| Dell' Rooster Restaurant & Bar |
| Restaurant | Wed–Sun | 3 PM – 6 PM | Corn Empanadas, Dell rooster Nachos +8 | $$ |
| Fry the Coop (West Town) |
| Restaurant | Mon–Sun | 3 PM – 5 PM | — | $ |
| Boeufhaus |
| Bar | Mon, Wed–Sun | 3:30 PM – 5:30 PM | — | $$$$ |
| Enoteca Roma Ristorante |
| Restaurant | Wed–Sun | 3:30 PM – 6 PM | — | $$ |
| ADORO FUSION KITCHEN + BAR |
| Restaurant | Thu–Sun | 4 PM – 6 PM | — | $ |
| Beatnik West Town |
| Restaurant | Wed–Sun | 4 PM – 6 PM | Baba Ganoush, Halloumi +4 | $$ |
| Boulevard |
| Sports Bar | Mon–Sun | 4 PM – 7 PM | Domestic Beer, Well Shot +8 | $$ |
| Easy Bar |
| Bar | Mon–Sun | 4 PM – 6 PM | Drafts (half-price), House Cocktails (half-price) +4 | $ |
| Irish Nobleman Pub |
| Pub | Mon–Sun | 4 PM – 6 PM | — | $$ |
| PERILLA korean fare |
| Restaurant | Mon–Sun | 4 PM – 6 PM | Raw oyster, Whole shrimp +30 | $$$ |
| Clever Coyote |
| Bar | Mon–Sun | 5 PM – 7 PM | — | $$ |
| Desert Hawk |
| Bar | Mon–Sun | 5 PM – 6 PM | House Margarita, Ranch Water +4 | $$ |
| Lilac Tiger |
| Bar | Thu–Sun | 5 PM – 7 PM | — | $$ |
| Port Union |
| Restaurant | Tue–Thu, Sun | 5 PM – 6 PM | All classic cocktails, Oysters +4 | $$ |
| Tsukiji Sushi Sake Bar |
| Restaurant | Tue–Sun | 5 PM – 6 PM | — | $$ |
| Valedor |
| Cocktails | Tue–Sun | 5 PM – 7 PM | TOKI'O FASHIONED, WE LOVE LYCHEE +22 | $$ |
| Dorian’s |
| Cocktails | Wed–Sun | 6 PM – 8 PM | Select Classic Cocktails | $$ |
| Sari's Restaurant & Bar |
| Sports Bar | Mon, Sun | 6 PM – 8 PM | — | $ |
| The California Clipper |
| Cocktails | Tue–Sun | 6 PM – 8 PM | Gran Centenario Mixers & Margaritas, Condesa Gin Mixers & Basil Gimlet +5 | $ |
| Aztec Dave's Cantina |
| Bar | Tue–Fri | 2 PM – 5 PM | Mimosa, Any Beer / Seltzer / Can Cocktail +11 | $$ |
| All Together Now |
| Restaurant | Tue–Thu | 3 PM – 6 PM | — | $$ |
| Cleos Bar and Grill |
| Bar | Mon–Thu | 3 PM – 6 PM | All Drafts, Well Liquors +1 | $ |
| Dog Haus Biergarten - Wicker Park |
| Bar | Mon–Thu | 3 PM – 6 PM | Any 3-Pack of Sliders, Draft Beer +4 | $$ |
| Dove's Luncheonette |
| Restaurant | Thu–Sat | 3 PM – 6 PM | El Animal Fries, Relish Tray +13 | $$ |
| Esther's Tavern |
| Bar | Mon | 3 PM – 6 PM | Draft Pint Beers, Beer Pitchers | $ |
| Forbidden Root Restaurant & Brewery |
| Brewery | Mon–Fri | 3 PM – 6 PM | FR Beer Flight, IPA of the day +5 | $$ |
| Gracie O' Malley's Wicker Park |
| Sports Bar | Mon–Fri | 3 PM – 6 PM | Busch Light, Miller Lite draft +5 | $$ |
| Handlebar |
| Restaurant | Mon–Thu | 3 PM – 6 PM | — | $$ |
| Little Wok - Wicker Park |
| Restaurant | Mon–Fri | 3 PM – 6 PM | ASAHI Cold-Draft, Sake Bomb +10 | $$ |
| Oggi Trattoria |
| Restaurant | Mon–Fri | 3 PM – 6 PM | Aperol Spritz, Limoncello +9 | $$ |
| Paradise Park | Pizza & Patio |
| Bar | Mon–Fri | 3 PM – 6 PM | Espresso Martini, Spritzes +12 | $$ |
| Rebel & Rye |
| Bar | Fri | 3 PM – 7 PM | half-price booze | $$ |
| Richmond Tavern |
| Cocktails | Mon–Fri | 3 PM – 6 PM | — | $ |
| The Dandy Crown |
| Cocktails | Mon–Fri | 3 PM – 6 PM | Chips & Dip, Beef or Veggie Slider +9 | $$ |
| Archie's Iowa Rockwell Tavern |
| Bar | Tue–Fri | 4 PM – 7 PM | — | $ |
| Big Star |
| Bar | Mon–Thu | 4 PM – 6 PM | Nachos, Classic Margarita +4 | $$ |
| Clara |
| Cocktails | Tue–Sat | 4 PM – 6 PM | — | $$ |
| Diego |
| Restaurant | Tue–Fri | 4 PM – 6 PM | Classico Tacos, Margaritas +2 | $$ |
| DSTRKT Bar & Grill |
| Sports Bar | Tue | 4 PM – 10 PM | Tacos, Margaritas | $$ |
| Elston Electric |
| Bar | Wed–Fri | 4 PM – 6 PM | Drafts | — |
| Estelle's Cafe & Lounge |
| Bar | Mon–Fri | 4 PM – 7 PM | — | $ |
| Flo |
| Restaurant | Fri–Sat | 4 PM – 7 PM | Wine Wednesday, glasses of select wines +1 | $$ |
| Good Funk |
| Wine Bar | Wed–Fri | 4 PM – 7 PM | — | $$ |
| Ina Mae |
| Restaurant | Tue–Fri | 4 PM – 6 PM | — | $$ |
| Lemon |
| Cocktails | Mon–Sat | 4 PM – 6 PM | Cheap Beer, Industry Standard +7 | $$ |
| Lone Owl |
| Gastropub | Wed | 4 PM – 7 PM | Beer and Cider, House Cocktails | $$ |
| Mama Delia |
| Bar | Tue–Sat | 4 PM – 7 PM | One Drink, One Pintxo | $$ |
| Nettare |
| Restaurant | Thu | 4 PM – 6 PM | — | $$$ |
| Pierogi Kitchen |
| Restaurant | Mon–Fri | 4 PM – 6 PM | Selected draft beer, Polish Handshake +3 | $$ |
| Recess |
| Restaurant | Tue–Thu | 4 PM – 6 PM | APPS, CRAFT COCKTAILS | $$ |
| Soul Prime |
| Restaurant | Tue–Wed, Fri | 4 PM – 6 PM | Short Rib Taco, Spicy Buffalo Wings +13 | $$ |
| The Aberdeen Tap |
| Bar | Mon–Fri | 4 PM – 6 PM | Tito's Mixed Drinks, Revolution Anti-Hero Cans | $$ |
| The Beetle Bar and Grill |
| Bar | Mon–Fri | 4 PM – 6 PM | Shared Plates, Wine by the Glass +3 | $$ |
| The Dawson |
| Restaurant | Tue–Fri | 4 PM – 6 PM | Cocktails, Wine by The Glass +2 | $$ |
| Black Hole Bar |
| Bar | Mon–Thu | 5 PM – 7 PM | — | $ |
| Brasero |
| Restaurant | Tue–Sat | 5 PM – 7 PM | Pork Sammy, Yellowfin Tuna Crudo +13 | $$$$ |
| Chop Shop |
| Restaurant | Wed–Fri | 5 PM – 7 PM | — | $$ |
| Damen Tavern |
| Bar | Thu–Fri | 5 PM – 8 PM | — | $ |
| Everything Bar |
| Bar | Wed–Sat | 5 PM – 7 PM | Margarita, Espresso Martini +4 | $$ |
| EZ Inn |
| Dive | Mon | 5 PM – close | High Life | $ |
| Fatpour Wicker Park: Ultimate Chicago Sports Bar |
| Sports Bar | Mon–Fri | 5 PM – 7 PM | Domestic Pitchers, Wine by the Glass +2 | $$ |
| Golden Years |
| Cocktails | Mon, Wed–Thu | 5 PM – 7 PM | Rotating Punch, 22° Whisky Highball +3 | $$ |
| Hiro Bar Izakaya |
| Bar | Tue–Fri | 5 PM – 6 PM | Sea and Smoke, Tony Choppers Sakura +14 | $$ |
| Parlor Pizza Bar Wicker Park |
| Pizzeria | Mon–Fri | 5 PM – 7 PM | Hummus, Hand Cut Frites +16 | $$ |
| Queen Mary |
| Bar | Mon | 5 PM – 7 PM | Classic martinis | $$ |
| Revolver |
| Cocktails | Tue–Sat | 5 PM – 6:30 PM | — | — |
| Standard Bar and Grill |
| Sports Bar | Mon | 5 PM – 7 PM | Plain Nachos, XL Pretzel +2 | $$ |
| Un amor |
| Restaurant | Thu–Sat | 5 PM – 6:30 PM | — | $$ |
| Dorothy |
| Bar | Mon–Fri | 6 PM – 7 PM | Summer Cocktails, Spirit Free Cocktails +2 | $ |
| Innjoy |
| Bar | Mon–Fri | 6 PM – 8 PM | 1/2 Price Happy Hour (all drinks & apps), 25% Off Appetizers +1 | $ |
| Tuman's Tap and Grill |
| Bar | Tue | 6 PM – 10 PM | Fidencio Espadin Mezcal, Real del Valle Tequila Blanco +1 | $$ |
| Bangers & Lace Wicker Park |
| Bar | Mon–Fri | Until 6 PM | Shots (Bourbon or Blanco Tequila), Miller High Life +7 | $$ |
| Big Mini Putt Club |
| Bar | Mon | Open to close | Select draft beers & ciders, Pitchers | $$ |
| Casa Tequila Chicago |
| Restaurant | Mon | Open to close | House margarita, Signature margarita +1 | $$ |
| Goose Island Salt Shed Pub |
| Bar | Wed | Open to close | Vintage BCS Pours, Kick Back Lagers | $$ |