| Henrietta |
| Restaurant | The Loop | Mon–Sun | 2 PM – 6 PM | Hangtime, Pinot Noir, Greenwing, Cabernet Sauvignon +25 | $ |
| Magoos Bar |
| Bar | Southwest Side | Sat–Sun | 2 PM – 5 PM | House Margaritas or Palomas, House Mexican Import Beers +2 | $ |
| Las Fuentes |
| Restaurant | Sheffield & DePaul | Mon–Sun | 3 PM – 5 PM | Classic Lime Margarita, Especial Margarita +10 | $$ |
| R Public House |
| Bar | Rogers Park | Mon–Thu, Sun | 3 PM – 5 PM | House cocktails, Margarita flights +3 | $$ |
| Tallboy Taco |
| Restaurant | Streeterville | Mon–Sun | 3 PM – 5 PM | Tallboy Margarita, Tallboy Margarita Pitcher +1 | $$ |
| Tierra y Fuego Mexican Steakhouse |
| Restaurant | Irving Park | Tue–Sun | 3 PM – 6 PM | Mini Flauta Rolls, Guac & Chips +4 | $$$ |
| Fernando's Tequila Bar &. Restaurant |
| Bar | Lakeview | Mon–Sun | 3:30 PM – 5:30 PM | Red Wine Sangria, Shaken Shot - Mexican Candy +13 | $$ |
| Barrio |
| Restaurant | River North | Mon–Sun | 4 PM – 6 PM | Margaritas, Margaritas - Grande +5 | $$ |
| 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 | $$ |
| Boulevard |
| Sports Bar | West Town | Mon–Sun | 4 PM – 7 PM | Domestic Beer, Well Shot +8 | $$ |
| HaiSous Vietnamese Kitchen |
| Restaurant | Pilsen | Wed–Sun | 4 PM – 5:30 PM | Old Fashioned, Seasonal Margarita +20 | $$ |
| La Licor Panamericana |
| Bar | Logan Square | Wed–Sun | 4 PM – 6:30 PM | 4AM Burger, Veggie Empanadas (2) +15 | $$ |
| Osito's Tap |
| Bar | Little Village | Wed–Thu, Sun | 4 PM – 6 PM | Wings (6 piece or 12 piece), Empanadas +7 | $$ |
| PERILLA korean fare |
| Restaurant | West Town | Mon–Sun | 4 PM – 6 PM | Raw oyster, Whole shrimp +30 | $$$ |
| Tuscany Taylor |
| Restaurant | Little Italy | Wed–Thu, Sun | 4 PM – 7 PM | Bruschetta, Sausage & Peppers +12 | $$ |
| Big Wig Tacos |
| Restaurant | Logan Square | Mon–Sun | 5 PM – 7 PM | Margarita - Small, Margarita - Large | $ |
| Desert Hawk |
| Bar | West Town | Mon–Sun | 5 PM – 6 PM | House Margarita, Ranch Water +4 | $$ |
| Mariscos San Pedro |
| Restaurant | Pilsen | Mon–Sun | 5 PM – 6 PM | Margarita Pitcher, Cocktail of the day +3 | $$ |
| Nine Bar |
| Cocktails | Armour Square | Mon, Wed–Thu, Sun | 5 PM – 6 PM | Classic Cocktails (Old Fashioned, Manhattan, Negroni, Margarita, Daiquiri, Gimlet), Sake Bombs +5 | $$ |
| The Duplex |
| Bar | Logan Square | Thu–Sun | 5 PM – 6:30 PM | Bottled Beer, House Wine +13 | $ |
| Valedor |
| Cocktails | West Town | Tue–Sun | 5 PM – 7 PM | TOKI'O FASHIONED, WE LOVE LYCHEE +22 | $$ |
| The California Clipper |
| Cocktails | West Town | Tue–Sun | 6 PM – 8 PM | Gran Centenario Mixers & Margaritas, Condesa Gin Mixers & Basil Gimlet +5 | $ |
| Moonflower |
| Bar | Portage Park | Tue–Sun | Until 6 PM | Paloma, Lemon Drop +4 | $$ |
| Aztec Dave's Cantina |
| Bar | West Town | Tue–Fri | 2 PM – 5 PM | Mimosa, Any Beer / Seltzer / Can Cocktail +11 | $$ |
| Carol's Pub |
| Dive | Sheridan Park | Thu | 2 PM – 6 PM | House Margarita, House Old Fashioned | $$ |
| Mesler Kitchen | Bar | Lounge |
| Bar | Hyde Park | Mon–Thu | 2 PM – 5 PM | Margarita, French 75 +5 | $$ |
| Alulu Brewery and Pub |
| Brewery | Pilsen | Mon–Fri | 3 PM – 5 PM | Pivo Liso, Happy Hour Beer Cheese Curds +7 | $ |
| AO Hawaiian Hideout |
| Bar | Near South Side | Mon | 3 PM – 6 PM | Ocean Breeze, Spicy Mandu-guk Dumpling Soup | $$ |
| Benihana - Chicago (John Hancock) |
| Restaurant | Streeterville | Mon–Fri | 3 PM – 6 PM | Signature Cocktails - Rocky's Margarita, Edamame +39 | $ |
| Boqueria Fulton Market |
| Restaurant | Fulton Market | Mon–Fri | 3 PM – 6 PM | Pan con Tomate, Croquetas de Jamón +12 | $$$ |
| Broken English Taco Pub |
| Bar | The Loop | Wed | 3 PM – 6 PM | Margarita | $$ |
| Cafe Con Leche |
| Restaurant | Logan Square | Mon–Fri | 3 PM – 6 PM | Margarita, Margarita with flavored add-on +9 | $$ |
| Chili's Grill & Bar |
| Restaurant | South Side | Mon–Fri | 3 PM – 6 PM | Bud Light 16 oz, Miller Lite 16 oz +11 | $ |
| Chili's Grill & Bar |
| Restaurant | — | Mon–Fri | 3 PM – 6 PM | Michelob Ultra 16 oz, Bud Light 16 oz +11 | $$ |
| Don Pez Taco Cantina |
| Restaurant | Lincoln Park | Mon–Fri | 3 PM – 6 PM | tacos, margaritas | $$ |
| Fat Rosie's Taco & Tequila Bar |
| Bar | North Side | Mon–Thu | 3 PM – 5:30 PM | Queso Dip Cup, Queso Fundido +14 | $$ |
| Ja' Grill Hyde Park |
| Restaurant | Hyde Park | Mon–Fri | 3 PM – 6 PM | Classic Daiquiri, Red Stripe +11 | $$ |
| Kaiser Tiger |
| Bar | Fulton Market | Mon–Fri | 3 PM – 5 PM | House Drafts, Margaritas +4 | $$ |
| Lalo's on Maxwell |
| Restaurant | Little Italy | Mon–Fri | 3 PM – 6 PM | Frozen Margaritas, Frozen Margarita flight +6 | $$ |
| Leña Brava |
| Bar | Fulton Market | Mon–Fri | 3 PM – 5 PM | MEZCALITA, MARGARITA +19 | $$$ |
| Lou Malnati's Pizzeria |
| Pizzeria | Clearing | Mon–Thu | 3 PM – 5 PM | Draft Beer, 6oz. Glasses of Wine - Lamarca Prosecco +19 | $$ |
| Lou Malnati's Pizzeria |
| Pizzeria | North Center | Mon–Thu | 3 PM – 5 PM | Draft Beer, 6oz. Glasses of Wine (LaMarca Prosecco, Ecco Domani Pinot Grigio, Seven Daughters Moscato, Josh Cabernet Sauvignon, La Crema Pinot Noir) +6 | $$ |
| Manchamanteles |
| Restaurant | Bucktown | Wed–Fri | 3 PM – 6 PM | Classic Lime Margarita, Modelo +7 | $$ |
| New Line Tavern |
| Restaurant | West Loop | Mon–Fri | 3 PM – 6 PM | Jose Cuervo Devil's Reserve Shots, Teeling Shot +11 | $$ |
| Shake A Leg |
| Restaurant | Austin | Wed–Thu | 3 PM – 7 PM | Margarita, Hurricane +4 | $$ |
| The Dandy Crown |
| Cocktails | West Town | Mon–Fri | 3 PM – 6 PM | Chips & Dip, Beef or Veggie Slider +9 | $$ |
| The Exchange |
| Bar | The Loop | Wed–Fri | 3 PM – 5 PM | Cheese Curds, Roasted Brussels Sprouts +10 | $$ |
| The Grillroom Chophouse & Wine Bar |
| Wine Bar | The Loop | Mon–Fri | 3 PM – 6 PM | Select Featured Wines, House Margarita +7 | $$$ |
| The Staley |
| Sports Bar | Near South Side | Mon–Fri | 3 PM – 6 PM | All Draft Beers, The Handshake +12 | $$ |
| Toro by Chef Richard Sandoval |
| Restaurant | The Loop | Mon–Fri | 3 PM – 5 PM | margaritas, margarita trio +1 | $$$ |
| Truth Be Told |
| Bar | Woodlawn | Mon–Thu | 3 PM – 5 PM | Pickled Roasted Beets, Cashew Hummus +21 | $$ |
| Tuco And Blondie |
| Restaurant | Lakeview | Mon–Fri | 3 PM – 5 PM | Mini Tacos, Classic Margaritas +3 | $$ |
| Yardbird |
| Restaurant | River North | Mon–Fri | 3 PM – 6 PM | Chef's Sampler Platter, Deviled Eggs +13 | $$$ |
| Zizi's Cafe |
| Restaurant | Lakeview East | Tue–Fri | 3 PM – 6 PM | Lamb Croquettes, Hummus +18 | $$ |
| BARDAVID |
| Restaurant | Woodlawn | Mon–Fri | 3:30 PM – 5:30 PM | Baba Ghanoush, Chicken Pita +11 | $$ |
| Kie-Gol-Lanee Uptown |
| Restaurant | Uptown | Mon, Wed–Fri | 3:30 PM – 5:30 PM | Margaritas, Cerveza +15 | $$ |
| A. J. Hudson's Public House |
| Pub | Lakeview | Mon–Fri | 4 PM – 6 PM | Espolon Margarita, Maplewood - Son of Juice +5 | $$ |
| Arbella Cocktail Bar |
| Cocktails | River North | Mon–Fri | 4 PM – 7 PM | Wine by the glass, All Arbella Classics cocktails +7 | $$ |
| Bandit |
| Bar | Fulton Market | Mon–Fri | 4 PM – 6 PM | Diplomat Slider, Spicy Chicken Slider +13 | $$ |
| Big Star |
| Bar | West Town | Mon–Thu | 4 PM – 6 PM | Nachos, Classic Margarita +4 | $$ |
| Big Star Wrigleyville |
| Bar | Lakeview East | Mon–Thu | 4 PM – 6 PM | Ranch Water, Nachos +4 | $$ |
| Cabra |
| Bar | Fulton Market | Mon–Tue | 4 PM – 6 PM | Chilcano, Margarita +15 | $$$ |
| Casa Chi by Chef Richard Sandoval |
| Cocktails | Streeterville | Mon–Fri | 4 PM – 7 PM | Gin Cucumber Fizz, Traditional Margarita +22 | $$$ |
| Chalet |
| Restaurant | Near North Side | Tue | 4 PM – 6 PM | Tacos, Reposado shots +1 | $$ |
| Charis Listening Bar |
| Bar | Bridgeport | Wed–Fri | 4 PM – 6 PM | Cocktail of the Day, Old Fashioned +4 | $$ |
| Cocina Tarascas Mexican Restaurant |
| Restaurant | Lincoln Park | Wed–Thu | 4 PM – 8 PM | FREE Margarita | $$ |
| Daisy's Po-Boy and Tavern |
| Restaurant | Hyde Park | Tue–Fri | 4 PM – 6 PM | Draft beer, Mardi Gras Punch +7 | $$ |
| Dave & Buster's Rosemont |
| Sports Bar | North Side | Mon–Fri | 4 PM – 7 PM | House wine, 7oz glass, 22oz select domestic draft beer +1 | $$ |
| Diego |
| Restaurant | West Town | Tue–Fri | 4 PM – 6 PM | Classico Tacos, Margaritas +2 | $$ |
| DSTRKT Bar & Grill |
| Sports Bar | West Town | Tue | 4 PM – 10 PM | Tacos, Margaritas | $$ |
| El Mariachi Restaurant |
| Bar | Lakeview East | Mon–Fri | 4 PM – 6 PM | House Lime Margarita, Mexican draft beers +1 | $$ |
| El Mariachi Tequila Bar & Grill |
| Bar | Lakeview East | Mon–Fri | 4 PM – 6 PM | House Lime Margaritas, Mexican draft beers +1 | $$ |
| Elixir Andersonville |
| Cocktails | Andersonville | Mon–Fri | 4 PM – 6 PM | Wine, Margaritas +5 | $ |
| Federales Tacos & Tequila - Fulton Market, Chicago |
| Bar | Fulton Market | Tue–Fri | 4 PM – 6 PM | Select Margaritas, Queso Blanco +4 | $$ |
| Federales Tacos & Tequila - Logan Square, Chicago |
| Bar | Logan Square | Mon–Thu | 4 PM – 6 PM | Grande Nachos, Pueblo Viejo Ice Shots +5 | $$ |
| Flight Club Chicago |
| Bar | The Loop | Mon–Fri | 4 PM – 6 PM | Beef Sliders (3), Pretzel Bites +10 | $$ |
| Gale Street Inn Chicago |
| Restaurant | Jefferson Park | Mon, Wed–Thu | 4 PM – 5 PM | Wines by the Glass, Krombacher Pints +13 | $$ |
| Gordo's Tiny Taco Bar |
| Restaurant | The Loop | Mon–Fri | 4 PM – 6 PM | Nachos, Tiny Quesadillas +9 | $ |
| Half Shell |
| Bar | Lakeview East | Mon–Fri | 4 PM – 6 PM | White Wine, Red Wine +5 | $$$ |
| La Calle Tacos y Tequila |
| Bar | Near South Side | Tue–Fri | 4 PM – 6 PM | Mexican Handshake, Quesadilla +5 | $ |
| La Josie |
| Bar | West Loop | Mon–Wed | 4 PM – 6 PM | Humble Tepache #7, Tardita Guapita +22 | $ |
| La Luna |
| Restaurant | Pilsen | Tue, Fri | 4 PM – 6 PM | Tacos (Pastor, Tinga, Pescado), Tequila or Mezcal Shot +2 | $$ |
| La Victoria Barra + Cocina Mexicana - Chicago |
| Bar | Logan Square | Tue–Fri | 4 PM – 6 PM | Margaritas, Cocktails +1 | $$ |
| Mexican Radio |
| Restaurant | The Loop | Mon | 4 PM – 6 PM | Martini Monday (tiny martini, cosmo, lemondrop, kolben) | $$ |
| Monday Blues Lounge |
| Bar | Rogers Park | Mon–Fri | 4 PM – 7 PM | Domestic Beer, Imported Beer +3 | $ |
| Nafsi South Shore Beach |
| Restaurant | South Shore | Tue–Thu | 4 PM – 7 PM | Garlic Truffle Fries, Nafsi Wings +14 | $$ |
| Ostras |
| Bar | North Side | Mon–Fri | 4 PM – 7 PM | Cosmopolitan, Espresso Martini +9 | $$ |
| Parlor Pizza Bar West Loop |
| Pizzeria | Fulton Market | Mon–Fri | 4 PM – 6 PM | Hummus, Hand Cut Frites +17 | $$ |
| Pour Decisions Chicago |
| Bar | Sheffield & DePaul | Tue | 4 PM – 11 PM | Tacos, Margaritas | $$ |
| Prime 57 Restaurant + Lounge |
| Restaurant | Little Italy | Tue | 4 PM – 7 PM | 2 Birria Tacos, 2 Salmon Tacos +8 | $$ |
| Roanoke Restaurant |
| Restaurant | The Loop | Mon–Fri | 4 PM – 6 PM | Marinated Olives & Marcona Almonds, Fried Local Cheese Curds +15 | $$ |
| Soul Prime |
| Restaurant | West Town | Tue–Wed, Fri | 4 PM – 6 PM | Short Rib Taco, Spicy Buffalo Wings +13 | $$ |
| Southern Chicago |
| Restaurant | Near South Side | Mon–Fri | 4 PM – 6 PM | House White, House Red +13 | $$$$ |
| Taco Maya |
| Restaurant | Logan Square | Mon–Fri | 4 PM – 7 PM | Beers, Margaritas +1 | $$ |
| Taco Maya |
| Restaurant | The Loop | Mon–Fri | 4 PM – 7 PM | Beers, Margaritas +1 | $ |
| Taco Maya |
| Restaurant | Lakeview | Mon–Fri | 4 PM – 7 PM | Beers, Margaritas +1 | $ |
| TECALITLAN MEXICAN KITCHEN & MARGARITA BAR |
| Bar | Goose Island | Wed–Thu | 4 PM – 7 PM | Nachitos, Trio +6 | $$ |
| The Cheesecake Factory |
| Restaurant | Streeterville | Mon–Fri | 4 PM – 6 PM | Roadside Sliders, Avocado Eggrolls +31 | $ |
| The Getaway |
| Bar | Lincoln Square | Mon–Thu | 4 PM – 6 PM | Karaoke Boulevardier, Murder, She Float +15 | $$ |
| The Oakville Grill & Cellar |
| Restaurant | Fulton Market | Mon–Fri | 4 PM – 6 PM | Bar snacks, Bottomless crispy parmesan fries +15 | $$$ |
| The Riu Rooftop Chicago |
| Bar | Streeterville | Mon–Fri | 4 PM – 6 PM | Flavor Margaritas, Lemon drop Martini +13 | $$ |
| Tzuco |
| Restaurant | River North | Mon–Fri | 4 PM – 5:30 PM | Tzuco Margarita, Mexican Negroni +13 | $$$$ |
| Whiskey Girl Tavern |
| Bar | Edgewater | Mon, Wed–Thu | 4 PM – 6 PM | Old Fashioned, Manhattan +7 | $$ |
| Wurst Behavior |
| Bar | Irving Park | Mon–Fri | 4 PM – 6 PM | Drafts, Margaritas +4 | $$ |
| XOchimilco Mexican Restaurant |
| Restaurant | Lincoln Square | Mon–Sat | 4 PM – 6 PM | Sangria, Margaritas +2 | $$ |
| Carnivale Chicago |
| Restaurant | West Loop | Tue–Fri | 4:30 PM – 6:30 PM | CAIPIRINHA, CLASSIC MARGARITA +27 | $ |
| Frontera Grill |
| Restaurant | River North | Tue–Wed | 4:30 PM – 6 PM | Rick's Margarita, Oaxacan Old Fashioned +19 | $$ |
| Cantina Rosa |
| Cocktails | Hyde Park | Wed–Thu | 5 PM – 7 PM | Guava Colada, Margarita Clarita +6 | $$$ |
| El Nandú Restaurant |
| Restaurant | Logan Square | Wed | 5 PM – 7 PM | Beer, Quilmes +6 | $$ |
| Everything Bar |
| Bar | West Town | Wed–Sat | 5 PM – 7 PM | Margarita, Espresso Martini +4 | $$ |
| Nia Restaurant & Wine Bar |
| Wine Bar | Fulton Market | Tue–Fri | 5 PM – 6 PM | Crispy Cauliflower, Veggie Croquettes +9 | $$$ |
| Palilgu |
| Bar | Logan Square | Wed–Sat | 5 PM – 6:30 PM | Rum Punch, Korean Tea Old Fashioned +8 | $$ |
| Parlor Pizza Bar Wicker Park |
| Pizzeria | West Town | Mon–Fri | 5 PM – 7 PM | Hummus, Hand Cut Frites +16 | $$ |
| Pueblito Viejo |
| Restaurant | Lincoln Square | Fri | 5 PM – 7 PM | Margaritas, Wine +1 | $$ |
| Standard Bar and Grill |
| Sports Bar | West Town | Mon | 5 PM – 7 PM | Plain Nachos, XL Pretzel +2 | $$ |
| The Owl |
| Bar | Logan Square | Mon–Thu | 5 PM – 8 PM | House Cocktails (half-price), Ghost Candy Margarita (half-price) +4 | $ |
| The Wellsey Tavern |
| Bar | River North | Mon | 5 PM – 8 PM | Half off nacho, Domestic Beer +3 | $$ |
| Tin Lizzie |
| Bar | Lincoln Park | Wed–Thu | 5 PM – 8 PM | Well Cocktail, Wine by The Glass +6 | $$ |
| El Berrinches Restaurant |
| Restaurant | Pilsen | Fri | 9 PM – 2 AM | Vegas bomb / Lime margaritas, House tequila shots / Twisted teas +2 | $$ |
| Asadito |
| Bar | West Loop | Mon | Open to close | House Margarita | $ |
| Beatrix |
| Restaurant | Streeterville | Mon | Open to close | Wine bottles | $$ |
| Beatrix |
| Restaurant | Fulton Market | Mon | Open to close | Wine Bottles | $$ |
| Casa Tequila Chicago |
| Restaurant | West Town | Mon | Open to close | House margarita, Signature margarita +1 | $$ |
| El Charro de San Francisco Mexican Restaurant |
| Restaurant | East Side | Mon | Open to close | Monday Martini | $ |
| La Lunita |
| Restaurant | Logan Square | Fri | Until 6 PM | Margarita, Palomas +4 | $$ |
| Las Fuentes |
| Restaurant | South Side | Mon | Open to close | Lime Margarita, Strawberry Margarita +4 | $$ |
| Panchos Rooftop Cantina |
| Restaurant | The Loop | Tue–Fri | Until 7:30 PM | margaritas, margarita towers +1 | $$ |
| Punch Bowl Social |
| Bar | Fulton Market | Mon | Open to close | Old Fashioned, Cosmopolitan +16 | $$ |
| Reclaimed Bar & Restaurant - Chicago | Southern |
| Restaurant | North Center | Mon–Thu | Until 6:30 PM | Draft Beer, House White +4 | $$ |
| Solazo |
| Bar | West Elsdon | Wed–Fri | Until 6 PM | Al Pastor Taco, Cochinita Pibil Taco +6 | $$ |