By Fiona Good-Sirota By Fiona Good-Sirota | April 17, 2025 | Food & Drink, Feature, Features, Food & Drink, Featured, 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.
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, Ruinart rosé, $10 mini martinis, $15 caviar bumps and small bites like the “Duck Inn” hot dog and the navy bean and feta dip served with grilled bread. 120 E. Delaware Place
From Sunday to Wednesday, Mag Mile luxury boutique hotel Pendry Chicago hosts its lavish happy hour from 5 to 7 p.m. at Bar Pendry. The bar offers a lineup of Social Hour deals, including $10 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 mozzarella, pomodoro sauce and giardiniera. 81 E. Wacker Place
Beatnik West Town has recently launched its deluxe happy hour, hosted Wednesday through Friday from 4 to 7 p.m. Swing by to indulge in $5 Estrella Lagers and rotating menu items, burgers and select cocktails for $10. 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. 1604 W. Chicago Ave.
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. in the all-season atrium. While you’re there, 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 wine. 817 W. Lake St.
The InterContinental’s cocktail-forward Nikkei lounge, helmed by chef Richard Sandoval, brings Japanese-influenced fare and libations to the Mag Mile. It also hosts a fan-favorite margarita hour, held daily from 3 to 5 p.m., featuring $12 chef-selected bites and traditional margaritas. 505 N. Michigan Ave.
This newly debuted River North steakhouse is shaking things up with a tempting selection of dry-aged beef, sustainably sourced seafood and a cocktail hour, available Monday through Friday from 5 to 6 p.m. Dine on freshly shucked oysters for $2 each and sip on $12 select signature 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. 500 N. La Salle Drive
Visit chef Gene Kato’s Japanese Robata restaurant from 4:30 to 6 p.m. Sunday through Thursday to dine on $5 to $8 maki rolls, like the beloved spicy tuna roll, and sip on $12 craft cocktails, like the bourbon-based Itoko and the rum-infused Aki No Kaori. Visitors can also opt for $12 happy hour entrees like the chicken katsu don and the chahan wagyu beef fried rice with kaiware, maitake, gailan and a soft poached egg. 3325 N. Southport Ave.
Enjoy an Italian-inspired happy hour at Logan Square dining destination Mano a Mano, hosted Monday through Friday from 4 to 6 p.m. Visitors who order any bottle of wine during happy hour receive a complimentary chef’s selection of small bites, available alongside $10 cocktails and a weekly rotating sandwich. 2534 N. Milwaukee Ave.
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 house red and white wines, martinis and old fashioneds for $15. 8 W. Maple St.
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. 2138 N. Halsted St.
Fans of Michael Jordan’s Streeterville steakhouse can now enjoy $10 mixed drinks and select wines from 2 to 5 p.m. Monday through Friday. The restaurant also serves garlic bread, mini sliders with fries and maple-glazed bacon chicken wings for $10 during happy hour, along with barbecue chicken or tomato flatbread, wedge salad, mini cheesecake bites and mini oyster platters. 505 N. Michigan Ave.
Pay a visit to chef Nobu Matsuhisa’s iconic West Loop restaurant for Tanoshi Hour, featuring $14 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. 854 W. Randolph St.
Led by renowned sushi chef Takashi Iida and executive chef Shoji Takahashi, this West Town eatery has recently 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. 1641 W. Chicago Ave.
James Beard Award-winning Fulton Market mainstay The Publican is the spot to go for oyster and martini-centric happy hour specials, available on weekdays from 4 to 6 p.m. Unwind and indulge with $2 oysters, $7 beef fat fries, $16 smashburgers and more, accompanied by a well-endowed selection of $12 cocktails, including martinis, Compassbox whiskey highballs and BAYAB gin and tonics. 837 W. Fulton Market
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. 401 N. Wabash Ave.
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 oysters for $10, prime steakburgers for $18 and more. Visitors can also enjoy libations like the Crystal Paloma and the classic martini, plus select beers, wines and zero-proof beverages. 317 N. Clark St.
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 double cheeseburger with crispy onions for just $20, the petite ember-roasted seafood tower for $35 and RPM’s Golden Kaluga caviar service for $85. 66 W. Kinzie St.
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 Monday through Thursday between 3 and 6 p.m. can pair their meal with half-off specialty cocktails and beer. 1112 N. State St.
Whether you’re craving handrolls, bar bites or craft cocktails, Sunda New Asian has got you covered with a lineup of tempting happy hour offerings, available on weekdays from 4 to 6 p.m. Dine on spicy tuna, salmon, shrimp and veggie handrolls, or opt for bar bites like shishito peppers, nori fries and Seoul wings for just $6. Pair your meal with $8 Bushido sake, $8 glasses of wine and the restaurant’s Satsuma Spritz craft cocktail for $10. 110 W. Illinois St.
Michelin-starred chef Carlos Gaytan and Somos Hospitality Group’s Mag Mile outpost offers specialty pricing on weekdays from 4 to 5:30 p.m. Happy hour highlights include tuna tostadas or guacamole for $10, roasted hamachi collars for $16, $5 Cervesas and $10 specialty cocktails like the signature margarita, the Mexican Negroni, the Mexique Sangria and the Carajillo. 720 N. State St.
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. Elevate your happy hour experience further with $12 espresso martinis or, for $18 per person, enjoy 90-minute bottomless rosé pours. 224 N. Michigan Ave.
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