| Adorn Bar & Restaurant |
| Restaurant | Streeterville | Mon–Thu, Sun | 3 PM – 6 PM | Brooks Dry Riesling, The Paring Bordeaux-Style Blend +10 | — |
| Land & Lake Rosemont |
| Restaurant | North Side | Mon–Thu, Sun | 3 PM – 5 PM | Homemade Chips, Fries +11 | $$ |
| Monarch & Lion, A British Restaurant |
| Pub | Streeterville | Mon–Sun | 3 PM – 5 PM | Blue Point Oysters, 1000 Layer Potatoes +11 | $$ |
| Pompette |
| Wine Bar | Bucktown | Mon, Wed–Sun | 3 PM – 6 PM | Sparkling Rose, Still Rosé +10 | $$ |
| Siena Tavern |
| Restaurant | River North | Mon–Sun | 3 PM – 6 PM | Arancini, Mini Wagyu Meatballs +13 | $$$ |
| Beatnik West Town |
| Restaurant | West Town | Wed–Sun | 4 PM – 6 PM | Baba Ganoush, Halloumi +4 | $$ |
| Boulevard |
| Sports Bar | West Town | Mon–Sun | 4 PM – 7 PM | Domestic Beer, Well Shot +8 | $$ |
| Butcher and the Bear |
| Bar | Lincoln Park | Tue–Sun | 4 PM – 7 PM | House Martinis, Dirtiest Martini +15 | $$$$ |
| Grant Park Bistro |
| Restaurant | The Loop | Mon–Thu, Sun | 4 PM – 6 PM | Fresh Cut Fries, House Made Chips with truffle cheddar powder +13 | $$ |
| HIDE+SEEK |
| Restaurant | Fulton Market | Mon–Thu, Sun | 4 PM – 6 PM | French Fries, Grilled Oysters +13 | $$ |
| La Licor Panamericana |
| Bar | Logan Square | Wed–Sun | 4 PM – 6:30 PM | 4AM Burger, Veggie Empanadas (2) +15 | $$ |
| Le Sud Mediterranean Kitchen |
| Restaurant | North Center | Tue–Sun | 4 PM – 6 PM | House Wine of the Day, Brut Prosecco +16 | $$ |
| Osito's Tap |
| Bar | Little Village | Wed–Thu, Sun | 4 PM – 6 PM | Wings (6 piece or 12 piece), Empanadas +7 | $$ |
| PERILLA korean fare |
| Restaurant | West Town | Mon–Sun | 4 PM – 6 PM | Raw oyster, Whole shrimp +30 | $$$ |
| Storyville Chicago |
| Bar | River North | Mon–Sun | 4 PM – 6 PM | House Cocktails, Old Fashioned +7 | $$ |
| Vincent |
| Restaurant | Andersonville | Mon–Sun | 4 PM – 6 PM | Marinated Olives, Happy Hour Board +17 | $$ |
| The Duplex |
| Bar | Logan Square | Thu–Sun | 5 PM – 6:30 PM | Bottled Beer, House Wine +13 | $ |
| Gilt Bar |
| Bar | River North | Mon–Sun | Until 5 PM | Sliders - American Cheeseburger, Sliders - Hot Fried Chicken +12 | $ |
| 90th Meridian Kitchen & Bar |
| Restaurant | The Loop | Tue–Thu | 3 PM – 7 PM | Roasted Brussels Sprouts, Wisconsin Cheese Curds +5 | $$ |
| Beatnik On The River |
| Restaurant | The Loop | Mon–Wed | 3 PM – 5 PM | Classic Cocktails, wine +1 | $$ |
| Benihana - Chicago (John Hancock) |
| Restaurant | Streeterville | Mon–Fri | 3 PM – 6 PM | Signature Cocktails - Rocky's Margarita, Edamame +39 | $ |
| Carmine's Italian Rosemont |
| Restaurant | North Side | Mon–Fri | 3 PM – 5 PM | Glass of House Selected Wine, Cocktail of the Week +16 | $$$ |
| Dove's Luncheonette |
| Restaurant | West Town | Thu–Sat | 3 PM – 6 PM | El Animal Fries, Relish Tray +13 | $$ |
| Fora |
| Restaurant | Fulton Market | Mon–Fri | 3 PM – 6 PM | Hugo, Orange Wine Sangria +26 | $$ |
| Fox's Restaurant & Pub |
| Restaurant | South Side | Tue–Fri | 3 PM – 6 PM | Shepherd's Pie, Tuscan Pasta with Chicken +12 | $ |
| 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 | $$ |
| Jake Melnick's Corner Tap |
| Restaurant | River North | Mon–Fri | 3 PM – 6 PM | Select Drafts, You Call It (Well Mixed Drinks) +6 | $$ |
| Leña Brava |
| Bar | Fulton Market | Mon–Fri | 3 PM – 5 PM | MEZCALITA, MARGARITA +19 | $$$ |
| New Line Tavern |
| Restaurant | West Loop | Mon–Fri | 3 PM – 6 PM | Jose Cuervo Devil's Reserve Shots, Teeling Shot +11 | $$ |
| Paradise Park | Pizza & Patio |
| Bar | West Town | Mon–Fri | 3 PM – 6 PM | Espresso Martini, Spritzes +12 | $$ |
| Pippin’s Tavern |
| Gastropub | River North | Mon–Fri | 3 PM – 6 PM | Burger, Draft Beer | $$ |
| Rounders Pub House |
| Sports Bar | Lakeview East | Mon–Fri | 3 PM – 6 PM | Old Style Draft, Kona Draft +4 | $$ |
| STK Steakhouse |
| Bar | River North | Mon–Fri | 3 PM – 5:30 PM | Oyster on The Half Shell, Tater Tots +20 | $$$$ |
| Summer House Santa Monica |
| Restaurant | Lincoln Park | Mon–Fri | 3 PM – 6 PM | Classic Martini, Espresso Martini +10 | $$ |
| Taureaux Tavern |
| Restaurant | The Loop | Mon–Fri | 3 PM – 6 PM | Buffalo Wings, Sliders +13 | $$ |
| Bar Siena |
| Restaurant | Fulton Market | Mon–Fri | 3:30 PM – 5:30 PM | Classic Martini, Espresso Martini +13 | $$ |
| Bub City |
| Bar | North Side | Mon–Fri | 3:30 PM – 5:30 PM | Single All American Burger, Single Cali Burger +10 | $$ |
| Land & Lake Kitchen |
| Restaurant | The Loop | Mon–Fri | 3:30 PM – 6 PM | Basket of fries, Loaded Fries +12 | $$ |
| McCormick & Schmick's Seafood & Steaks |
| Restaurant | North Side | Mon–Fri | 3:30 PM – 6:30 PM | Truffle Fries, Roasted Garlic Hummus +15 | $ |
| Cobblestone Cafe & Bistro |
| Restaurant | North Center | Tue–Fri | 4 PM – 6 PM | Old Fashioned, Daiquiri +13 | $$ |
| Daisy's Po-Boy and Tavern |
| Restaurant | Hyde Park | Tue–Fri | 4 PM – 6 PM | Draft beer, Mardi Gras Punch +7 | $$ |
| Drew's on Halsted |
| Restaurant | Lakeview East | Mon–Fri | 4 PM – 6 PM | Beer, Wine +5 | $$ |
| DSTRKT Bar & Grill |
| Sports Bar | West Town | Tue | 4 PM – 10 PM | Tacos, Margaritas | $$ |
| FireLake Grill House and Cocktail Bar |
| Restaurant | The Loop | Mon–Thu | 4 PM – 7 PM | Mega Pretzel, FireLake Smash Burger +9 | $$ |
| Fiya |
| Restaurant | Andersonville | Mon–Fri | 4 PM – 6 PM | Fries, Amba Mayo, Ketchup, Marinated Olives +12 | $$ |
| Gale Street Inn Chicago |
| Restaurant | Jefferson Park | Mon, Wed–Thu | 4 PM – 5 PM | Wines by the Glass, Krombacher Pints +13 | $$ |
| Gordo's Tiny Taco Bar |
| Restaurant | The Loop | Mon–Fri | 4 PM – 6 PM | Nachos, Tiny Quesadillas +9 | $ |
| Innjoy Logan Square |
| Bar | Logan Square | Mon–Fri | 4 PM – 6 PM | 312 Pints, Malort Shots | $$ |
| Kindling | Downtown Cookout & Cocktails |
| Restaurant | The Loop | Mon–Fri | 4 PM – 6 PM | The OKC Onion Smashburger, Raw Oysters +7 | $$$ |
| La Grande Boucherie Chicago |
| Restaurant | River North | Mon–Fri | 4 PM – 7 PM | Stella, House Wine (Sparkling, White, Red, Rosé) +15 | $$$ |
| Moon Star Kitchen & Bar |
| Bar | Old Town Triangle | Mon–Fri | 4 PM – 6 PM | Wagyu Cheeseburger Sliders (3), Steak Skewars +10 | $$ |
| Off Hours Beer Co. |
| Brewery | Bridgeport | Wed | 4 PM – 10 PM | Burger, Beer & Shot Combo | $$ |
| Park & Field |
| Bar | Logan Square | Fri | 4 PM – 6 PM | AYCD Beer, AYCD Wine +2 | $$ |
| Pour Decisions Chicago |
| Bar | Sheffield & DePaul | Tue | 4 PM – 11 PM | Tacos, Margaritas | $$ |
| Roanoke Restaurant |
| Restaurant | The Loop | Mon–Fri | 4 PM – 6 PM | Marinated Olives & Marcona Almonds, Fried Local Cheese Curds +15 | $$ |
| Southern Chicago |
| Restaurant | Near South Side | Mon–Fri | 4 PM – 6 PM | House White, House Red +13 | $$$$ |
| Spectrum Bar & Grill |
| Bar | West Loop | Mon | 4 PM – 7 PM | Chicken Tenders, Onion Rings, Fried Zucchini, Halloumi Rolls | $$ |
| Spice by CMB |
| Restaurant | Avondale | Wed–Fri | 4 PM – 6:30 PM | Crispy Black-Eyed Pea Fritters, Date-Glazed Sweet Potatoes +8 | $$$ |
| The Cheesecake Factory |
| Restaurant | Streeterville | Mon–Fri | 4 PM – 6 PM | Roadside Sliders, Avocado Eggrolls +31 | $ |
| The Oakville Grill & Cellar |
| Restaurant | Fulton Market | Mon–Fri | 4 PM – 6 PM | Bar snacks, Bottomless crispy parmesan fries +15 | $$$ |
| The Publican |
| Restaurant | Fulton Market | Mon–Fri | 4 PM – 6 PM | Pimento Cheese, Caesar Frites +14 | $ |
| Peckish Pig |
| Restaurant | North Side | Mon–Fri | 4:30 PM – 6 PM | Draft beers, House wines +2 | $$ |
| S.K.Y. |
| Restaurant | Lincoln Park | Mon–Thu | 4:30 PM – 6:30 PM | Chilled Oyster, Marinated Japanese Cucumbers +9 | $ |
| Swift Tavern - Wrigleyville |
| Bar | Lakeview East | Mon–Fri | 4:30 PM – 6:30 PM | Oysters, Tavern Burger +3 | $$ |
| Everything Bar |
| Bar | West Town | Wed–Sat | 5 PM – 7 PM | Margarita, Espresso Martini +4 | $$ |
| Golden Years |
| Cocktails | West Town | Mon, Wed–Thu | 5 PM – 7 PM | Rotating Punch, 22° Whisky Highball +3 | $$ |
| Palilgu |
| Bar | Logan Square | Wed–Sat | 5 PM – 6:30 PM | Rum Punch, Korean Tea Old Fashioned +8 | $$ |
| Standard Bar and Grill |
| Sports Bar | West Town | Mon | 5 PM – 7 PM | Plain Nachos, XL Pretzel +2 | $$ |
| The Royal Grocer & Co. |
| Bar | Bucktown | Tue–Fri | 5 PM – 7 PM | Potato Chips, House Cut Fries +13 | $$ |
| Innjoy |
| Bar | West Town | Mon–Fri | 6 PM – 8 PM | 1/2 Price Happy Hour (all drinks & apps), 25% Off Appetizers +1 | $ |
| Bar Parisette |
| Wine Bar | Logan Square | Mon | Open to close | champagne, cava +19 | $ |
| Beatrix |
| Restaurant | Streeterville | Mon | Open to close | Wine bottles | $$ |
| Beatrix |
| Restaurant | Fulton Market | Mon | Open to close | Wine Bottles | $$ |
| Cheesie's Pub & Grub - Lakeview |
| Pub | Lakeview East | Mon | Open to close | Any Drink, Smashed Cheesie + Domestic Beer | $ |
| Cheesie's Pub & Grub - Wrigleyville |
| Bar | Lakeview East | Mon | Open to close | Any Drink, Smashed Cheesie + Domestic Beer | $ |