Manchamanteles invites guests to “come early, stay for the mole” with Happy Hour specials Wednesday through Friday from 3 - 6 p.m. The offering features handcrafted cocktails, cold beer and mole-inspired bites, including a $10 Mole Trio, $10 Queso con Chiles, $10 classic lime margaritas and $5 Modelo beers. Guests can also enjoy heartier favorites like the La Mole Hamburguesa and Torta Ahogada. Wednesday specials include margarita pitchers, guacamole and half-off wine bottles.
Credit: Manchamanteles
Gold Coast
Maple & Ash / Eight Bar
Maple & Ash puts a luxurious spin on happy hour with Tower Hour, a daily offering in the Gold Coast steakhouse’s bar and lounge. Available Sunday through Thursday from 5 - 6 p.m. and Friday and Saturday from 4:30 - 6 p.m., the experience centers on a $45 fire-roasted seafood tower featuring Manila clams, scallops, black tiger prawns and Alaskan king crab, all roasted in the hearth and finished with garlic butter and chili oil. Guests can pair the signature tower with $15 cocktails, including martinis, an Espresso Martini and an Old Fashioned, alongside $15 house red and white wines.
Just downstairs, Eight Bar offers its own Happy Hour Monday - Friday from 2 - 5 p.m., with $8 mini martinis, including the Tito’s Martini, Cosmo-ish and Espressotini, alongside $8 hand rolls like King Crab, Spicy Tuna and Hamachi Jalapeño, plus Crispy Fried Chicken Karaage. Guests can also enjoy an $12 Summer Affair frozen cocktail, $8 wines by the glass and a $50 Aperol Spritz bucket made to share.
The Alston
The Alston, led by Michelin-starred Chef Jenner Tomaska, brings a touch of luxury to happy hour with half-off wines by the glass and signature cocktails, alongside a selection of elevated bites. Highlights include $1 oysters served with classic mignonette and cocktail sauce, $15 prime ribeye brochette skewers, $15 tuna crudo and the restaurant's signature burger for $20. Guests can also indulge in $28 steak frites or $40 caviar service.
Credit: Maple & Ash / Eight Bar
Logan Square
Daisies
Daisies offers a distinctive take on happy hour with an Italian-inspired spread of aperitivo cocktails, wine, vermouth and elevated snacks. Available Tuesday through Saturday from 3 - 5 p.m., the Logan Square restaurant features $7 cocktails, including a House Aperitivo Spritz, Logan Sour and Torino Torino, alongside wines by the glass starting at $7 and a selection of vermouth and sherry. Guests can pair their drinks with bites like $5 gnocco fritto with Cool Ranch seasoning, $7 housemade onion dip with Ruffles, $12 fritto misto and an assortment of tinned seafood. For a more indulgent experience, Daisies also offers curated wine assortments for two, pairing wine, fortified pours and snacks starting at $30.
Loop
Mariela
For a coastal-inspired twist to happy hour in the heart of the Loop, Mariela offers a spot to unwind after work, Tuesday through Saturday from 4 - 6 p.m. The menu features $1 oysters served with guava-habanero salsa, alongside $8 bites like citrus-cured albacore ceviche, shrimp cocktail and Fried Chicken 65 with cilantro crema. For drinks, enjoy $9 wines by the glass and $12 signature cocktails, including the Mariela Martini with peach and black lemon and the Mariela Punch featuring apricot, ginger and carrot.
Credit: Mariela
River North
Carlyle Club
Carlyle Club set along the Chicago River inside the historic Reid Murdoch Building, offers an elevated after-work escape with happy hour from 3–6 p.m. at its marble bar. Guests can sip cocktails, Champagne and sake while exploring a bar menu featuring hand rolls, the signature Carlyle Burger, French Dip and other elevated favorites.
Olio e Più
Every Monday the River North trattoria invites guests to sip and unwind with $10 featured martinis, available all day at the bar. Featured martinis include the Dirty Martini, French Martini, Espresso Martini, Cosmopolitan, and Lemon Drop Martini, which can be enjoyed alongside handmade pastas, and classic Italian comfort dishes. Olio e Più also hosts an aperitivo hour with a daily bar-side experience designed for lingering, sipping, and snacking. Available Tuesday through Saturday from 4–7pm, Aperitivo Hour invites guests to unwind with $10 wines, cocktails, and Italian small plates, served at the bar and patio.
The Gwen Hotel
Elevate your after-work plans with The Lux Happy Hour at Upstairs at The Gwen, available Monday through Thursday from 4–5:30 p.m. Located on the fifth floor of The Gwen, guests can unwind on the rooftop terrace or in the indoor lounge with specially priced cocktails, wine, beer and elevated bites. Sip on $10 draft beers, Tommy’s Margarita ($14). Pair your drinks with shareable favorites like Truffle Fries ($12) and gourmet flatbreads ($15). On Wednesdays, keep the evening going with Wine Wednesdays, featuring half-priced bottles of wine and exclusive by-the-glass specials. From 6–8 p.m., the lounge comes alive with live jazz performances by the Cosmic Jaywalkers.
South Loop
Martini Lounge
Located in Chicago’s South Loop, Martini Lounge puts a spin on happy hour, offered Thursday through Sunday from 5–7 p.m., with $10 cocktails, $6 Dirty Martini Shots and $5 beers. Guests can sip on classic and contemporary cocktails, including the Daiquiri, crafted with white rum, aged cachaça, lime and cane sugar; the Manhattan, featuring wheated bourbon, sweet vermouth and house bitters; and the Berry Bramble, combining berry vodka, berry gin, Pimm’s, Oloroso sherry and lemon. For those looking to keep things playful, $6 Dirty Martini Shots offer a fun twist on the lounge’s namesake cocktail, while $5 Stella Artois, Stella Artois 0.0 and Miller Lite round out the offerings.
Credit: Kim Kovacik for Olio e Più
West Loop
Cache 310
Happy Hour at Cache 310in the West Loop is calling! Enjoy signature cocktails for $10 and beer & seltzers for $5 Mondays–Thursdays from 4–6 PM, or take advantage of $7 Heaven Fridays & Saturdays until 7 PM, featuring signature cocktails for just $7! Plus, enjoy 2 hours of complimentary parking on Fridays and Saturdays. Seating is first-come, first-served.
Canal Street Eatery & Market
Canal Street Eatery & Market, located in the BMO Bank building, offers Happy Hour Monday through Friday from 3 p.m. - 6 p.m. Their happy hour menu features $12 pizzas (like their Spicy Sopressata made with pepperoni, fresh mozzarella, fresno honey, oregano), $9 house wines, and select beers for $5.
West Town
Omakase Shoji
For an elevated start to the evening, Omakase Shojioffers Happy Hour Sunday, Tuesday and Wednesday from 5 - 6:30 p.m. Guests can enjoy a selection of food and drinks.
Wicker Park
Clever Coyote
Swing by Clever Coyote located inside The Robey in Wicker Park for daily Happy Hour from 5–7 PM, where all menu items are just $9 (excluding The Fishbowl)! Sip on tiki style drinks, dig into flavor-packed wings and nostalgic bar bites, and enjoy throwback vibes with pool, games, and all your favorite 80s, 90s, and early 2000s hits. Walk-Ins are welcome.
Valedor
Inspired by Mexico City's Little Tokyo neighborhood, Valedor’s Cantina Hour features cocktails and bites with Mexican-Japanese inflection. From Tuesday to Sunday, from 5 - 7 p.m., the Wicker Park cocktail bar offers $12 cocktails (like the Toki'o Fashioned with oki Japanese whisky, Lapsang-kokuto syrup, house bitters and orange expression) and $8 tapas (like the Tuna Poke Tacos with wonton shell, wasabi salsa verde and sesame slaw). Guests also enjoy complimentary bites from a rotating selection of tapas during Cantina Hour while they enjoy drinks.
The Rundown
Bucktown
Manchamanteles invites guests to “come early, stay for the mole” with Happy Hour specials Wednesday through Friday from 3 - 6 p.m. The offering features handcrafted cocktails, cold beer and mole-inspired bites, including a $10 Mole Trio, $10 Queso con Chiles, $10 classic lime margaritas and $5 Modelo beers. Guests can also enjoy heartier favorites like the La Mole Hamburguesa and Torta Ahogada. Wednesday specials include margarita pitchers, guacamole and half-off wine bottles.
Gold Coast
Maple & Ash puts a luxurious spin on happy hour with Tower Hour, a daily offering in the Gold Coast steakhouse’s bar and lounge. Available Sunday through Thursday from 5 - 6 p.m. and Friday and Saturday from 4:30 - 6 p.m., the experience centers on a $45 fire-roasted seafood tower featuring Manila clams, scallops, black tiger prawns and Alaskan king crab, all roasted in the hearth and finished with garlic butter and chili oil. Guests can pair the signature tower with $15 cocktails, including martinis, an Espresso Martini and an Old Fashioned, alongside $15 house red and white wines.
Just downstairs, Eight Bar offers its own Happy Hour Monday - Friday from 2 - 5 p.m., with $8 mini martinis, including the Tito’s Martini, Cosmo-ish and Espressotini, alongside $8 hand rolls like King Crab, Spicy Tuna and Hamachi Jalapeño, plus Crispy Fried Chicken Karaage. Guests can also enjoy an $12 Summer Affair frozen cocktail, $8 wines by the glass and a $50 Aperol Spritz bucket made to share.
The Alston, led by Michelin-starred Chef Jenner Tomaska, brings a touch of luxury to happy hour with half-off wines by the glass and signature cocktails, alongside a selection of elevated bites. Highlights include $1 oysters served with classic mignonette and cocktail sauce, $15 prime ribeye brochette skewers, $15 tuna crudo and the restaurant's signature burger for $20. Guests can also indulge in $28 steak frites or $40 caviar service.
Logan Square
Daisies offers a distinctive take on happy hour with an Italian-inspired spread of aperitivo cocktails, wine, vermouth and elevated snacks. Available Tuesday through Saturday from 3 - 5 p.m., the Logan Square restaurant features $7 cocktails, including a House Aperitivo Spritz, Logan Sour and Torino Torino, alongside wines by the glass starting at $7 and a selection of vermouth and sherry. Guests can pair their drinks with bites like $5 gnocco fritto with Cool Ranch seasoning, $7 housemade onion dip with Ruffles, $12 fritto misto and an assortment of tinned seafood. For a more indulgent experience, Daisies also offers curated wine assortments for two, pairing wine, fortified pours and snacks starting at $30.
Loop
For a coastal-inspired twist to happy hour in the heart of the Loop, Mariela offers a spot to unwind after work, Tuesday through Saturday from 4 - 6 p.m. The menu features $1 oysters served with guava-habanero salsa, alongside $8 bites like citrus-cured albacore ceviche, shrimp cocktail and Fried Chicken 65 with cilantro crema. For drinks, enjoy $9 wines by the glass and $12 signature cocktails, including the Mariela Martini with peach and black lemon and the Mariela Punch featuring apricot, ginger and carrot.
River North
Carlyle Club set along the Chicago River inside the historic Reid Murdoch Building, offers an elevated after-work escape with happy hour from 3–6 p.m. at its marble bar. Guests can sip cocktails, Champagne and sake while exploring a bar menu featuring hand rolls, the signature Carlyle Burger, French Dip and other elevated favorites.
Every Monday the River North trattoria invites guests to sip and unwind with $10 featured martinis, available all day at the bar. Featured martinis include the Dirty Martini, French Martini, Espresso Martini, Cosmopolitan, and Lemon Drop Martini, which can be enjoyed alongside handmade pastas, and classic Italian comfort dishes. Olio e Più also hosts an aperitivo hour with a daily bar-side experience designed for lingering, sipping, and snacking. Available Tuesday through Saturday from 4–7pm, Aperitivo Hour invites guests to unwind with $10 wines, cocktails, and Italian small plates, served at the bar and patio.
Elevate your after-work plans with The Lux Happy Hour at Upstairs at The Gwen, available Monday through Thursday from 4–5:30 p.m. Located on the fifth floor of The Gwen, guests can unwind on the rooftop terrace or in the indoor lounge with specially priced cocktails, wine, beer and elevated bites. Sip on $10 draft beers, Tommy’s Margarita ($14). Pair your drinks with shareable favorites like Truffle Fries ($12) and gourmet flatbreads ($15). On Wednesdays, keep the evening going with Wine Wednesdays, featuring half-priced bottles of wine and exclusive by-the-glass specials. From 6–8 p.m., the lounge comes alive with live jazz performances by the Cosmic Jaywalkers.
South Loop
Located in Chicago’s South Loop, Martini Lounge puts a spin on happy hour, offered Thursday through Sunday from 5–7 p.m., with $10 cocktails, $6 Dirty Martini Shots and $5 beers. Guests can sip on classic and contemporary cocktails, including the Daiquiri, crafted with white rum, aged cachaça, lime and cane sugar; the Manhattan, featuring wheated bourbon, sweet vermouth and house bitters; and the Berry Bramble, combining berry vodka, berry gin, Pimm’s, Oloroso sherry and lemon. For those looking to keep things playful, $6 Dirty Martini Shots offer a fun twist on the lounge’s namesake cocktail, while $5 Stella Artois, Stella Artois 0.0 and Miller Lite round out the offerings.
West Loop
Happy Hour at Cache 310 in the West Loop is calling! Enjoy signature cocktails for $10 and beer & seltzers for $5 Mondays–Thursdays from 4–6 PM, or take advantage of $7 Heaven Fridays & Saturdays until 7 PM, featuring signature cocktails for just $7! Plus, enjoy 2 hours of complimentary parking on Fridays and Saturdays. Seating is first-come, first-served.
Canal Street Eatery & Market, located in the BMO Bank building, offers Happy Hour Monday through Friday from 3 p.m. - 6 p.m. Their happy hour menu features $12 pizzas (like their Spicy Sopressata made with pepperoni, fresh mozzarella, fresno honey, oregano), $9 house wines, and select beers for $5.
West Town
For an elevated start to the evening, Omakase Shoji offers Happy Hour Sunday, Tuesday and Wednesday from 5 - 6:30 p.m. Guests can enjoy a selection of food and drinks.
Wicker Park
Swing by Clever Coyote located inside The Robey in Wicker Park for daily Happy Hour from 5–7 PM, where all menu items are just $9 (excluding The Fishbowl)! Sip on tiki style drinks, dig into flavor-packed wings and nostalgic bar bites, and enjoy throwback vibes with pool, games, and all your favorite 80s, 90s, and early 2000s hits. Walk-Ins are welcome.
Inspired by Mexico City's Little Tokyo neighborhood, Valedor’s Cantina Hour features cocktails and bites with Mexican-Japanese inflection. From Tuesday to Sunday, from 5 - 7 p.m., the Wicker Park cocktail bar offers $12 cocktails (like the Toki'o Fashioned with oki Japanese whisky, Lapsang-kokuto syrup, house bitters and orange expression) and $8 tapas (like the Tuna Poke Tacos with wonton shell, wasabi salsa verde and sesame slaw). Guests also enjoy complimentary bites from a rotating selection of tapas during Cantina Hour while they enjoy drinks.
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