 PM – 7 PM | Shrimp Cocktail, Oysters on the Half Shell +10 | $$$$ |
| CheSa’s Bistro & Bar Chicago |
| Restaurant | Avondale | Wed–Fri | 5 PM – 6:30 PM | Lamb Meatballs, New Orleans BBQ +4 | $$ |
| Port Union |
| Restaurant | West Town | Tue–Thu, Sun | 5 PM – 6 PM | All classic cocktails, Oysters +4 | $$ |
| Uvae Kitchen and Wine Bar |
| Wine Bar | Andersonville | Tue–Fri | 5 PM – 6:30 PM | Oysters, Shrimp Cocktail +6 | $$ |
| Bar Sótano |
| Bar | River North | Wed–Sat | Until 6 PM | Fire Fried Chicken, Dry Aged Beef Albondigas +9 | $$ |
| Venteux Brasserie, Cafe & Oyster Bar |
| Restaurant | The Loop | Tue | Open to close | East Coast Oysters | $ |