| Gao's BBQ & Crab | Ends in 17h 41m | Restaurant | Armour Square | Mon–Sun | Until 6:30 PM | — | $$ |
| Paterno's Pizza |
| Pizzeria | Jefferson Park | Mon, Wed–Sun | 9 AM – 5 PM | — | $ |
| Gyu-Kaku Japanese BBQ |
| Restaurant | Lakeview East | Mon–Sun | 11 AM – 5 PM | Takoyaki, Gyu-Sushi Yuzu Miso (4 pcs) +63 | $$ |
| Gyu-Kaku Japanese BBQ |
| Restaurant | Fulton Market | Mon–Sun | 11 AM – 6 PM | — | $$ |
| Si-Pie Pizzeria in Lakeview, Chicago |
| Pizzeria | Lakeview East | Mon–Sun | 11 AM – 6 PM | — | $ |
| El Taco Ázteca - Pilsen |
| Restaurant | Pilsen | Mon–Sun | 2 PM – 5 PM | All cocktails | $$ |
| Henrietta |
| Restaurant | The Loop | Mon–Sun | 2 PM – 6 PM | Hangtime, Pinot Noir, Greenwing, Cabernet Sauvignon +25 | $ |
| The Purple Pig Restaurant |
| Restaurant | River North | Mon–Wed, Sun | 2 PM – 5 PM | — | $$$ |
| The Village Inn Bar |
| Bar | New City | Mon–Tue, Thu | 2 PM – 6 PM | Martinis, Blue Moons +1 | $ |
| Adorn Bar & Restaurant |
| Restaurant | Streeterville | Mon–Thu, Sun | 3 PM – 6 PM | Brooks Dry Riesling, The Paring Bordeaux-Style Blend +10 | — |
| BiXi Beer |
| Bar | Logan Square | Mon, Thu–Fri, Sun | 3 PM – 5 PM | — | $$ |
| Boqueria Fulton Market |
| Restaurant | Fulton Market | Mon–Fri | 3 PM – 6 PM | Pan con Tomate, Croquetas de Jamón +12 | $$$ |
| Brown Bag Seafood Co. |
| Restaurant | The Loop | Mon–Sun | 3 PM – 6 PM | Dinner Plate, Shareables +1 | $ |
| Brown Bag Seafood Co. |
| Restaurant | Lakeview | Mon–Sun | 3 PM – 6 PM | Dinner Plate, Shareables +1 | $ |
| Cafe Con Leche |
| Restaurant | Logan Square | Mon–Fri | 3 PM – 6 PM | Margarita, Margarita with flavored add-on +9 | $$ |
| Fry the Coop (West Town) |
| Restaurant | West Town | Mon–Sun | 3 PM – 5 PM | — | $ |
| George Street Pub |
| Pub | Lakeview East | Mon–Fri | 3 PM – 6 PM | Pub Chips, Spinach & Artichoke Dip +10 | $$ |
| Land & Lake Rosemont |
| Restaurant | North Side | Mon–Thu, Sun | 3 PM – 5 PM | Homemade Chips, Fries +11 | $$ |
| Las Fuentes |
| Restaurant | Sheffield & DePaul | Mon–Sun | 3 PM – 5 PM | Classic Lime Margarita, Especial Margarita +10 | $$ |
| Monarch & Lion, A British Restaurant |
| Pub | Streeterville | Mon–Sun | 3 PM – 5 PM | Blue Point Oysters, 1000 Layer Potatoes +11 | $$ |
| Moretti's Ristorante and Pizzeria |
| Restaurant | Edison Park | Mon–Fri | 3 PM – 6 PM | 10" Thin Crust 1-Topping Pizza, Brussels Sprouts +12 | $ |
| Nora Ristorante & Bar |
| Restaurant | Streeterville | Mon–Sun | 3 PM – 6 PM | — | $$ |
| Pompette |
| Wine Bar | Bucktown | Mon, Wed–Sun | 3 PM – 6 PM | Sparkling Rose, Still Rosé +10 | $$ |
| Present Tense Bar |
| Cocktails | Garfield Park | Mon–Sun | 3 PM – 7 PM | — | — |
| R Public House |
| Bar | Rogers Park | Mon–Thu, Sun | 3 PM – 5 PM | House cocktails, Margarita flights +3 | $$ |
| ROCKS lakeview |
| Bar | Lakeview East | Mon–Fri | 3 PM – 6 PM | — | $$ |
| Rosebud Taylor Street |
| Restaurant | Little Italy | Mon–Sun | 3 PM – 5 PM | — | $$ |
| Senoritas Cantina On Dearborn |
| Bar | The Loop | Mon–Fri | 3 PM – 6 PM | Appetizers, All Beer | $$ |
| Siena Tavern |
| Restaurant | River North | Mon–Sun | 3 PM – 6 PM | Arancini, Mini Wagyu Meatballs +13 | $$$ |
| STK Steakhouse |
| Bar | River North | Mon–Fri | 3 PM – 5:30 PM | Oyster on The Half Shell, Tater Tots +20 | $$$$ |
| Tallboy Taco |
| Restaurant | Streeterville | Mon–Sun | 3 PM – 5 PM | Tallboy Margarita, Tallboy Margarita Pitcher +1 | $$ |
| Tavern On Rush |
| Bar | Gold Coast | Mon–Thu, Sun | 3 PM – 6 PM | Caesar Salad, Feta Hummus +11 | $$$ |
| Truth Chicago |
| Restaurant | Douglas | Mon–Tue, Thu–Sun | 3 PM – 6 PM | — | — |
| Union Sushi + BBQ + Izakaya |
| Bar | Goose Island | Mon–Sun | 3 PM – 5 PM | — | $$ |
| Boeufhaus |
| Bar | West Town | Mon, Wed–Sun | 3:30 PM – 5:30 PM | — | $$$$ |
| Bub City |
| Bar | North Side | Mon–Fri | 3:30 PM – 5:30 PM | Single All American Burger, Single Cali Burger +10 | $$ |
| Fernando's Tequila Bar &. Restaurant |
| Bar | Lakeview | Mon–Sun | 3:30 PM – 5:30 PM | Red Wine Sangria, Shaken Shot - Mexican Candy +13 | $$ |
| Leiya |
| Restaurant | The Loop | Mon–Sun | 3:30 PM – 6:30 PM | Edamame, Vegetable Potstickers +13 | $$ |
| Axum Ethiopian Restaurant |
| Restaurant | Magnolia Glen | Mon–Thu, Sun | 4 PM – 6 PM | — | — |
| 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 | $$ |
| Bub City |
| Restaurant | River North | Mon–Fri | 4 PM – 6 PM | — | $$ |
| Cafe Ba-Ba-Reeba! |
| Restaurant | Lincoln Park | Mon–Sun | 4 PM – 6 PM | Sangria pitchers, Estrella Damm bottles +2 | $$ |
| Cafecito |
| Café | Streeterville | Mon–Fri | 4 PM – 7 PM | Specialty cocktails, Wine glasses | $ |
| Chapel Street Café and Restaurant |
| Restaurant | Streeterville | Mon–Sun | 4 PM – 6 PM | — | — |
| Dave & Buster's Rosemont |
| Sports Bar | North Side | Mon–Fri | 4 PM – 7 PM | House wine, 7oz glass, 22oz select domestic draft beer +1 | $$ |
| Double Fun |
| Cocktails | Rush & Division | Mon–Thu | 4 PM – 6 PM | — | $$ |
| Easy Bar |
| Bar | West Town | Mon–Sun | 4 PM – 6 PM | Drafts (half-price), House Cocktails (half-price) +4 | $ |
| Fireside Restaurant & Lounge |
| Restaurant | Andersonville | Mon–Fri | 4 PM – 6 PM | House Red & White Wine, Homemade Sangria (Peach, White, Red, Raspberry) +2 | $$ |
| Grant Park Bistro |
| Restaurant | The Loop | Mon–Thu, Sun | 4 PM – 6 PM | Fresh Cut Fries, House Made Chips with truffle cheddar powder +13 | $$ |
| GREEK PRIME |
| Restaurant | Bridgeport | Mon–Sun | 4 PM – 6 PM | — | $$ |
| Grill on 21 |
| Bar | The Loop | Mon–Sun | 4 PM – 6 PM | — | $$$ |
| Happy Day Tavern |
| Bar | Old Irving Park | Mon–Tue | 4 PM – 7 PM | — | $ |
| HIDE+SEEK |
| Restaurant | Fulton Market | Mon–Thu, Sun | 4 PM – 6 PM | French Fries, Grilled Oysters +13 | $$ |
| Irish Nobleman Pub |
| Pub | West Town | Mon–Sun | 4 PM – 6 PM | — | $$ |
| La peña Cantina & Grill |
| Restaurant | Humboldt Park | Mon–Sun | 4 PM – 7 PM | — | — |
| Le Bar Chicago |
| Hotel | Rush & Division | Mon–Sun | 4 PM – 6 PM | — | $ |
| Mercat a la Planxa |
| Restaurant | The Loop | Mon–Sun | 4 PM – 5:30 PM | — | $$ |
| Mexican Radio |
| Restaurant | The Loop | Mon | 4 PM – 6 PM | Martini Monday (tiny martini, cosmo, lemondrop, kolben) | $$ |
| Nando's PERi-PERi |
| Restaurant | The Loop | Mon–Sun | 4 PM – 6 PM | — | $$ |
| 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 | — | $ |
| New Celebrity Lounge |
| Bar | South Side | Mon–Tue, Fri, Sun | 4 PM – 6 PM | — | $$ |
| Nicky's of Beverly |
| Bar | South Side | Mon–Fri | 4 PM – 7 PM | Buffalo Shrimp, Parmesan Truffle Fries +8 | $ |
| PERILLA korean fare |
| Restaurant | West Town | Mon–Sun | 4 PM – 6 PM | Raw oyster, Whole shrimp +30 | $$$ |
| River North Bistro |
| Restaurant | River North | Mon–Tue, Thu, Sun | 4 PM – 6 PM | — | $$ |
| Rooftop Chicago (J Parker) |
| Bar | Old Town Triangle | Mon–Thu, Sun | 4 PM – 6 PM | Espresso Martini & Classic Gin/Vodka Martinis, Old Fashioned +10 | $ |
| Storyville Chicago |
| Bar | River North | Mon–Sun | 4 PM – 6 PM | House Cocktails, Old Fashioned +7 | $$ |
| Sushi-san |
| Restaurant | Lincoln Park | Mon–Thu | 4 PM – 6 PM | Sake, Wine +9 | $$ |
| The J. Parker |
| Hotel | Old Town Triangle | Mon–Thu, Sun | 4 PM – 6 PM | Espresso Martini & Classic Gin/Vodka Martinis, Old Fashioned +10 | $$ |
| The Lodge Tavern |
| Bar | Rush & Division | Mon–Fri | 4 PM – 6 PM | Busch Light | $ |
| Truluck's Ocean's Finest Seafood and Crab |
| Restaurant | North Side | Mon–Sun | 4 PM – 6 PM | Handcrafted cocktails, Premium spirits +2 | $$$$ |
| Vincent |
| Restaurant | Andersonville | Mon–Sun | 4 PM – 6 PM | Marinated Olives, Happy Hour Board +17 | $$ |
| W XYZ Bar |
| Restaurant | Streeterville | Mon–Thu, Sun | 4 PM – 6 PM | — | $$ |
| Wang's |
| Bar | Lakeview East | Mon–Sun | 4 PM – 6 PM | — | $$ |
| Wrigleyville North |
| Bar | Lakeview East | Mon–Sun | 4 PM – 6 PM | drafts, Domestic bottles | $ |
| Kayao Restaurant |
| Restaurant | Near North Side | Mon–Fri | 4:30 PM – 7 PM | Pisco Sour, House Wines +11 | $$$ |
| Lula Cafe |
| Restaurant | Logan Square | Mon, Wed–Sun | 4:30 PM – 7 PM | That's a Caper, The Rhuby Martini +10 | $$ |
| 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 | $$ |
| Sofi Restaurant |
| Restaurant | The Loop | Mon–Thu, Sun | 4:30 PM – 6 PM | Soup of the Day, Burrata with Roasted Bell Peppers +11 | $$$ |
| Swift & Sons |
| Restaurant | Fulton Market | Mon–Sun | 4:30 PM – 6 PM | whiskey classics | $$$$ |
| Beaumont's |
| Bar | Lincoln Park | Mon–Tue | 5 PM – 6:30 PM | Tini Martinis, All Menu Cocktails & Wines By The Glass +1 | $$ |
| 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 | $ |
| Bokeh |
| Cocktails | Albany Park | Mon–Thu, Sun | 5 PM – 6 PM | Cocktails | $$ |
| Chef’s Special Cocktail Bar |
| Cocktails | Bucktown | Mon–Sun | 5 PM – 6 PM | Egg roll with pork & shrimp (2pc), Vegetable spring rolls (2pc) +9 | $$ |
| Clever Coyote |
| Bar | West Town | Mon–Sun | 5 PM – 7 PM | — | $$ |
| Desert Hawk |
| Bar | West Town | Mon–Sun | 5 PM – 6 PM | House Margarita, Ranch Water +4 | $$ |
| Fathom |
| Bar | Lakeview | Mon–Fri | 5 PM – 6 PM | — | $$ |
| Fioretta |
| Bar | Fulton Market | Mon–Sun | 5 PM – 6:30 PM | Classic Martini, Classic Espresso Martini +4 | $$$$ |
| Golden Years |
| Cocktails | West Town | Mon, Wed–Thu | 5 PM – 7 PM | Rotating Punch, 22° Whisky Highball +3 | $$ |
| King of Cups |
| Cocktails | Lincoln Park | Mon–Sun | 5 PM – 7 PM | — | $$ |
| Longman & Eagle |
| Restaurant | Logan Square | Mon, Fri–Sun | 5 PM – 10 PM | whiskey shots and other | $ |
| LÝRA |
| Restaurant | Fulton Market | Mon–Sat | 5 PM – 6:30 PM | House Red or White, Classic Martini +12 | $$$$ |
| Maple & Ash |
| Restaurant | Rush & Division | Mon–Thu, Sun | 5 PM – 6 PM | — | $$$$ |
| Mariscos San Pedro |
| Restaurant | Pilsen | Mon–Sun | 5 PM – 6 PM | Margarita Pitcher, Cocktail of the day +3 | $$ |
| Minyoli |
| Restaurant | Andersonville | Mon–Sun | 5 PM – 7 PM | Sweet Potato Fries, Cucumber Salad +16 | $$ |
| Nighthawk |
| Bar | Albany Park | Mon–Fri | 5 PM – 7 PM | Commuter Special | $ |
| Nine Bar |
| Cocktails | Armour Square | Mon, Wed–Thu, Sun | 5 PM – 6 PM | Classic Cocktails (Old Fashioned, Manhattan, Negroni, Margarita, Daiquiri, Gimlet), Sake Bombs +5 | $$ |
| Queen Mary |
| Bar | West Town | Mon | 5 PM – 7 PM | Classic martinis | $$ |
| Rebar |
| Bar | River North | Mon–Sun | 5 PM – 7 PM | — | — |
| Streeter's Tavern |
| Bar | Rush & Division | Mon–Thu | 5 PM – 7 PM | Bud Light Drafts, Patron | $$ |
| Tapas Valencia Restaurant |
| Restaurant | Near South Side | Mon–Sun | 5 PM – 7 PM | — | $$ |
| The Bull Moose |
| Bar | Lincoln Park | Mon–Tue | 5 PM – 6:30 PM | Martini (any menu cocktail), Wines by the glass +1 | $$$$ |
| The District House |
| Bar | Jefferson Park | Mon–Thu | 5 PM – 7 PM | — | $$ |
| Innjoy |
| Bar | West Town | Mon–Fri | 6 PM – 8 PM | 1/2 Price Happy Hour (all drinks & apps), 25% Off Appetizers +1 | $ |
| Sari's Restaurant & Bar |
| Sports Bar | West Town | Mon, Sun | 6 PM – 8 PM | — | $ |
| Lincoln Karaoke |
| Cocktails | Lincoln Square | Mon–Thu, Sun | 7 PM – 9 PM | — | $$ |
| Redhead Piano Bar |
| Bar | River North | Mon–Thu, Sun | 7 PM – 9 PM | Tullamore D.E.W. Manhattan | $$ |
| Gyu-Kaku Japanese BBQ |
| Restaurant | Streeterville | Mon–Sun | 8:45 PM – 10 PM | — | $$ |
| Five Iron Golf |
| Bar | Bucktown | Mon–Sun | 9 PM – close | Boneless Wings, Bone-In Wings +4 | $ |
| Five Iron Golf |
| Bar | River North | Mon–Sun | 9 PM – close | Simulator Rentals, Boneless Wings +5 | $ |
| Big Mini Putt Club |
| Bar | Lakeview East | Mon | Open to close | Select Draft beers & ciders, Pitchers | $ |
| Big Mini Putt Club |
| Bar | West Town | Mon | Open to close | Select draft beers & ciders, Pitchers | $$ |
| El Charro de San Francisco Mexican Restaurant |
| Restaurant | East Side | Mon | Open to close | Monday Martini | $ |
| 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 | $$ |
| Inkwell |
| Bar | Fulton Market | Mon–Sun | Until 6 PM | Bar Mix, Olives +1 | $$ |
| La Bella Trattoria Loop |
| Restaurant | The Loop | Mon | Open to close | Pizza | $$ |
| Las Fuentes |
| Restaurant | South Side | Mon | Open to close | Lime Margarita, Strawberry Margarita +4 | $$ |
| Lockwood Restaurant |
| Hotel | The Loop | Mon–Sun | Until 4 PM | Palmer House Bloody Mary or Mimosa | $$ |
| The Moonlighter |
| Bar | Logan Square | Mon | Open to close | Hidden Hands Lager, High Life Can +4 | $$ |
| Nori Sushi Chicago |
| Restaurant | Lakeview East | Fri–Sun | 12 PM – 3:30 PM | — | $$ |
| Palm Court |
| Restaurant | Streeterville | Sun | 12 PM – 3:30 PM | — | — |
| Replay Lincoln Park |
| Bar | Lakeview East | Sat–Sun | 1 PM – 5 PM | — | $$ |
| Magoos Bar |
| Bar | Southwest Side | Sat–Sun | 2 PM – 5 PM | House Margaritas or Palomas, House Mexican Import Beers +2 | $ |
| All Together Now |
| Restaurant | West Town | Tue–Thu | 3 PM – 6 PM | — | $$ |
| Dell' Rooster Restaurant & Bar |
| Restaurant | West Town | Wed–Sun | 3 PM – 6 PM | Corn Empanadas, Dell rooster Nachos +8 | $$ |
| Honky Tonk BBQ / The Tonk |
| Bar | Pilsen | Wed–Fri | 3 PM – 5 PM | — | $$ |
| Jackhammer |
| Bar | Rogers Park | Sun | 3 PM – 7 PM | House Shots, Premium Well Cocktails +1 | $$ |
| La Dolce Vita Cucina - Chicago |
| Restaurant | Portage Park | Tue–Sun | 3 PM – 5 PM | Draft Beers, Hard Seltzers +8 | $$ |
| Oak and Honey |
| Restaurant | Lakeview East | Wed–Sun | 3 PM – 6 PM | — | $$ |
| Pilsen Yards |
| Bar | Pilsen | Wed–Sun | 3 PM – 5:30 PM | Draft beer, Draft cocktails | $$ |
| Shake A Leg |
| Restaurant | Austin | Wed–Thu | 3 PM – 7 PM | Margarita, Hurricane +4 | $$ |
| Tierra y Fuego Mexican Steakhouse |
| Restaurant | Irving Park | Tue–Sun | 3 PM – 6 PM | Mini Flauta Rolls, Guac & Chips +4 | $$$ |
| Enoteca Roma Ristorante |
| Restaurant | West Town | Wed–Sun | 3:30 PM – 6 PM | — | $$ |
| 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 | $$ |
| Beatnik West Town |
| Restaurant | West Town | Wed–Sun | 4 PM – 6 PM | Baba Ganoush, Halloumi +4 | $$ |
| Black & Caspian |
| Restaurant | Lakeview East | Tue–Sun | 4 PM – 6 PM | — | $$ |
| Bungalow by Middle Brow |
| Bar | Logan Square | Wed–Fri | 4 PM – 6 PM | — | $$ |
| Butcher and the Bear |
| Bar | Lincoln Park | Tue–Sun | 4 PM – 7 PM | House Martinis, Dirtiest Martini +15 | $$$$ |
| Buttercup |
| Cocktails | Near South Side | Tue–Thu, Sun | 4 PM – 6 PM | Lambrusco, Peroni Italian Pilsner +5 | $ |
| Cafe El Tapatio |
| Restaurant | Lakeview | Tue–Sun | 4 PM – 6 PM | — | $$ |
| Centennial Crafted Beer & Eatery |
| Bar | River North | Tue–Fri | 4 PM – 6 PM | All draft pours, Classic cocktails +4 | $$ |
| Clara |
| Cocktails | West Town | Tue–Sat | 4 PM – 6 PM | — | $$ |
| Dearly Beloved |
| Cocktails | Near North Side | Wed–Sun | 4 PM – 7 PM | Oysters, Wine by the Glass +2 | $$$ |
| Fuego Logan Square |
| Restaurant | Logan Square | Wed–Fri | 4 PM – 7 PM | — | $$ |
| HaiSous Vietnamese Kitchen |
| Restaurant | Pilsen | Wed–Sun | 4 PM – 5:30 PM | Old Fashioned, Seasonal Margarita +20 | $$ |
| La Licor Panamericana |
| Bar | Logan Square | Wed–Sun | 4 PM – 6:30 PM | 4AM Burger, Veggie Empanadas (2) +15 | $$ |
| Le Sud Mediterranean Kitchen |
| Restaurant | North Center | Tue–Sun | 4 PM – 6 PM | House Wine of the Day, Brut Prosecco +16 | $$ |
| NoodleBird |
| Restaurant | Logan Square | Wed–Fri | 4 PM – 6 PM | — | $$ |
| Off Hours Beer Co. |
| Brewery | Bridgeport | Wed | 4 PM – 10 PM | Burger, Beer & Shot Combo | $$ |
| Osito's Tap |
| Bar | Little Village | Wed–Thu, Sun | 4 PM – 6 PM | Wings (6 piece or 12 piece), Empanadas +7 | $$ |
| Port & Park Bistro | Bar |
| Bar | Lakeview | Wed–Sun | 4 PM – 6:30 PM | Grilled Chicken Sandwich, Port & Park Quarter-Pounder +9 | $ |
| Prime 57 Restaurant + Lounge |
| Restaurant | Little Italy | Tue | 4 PM – 7 PM | 2 Birria Tacos, 2 Salmon Tacos +8 | $$ |
| Sweethearts |
| Bar | Andersonville | Wed–Sun | 4 PM – 6 PM | — | $$ |
| The L Station ChopHouse |
| Restaurant | Near North Side | Wed–Sun | 4 PM – 7 PM | — | — |
| Tuscany Taylor |
| Restaurant | Little Italy | Wed–Thu, Sun | 4 PM – 7 PM | Bruschetta, Sausage & Peppers +12 | $$ |
| Frontera Grill |
| Restaurant | River North | Tue–Wed | 4:30 PM – 6 PM | Rick's Margarita, Oaxacan Old Fashioned +19 | $$ |
| ArePA George Cantina |
| Restaurant | Logan Square | Tue–Sun | 5 PM – 7 PM | Berraco, Orquidea +9 | $$ |
| Artango Bar & Steakhouse |
| Restaurant | Lincoln Square | Tue–Fri, Sun | 5 PM – 7 PM | cocktails, wine +2 | $$$ |
| Boutique |
| Cocktails | Gold Coast | Wed–Thu, Sun | 5 PM – 7 PM | — | — |
| Brasero |
| Restaurant | West Town | Tue–Sat | 5 PM – 7 PM | Pork Sammy, Yellowfin Tuna Crudo +13 | $$$$ |
| Cafe Yaya |
| Café | Sheffield & DePaul | Tue, Thu–Sun | 5 PM – 6 PM | — | $$ |
| Cantina Rosa |
| Cocktails | Hyde Park | Wed–Thu | 5 PM – 7 PM | Guava Colada, Margarita Clarita +6 | $$$ |
| Community Tavern |
| Restaurant | Portage Park | Tue–Sun | 5 PM – 6 PM | Select Appetizers, Select Classic Cocktails +2 | $$ |
| Declan's Irish Pub |
| Pub | Near North Side | Tue | 5 PM – 9 PM | Taco Tuesday - $3.00 Tacos | $ |
| 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 | — | $$ |
| Ox Bar & Hearth |
| Restaurant | Goose Island | Wed–Sun | 5 PM – 6 PM | hamm, select wines btg +1 | $$$ |
| Port Union |
| Restaurant | West Town | Tue–Thu, Sun | 5 PM – 6 PM | All classic cocktails, Oysters +4 | $$ |
| Revolver |
| Cocktails | West Town | Tue–Sat | 5 PM – 6:30 PM | — | — |
| The Duplex |
| Bar | Logan Square | Thu–Sun | 5 PM – 6:30 PM | Bottled Beer, House Wine +13 | $ |
| Tsukiji Sushi Sake Bar |
| Restaurant | West Town | Tue–Sun | 5 PM – 6 PM | — | $$ |
| Uvae Kitchen and Wine Bar |
| Wine Bar | Andersonville | Tue–Fri | 5 PM – 6:30 PM | Oysters, Shrimp Cocktail +6 | $$ |
| Valedor |
| Cocktails | West Town | Tue–Sun | 5 PM – 7 PM | TOKI'O FASHIONED, WE LOVE LYCHEE +22 | $$ |
| Way Out |
| Bar | Logan Square | Tue–Thu, Sun | 5 PM – 7 PM | — | — |
| Winter's Jazz Club |
| Cocktails | Streeterville | Wed–Thu | 5 PM – 6 PM | Select drinks | $$ |
| W. Hideaway Lounge |
| Cocktails | Douglas | Tue–Thu | 5:30 PM – 7:30 PM | — | $$ |
| Dorian’s |
| Cocktails | West Town | Wed–Sun | 6 PM – 8 PM | Select Classic Cocktails | $$ |
| The California Clipper |
| Cocktails | West Town | Tue–Sun | 6 PM – 8 PM | Gran Centenario Mixers & Margaritas, Condesa Gin Mixers & Basil Gimlet +5 | $ |
| Tuman's Tap and Grill |
| Bar | West Town | Tue | 6 PM – 10 PM | Fidencio Espadin Mezcal, Real del Valle Tequila Blanco +1 | $$ |
| The Avondale Tap |
| Bar | Avondale | Sun | 9 PM – 11 PM | All appetizers, Well drinks +1 | $$ |
| Coalfire |
| Pizzeria | Wrigleyville | Tue–Sun | Until 7 PM | Draft Beers, Wine Pours +2 | $$ |
| Moonflower |
| Bar | Portage Park | Tue–Sun | Until 6 PM | Paloma, Lemon Drop +4 | $$ |