| Cheesie's Pub & Grub - Lakeview | Dine-in only | Pub | Lakeview East | Mon | Open to close | Any Drink, Smashed Cheesie + Domestic Beer | $ |
| El Taco Ázteca - Pilsen |
| Restaurant | Pilsen | Mon–Sun | 2 PM – 5 PM | All cocktails | $$ |
| IO Godfrey Rooftop Lounge |
| Bar | River North | Mon–Thu | 2 PM – 5 PM | Hummus, Wagyu Beef Sliders +14 | $$ |
| Old Irving Brewing Co. |
| Brewery | Old Irving Park | Mon–Thu | 2 PM – 5 PM | Beer, Wine +10 | $$ |
| Alulu Brewery and Pub |
| Brewery | Pilsen | Mon–Fri | 3 PM – 5 PM | Pivo Liso, Happy Hour Beer Cheese Curds +7 | $ |
| Beatnik On The River |
| Restaurant | The Loop | Mon–Wed | 3 PM – 5 PM | Classic Cocktails, wine +1 | $$ |
| Benihana - Chicago (John Hancock) |
| Restaurant | Streeterville | Mon–Fri | 3 PM – 6 PM | Signature Cocktails - Rocky's Margarita, Edamame +39 | $ |
| Brass Tack |
| Restaurant | Rush & Division | Mon–Thu | 3 PM – 6 PM | Lazy Old Fashioned, Manhattan +9 | $ |
| Canal Street Eatery and Market |
| Restaurant | West Loop | Mon–Fri | 3 PM – 6 PM | pizzas to share plus, spritz +3 | $$ |
| Carmine's |
| Restaurant | Gold Coast | Mon–Fri | 3 PM – 5 PM | Happy Hour cocktails, Martinis +8 | $$$$ |
| Carmine's Italian Rosemont |
| Restaurant | North Side | Mon–Fri | 3 PM – 5 PM | Glass of House Selected Wine, Cocktail of the Week +16 | $$$ |
| D4 Irish Pub & Cafe |
| Restaurant | Streeterville | Mon–Fri | 3 PM – 6 PM | Drafts, House Wines +8 | $$ |
| Dog Haus Biergarten - Lincoln Park |
| Bar | Sheffield & DePaul | Mon–Fri | 3 PM – 6 PM | Draft Beer, Wine +4 | — |
| Dog Haus Biergarten - Wicker Park |
| Bar | West Town | Mon–Thu | 3 PM – 6 PM | Any 3-Pack of Sliders, Draft Beer +4 | $$ |
| Esther's Tavern |
| Bar | West Town | Mon | 3 PM – 6 PM | Draft Pint Beers, Beer Pitchers | $ |
| Fora |
| Restaurant | Fulton Market | Mon–Fri | 3 PM – 6 PM | Hugo, Orange Wine Sangria +26 | $$ |
| Forbidden Root Restaurant & Brewery |
| Brewery | West Town | Mon–Fri | 3 PM – 6 PM | FR Beer Flight, IPA of the day +5 | $$ |
| Harry Caray's Italian Steakhouse |
| Restaurant | North Side | Mon–Fri | 3 PM – 5 PM | Draft Beer, Wild Card Cocktail +2 | $$ |
| Labriola Ristorante - Chicago |
| Restaurant | Streeterville | Mon–Thu | 3 PM – 5 PM | Select Beer, Wine +3 | $$ |
| 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 | $$ |
| Mon Ami Gabi |
| Restaurant | Lincoln Park | Mon–Thu | 3 PM – 5 PM | French 75, Aperol Spritz +3 | $$$ |
| Moretti's Ristorante and Pizzeria |
| Restaurant | Southwest Side | Mon–Fri | 3 PM – 6 PM | Pizzas: 10" Thin Crust 1-Topping, Brussels Sprouts +12 | $ |
| Moretti's Ristorante and Pizzeria |
| Restaurant | Edison Park | Mon–Fri | 3 PM – 6 PM | 10" Thin Crust 1-Topping Pizza, Brussels Sprouts +12 | $ |
| Pompette |
| Wine Bar | Bucktown | Mon, Wed–Sun | 3 PM – 6 PM | Sparkling Rose, Still Rosé +10 | $$ |
| R Public House |
| Bar | Rogers Park | Mon–Thu, Sun | 3 PM – 5 PM | House cocktails, Margarita flights +3 | $$ |
| Ranalli's of Andersonville |
| Pizzeria | Andersonville | Mon–Fri | 3 PM – 6 PM | $1 off Any SlicE, $2 off ANY APP +4 | $$ |
| Reunion by Chef Art Smith |
| Restaurant | Streeterville | Mon–Fri | 3 PM – 6 PM | Domestic Draft Beer, Chicken Wings +5 | $$ |
| Rounders Pub House |
| Sports Bar | Lakeview East | Mon–Fri | 3 PM – 6 PM | Old Style Draft, Kona Draft +4 | $$ |
| STK Steakhouse |
| Bar | River North | Mon–Fri | 3 PM – 5:30 PM | Oyster on The Half Shell, Tater Tots +20 | $$$$ |
| Taureaux Tavern |
| Restaurant | The Loop | Mon–Fri | 3 PM – 6 PM | Buffalo Wings, Sliders +13 | $$ |
| Tavern On Rush |
| Bar | Gold Coast | Mon–Thu, Sun | 3 PM – 6 PM | Caesar Salad, Feta Hummus +11 | $$$ |
| The Butcher’s Tap |
| Gastropub | Lakeview | Mon–Fri | 3 PM – 6 PM | Call Cocktails, Prickly Dragon Lemonade Mocktail +2 | $$ |
| The Embassy |
| Bar | Little Italy | Mon–Fri | 3 PM – 6 PM | Tito's Cocktails, Crane Lake (Cab, Chard, Merlot, Moscato, Pinot Grigio, White Zin) +7 | $$ |
| The Evie |
| Restaurant | Streeterville | Mon–Fri | 3 PM – 6 PM | White wine by the glass, Red wine by the glass +15 | $$ |
| The Gman Tavern |
| Bar | Lakeview East | Mon–Fri | 3 PM – 6 PM | $2 off all drafts, $2 off well drinks +3 | $ |
| The Smith |
| Restaurant | River North | Mon–Fri | 3 PM – 6 PM | Martinis (assorted), The Raw Bar Special - Pickle Rick and three oysters +7 | $$ |
| Timothy O'Toole's Pub Chicago |
| Pub | Streeterville | Mon–Fri | 3 PM – 6 PM | Domestic Drafts, Domestic Bottles & Cans +15 | $$ |
| avec Restaurant |
| Restaurant | West Loop | Mon–Fri | 3:30 PM – 5 PM | bartender's choice cocktail, wine by the carafina (sparkling, white, rosé or red) +3 | $$$ |
| avec River North |
| Restaurant | River North | Mon–Fri | 3:30 PM – 5 PM | Bartender's choice cocktail, Wine by the carafina (sparkling, white, rosé or red) +3 | $$$ |
| Land & Lake Kitchen |
| Restaurant | The Loop | Mon–Fri | 3:30 PM – 6 PM | Basket of fries, Loaded Fries +12 | $$ |
| Leiya |
| Restaurant | The Loop | Mon–Sun | 3:30 PM – 6:30 PM | Edamame, Vegetable Potstickers +13 | $$ |
| McCormick & Schmick's Seafood & Steaks |
| Restaurant | North Side | Mon–Fri | 3:30 PM – 6:30 PM | Truffle Fries, Roasted Garlic Hummus +15 | $ |
| Robert's Pizza and Dough Company |
| Pizzeria | Streeterville | Mon–Fri | 3:30 PM – 5:30 PM | Draft beers (selected), Cans & bottles +10 | $$ |
| Andros Taverna |
| Restaurant | Logan Square | Mon–Thu | 4 PM – 6 PM | cocktails, Complimentary mini Olive Oil Martini with any order from RAW seafood section | $$ |
| Arbella Cocktail Bar |
| Cocktails | River North | Mon–Fri | 4 PM – 7 PM | Wine by the glass, All Arbella Classics cocktails +7 | $$ |
| Bisous |
| Cocktails | Fulton Market | Mon–Fri | 4 PM – 6 PM | glass, bottle +4 | $$ |
| Cafecito |
| Café | Streeterville | Mon–Fri | 4 PM – 7 PM | Specialty cocktails, Wine glasses | $ |
| Central Park Bar |
| Bar | Avondale | Mon–Fri | 4 PM – 7 PM | CPB Cocktails, Wine | $$ |
| City Winery Chicago |
| Bar | Fulton Market | Mon–Thu | 4 PM – 7 PM | — | — |
| Dave & Buster's Rosemont |
| Sports Bar | North Side | Mon–Fri | 4 PM – 7 PM | House wine, 7oz glass, 22oz select domestic draft beer +1 | $$ |
| Drew's on Halsted |
| Restaurant | Lakeview East | Mon–Fri | 4 PM – 6 PM | Beer, Wine +5 | $$ |
| Easy Bar |
| Bar | West Town | Mon–Sun | 4 PM – 6 PM | Drafts (half-price), House Cocktails (half-price) +4 | $ |
| Felix: Modern American Dining |
| Restaurant | Lakeview East | Mon, Wed–Fri | 4 PM – 6 PM | Crispy Brussel Sprouts, Parmesan Fries +18 | $$ |
| Fireside Restaurant & Lounge |
| Restaurant | Andersonville | Mon–Fri | 4 PM – 6 PM | House Red & White Wine, Homemade Sangria (Peach, White, Red, Raspberry) +2 | $$ |
| Fiya |
| Restaurant | Andersonville | Mon–Fri | 4 PM – 6 PM | Fries, Amba Mayo, Ketchup, Marinated Olives +12 | $$ |
| Gus' Sip & Dip |
| Bar | River North | Mon–Fri | 4 PM – 5 PM | All Mixed Drinks, Rotating Cocktail of the Day | $$ |
| Heineken 2nd Star Tavern |
| Bar | North Center | Mon–Fri | 4 PM – 7 PM | Drafts, Well Cocktails +1 | $$ |
| HIDE+SEEK |
| Restaurant | Fulton Market | Mon–Thu, Sun | 4 PM – 6 PM | French Fries, Grilled Oysters +13 | $$ |
| La Grande Boucherie Chicago |
| Restaurant | River North | Mon–Fri | 4 PM – 7 PM | Stella, House Wine (Sparkling, White, Red, Rosé) +15 | $$$ |
| 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 | $$$ |
| River Roast |
| Restaurant | River North | Mon–Fri | 4 PM – 5:45 PM | Specialty Cocktails, Wines by the glass +2 | $$ |
| Snorkelbox |
| Cocktails | West Loop | Mon–Fri | 4 PM – 6 PM | HH Cocktail, HH Red +2 | $ |
| Spectrum Bar & Grill |
| Bar | West Loop | Mon | 4 PM – 7 PM | Chicken Tenders, Onion Rings, Fried Zucchini, Halloumi Rolls | $$ |
| Storyville Chicago |
| Bar | River North | Mon–Sun | 4 PM – 6 PM | House Cocktails, Old Fashioned +7 | $$ |
| Surge Billiards |
| Bar | Logan Square | Mon–Fri | 4 PM – 7 PM | Bottles, Drafts +1 | $ |
| The Broken Barrel Bar |
| Sports Bar | Lincoln Park | Mon–Fri | 4 PM – 6 PM | Crafted Cocktails, House Wines +2 | $ |
| The Chicago Firehouse Restaurant |
| Restaurant | Near South Side | Mon–Thu | 4 PM – 5 PM | Oysters on the Half Shell, Beef Empanada +6 | $$$ |
| The Pony Inn |
| Bar | Lakeview | Mon–Fri | 4 PM – 7 PM | Draft Beers, Wine by the Glass +2 | $$ |
| Truluck's Ocean's Finest Seafood and Crab |
| Restaurant | North Side | Mon–Sun | 4 PM – 6 PM | Handcrafted cocktails, Premium spirits +2 | $$$$ |
| Vincent |
| Restaurant | Andersonville | Mon–Sun | 4 PM – 6 PM | Marinated Olives, Happy Hour Board +17 | $$ |
| Adamus Lounge |
| Hotel | The Loop | Mon–Fri | 4:30 PM – 7:30 PM | Wine by the glass, Beer bottles & cans +1 | $ |
| Itoko |
| Restaurant | Lakeview | Mon–Sat | 4:30 PM – 6 PM | Signature cocktails, Sake +5 | $ |
| 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 | $$ |
| Peckish Pig |
| Restaurant | North Side | Mon–Fri | 4:30 PM – 6 PM | Draft beers, House wines +2 | $$ |
| 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 | $$ |
| Beaumont's |
| Bar | Lincoln Park | Mon–Tue | 5 PM – 6:30 PM | Tini Martinis, All Menu Cocktails & Wines By The Glass +1 | $$ |
| Benchmark |
| Sports Bar | Near North Side | Mon–Fri | 5 PM – 7 PM | Select Wine (6oz), Draft Beers +3 | $$ |
| Bokeh |
| Cocktails | Albany Park | Mon–Thu, Sun | 5 PM – 6 PM | Cocktails | $$ |
| Headquarters Beercade |
| Bar | Near North Side | Mon–Fri | 5 PM – 7 PM | Cocktails, White Claw Buckets (5 cans) +2 | $$ |
| Mariscos San Pedro |
| Restaurant | Pilsen | Mon–Sun | 5 PM – 6 PM | Margarita Pitcher, Cocktail of the day +3 | $$ |
| 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 | $$ |
| The Bull Moose |
| Bar | Lincoln Park | Mon–Tue | 5 PM – 6:30 PM | Martini (any menu cocktail), Wines by the glass +1 | $$$$ |
| The Owl |
| Bar | Logan Square | Mon–Thu | 5 PM – 8 PM | House Cocktails (half-price), Ghost Candy Margarita (half-price) +4 | $ |
| Woodie's Flat |
| Bar | Near North Side | Mon–Fri | 5 PM – 7 PM | Specialty Cocktails, Ketel One Espresso Martinis +4 | $$ |
| Dorothy |
| Bar | West Town | Mon–Fri | 6 PM – 7 PM | Summer Cocktails, Spirit Free Cocktails +2 | $ |
| Innjoy |
| Bar | West Town | Mon–Fri | 6 PM – 8 PM | 1/2 Price Happy Hour (all drinks & apps), 25% Off Appetizers +1 | $ |
| Teddy Bear Lounge |
| Bar | Avondale | Mon–Tue | 7 PM – 10 PM | House Cocktails, Draft Beer +2 | $$ |
| Clover Lincoln Park |
| Sports Bar | Lakeview East | Mon | 7:30 PM – 11 PM | Frozen Cocktails | $ |
| Five Iron Golf |
| Bar | Bucktown | Mon–Sun | 9 PM – close | Boneless Wings, Bone-In Wings +4 | $ |
| Five Iron Golf |
| Bar | River North | Mon–Sun | 9 PM – close | Simulator Rentals, Boneless Wings +5 | $ |
| Bar Parisette |
| Wine Bar | Logan Square | Mon | Open to close | champagne, cava +19 | $ |
| Beatrix |
| Restaurant | Streeterville | Mon | Open to close | Wine bottles | $$ |
| 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 | $$ |
| Inkwell |
| Bar | Fulton Market | Mon–Sun | Until 6 PM | Bar Mix, Olives +1 | $$ |
| Punch Bowl Social |
| Bar | Fulton Market | Mon | Open to close | Old Fashioned, Cosmopolitan +16 | $$ |
| Offshore Rooftop |
| Bar | Streeterville | Tue–Fri | 1 PM – 5 PM | Specialty cocktails, Beers +2 | $ |
| Aztec Dave's Cantina |
| Bar | West Town | Tue–Fri | 2 PM – 5 PM | Mimosa, Any Beer / Seltzer / Can Cocktail +11 | $$ |
| 14 Parish Restaurant & Rhum Bar |
| Bar | Hyde Park | Tue–Thu | 3 PM – 6 PM | Cocktails, Caribbean Wings +2 | $$ |
| Dell' Rooster Restaurant & Bar |
| Restaurant | West Town | Wed–Sun | 3 PM – 6 PM | Corn Empanadas, Dell rooster Nachos +8 | $$ |
| Jackhammer |
| Bar | Rogers Park | Sun | 3 PM – 7 PM | House Shots, Premium Well Cocktails +1 | $$ |
| Pilsen Yards |
| Bar | Pilsen | Wed–Sun | 3 PM – 5:30 PM | Draft beer, Draft cocktails | $$ |
| Pinched on the River |
| Restaurant | Streeterville | Tue–Thu | 3 PM – 6 PM | Beef Sliders (3), Greek Handcut Fries for Two +12 | $$ |
| Beatnik West Town |
| Restaurant | West Town | Wed–Sun | 4 PM – 6 PM | Baba Ganoush, Halloumi +4 | $$ |
| Blue Bayou |
| Sports Bar | Lakeview | Fri | 4 PM – 7 PM | Domestics, Jameson Shots +1 | $$ |
| Bunker |
| Bar | West Loop | Tue–Fri | 4 PM – 6 PM | 1/2 Priced Appetizers, 1/2 Priced Cocktails +1 | $$ |
| Butcher and the Bear |
| Bar | Lincoln Park | Tue–Sun | 4 PM – 7 PM | House Martinis, Dirtiest Martini +15 | $$$$ |
| Centennial Crafted Beer & Eatery |
| Bar | River North | Tue–Fri | 4 PM – 6 PM | All draft pours, Classic cocktails +4 | $$ |
| Charis Listening Bar |
| Bar | Bridgeport | Wed–Fri | 4 PM – 6 PM | Cocktail of the Day, Old Fashioned +4 | $$ |
| DJ's Great Room |
| Bar | Near North Side | Tue–Fri | 4 PM – 6 PM | Brussel sprouts, Buffalo Bites +7 | $$ |
| Donny G's Ristorante |
| Bar | North Side | Tue–Fri | 4 PM – 6 PM | Half Priced Cocktails, Half Priced Appetizers | $$ |
| La Parrilla Latin Food Broadway |
| Restaurant | Magnolia Glen | Wed–Fri | 4 PM – 7 PM | Beers, Cocktails +1 | $$ |
| La Victoria Barra + Cocina Mexicana - Chicago |
| Bar | Logan Square | Tue–Fri | 4 PM – 6 PM | Margaritas, Cocktails +1 | $$ |
| Lone Owl |
| Gastropub | West Town | Wed | 4 PM – 7 PM | Beer and Cider, House Cocktails | $$ |
| Off Hours Beer Co. |
| Brewery | Bridgeport | Wed | 4 PM – 10 PM | Burger, Beer & Shot Combo | $$ |
| Port & Park Bistro | Bar |
| Bar | Lakeview | Wed–Sun | 4 PM – 6:30 PM | Grilled Chicken Sandwich, Port & Park Quarter-Pounder +9 | $ |
| Recess |
| Restaurant | West Town | Tue–Thu | 4 PM – 6 PM | APPS, CRAFT COCKTAILS | $$ |
| Surge Billiards |
| Venue | Irving Park | Tue–Fri | 4 PM – 7 PM | Bottles, Drafts +1 | $ |
| The Dawson |
| Restaurant | West Town | Tue–Fri | 4 PM – 6 PM | Cocktails, Wine by The Glass +2 | $$ |
| The Rabbit Hole Wrigley |
| Bar | Lakeview East | Wed–Fri | 4 PM – 7 PM | Bud Light Cans, Green Tea Shots +5 | $$ |
| Artango Bar & Steakhouse |
| Restaurant | Lincoln Square | Tue–Fri, Sun | 5 PM – 7 PM | cocktails, wine +2 | $$$ |
| Charlie Martin's |
| Restaurant | River North | Tue–Sat | 5 PM – 7 PM | Shrimp Cocktail, Oysters on the Half Shell +10 | $$$$ |
| CheSa’s Bistro & Bar Chicago |
| Restaurant | Avondale | Wed–Fri | 5 PM – 6:30 PM | Lamb Meatballs, New Orleans BBQ +4 | $$ |
| Community Tavern |
| Restaurant | Portage Park | Tue–Sun | 5 PM – 6 PM | Select Appetizers, Select Classic Cocktails +2 | $$ |
| Figo Wine Bar |
| Wine Bar | Lakeview East | Tue–Wed | 5 PM – 6 PM | Select Wine, Select Cocktails +2 | $$$ |
| 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 | $$ |
| Machine Cocktail Bar |
| Cocktails | Near North Side | Wed–Fri | 5 PM – 6:30 PM | Select Cocktails | $$ |
| Paulie Gee's Logan Square |
| Pizzeria | Logan Square | Tue–Wed | 5 PM – 7 PM | Margherita pizzas, Mocktail and Drafts +2 | $$ |
| Port Union |
| Restaurant | West Town | Tue–Thu, Sun | 5 PM – 6 PM | All classic cocktails, Oysters +4 | $$ |
| The Fieldhouse LP |
| Bar | Lincoln Park | Wed–Fri | 5 PM – 7 PM | Domestics, Imports +2 | $ |
| The Royal Grocer & Co. |
| Bar | Bucktown | Tue–Fri | 5 PM – 7 PM | Potato Chips, House Cut Fries +13 | $$ |
| Tin Lizzie |
| Bar | Lincoln Park | Wed–Thu | 5 PM – 8 PM | Well Cocktail, Wine by The Glass +6 | $$ |
| Uvae Kitchen and Wine Bar |
| Wine Bar | Andersonville | Tue–Fri | 5 PM – 6:30 PM | Oysters, Shrimp Cocktail +6 | $$ |
| Dorian’s |
| Cocktails | West Town | Wed–Sun | 6 PM – 8 PM | Select Classic Cocktails | $$ |
| GG Piano Bar Cocktail Lounge |
| Cocktails | Fulton Market | Wed–Fri | 6 PM – 8 PM | Signature cocktails | $$ |
| The Black Lion |
| Bar | Logan Square | Fri–Sat | 6 PM – 8 PM | cocktail | $$ |
| Duffy's Tavern and Grille |
| Sports Bar | Lakeview East | Wed | 7 PM – close | Specialty Cocktails, Glasses of Wine | $$ |
| R.J. Grunts |
| Restaurant | Lincoln Park | Thu–Sat | 8 PM – 10 PM | Classic Cocktails, Beers +1 | $$ |
| The Country Club |
| Bar | Lakeview East | Thu | 8 PM – close | All Drafts | $ |
| Coalfire |
| Pizzeria | Wrigleyville | Tue–Sun | Until 7 PM | Draft Beers, Wine Pours +2 | $$ |