Waiting for Friday after a tedious work week can feel like light-years away, especially if it’s a dreaded Monday. However, we don’t have to wait until the weekend to see friends and pay for overpriced drinks at a crowded bar to get boozy—a budget-friendly outing awaits you after completing the day’s worth of tasks.
Whether your office is in Fulton Market or your River North bedroom, head to the nearest neighborhood bar and take advantage of the best happy hours Chicago has for a midweek excursion.
RPM Seafood
RPM Seafood has just launched its first-ever happy hour! It doesn’t get better than unwinding on the Chicago Riverfront and sipping on their signature cocktails, including the Crystal Paloma, Classic Martini, and Winter Old Fashioned, all for just $10 each. Don’t miss out on the bar bites deals, featuring items like Yellowfin Tuna Crispy Rice, Prime Steakburger, and char-broiled RPM Prestige Oysters, with prices ranging from $5 to $75.
📍Address: 317 N Clark St, Chicago, IL 60654
📅 When: Monday – Friday: 4:00 – 5:30 PM
🍽️ Reservation: Make a reservation at RPM Seafood
Sushi-San
Goodbye Taco Tuesday and hello Sushi Wednesday (any other day works, but Wednesday sounds better.) This is one of the best happy hours in Chicago if you love sushi. The deal includes $6 Spicy Tuna Maki, Spicy Tuna Aburi, Roasted Edamame, Japanese Eggplant, and more.
📍Address: 63 W. Grand Ave Chicago, Chicago
📅 When: Monday—Friday: 3:00-6:00 PM
🍽️ Reservation: Make a reservation at Sushi-san
Olio E Più
Olio E Più is an authentic trattoria serving classic Italian dishes, with a focus on house-made pasta, hand-stretched pizza, and traditional favorites like Caprese salad, fritto misto, and tiramisu. The open dining area, rustic interior, and lovely patio space bring a piece of old-world Italy to Chicago’s River North neighborhood.
The lineup changes based on the season. One of our favorite happy hours in Chicago, the menu includes $10 house wine, cocktails, and various small bites like Focaccina Napoli, Caponatina, and Bruschetta Al Pomodoro, each priced at $10.
📍Address: 445 N Dearborn St, Chicago, IL 60654
📅 When: Monday—Sunday: 2:00-6:00 PM
🍽️ Reservation: First come, first served at the bar area
Avli on the Park
Block out the city noise and head to this restaurant overlooking a charming park as you sip wine and, for once, breathe in polluted-freeish air. You’ll be undisturbed at what we designated as one of the prettiest restaurants in the city. Avli on the Park’s happy hour menu includes $6 glasses of wine, $10 featured cocktail, $5 selected beers, $8 Greek salad, $6 spreads, and $8 small bites.
📍Address: 180 N Field Blvd, Chicago
📅 When: Tuesday – Friday: 2:30-5:30 PM
🍽️ Reservation: Make a reservation at Avli on the Park
Upstairs at the Gwen
This opulent New American restaurant perspires Chicago happy hour elegance with its terrace skyline views paired with small plates and sweet cocktails. The happy hour menu includes a $10 Tommy Margarita, $10 Gin & Tonic, $10 Creole Maple Old Fashioned, $10 house wine, $8 draft beer, $6 fries, $11 Chicken Wings, and $11 Fried Brussels Sprouts.
📍Address: 521 N Rush St 5th Floor, Chicago
📅 When: Monday—Friday: 4:00-5:30 PM
🍽️ Reservation: Make a reservation at Upstairs at the Gwen
Middle Brow Bungalow
Wooden beams and string lights cover the patio of this delightful bucolic-decorated restaurant, giving a refreshing aura. Take a seat at one of their picnic tables and enjoy their happy hour menu, which includes $5 beer, $6 wine, and a selection of bread, salad, and pizza that range in price. On Wednesdays, stay past 6 PM and become drenched in the music from live performances.
📍Address: 2840 W Armitage Ave, Chicago
📅 When: Wednesday—Frida, 4:00-6:00 PM
🍽️ Reservation: Make a reservation at Middle Brow Bungalow
Nisos Prime
If you’re seeking a luxurious happy hour in Chicago, make your way to Nisos Prime as soon as possible. Enjoy a selection of opulent offerings, including $15 caviar bites such as crab beignets, prosciutto crostini, and truffle arancini. For $12 to $13, you can choose from bar bites like gin and tonic cheese curds, croquettes, and truffle fries. Don’t miss out on their cocktails, priced at just $9. It’s the perfect spot to indulge after hours.
📍Address: 802 W Randolph St Floor 2, Chicago, IL 60607
📅 When: Every day, 4:00-6:00 PM at the Prime Bar
🍽️ Reservation: Make a reservation at Nisos Prime
Cafe Ba-Ba Reeba
Cafe Ba-Ba Reeba is noted as one of the best Chicago happy hours because the happy hour never stops—come by the restaurant seven days a week and choose food from their mouth-watering menu while slowly becoming inebriated by the sangria pitchers. The menu includes $20 Sangria pitchers, $1.50 pintxos, $3.50 tapas, $5 Estrella Damm bottles, and more.
📍Address: 2024 N Halsted St, Chicago
📅 When: Monday—Sunday, 4:00-6:00 PM
🍽️ Reservation: First come, first served at the bar area
Tanta
Walk into the first-floor bar of this Peruvian-inspired space to devour a few of their inventive Chicago happy-hours specials. From $8 to $10, indulge in everything from Boliyucas to Tequeños De Pollo. The drink specials include $10 cocktails, $10 wine by the glass, and $6 beer.
📍Address: 118 W Grand Ave, Chicago
📅 When: Monday—Friday: 4:00-6:00 PM
🍽️ Reservation: First come, first served at the first-floor bar
City Social
Amid every financial district in America, there is ostensibly an American Pub nearby. Whether you need an escape from an arduous day crunching numbers or long-winded, monotonous business calls, you’ll never want to leave once arriving. City Social’s Chicago happy hour specials include $4 Draft Krombacher, $6 glasses of Rose-All-Day Bubbly, $4 City Pale Ale, and $5 Mini Black & Tan.
📍Address: 120 North LaSalle, Chicago
📅 When: Monday—Wednesday: 4:00-6:00 PM
🍽️ Reservation: Make a reservation at City Social
La Grande Boucherie
La Grande Boucherie is a unique culinary destination that seamlessly combines the elegance of a Parisian brasserie with the robust flavors of a classic steakhouse.
Nestled in the historic Belle Époque building in the heart of Chicago, this restaurant offers an exquisite dining experience set against an Art Nouveau-inspired backdrop. Guests can indulge in a vibrant happy hour menu, which includes $10 house wine, $11 cocktails, $15 for a dozen Oysters, $16 Escargots, $19 Pâté, and more.
📍Address: 431 N. Dearborn Street, Chicago, IL 60654
📅 When: Monday—Sunday: 2:00-6:00 PM
🍽️ Reservation: First come, first served at the bar area
Virtue
Usually, when you want to consume award-winning food, it comes at a price. However, Virtue’s happy hour menu is delectable, affordable southern food. Ranging from $7 to $13, order a cup of Gumbo, a catfish slider, buffalo mac & cheese croquette, and other savory items. The happy hour drinks include a $10 cocktail and $9 glasses of wine.
📍Address: 1462 E 53rd St, Chicago
📅 When: Wednesday—Friday: 4:00-5:30 PM
🍽️ Reservation: Make a reservation at Virtue
Aba
Leave your dreary cubicle and head to this luscious greenery oasis rooftop after work. Aba is the perfect post-work solution to rejuvenate a hungry group of co-workers. One of the best Chicago happy hours, the specials at Aba include $7 sommelier-selected white and red wine pours, $5 locally-brewed beer, $10 for a classic martini and margarita drink, and $15.95 for the spread sampler.
📍Address: 302 N Green St, 3rd Floor, Chicago
📅 When: Sunday—Thursday: 4:00-6:00 PM
🍽️ Reservation: Make a reservation at Aba
Bub City
This sprawling and buzzy BBQ bar is perfect for howling out the tunes of Luke Bryan or Tim McGraw. While twirling to live music in the country-themed bar, check out their happy hour, which includes a $5 draft beer and hard seltzers available at the bar and dining room.
📍Address: 435 N Clark St, Chicago
📅 When: Monday—Friday: 3:00 PM–5:00 PM
🍽️ Reservation: Make a reservation at Bub City
Sifr
Awarded as a 2024 Michelin Bib Gourmand, Sifr, known for its hearth-fired twist on Middle Eastern cuisine, has one of the best happy hours in Chicago. From crafted cocktails for $7 to $6 Middle Eastern wines and $5 beers. To pair, guests can select the exclusive Halal Lamb Kebab Burger with tzatziki, cheese, house pickles, and classic dips like Hummus and Manoushe.
📍Address: 660 N Orleans St, Chicago, IL 60654
📅 When: Sunday—Thursday: 4:00 PM–6:00 PM
🍽️ Reservation: Make a reservation here
Ema
A Mediterranean restaurant in River North, their menu is full of small plates, fresh bread, and regional wines that will take you to the coast of the Aegean Sea. The happy hour menu includes $7 mezze, $6 craft beer, $10 House Margarita, and $8 happy hour white & red pours for bar dine-in only.
📍Address: 74 W Illinois St, Chicago
📅 When: Monday—Thursday: 4:00 PM – 6:00 PM
🍽️ Reservation: Make a reservation at Ema
RPM Italian
Backed by Giuliana and Bill Rancic, this Italian restaurant will cure all your Italian cravings. This sleek, modern hot spot has an essential happy hour menu that includes $8 cicchetti and signature cocktails, beer, and wine by the glass starting at $8
📍Address: 52 W Illinois St, Chicago
📅 When: Monday—Friday: 4:00 PM–6:00 PM
🍽️ Reservation: first come, first served at that bar
Tallboy Taco
Tallboy Taco boats a fresh and inspired menu that serves tacos on hand-pressed corn tortillas, margaritas, and tall beers. If you’re a Mexican cuisine fanatic, you must stop here for the happy hour, including $5 Classic Margaritas, $5 Palomas, and $5 Nachitos.
📍Address: 302 N Green St, 3rd Floor, Chicago
📅 When: Monday—Friday: 3:00 PM – 6:00 PM
🍽️ Reservation: First come, first served
Diego
A nod to street food, Diego is a culinary voyage that intertwines the artistry of Mexican mixology and the authentic food you find on the street. Founded by Chef Stephen Sandoval, the craft cocktail bar is infused with the spirit of Baja in Chicago’s hip heart of West Town. Their happy hour includes bright cocktails, beer, and bites.
📍Address: 459 N Ogden Ave, Chicago, IL 60642
📅 When: Monday—Friday: 4:00 PM – 6:00 PM
🍽️ Reservation: First come, first served
Beatrix
This modern, all-day venue combines an American eatery, cocktail lounge, and bakery, molding the perfect happy hour in Chicago for drinks and delectables. The menu includes $5 local beers, $6 select wines, $7 hand-crafted cocktails, and rotating bar bites.
📍Address: 519 N Clark St, Chicago
📅 When: Tuesday—Friday: 3:00 PM–6:00 PM
🍽️ Reservation: Make a reservation at Beatrix
Casa Chi by Chef Richard Sandoval
Enjoy a one-of-a-kind margarita happy hour at Casa Chi by Chef Richard Sandoval. For just $12, sip on the refreshing traditional margarita. Other specialty margaritas, like the MagMile Margarita, Cucumber Tortilla Margarita, and Watermelon Margarita, will be offered at $14. If you’re looking to go crazy, the Margarita Flight is $24.
Paired with $12 Nikkei-inspired bites like Tuna Ponzu Guacamole, featuring jalapeño, chipotle aioli, and lime, it’s the perfect way to unwind after a busy workday or start the night out.
📍Address: 505 N Michigan Ave., Chicago, IL 60611
📅 When: Every day: 3:00 PM–5:00 PM
🍽️ Reservation: Make a reservation here
aliveOne
Any night of the week, you can enjoy the half-price happy hour at aliveOne. Everything on the menu is half-price, including their signature cocktails like The Becky with Tito’s, Pamplemousse La Croix, fresh lime juice, and demerara syrup or You’re a Daisy If You Do with Titos, St. Germain, Aperol, and lemon juice.
📍Address: 2683 N Halsted St, Chicago, IL 60614
📅 When: Sunday—Thursday: 5:00-7:00 PM | Sunday—Thursday: 5:00-7:00 PM
Central Park Bar
If you’re looking to unwind, make your way to happy hour at Central Park Bar. Enjoy a rotating selection of local brews, ciders, wines, and house cocktails, all offered at half price. Drink indoors or outside in the 3,500-square-foot “backyard bar,” which features picnic tables, bumper pool, porch swings, tiki torches, and more.
📍Address: 2924 N Central Park Ave, Chicago, IL 60618
📅 When: Monday—Friday: 4:00-7:00 PM
Easy Bar
Let’s raise a glass to one of our favorite bars in Wicker Park: Easy Bar. The spot has a half-price happy hour every day that includes a rotating selection of beer, wine, and house cocktails, featuring seasonal craft brews from local favorites like Revolution Brewing, Bell’s Brewery, Maplewood Brewing, and more.
📍Address: 1944 W Division St., Chicago, IL 60622
📅 When: Everyday: 4:00-6:00 PM
Estelle’s
A late-night staple, Estelle’s is the go-to spot for clinking drinks. It’s even better when there are deals, which include everything on the menu, excluding shots and food.
📍Address: 2013 W North Ave. Chicago, IL 60647
📅 When: Everyday: 4:00-6:00 PM