| Declan's Irish Pub |
| Pub | Near North Side | Sat–Sun | 11 AM – close | Bloody Mary's | $ |
| El Taco Ázteca - Pilsen |
| Restaurant | Pilsen | Mon–Sun | 2 PM – 5 PM | All cocktails | $$ |
| Las Fuentes |
| Restaurant | Sheffield & DePaul | Mon–Sun | 3 PM – 5 PM | Classic Lime Margarita, Especial Margarita +10 | $$ |
| Tallboy Taco |
| Restaurant | Streeterville | Mon–Sun | 3 PM – 5 PM | Tallboy Margarita, Tallboy Margarita Pitcher +1 | $$ |
| Tavern On Rush |
| Bar | Gold Coast | Mon–Thu, Sun | 3 PM – 6 PM | Caesar Salad, Feta Hummus +11 | $$$ |
| Tierra y Fuego Mexican Steakhouse |
| Restaurant | Irving Park | Tue–Sun | 3 PM – 6 PM | Mini Flauta Rolls, Guac & Chips +4 | $$$ |
| Fernando's Tequila Bar &. Restaurant |
| Bar | Lakeview | Mon–Sun | 3:30 PM – 5:30 PM | Red Wine Sangria, Shaken Shot - Mexican Candy +13 | $$ |
| 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 | $$ |
| Boulevard |
| Sports Bar | West Town | Mon–Sun | 4 PM – 7 PM | Domestic Beer, Well Shot +8 | $$ |
| Grant Park Bistro |
| Restaurant | The Loop | Mon–Thu, Sun | 4 PM – 6 PM | Fresh Cut Fries, House Made Chips with truffle cheddar powder +13 | $$ |
| ArePA George Cantina |
| Restaurant | Logan Square | Tue–Sun | 5 PM – 7 PM | Berraco, Orquidea +9 | $$ |
| Valedor |
| Cocktails | West Town | Tue–Sun | 5 PM – 7 PM | TOKI'O FASHIONED, WE LOVE LYCHEE +22 | $$ |
| Aztec Dave's Cantina |
| Bar | West Town | Tue–Fri | 2 PM – 5 PM | Mimosa, Any Beer / Seltzer / Can Cocktail +11 | $$ |
| Cafe Con Leche |
| Restaurant | Logan Square | Mon–Fri | 3 PM – 6 PM | Margarita, Margarita with flavored add-on +9 | $$ |
| Carmine's |
| Restaurant | Gold Coast | Mon–Fri | 3 PM – 5 PM | Happy Hour cocktails, Martinis +8 | $$$$ |
| Carmine's Italian Rosemont |
| Restaurant | North Side | Mon–Fri | 3 PM – 5 PM | Glass of House Selected Wine, Cocktail of the Week +16 | $$$ |
| Don Pez Taco Cantina |
| Restaurant | Lincoln Park | Mon–Fri | 3 PM – 6 PM | tacos, margaritas | $$ |
| El Cid |
| Restaurant | Logan Square | Tue–Thu | 3 PM – 7 PM | $1 off Tacos | $$ |
| Happy Camper Pizza |
| Pizzeria | Lakeview East | Mon–Thu | 3 PM – 6 PM | Espresso Martini, Spritzes +10 | $$ |
| Happy Camper Pizza |
| Bar | Near North Side | Mon–Thu | 3 PM – 6 PM | Espresso Martini, Spritzes +10 | $$ |
| Homeslice Pizza + Patio |
| Bar | Sheffield & DePaul | Mon–Fri | 3 PM – 6 PM | Espresso Martini, Spritzes (Aperol Spritz, Sarti Spritz, Sparkling Gerry) +9 | $$ |
| Ja' Grill Hyde Park |
| Restaurant | Hyde Park | Mon–Fri | 3 PM – 6 PM | Classic Daiquiri, Red Stripe +11 | $$ |
| Paradise Park | Pizza & Patio |
| Bar | West Town | Mon–Fri | 3 PM – 6 PM | Espresso Martini, Spritzes +12 | $$ |
| STK Steakhouse |
| Bar | River North | Mon–Fri | 3 PM – 5:30 PM | Oyster on The Half Shell, Tater Tots +20 | $$$$ |
| The Staley |
| Sports Bar | Near South Side | Mon–Fri | 3 PM – 6 PM | All Draft Beers, The Handshake +12 | $$ |
| Toro by Chef Richard Sandoval |
| Restaurant | The Loop | Mon–Fri | 3 PM – 5 PM | margaritas, margarita trio +1 | $$$ |
| Tuco And Blondie |
| Restaurant | Lakeview | Mon–Fri | 3 PM – 5 PM | Mini Tacos, Classic Margaritas +3 | $$ |
| Kie-Gol-Lanee Uptown |
| Restaurant | Uptown | Mon, Wed–Fri | 3:30 PM – 5:30 PM | Margaritas, Cerveza +15 | $$ |
| McCormick & Schmick's Seafood & Steaks |
| Restaurant | North Side | Mon–Fri | 3:30 PM – 6:30 PM | Truffle Fries, Roasted Garlic Hummus +15 | $ |
| A. J. Hudson's Public House |
| Pub | Lakeview | Mon–Fri | 4 PM – 6 PM | Espolon Margarita, Maplewood - Son of Juice +5 | $$ |
| Casa Chi by Chef Richard Sandoval |
| Cocktails | Streeterville | Mon–Fri | 4 PM – 7 PM | Gin Cucumber Fizz, Traditional Margarita +22 | $$$ |
| Chalet |
| Restaurant | Near North Side | Tue | 4 PM – 6 PM | Tacos, Reposado shots +1 | $$ |
| Diego |
| Restaurant | West Town | Tue–Fri | 4 PM – 6 PM | Classico Tacos, Margaritas +2 | $$ |
| DSTRKT Bar & Grill |
| Sports Bar | West Town | Tue | 4 PM – 10 PM | Tacos, Margaritas | $$ |
| Flight Club Chicago |
| Bar | The Loop | Mon–Fri | 4 PM – 6 PM | Beef Sliders (3), Pretzel Bites +10 | $$ |
| Gordo's Tiny Taco Bar |
| Restaurant | The Loop | Mon–Fri | 4 PM – 6 PM | Nachos, Tiny Quesadillas +9 | $ |
| Innjoy Logan Square |
| Bar | Logan Square | Mon–Fri | 4 PM – 6 PM | 312 Pints, Malort Shots | $$ |
| La Calle Tacos y Tequila |
| Bar | Near South Side | Tue–Fri | 4 PM – 6 PM | Mexican Handshake, Quesadilla +5 | $ |
| La Luna |
| Restaurant | Pilsen | Tue, Fri | 4 PM – 6 PM | Tacos (Pastor, Tinga, Pescado), Tequila or Mezcal Shot +2 | $$ |
| Mexican Radio |
| Restaurant | The Loop | Mon | 4 PM – 6 PM | Martini Monday (tiny martini, cosmo, lemondrop, kolben) | $$ |
| Pour Decisions Chicago |
| Bar | Sheffield & DePaul | Tue | 4 PM – 11 PM | Tacos, Margaritas | $$ |
| Prime 57 Restaurant + Lounge |
| Restaurant | Little Italy | Tue | 4 PM – 7 PM | 2 Birria Tacos, 2 Salmon Tacos +8 | $$ |
| Raiz Kitchen Sushi Bar |
| Bar | Logan Square | Tue–Thu | 4 PM – 6 PM | Hamachi Nigiri, Spicy Salmon +20 | $$ |
| Soul Prime |
| Restaurant | West Town | Tue–Wed, Fri | 4 PM – 6 PM | Short Rib Taco, Spicy Buffalo Wings +13 | $$ |
| The Oakville Grill & Cellar |
| Restaurant | Fulton Market | Mon–Fri | 4 PM – 6 PM | Bar snacks, Bottomless crispy parmesan fries +15 | $$$ |
| Tzuco |
| Restaurant | River North | Mon–Fri | 4 PM – 5:30 PM | Tzuco Margarita, Mexican Negroni +13 | $$$$ |
| Frontera Grill |
| Restaurant | River North | Tue–Wed | 4:30 PM – 6 PM | Rick's Margarita, Oaxacan Old Fashioned +19 | $$ |
| CheSa’s Bistro & Bar Chicago |
| Restaurant | Avondale | Wed–Fri | 5 PM – 6:30 PM | Lamb Meatballs, New Orleans BBQ +4 | $$ |
| Standard Bar and Grill |
| Sports Bar | West Town | Mon | 5 PM – 7 PM | Plain Nachos, XL Pretzel +2 | $$ |
| The Wellsey Tavern |
| Bar | River North | Mon | 5 PM – 8 PM | Half off nacho, Domestic Beer +3 | $$ |
| Chemistry Chicago |
| Bar | Hyde Park | Mon | 6 PM – 8 PM | First Kiss, Watermelon Splash +12 | $$$$ |
| Casa Tequila Chicago |
| Restaurant | West Town | Mon | Open to close | House margarita, Signature margarita +1 | $$ |
| Las Fuentes |
| Restaurant | South Side | Mon | Open to close | Lime Margarita, Strawberry Margarita +4 | $$ |
| Solazo |
| Bar | West Elsdon | Wed–Fri | Until 6 PM | Al Pastor Taco, Cochinita Pibil Taco +6 | $$ |