By Fiona Good-Sirota By Fiona Good-Sirota | January 14, 2025 | Food & Drink, Feature, Features, Featured, Food & Drink, Guides,
Happy hour offerings at Maple & Ash
From caviar service to wagyu gyoza, we’ve rounded up the most luxurious happy hour offerings in Chicago.
120 E. Delaware Place / Website
Restaurant-goers can indulge and unwind with this upscale dining destination’s Champagne and caviar-centric happy hour, hosted Sunday through Thursday from 4 to 6 p.m. Enjoy Laurent-Perrier brut or rosé, Far Niente chardonnay, half-bottles of Krug, $12 vodka or gin freezer martinis, $15 caviar and eggs, $20 caviar bumps and $100 caviar service, complete with Antonius caviar, egg whites, yolk, creme fraiche and blinis.
81 E. Wacker Place / Website
Mag Mile luxury boutique hotel Pendry Chicago is hosting happy hour from Wednesday through Sunday from 5 to 7 p.m. at Bar Pendry. The bar offers a lineup of In The Loop Social Hour deals, including $8 mini dirty, espresso or lemon drop martinis, $10 shrimp cocktails, $5 draft beers, $5 fries with herb aioli, $10 house wines and $10 West Town sliders with breaded chicken cutlets, mozzarella, pomodoro sauce and giardiniera.
1604 W. Chicago Ave. / Website
Beatnik West Town has recently launched its deluxe happy hour, featuring $5 beers and spreads, burgers, ceviche, wines by the glass and select cocktails for $10 every Wednesday through Friday from 4 to 7 p.m. Choose from popular craft cocktails like the “Chartreuse Swizzle” with herbal liqueur, Falernum, pineapple and lime and the “Coco Toronto” with coconut-washed rye whiskey, Fernet Branca and Pandan.
817 W. Lake St. / Website
Celebrity chef Joe Flamm and Day Off Group’s chic Fulton Market steakhouse hosts happy hour Monday through Friday from 4:30 to 6 p.m., during which visitors can enjoy a burger, fries, beer and a shot for $25. Diners can also indulge in $2 oysters, a chef’s charcuterie selection, half-off martinis and select bottles of vintage wine.
505 N. Michigan Ave. / Website
The InterContinental’s cocktail-forward Nikkei lounge, helmed by chef Richard Sandoval, brings Japanese-influenced fare and libations to the Mag Mile, along with a fan-favorite margarita hour, held Tuesday through Friday from 3 to 5 p.m., featuring chef-selected appetizers and inventive margaritas.
12 S. Michigan Ave. / Website
Situated in the Chicago Athletic Association, this James Beard Award-winning dining establishment hosts happy hour every day from 5 to 6 p.m. Dine on $13 popcorn chicken with house giardiniera, yuzu aioli, togarashi and lime, $12 golden truffle fries, $8 warm marinated Spanish olives and $55 seafood towers stocked with shrimp cocktail, market oysters, tartare with the fresh catch of the day, mignonette, cocktail sauce, Dijonnaise and crackers.
2429 N. Lincoln Ave. / Website
Owned and operated by Andrés Clavero and James Beard Award-winning chef Zach Engel, this Lincoln Park eatery brings indulgent Middle Eastern fare to the local dining scene. Visit on Tuesdays, Wednesdays and Thursdays from 5 to 6 p.m. through the end of February to partake in Galit’s newly debuted happy hour. Visitors can enjoy a selection of wines, cocktails, hummus and arak service for $10 and opt for the salatim platter for $18. During happy hour, 16-ounce brews are priced at $6, and 12-ounce cans of Middle Brow White Light are available for $5. The happy hour and a la carte menu will be available at Galit’s communal table and bar seating.
500 N. La Salle Drive / Website
This newly debuted River North steakhouse is shaking things up with a tempting selection of dry-aged beef, sustainably sourced seafood and a new cocktail hour from Monday through Friday from 5 to 7 p.m. Sip on $12 signature Hawksmoor cocktails like the Glendalough rose gin and apricot brandy-infused Charlie Chaplin and the Morning Glory Fizz with Glendalough pot still whiskey, apple brandy, lemon, egg whites and absinth.
3325 N. Southport Ave. / Website
Visit chef Gene Kato’s Japanese Robata restaurant from 4:30 to 6 p.m. Sunday through Thursday to dine on $8 to $10 maki rolls, like the beloved spicy tuna roll, and sip on $10 craft cocktails, like the bourbon-based Itoko and the spirit-free Madai Sour. Visitors can also opt for $20 happy hour pairings, like beer with a charcoal burger or the Ebi Tom Yum Temaki course with sake.
2534 N. Milwaukee Ave. / Website
Enjoy an Italian-inspired happy hour at Logan Square dining destination Mano a Mano, hosted daily from 4 to 6 p.m. Visitors who order any bottle of wine during happy hour receive a complimentary Tonda Romana pizza, a handmade, cracker-thin Roman specialty that pairs with wine selections from Lazio, including the Riva de la Rosa Frascati SOC and the Rapillo Cesanese.
8 W. Maple St. / Website
Every day through 6 p.m., visitors to Gold Coast mainstay Maple & Ash can order the spot’s signature hearth fire-roasted seafood tower for just $45, complete with manila clams, scallops, black tiger prawns and Alaskan king crab, topped with garlic butter and chili oil. During Tower Hour, guests can pair the specialty with espresso martinis and old fashioneds for just $15.
2138 N. Halsted St. / Website
Mediterranean dining destination Medi Kitchen & Cocktail offers special pricing on favorites like falafels, sambousek and savory wraps Tuesday through Friday from 4 to 6 p.m. During happy hour, diners can pair menu favorites like chicken and beef shawarma wraps and trios of hummus, jajik and baba ganoush with $10 espresso martinis, specialty-priced Aperol spritzes, wine and more.
505 N. Michigan Ave. / Website
Fans of Michael Jordan’s Streeterville steakhouse can now enjoy $12 martinis, including cosmos and dirty martinis, on Mondays from 2 to 5 p.m., and $12 Chandon Garden Spritz cocktails and fresh oysters paired with a sauce trio on Tuesdays from 2 to 5 p.m. During the restaurant’s midweek happy hour, Wednesday through Thursday from 2 to 5 p.m., visitors can pair $8 drinks with tempting small bites like maple-glazed bacon chicken wings and mini cheesecake bites.
854 W. Randolph St. / Website
Chef Nobu Matsuhisa’s iconic West Loop restaurant has instated its Tanoshi Hour, featuring $12 specialty cocktails like the Lychee & Elderflower Martini and happy hour pricing on signature dishes like the rock shrimp tempura, wagyu gyoza and yellowtail jalapeño on weekdays from 3 to 6 p.m.
1641 W. Chicago Ave. / Website
Led by renowned sushi chef Takashi Iida and executive chef Shoji Takahashi, this West Town eatery has just introduced a new special featuring $10 to $15 Otokoyama, Koshino Kanbai Junmai and Shiro Kirishima Shochu sake and a lineup of small plates like California rolls, takoyaki and gyoza. Held on Sunday, Tuesday and Wednesday from 5 to 6:30 p.m., Omakase Shoji & Izakaya’s happy hour also features $40 Uka, Dassai 39 and Born sake flights and $5 Japanese beers like Sapporo, Kirin Ichiban, Kirin Light and Asahi.
500 N. Clark St. / Website
River North speakeasy Pigtail hosts Social Hour Tuesday through Friday from 5 to 6 p.m., featuring $5 small bites and $12 cocktails. Choose from a lineup of Spanish-inspired specialty cocktails, curated by beverage innovator Miguel Lancha, like the “Around the World in 80 Days” with manzanilla, Del Maguey Ibérico, oude genever and Junmai Daiginjo sparkling sake or the Negroni Cristal, an Ibérico fat-washed blend of Gin Mare gin, blanc vermouth and Luxardo Bitter Bianco.
401 N. Wabash Ave. / Website
Located on the first mezzanine level of the Trump International Hotel & Tower, this high-end lounge is one to visit for Japanese-inspired bites, skyline views and inventive craft cocktails. Rebar’s happy hour experience is now available daily from 5 to 7 p.m., featuring half-off pricing on wine by the glass and $12 specialty cocktails, including the Pink Lemonade with Wheatley vodka, strawberry purée, lemon and simple syrup and the passion fruit margarita with Corazon reposado, passion fruit purée, lime and simple syrup.
317 N. Clark St. / Website
Lettuce Entertain You Enterprises’ upscale seafood joint, RPM Seafood, recently debuted its first happy hour, hosted in the bar Monday through Friday from 4 to 5:30 p.m. The menu includes highlights like signature rolls, yellowfin tuna crispy rice and char-broiled RPM Prestige oysters for $10, prime steakburgers for $18 and more. Visitors can also enjoy libations like the Crystal Paloma, the classic martini and the Winter Old Fashioned, plus select beers and zero-proof beverages like the Tropical Spritz for $5 each and select wines for $10, plus tax (gratuity not included). Reservations can be made here.
66 W. Kinzie St. / Website
Celebrity couple Bill and Giuliana Rancic and siblings R.J., Jerrod and Molly Melman of Lettuce Entertain You Enterprises own and helm this sleek, upscale establishment, which recently instated its 4 to 5:30 p.m. happy hour at Proper Bar. Try offerings like the wagyu smash burger with yuzu aioli for just $20, the petite ember-roasted seafood tower for $35 and RPM’s Golden Kaluga caviar service for $85.
1112 N. State St. / Website
Located in the Viceroy Chicago, this dining spot is known for its craft cocktails, market salads and tasty entrees like spinach tagliatelle, short ribs and wagyu burgers. Guests who visit Mondays through Thursdays between 3 and 6 p.m. can pair their meal with half-off specialty cocktails, wine and beer.
110 W. Illinois St. / Website
Whether you’re craving handrolls, bar bites or craft cocktails, Sunda has got you covered with its Monday through Friday happy hour, held from 4 to 6 p.m. Dine on sake, spicy tuna, shrimp and veggie handrolls and bar bites like shishito peppers, nori fries and Seoul wings for just $6. Or, elevate your meal with $7 Bushido sake, $6 glasses of red and white wine and the restaurant’s “Time of Your Life” craft cocktail for $8.
720 N. State St. / Website
Michelin-starred chef Carlos Gaytan and Somos Hospitality Group’s Mag Mile outpost offers specialty pricing on favorites Monday through Friday from 4 to 5:30 p.m. Pair $10 tuna tostadas, Chicharron de Pulpo lime-topped tempura octopus and $18 flank steak Esquites con Carne with $10 glasses of wine, $5 Cervesas and $10 specialty cocktails like the signature margarita, the Mexican Negroni, the Mexique Sangria and the Carajillo.
224 N. Michigan Ave. / Website
Visit French bistro Venteux Monday through Saturday from 4 to 6 p.m. to dine on half a dozen freshly shucked oysters for $12 while enjoying Parisian classics like steak tartare and buttery escargot. Amp up your happy hour experience with $12 espresso martinis or, for $18 per person, enjoy 90-minute bottomless rosé pours.
See also: The 10 Most Extravagant Dining And Drinking Experiences In Chicago
Photography by: Photos of Maple & Ash courtesy of Matt Haas; photo of Medi Kitchen & Cocktail by Ryan Beshel; photo of Beatnik West Town by Greg Chmiel; PHOTO OF HAWKSMOOR’S SOUR CHERRY NEGRONI COURTESY OF HAWKSMOOR