Whether you're working in the office or at home, when five o'clock hits, use this guide to find the best budget-friendly deals in your neighborhood.
Tori Levy - Staff Writer•
Waiting for Friday after a tedious work week can feel 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.
1. 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
2. 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, co*cktails, 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—Friday: 3:00-6:00 PM
🍽️ Reservation: First come, first served at the bar area
3. 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 co*cktail, $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
4. 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 co*cktails. 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
5. 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
6. 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—Friday: 4:00-6:00 PM
🍽️ Reservation: Make a reservation at Middle Brow Bungalow
7. 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 co*cktails, $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
8. 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
9. 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 co*cktails, $15 for a dozen Oysters, $16 Escargots, $19 Pâté, and more.
📍Address: 431 N. Dearborn Street, Chicago, IL 60654
📅 When: Monday—Friday: 3:00-6:00 PM
🍽️ Reservation: First come, first served at the bar area
10. 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 co*cktail 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
11. 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
12. 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
13. 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
14. 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 co*cktails, 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
15. 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
16. 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 co*cktail bar is infused with the spirit of Baja in Chicago’s hip heart of West Town. Their happy hour includes bright co*cktails, 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
17. Celeste
Head to Celeste’s happy hour in Chicago with bites starting at $6 bites, $8 wine, $10 co*cktails, and $6 Modelo. Bites include Shish*to Peppers, Arancini, a Nashville Hot Chicken Sandwich, and a Smash Burger. For the co*cktails, choose from Celeste Margarita, Cucumber Collins, Melon Melon, and Espresso Martini for co*cktails. The fourth-floor Garden space offers a year-round escapist experience due to the retractable glass rooftop. However, the charm comes from the interiors decorated with natural tropical greenery, vine-covered brick walls, and floral-print Victorian furniture.
📍Address: 111 W Hubbard St, Chicago, IL 60654
📅 When: Wednesday—Friday: 5:00 PM – 7:00 PM
🍽️ Reservation: First come, first served
18. Beatrix
This modern, all-day venue combines an American eatery, co*cktail lounge, and bakery, molding the perfect afternoon spot for happy hour drinks and delectables. The menu includes $5 local beers, $6 select wines, $7 hand-crafted co*cktails, 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
See More: The Best Bars In Chicago Right Now
