| Henrietta |
| Restaurant | Mon–Sun | 2 PM – 6 PM | Hangtime, Pinot Noir, Greenwing, Cabernet Sauvignon +25 | $ |
| Brown Bag Seafood Co. |
| Restaurant | Mon–Sun | 3 PM – 6 PM | Dinner Plate, Shareables +1 | $ |
| Leiya |
| Restaurant | Mon–Sun | 3:30 PM – 6:30 PM | Edamame, Vegetable Potstickers +13 | $$ |
| Grant Park Bistro |
| Restaurant | Mon–Thu, Sun | 4 PM – 6 PM | Fresh Cut Fries, House Made Chips with truffle cheddar powder +13 | $$ |
| Grill on 21 |
| Bar | Mon–Sun | 4 PM – 6 PM | — | $$$ |
| Mercat a la Planxa |
| Restaurant | Mon–Sun | 4 PM – 5:30 PM | — | $$ |
| Mexican Radio |
| Restaurant | Mon–Sun | 4 PM – 6 PM | House Margarita, La Jefa Margarita +12 | $$ |
| Nando's PERi-PERi |
| Restaurant | Mon–Sun | 4 PM – 6 PM | — | $ |
| Nando's PERi-PERi |
| Restaurant | Mon–Sun | 4 PM – 6 PM | — | $$ |
| Nando's PERi-PERi |
| Restaurant | Mon–Sun | 4 PM – 6 PM | — | $ |
| Sofi Restaurant |
| Restaurant | Mon–Thu, Sun | 4:30 PM – 6 PM | Soup of the Day, Burrata with Roasted Bell Peppers +11 | $$$ |
| Lockwood Restaurant |
| Hotel | Mon–Sun | Until 4 PM | Palmer House Bloody Mary or Mimosa | $$ |
| Acanto |
| Wine Bar | Mon–Fri | 2 PM – 5 PM | — | $$$ |
| Bistro Monadnock |
| Restaurant | Tue–Sat | 2:30 PM – 5:30 PM | Gimlet, Sazerac +8 | $$ |
| MingHin Cuisine - Lakeshore East |
| Restaurant | Mon–Fri | 2:30 PM – 5 PM | other | $$ |
| 90th Meridian Kitchen & Bar |
| Restaurant | Tue–Thu | 3 PM – 7 PM | Roasted Brussels Sprouts, Wisconsin Cheese Curds +5 | $$ |
| About Last Knife (ALK) |
| Restaurant | Mon–Fri | 3 PM – 7 PM | — | $$ |
| Avli on The Park |
| Bar | Mon–Fri | 3 PM – 6 PM | A-Gouri, Klima Klub +17 | $$ |
| Beatnik On The River |
| Restaurant | Mon–Wed | 3 PM – 5 PM | Classic Cocktails, wine +1 | $$ |
| Broken English Taco Pub |
| Bar | Wed | 3 PM – 6 PM | Margarita | $$ |
| Drawing Room |
| Bar | Mon–Fri | 3 PM – 5 PM | Fries, Crab & Artichoke Dip +8 | $$ |
| Elephant & Castle |
| Pub | Mon–Fri | 3 PM – 6 PM | Share Plates, Domestic Draught +1 | $ |
| Elephant & Castle |
| Sports Bar | Mon–Fri | 3 PM – 6 PM | Share Plates (Crisps & Dips, Mini-Sausage Rolls, Sweet Potato Fries, Roasted Tomato & Whipped Feta, Fried Pickles), Domestic Draught (Carlsberg, Miller Light, Michelob Ultra, Modelo Especial) +1 | $$ |
| Emerald Loop Bar & Grill |
| Bar | Mon–Fri | 3 PM – 7 PM | Modelo Pints, Signature Spritzzes +8 | $$ |
| Flaco's Tacos |
| Restaurant | Mon–Fri | 3 PM – 6 PM | — | $ |
| Senoritas Cantina On Dearborn |
| Bar | Mon–Fri | 3 PM – 6 PM | Appetizers, All Beer | $$ |
| Stocks & Blondes |
| Bar | Mon–Fri | 3 PM – 5 PM | Nachos, Cheese Curds, Titos and Buffalo Trace Highballs +4 | $$ |
| Taureaux Tavern |
| Restaurant | Mon–Fri | 3 PM – 6 PM | Buffalo Wings, Sliders +13 | $$ |
| The Exchange |
| Bar | Wed–Fri | 3 PM – 5 PM | Cheese Curds, Roasted Brussels Sprouts +10 | $$ |
| The Game Room |
| Restaurant | Mon–Fri | 3 PM – 5 PM | wings and Old Style | $$ |
| The Grillroom Chophouse & Wine Bar |
| Wine Bar | Mon–Fri | 3 PM – 6 PM | Select Featured Wines, House Margarita +7 | $$$ |
| The Palm - Chicago |
| Restaurant | Mon–Fri | 3 PM – 6 PM | — | — |
| Toro by Chef Richard Sandoval |
| Restaurant | Mon–Fri | 3 PM – 5 PM | margaritas, margarita trio +1 | $$$ |
| Land & Lake Kitchen |
| Restaurant | Mon–Fri | 3:30 PM – 6 PM | Basket of fries, Loaded Fries +12 | $$ |
| Seville Chicago |
| Restaurant | Mon–Fri | 3:30 PM – 5:30 PM | Marinated Olives, Ceviche +10 | $$ |
| AceBounce |
| Bar | Tue–Fri | 4 PM – 7 PM | Rotating Martini, House Spirit & Mixer +6 | $ |
| Bar Pendry Chicago |
| Cocktails | Tue | 4 PM – 9 PM | Chef's Choice Oysters | $$ |
| Beer Garden at Millennium Hall |
| Restaurant | Mon–Fri | 4 PM – 6 PM | — | $$ |
| Brando's Speakeasy |
| Bar | Mon–Fri | 4 PM – 7 PM | — | $$ |
| Copper Club |
| Bar | Mon–Fri | 4 PM – 6 PM | Buffalo Chicken Sliders, Detroit Style Sliders +3 | $$ |
| FireLake Grill House and Cocktail Bar |
| Restaurant | Mon–Thu | 4 PM – 7 PM | Mega Pretzel, FireLake Smash Burger +9 | $$ |
| First Draft |
| Bar | Mon–Fri | 4 PM – 7 PM | Domestic Bottles, Well Drinks +2 | $$ |
| Flight Club Chicago |
| Bar | Mon–Fri | 4 PM – 6 PM | Beef Sliders (3), Pretzel Bites +10 | $$ |
| Gino’s East - South Loop |
| Pizzeria | Mon–Thu | 4 PM – 6 PM | Thin crust pizzas, Mixed drinks +4 | $$ |
| Gordo's Tiny Taco Bar |
| Restaurant | Mon–Fri | 4 PM – 6 PM | Nachos, Tiny Quesadillas +9 | $ |
| Kindling | Downtown Cookout & Cocktails |
| Restaurant | Mon–Fri | 4 PM – 6 PM | The OKC Onion Smashburger, Raw Oysters +7 | $$$ |
| Millennium Hall Restaurant |
| Restaurant | Mon–Fri | 4 PM – 6 PM | — | $$ |
| Niu B |
| Restaurant | Mon–Fri | 4 PM – 6 PM | Ramen, Tonkotsu Ramen +8 | $$ |
| Remington's |
| Restaurant | Mon–Fri | 4 PM – 6 PM | — | $$$ |
| Roanoke Restaurant |
| Restaurant | Mon–Fri | 4 PM – 6 PM | Marinated Olives & Marcona Almonds, Fried Local Cheese Curds +15 | $$ |
| State and Lake Chicago Tavern |
| Restaurant | Mon–Thu | 4 PM – 6 PM | — | — |
| Taco Maya |
| Restaurant | Mon–Fri | 4 PM – 7 PM | Beers, Margaritas +1 | $ |
| The Dearborn |
| Restaurant | Mon | 4 PM – 6 PM | starters, martinis | $$ |
| Adamus Lounge |
| Hotel | Mon–Fri | 4:30 PM – 7:30 PM | Wine by the glass, Beer bottles & cans +1 | $ |
| Printers Row Wine Bar and Shop |
| Wine Bar | Tue | 5 PM – 7 PM | — | $ |
| La Bella Trattoria Loop |
| Restaurant | Mon | Open to close | Pizza | $$ |
| Panchos Rooftop Cantina |
| Restaurant | Tue–Fri | Until 7:30 PM | margaritas, margarita towers +1 | $$ |
| Venteux Brasserie, Cafe & Oyster Bar |
| Restaurant | Tue | Open to close | East Coast Oysters | $ |