| Declan's Irish Pub |
| Pub | Near North Side | Sat–Sun | 11 AM – close | Bloody Mary's | $ |
| The Moonlighter | Weekend bucket specials | Bar | Logan Square | Sat–Sun | Open to close | High Life Buckets, Miller Lite Buckets | $$ |
| The Village Inn Bar | All day | Bar | New City | Sun | Open to close | Loaded Bloody Marys, Mimosas | $ |
| Paterno's Pizza |
| Pizzeria | Jefferson Park | Mon, Wed–Sun | 9 AM – 5 PM | — | $ |
| Gyu-Kaku Japanese BBQ |
| Restaurant | Lakeview East | Mon–Sun | 11 AM – 5 PM | Takoyaki, Gyu-Sushi Yuzu Miso (4 pcs) +63 | $$ |
| Gyu-Kaku Japanese BBQ |
| Restaurant | Fulton Market | Mon–Sun | 11 AM – 6 PM | — | $$ |
| Si-Pie Pizzeria in Lakeview, Chicago |
| Pizzeria | Lakeview East | Mon–Sun | 11 AM – 6 PM | — | $ |
| Nori Sushi Chicago |
| Restaurant | Lakeview East | Fri–Sun | 12 PM – 3:30 PM | — | $$ |
| Replay Lincoln Park |
| Bar | Lakeview East | Sat–Sun | 1 PM – 5 PM | — | $$ |
| El Taco Ázteca - Pilsen |
| Restaurant | Pilsen | Mon–Sun | 2 PM – 5 PM | All cocktails | $$ |
| 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 | $ |
| Brown Bag Seafood Co. |
| Restaurant | The Loop | Mon–Sun | 3 PM – 6 PM | Dinner Plate, Shareables +1 | $ |
| Brown Bag Seafood Co. |
| Restaurant | Lakeview | Mon–Sun | 3 PM – 6 PM | Dinner Plate, Shareables +1 | $ |
| Dell' Rooster Restaurant & Bar |
| Restaurant | West Town | Wed–Sun | 3 PM – 6 PM | Corn Empanadas, Dell rooster Nachos +8 | $$ |
| Fry the Coop (West Town) |
| Restaurant | West Town | Mon–Sun | 3 PM – 5 PM | — | $ |
| La Dolce Vita Cucina - Chicago |
| Restaurant | Portage Park | Tue–Sun | 3 PM – 5 PM | Draft Beers, Hard Seltzers +8 | $$ |
| Las Fuentes |
| Restaurant | Sheffield & DePaul | Mon–Sun | 3 PM – 5 PM | Classic Lime Margarita, Especial Margarita +10 | $$ |
| Monarch & Lion, A British Restaurant |
| Pub | Streeterville | Mon–Sun | 3 PM – 5 PM | Blue Point Oysters, 1000 Layer Potatoes +11 | $$ |
| Nora Ristorante & Bar |
| Restaurant | Streeterville | Mon–Sun | 3 PM – 6 PM | — | $$ |
| Oak and Honey |
| Restaurant | Lakeview East | Wed–Sun | 3 PM – 6 PM | — | $$ |
| Pilsen Yards |
| Bar | Pilsen | Wed–Sun | 3 PM – 5:30 PM | Draft beer, Draft cocktails | $$ |
| Pompette |
| Wine Bar | Bucktown | Mon, Wed–Sun | 3 PM – 6 PM | Sparkling Rose, Still Rosé +10 | $$ |
| Present Tense Bar |
| Cocktails | Garfield Park | Mon–Sun | 3 PM – 7 PM | — | — |
| Rosebud Taylor Street |
| Restaurant | Little Italy | Mon–Sun | 3 PM – 5 PM | — | $$ |
| Siena Tavern |
| Restaurant | River North | Mon–Sun | 3 PM – 6 PM | Arancini, Mini Wagyu Meatballs +13 | $$$ |
| Tallboy Taco |
| Restaurant | Streeterville | Mon–Sun | 3 PM – 5 PM | Tallboy Margarita, Tallboy Margarita Pitcher +1 | $$ |
| Tierra y Fuego Mexican Steakhouse |
| Restaurant | Irving Park | Tue–Sun | 3 PM – 6 PM | Mini Flauta Rolls, Guac & Chips +4 | $$$ |
| Truth Chicago |
| Restaurant | Douglas | Mon–Tue, Thu–Sun | 3 PM – 6 PM | — | — |
| Union Sushi + BBQ + Izakaya |
| Bar | Goose Island | Mon–Sun | 3 PM – 5 PM | — | $$ |
| Boeufhaus |
| Bar | West Town | Mon, Wed–Sun | 3:30 PM – 5:30 PM | — | $$$$ |
| Enoteca Roma Ristorante |
| Restaurant | West Town | Wed–Sun | 3:30 PM – 6 PM | — | $$ |
| Fernando's Tequila Bar &. Restaurant |
| Bar | Lakeview | Mon–Sun | 3:30 PM – 5:30 PM | Red Wine Sangria, Shaken Shot - Mexican Candy +13 | $$ |
| Leiya |
| Restaurant | The Loop | Mon–Sun | 3:30 PM – 6:30 PM | Edamame, Vegetable Potstickers +13 | $$ |
| ADORO FUSION KITCHEN + BAR |
| Restaurant | West Town | Thu–Sun | 4 PM – 6 PM | — | $ |
| Alhambra Palace Chicago |
| Restaurant | Fulton Market | Wed–Sun | 4 PM – 7 PM | — | — |
| Bar Roma |
| Restaurant | Uptown | Tue–Sun | 4 PM – 6 PM | House Red, White or Rosé, Seasonal Collins +7 | $$ |
| Barrio |
| Restaurant | River North | Mon–Sun | 4 PM – 6 PM | Margaritas, Margaritas - Grande +5 | $$ |
| Beatnik West Town |
| Restaurant | West Town | Wed–Sun | 4 PM – 6 PM | Baba Ganoush, Halloumi +4 | $$ |
| Black & Caspian |
| Restaurant | Lakeview East | Tue–Sun | 4 PM – 6 PM | — | $$ |
| Boulevard |
| Sports Bar | West Town | Mon–Sun | 4 PM – 7 PM | Domestic Beer, Well Shot +8 | $$ |
| Butcher and the Bear |
| Bar | Lincoln Park | Tue–Sun | 4 PM – 7 PM | House Martinis, Dirtiest Martini +15 | $$$$ |
| Cafe Ba-Ba-Reeba! |
| Restaurant | Lincoln Park | Mon–Sun | 4 PM – 6 PM | Sangria pitchers, Estrella Damm bottles +2 | $$ |
| Cafe El Tapatio |
| Restaurant | Lakeview | Tue–Sun | 4 PM – 6 PM | — | $$ |
| Chapel Street Café and Restaurant |
| Restaurant | Streeterville | Mon–Sun | 4 PM – 6 PM | — | — |
| Dearly Beloved |
| Cocktails | Near North Side | Wed–Sun | 4 PM – 7 PM | Oysters, Wine by the Glass +2 | $$$ |
| Easy Bar |
| Bar | West Town | Mon–Sun | 4 PM – 6 PM | Drafts (half-price), House Cocktails (half-price) +4 | $ |
| GREEK PRIME |
| Restaurant | Bridgeport | Mon–Sun | 4 PM – 6 PM | — | $$ |
| Grill on 21 |
| Bar | The Loop | Mon–Sun | 4 PM – 6 PM | — | $$$ |
| HaiSous Vietnamese Kitchen |
| Restaurant | Pilsen | Wed–Sun | 4 PM – 5:30 PM | Old Fashioned, Seasonal Margarita +20 | $$ |
| Irish Nobleman Pub |
| Pub | West Town | Mon–Sun | 4 PM – 6 PM | — | $$ |
| La Licor Panamericana |
| Bar | Logan Square | Wed–Sun | 4 PM – 6:30 PM | 4AM Burger, Veggie Empanadas (2) +15 | $$ |
| La peña Cantina & Grill |
| Restaurant | Humboldt Park | Mon–Sun | 4 PM – 7 PM | — | — |
| Le Bar Chicago |
| Hotel | Rush & Division | Mon–Sun | 4 PM – 6 PM | — | $ |
| Le Sud Mediterranean Kitchen |
| Restaurant | North Center | Tue–Sun | 4 PM – 6 PM | House Wine of the Day, Brut Prosecco +16 | $$ |
| Mercat a la Planxa |
| Restaurant | The Loop | Mon–Sun | 4 PM – 5:30 PM | — | $$ |
| Nando's PERi-PERi |
| Restaurant | The Loop | Mon–Sun | 4 PM – 6 PM | — | $$ |
| Nando's PERi-PERi |
| Restaurant | Goose Island | Mon–Sun | 4 PM – 6 PM | — | $ |
| Nando's PERi-PERi |
| Restaurant | Hyde Park | Mon–Sun | 4 PM – 6 PM | — | $ |
| Nando's PERi-PERi |
| Restaurant | The Loop | Mon–Sun | 4 PM – 6 PM | — | $ |
| Nando's PERi-PERi |
| Restaurant | Lakeview East | Mon–Sun | 4 PM – 6 PM | — | $ |
| Nando's PERi-PERi |
| Restaurant | Streeterville | Mon–Sun | 4 PM – 6 PM | — | $ |
| Nando's PERi-PERi |
| Restaurant | The Loop | Mon–Sun | 4 PM – 6 PM | — | $ |
| PERILLA korean fare |
| Restaurant | West Town | Mon–Sun | 4 PM – 6 PM | Raw oyster, Whole shrimp +30 | $$$ |
| Port & Park Bistro | Bar |
| Bar | Lakeview | Wed–Sun | 4 PM – 6:30 PM | Grilled Chicken Sandwich, Port & Park Quarter-Pounder +9 | $ |
| Storyville Chicago |
| Bar | River North | Mon–Sun | 4 PM – 6 PM | House Cocktails, Old Fashioned +7 | $$ |
| Sweethearts |
| Bar | Andersonville | Wed–Sun | 4 PM – 6 PM | — | $$ |
| The L Station ChopHouse |
| Restaurant | Near North Side | Wed–Sun | 4 PM – 7 PM | — | — |
| Truluck's Ocean's Finest Seafood and Crab |
| Restaurant | North Side | Mon–Sun | 4 PM – 6 PM | Handcrafted cocktails, Premium spirits +2 | $$$$ |
| Vincent |
| Restaurant | Andersonville | Mon–Sun | 4 PM – 6 PM | Marinated Olives, Happy Hour Board +17 | $$ |
| Wang's |
| Bar | Lakeview East | Mon–Sun | 4 PM – 6 PM | — | $$ |
| Wrigleyville North |
| Bar | Lakeview East | Mon–Sun | 4 PM – 6 PM | drafts, Domestic bottles | $ |
| Lula Cafe |
| Restaurant | Logan Square | Mon, Wed–Sun | 4:30 PM – 7 PM | That's a Caper, The Rhuby Martini +10 | $$ |
| Old Pueblo Cantina |
| Bar | Lincoln Park | Mon–Sun | 4:30 PM – 5:30 PM | Queso (Chihuahua, Longhorn Cheddar, Cotija), Green Chile (Mild Chiles, Cotija) +9 | $$ |
| Swift & Sons |
| Restaurant | Fulton Market | Mon–Sun | 4:30 PM – 6 PM | whiskey classics | $$$$ |
| ArePA George Cantina |
| Restaurant | Logan Square | Tue–Sun | 5 PM – 7 PM | Berraco, Orquidea +9 | $$ |
| Big Wig Tacos |
| Restaurant | Logan Square | Mon–Sun | 5 PM – 7 PM | Margarita - Small, Margarita - Large | $ |
| Billy Sunday |
| Cocktails | Logan Square | Mon–Sun | 5 PM – 7 PM | Ranch Water, Suffering Bastard +7 | $ |
| Boutique |
| Cocktails | Gold Coast | Wed–Thu, Sun | 5 PM – 7 PM | — | — |
| Cafe Yaya |
| Café | Sheffield & DePaul | Tue, Thu–Sun | 5 PM – 6 PM | — | $$ |
| Chef’s Special Cocktail Bar |
| Cocktails | Bucktown | Mon–Sun | 5 PM – 6 PM | Egg roll with pork & shrimp (2pc), Vegetable spring rolls (2pc) +9 | $$ |
| Clever Coyote |
| Bar | West Town | Mon–Sun | 5 PM – 7 PM | — | $$ |
| Community Tavern |
| Restaurant | Portage Park | Tue–Sun | 5 PM – 6 PM | Select Appetizers, Select Classic Cocktails +2 | $$ |
| Desert Hawk |
| Bar | West Town | Mon–Sun | 5 PM – 6 PM | House Margarita, Ranch Water +4 | $$ |
| Fioretta |
| Bar | Fulton Market | Mon–Sun | 5 PM – 6:30 PM | Classic Martini, Classic Espresso Martini +4 | $$$$ |
| King of Cups |
| Cocktails | Lincoln Park | Mon–Sun | 5 PM – 7 PM | — | $$ |
| Life on Marz Community Club |
| Brewery | Logan Square | Tue–Sun | 5 PM – 7 PM | — | — |
| Lilac Tiger |
| Bar | West Town | Thu–Sun | 5 PM – 7 PM | — | $$ |
| Longman & Eagle |
| Restaurant | Logan Square | Mon, Fri–Sun | 5 PM – 10 PM | whiskey shots and other | $ |
| Maple & Ash |
| Restaurant | Rush & Division | Mon–Thu, Sun | 5 PM – 6 PM | — | $$$$ |
| Mariscos San Pedro |
| Restaurant | Pilsen | Mon–Sun | 5 PM – 6 PM | Margarita Pitcher, Cocktail of the day +3 | $$ |
| Minyoli |
| Restaurant | Andersonville | Mon–Sun | 5 PM – 7 PM | Sweet Potato Fries, Cucumber Salad +16 | $$ |
| Ox Bar & Hearth |
| Restaurant | Goose Island | Wed–Sun | 5 PM – 6 PM | hamm, select wines btg +1 | $$$ |
| Rebar |
| Bar | River North | Mon–Sun | 5 PM – 7 PM | — | — |
| Tapas Valencia Restaurant |
| Restaurant | Near South Side | Mon–Sun | 5 PM – 7 PM | — | $$ |
| The Duplex |
| Bar | Logan Square | Thu–Sun | 5 PM – 6:30 PM | Bottled Beer, House Wine +13 | $ |
| Tsukiji Sushi Sake Bar |
| Restaurant | West Town | Tue–Sun | 5 PM – 6 PM | — | $$ |
| Valedor |
| Cocktails | West Town | Tue–Sun | 5 PM – 7 PM | TOKI'O FASHIONED, WE LOVE LYCHEE +22 | $$ |
| Dorian’s |
| Cocktails | West Town | Wed–Sun | 6 PM – 8 PM | Select Classic Cocktails | $$ |
| The California Clipper |
| Cocktails | West Town | Tue–Sun | 6 PM – 8 PM | Gran Centenario Mixers & Margaritas, Condesa Gin Mixers & Basil Gimlet +5 | $ |
| Gyu-Kaku Japanese BBQ |
| Restaurant | Streeterville | Mon–Sun | 8:45 PM – 10 PM | — | $$ |
| Five Iron Golf |
| Bar | Bucktown | Mon–Sun | 9 PM – close | Boneless Wings, Bone-In Wings +4 | $ |
| Five Iron Golf |
| Bar | River North | Mon–Sun | 9 PM – close | Simulator Rentals, Boneless Wings +5 | $ |
| Coalfire |
| Pizzeria | Wrigleyville | Tue–Sun | Until 7 PM | Draft Beers, Wine Pours +2 | $$ |
| Gao's BBQ & Crab |
| Restaurant | Armour Square | Mon–Sun | Until 6:30 PM | — | $$ |
| Gilt Bar |
| Bar | River North | Mon–Sun | Until 5 PM | Sliders - American Cheeseburger, Sliders - Hot Fried Chicken +12 | $ |
| Giordano's |
| Restaurant | Hyde Park | Mon–Sun | Until 3 PM | Personal Deep Dish Pizza, Any Sandwich on Menu +1 | $$ |
| Inkwell |
| Bar | Fulton Market | Mon–Sun | Until 6 PM | Bar Mix, Olives +1 | $$ |
| Lockwood Restaurant |
| Hotel | The Loop | Mon–Sun | Until 4 PM | Palmer House Bloody Mary or Mimosa | $$ |
| Moonflower |
| Bar | Portage Park | Tue–Sun | Until 6 PM | Paloma, Lemon Drop +4 | $$ |
| Blue Sushi Sake Grill |
| Restaurant | Lincoln Park | Mon–Fri | 11 AM – 6:30 PM | — | $$ |
| Bistro Monadnock |
| Restaurant | The Loop | Tue–Sat | 2:30 PM – 5:30 PM | Gimlet, Sazerac +8 | $$ |
| Boqueria Fulton Market |
| Restaurant | Fulton Market | Mon–Fri | 3 PM – 6 PM | Pan con Tomate, Croquetas de Jamón +12 | $$$ |
| City Tap and Grill |
| Sports Bar | North Side | Fri | 3 PM – 6 PM | Martini, Tito's +1 | $ |
| Daisies |
| Restaurant | Logan Square | Tue–Sat | 3 PM – 5 PM | House Aperitivo Spritz, Logan Sour +39 | $$$ |
| Dove's Luncheonette |
| Restaurant | West Town | Thu–Sat | 3 PM – 6 PM | El Animal Fries, Relish Tray +13 | $$ |
| George Street Pub |
| Pub | Lakeview East | Mon–Fri | 3 PM – 6 PM | Pub Chips, Spinach & Artichoke Dip +10 | $$ |
| Honky Tonk BBQ / The Tonk |
| Bar | Pilsen | Wed–Fri | 3 PM – 5 PM | — | $$ |
| Moretti's Ristorante and Pizzeria |
| Restaurant | Edison Park | Mon–Fri | 3 PM – 6 PM | 10" Thin Crust 1-Topping Pizza, Brussels Sprouts +12 | $ |
| New Line Tavern |
| Restaurant | West Loop | Mon–Fri | 3 PM – 6 PM | Jose Cuervo Devil's Reserve Shots, Teeling Shot +11 | $$ |
| Shake A Leg |
| Restaurant | Austin | Wed–Thu | 3 PM – 7 PM | Margarita, Hurricane +4 | $$ |
| STK Steakhouse |
| Bar | River North | Mon–Fri | 3 PM – 5:30 PM | Oyster on The Half Shell, Tater Tots +20 | $$$$ |
| The Ivy Bar and Kitchen |
| Sports Bar | Lakeview | Mon–Thu | 3 PM – 5 PM | — | $$ |
| Bub City |
| Bar | North Side | Mon–Fri | 3:30 PM – 5:30 PM | Single All American Burger, Single Cali Burger +10 | $$ |
| aliveOne |
| Bar | Lincoln Park | Fri–Sat | 4 PM – 6 PM | — | $ |
| Bar Pendry Chicago |
| Cocktails | The Loop | Tue | 4 PM – 9 PM | Chef's Choice Oysters | $$ |
| Bub City |
| Restaurant | River North | Mon–Fri | 4 PM – 6 PM | — | $$ |
| Bungalow by Middle Brow |
| Bar | Logan Square | Wed–Fri | 4 PM – 6 PM | — | $$ |
| Caché 310 |
| Cocktails | West Loop | Mon–Thu | 4 PM – 6 PM | Signature libations, Beer & seltzer | $$ |
| Cafecito |
| Café | Streeterville | Mon–Fri | 4 PM – 7 PM | Specialty cocktails, Wine glasses | $ |
| CH Distillery | Jōtō Sushi |
| Restaurant | West Loop | Tue–Sat | 4 PM – 6 PM | — | $$$ |
| Clara |
| Cocktails | West Town | Tue–Sat | 4 PM – 6 PM | — | $$ |
| Daisy's Po-Boy and Tavern |
| Restaurant | Hyde Park | Tue–Fri | 4 PM – 6 PM | Draft beer, Mardi Gras Punch +7 | $$ |
| Dave & Buster's Rosemont |
| Sports Bar | North Side | Mon–Fri | 4 PM – 7 PM | House wine, 7oz glass, 22oz select domestic draft beer +1 | $$ |
| Flo |
| Restaurant | West Town | Fri–Sat | 4 PM – 7 PM | Wine Wednesday, glasses of select wines +1 | $$ |
| Fuego Logan Square |
| Restaurant | Logan Square | Wed–Fri | 4 PM – 7 PM | — | $$ |
| Gale Street Inn Chicago |
| Restaurant | Jefferson Park | Mon, Wed–Thu | 4 PM – 5 PM | Wines by the Glass, Krombacher Pints +13 | $$ |
| Happy Day Tavern |
| Bar | Old Irving Park | Mon–Tue | 4 PM – 7 PM | — | $ |
| Le Petit Marcel |
| Restaurant | Lakeview East | Mon–Thu | 4 PM – 6 PM | — | $$$ |
| Lemon |
| Cocktails | West Town | Mon–Sat | 4 PM – 6 PM | Cheap Beer, Industry Standard +7 | $$ |
| Mama Delia |
| Bar | West Town | Tue–Sat | 4 PM – 7 PM | One Drink, One Pintxo | $$ |
| Mexican Radio |
| Restaurant | The Loop | Mon | 4 PM – 6 PM | Martini Monday (tiny martini, cosmo, lemondrop, kolben) | $$ |
| Nettare |
| Restaurant | West Town | Thu | 4 PM – 6 PM | — | $$$ |
| Nicky's of Beverly |
| Bar | South Side | Mon–Fri | 4 PM – 7 PM | Buffalo Shrimp, Parmesan Truffle Fries +8 | $ |
| NoodleBird |
| Restaurant | Logan Square | Wed–Fri | 4 PM – 6 PM | — | $$ |
| Prime 57 Restaurant + Lounge |
| Restaurant | Little Italy | Tue | 4 PM – 7 PM | 2 Birria Tacos, 2 Salmon Tacos +8 | $$ |
| Roscoe's Tavern |
| Bar | Lakeview East | Sat | 4 PM – 7 PM | Sarti Spritz, Hugo Spritz +1 | $$ |
| Soul Prime |
| Restaurant | West Town | Tue–Wed, Fri | 4 PM – 6 PM | Short Rib Taco, Spicy Buffalo Wings +13 | $$ |
| Sushi-san |
| Restaurant | Lincoln Park | Mon–Thu | 4 PM – 6 PM | Sake, Wine +9 | $$ |
| The Park Bar & Grill |
| Bar | East Side | Thu–Sat | 4 PM – 7 PM | Martinis, Appetizers | $$ |
| Volo Restaurant Wine Bar |
| Wine Bar | North Center | Tue–Sat | 4 PM – 6 PM | Oysters, Limoncello Fizz Shots +6 | $$ |
| VU Rooftop |
| Bar | Near South Side | Mon–Thu | 4 PM – 5 PM | Tiny 'Tini (happy hour special), Glass of Wine (happy hour special) | $$ |
| XOchimilco Mexican Restaurant |
| Restaurant | Lincoln Square | Mon–Sat | 4 PM – 6 PM | Sangria, Margaritas +2 | $$ |
| Frontera Grill |
| Restaurant | River North | Tue–Wed | 4:30 PM – 6 PM | Rick's Margarita, Oaxacan Old Fashioned +19 | $$ |
| Itoko |
| Restaurant | Lakeview | Mon–Sat | 4:30 PM – 6 PM | Signature cocktails, Sake +5 | $ |
| Kayao Restaurant |
| Restaurant | Near North Side | Mon–Fri | 4:30 PM – 7 PM | Pisco Sour, House Wines +11 | $$$ |
| Peckish Pig |
| Restaurant | North Side | Mon–Fri | 4:30 PM – 6 PM | Draft beers, House wines +2 | $$ |
| Beaumont's |
| Bar | Lincoln Park | Mon–Tue | 5 PM – 6:30 PM | Tini Martinis, All Menu Cocktails & Wines By The Glass +1 | $$ |
| Black Hole Bar |
| Bar | West Town | Mon–Thu | 5 PM – 7 PM | — | $ |
| Brando's Lincoln Park |
| Bar | Lincoln Park | Wed–Sat | 5 PM – 7 PM | — | $$ |
| Brasero |
| Restaurant | West Town | Tue–Sat | 5 PM – 7 PM | Pork Sammy, Yellowfin Tuna Crudo +13 | $$$$ |
| Cebu Chicago |
| Restaurant | Lakeview | Thu–Sat | 5 PM – 6:30 PM | All Bottle Wines, Popcorn Chicken +8 | $$ |
| Charlie Martin's |
| Restaurant | River North | Tue–Sat | 5 PM – 7 PM | Shrimp Cocktail, Oysters on the Half Shell +10 | $$$$ |
| Everything Bar |
| Bar | West Town | Wed–Sat | 5 PM – 7 PM | Margarita, Espresso Martini +4 | $$ |
| Fathom |
| Bar | Lakeview | Mon–Fri | 5 PM – 6 PM | — | $$ |
| Golden Years |
| Cocktails | West Town | Mon, Wed–Thu | 5 PM – 7 PM | Rotating Punch, 22° Whisky Highball +3 | $$ |
| Icon Bar & Lounge |
| Cocktails | Lincoln Park | Thu–Sat | 5 PM – 10 PM | Craft cocktails, Select martinis +3 | $ |
| Lark Restaurant & Bar |
| Restaurant | Lakeview East | Tue–Fri | 5 PM – 6:30 PM | Bud Light, Select Red & White Wine +2 | $$ |
| Ludlow Liquors |
| Bar | Avondale | Mon–Fri | 5 PM – 6 PM | — | $$ |
| LÝRA |
| Restaurant | Fulton Market | Mon–Sat | 5 PM – 6:30 PM | House Red or White, Classic Martini +12 | $$$$ |
| Nighthawk |
| Bar | Albany Park | Mon–Fri | 5 PM – 7 PM | Commuter Special | $ |
| Nobody's Darling |
| Bar | Andersonville | Wed–Thu | 5 PM – 7 PM | — | $$ |
| Palilgu |
| Bar | Logan Square | Wed–Sat | 5 PM – 6:30 PM | Rum Punch, Korean Tea Old Fashioned +8 | $$ |
| Revolver |
| Cocktails | West Town | Tue–Sat | 5 PM – 6:30 PM | — | — |
| Stardust |
| Cocktails | River North | Thu–Sat | 5 PM – 8 PM | — | $ |
| The Bull Moose |
| Bar | Lincoln Park | Mon–Tue | 5 PM – 6:30 PM | Martini (any menu cocktail), Wines by the glass +1 | $$$$ |
| Un amor |
| Restaurant | West Town | Thu–Sat | 5 PM – 6:30 PM | — | $$ |
| Uvae Kitchen and Wine Bar |
| Wine Bar | Andersonville | Tue–Fri | 5 PM – 6:30 PM | Oysters, Shrimp Cocktail +6 | $$ |
| Winter's Jazz Club |
| Cocktails | Streeterville | Wed–Thu | 5 PM – 6 PM | Select drinks | $$ |
| W. Hideaway Lounge |
| Cocktails | Douglas | Tue–Thu | 5:30 PM – 7:30 PM | — | $$ |
| Botanero |
| Cocktails | Pulaski Park | Wed–Sat | 6 PM – 7:30 PM | — | $$ |
| Innjoy |
| Bar | West Town | Mon–Fri | 6 PM – 8 PM | 1/2 Price Happy Hour (all drinks & apps), 25% Off Appetizers +1 | $ |
| Rizzo's |
| Bar | Lakeview East | Fri–Sat | 6 PM – 9 PM | — | $$ |
| The Black Lion |
| Bar | Logan Square | Fri–Sat | 6 PM – 8 PM | cocktail | $$ |
| Alibaba Retro Club |
| Club | Union Ridge | Fri–Sat | 7 PM – 9 PM | — | $ |
| The Original Mother's |
| Bar | Gold Coast | Thu–Sat | 7 PM – 9 PM | — | $$ |
| Big City Tap |
| Bar | Lakeview East | Fri | 7:30 PM – 9:30 PM | Miller Lite Pint | $$ |
| Home Away From Home |
| Restaurant | Lakeview East | Fri–Sat | 8 PM – 10 PM | — | $$ |
| Late Bar |
| Bar | Avondale | Thu–Sat | 8 PM – 10 PM | Sangria, PBR + choice of well shot/Malört | $ |
| R.J. Grunts |
| Restaurant | Lincoln Park | Thu–Sat | 8 PM – 10 PM | Classic Cocktails, Beers +1 | $$ |
| El Berrinches Restaurant |
| Restaurant | Pilsen | Fri | 9 PM – 2 AM | Vegas bomb / Lime margaritas, House tequila shots / Twisted teas +2 | $$ |
| Tack Room |
| Cocktails | Pilsen | Sat | 9 PM – 12 AM | Pilsen | $$ |
| Bar Parisette |
| Wine Bar | Logan Square | Mon | Open to close | champagne, cava +19 | $ |
| Bar Sótano |
| Bar | River North | Wed–Sat | Until 6 PM | Fire Fried Chicken, Dry Aged Beef Albondigas +9 | $$ |
| El Charro de San Francisco Mexican Restaurant |
| Restaurant | East Side | Mon | Open to close | Monday Martini | $ |
| La Bella Trattoria Loop |
| Restaurant | The Loop | Mon | Open to close | Pizza | $$ |
| La Lunita |
| Restaurant | Logan Square | Fri | Until 6 PM | Margarita, Palomas +4 | $$ |
| Las Fuentes |
| Restaurant | South Side | Mon | Open to close | Lime Margarita, Strawberry Margarita +4 | $$ |