Every day, you show up to work and either accomplish a sufficient amount or look productive enough not to get fired. And when you’ve either crossed enough tasks off your to-do list or read the entire internet, you deserve to leave the office and get a drink that doesn’t cost $20. So here’s a guide to the best Happy Hours in the city with all the details you’ll need on days, times, and the drink and food deals.
All restaurants featured on The Infatuation are selected by our editorial team. The Best Happy Hours In Chicago is presented by Kenneth Cole.
The Spots
When Mon-Thu 5-7pm The Deal: $4 Beer, $6 Wine, And $8 Drinks At The Bar If You Spend $12 At Any Vendor
Remember playing games at the arcade and redeeming tickets for prizes? That’s a little like the Happy Hour at Time Out Market. This two-level food hall has 18 restaurants (all successful places that already exist like Mini Mott and Fat Rice) and three bars. And if you show a receipt at one of the bars proving you spent $12 or more on food, you get a deal on drinks. More importantly, you don’t have to spend $590 dollars to win glow-in-the-dark dice.
When: Mon-Fri 3-6pm The Deal: $6 Wine
Like a very special episode of This Is Us, Beatrix’s food is well-made and designed to appeal to a large amount of people. The menu has a wide range of options to choose from, like grain bowls, salmon, salads, tacos, and a burger. So if you want a place to catch up with friends and the only thing you can all agree on is wine, come here.
When: Mon-Fri 4-5:45pm The Deal: $7 Wine, $8 Drinks, $3-$4 Beer, $5-6 Snacks, And A $10 Butcher Board
This bright and airy Southern restaurant is one of our favorite upscale dinner spots in Hyde Park, but there’s also a separate, dimly lit bar area that’s great for just grabbing drinks and snacks. There you can get $7 glasses of wine, and share small plates like catfish sliders, mac and cheese fritters, or split a butcher board for $10. It isn’t the lightest food in the city, so you might not want to plan on doing much else after.
When Sun-Thu 4-6:30pm The Deal: $5-$8 Wine, Beer, And Select Drinks, $5-$8 Select Appetizers
Rooh is an upscale Indian restaurant in the West Loop that has very good cocktails, and bar food that’s more interesting than things like mozzarella sticks or tater tots. Along with wine, beer, and cocktails, you get deals on snacks like a chutney sampler and beet and yogurt kebabs. The large space has two levels, but you can only get Happy Hour downstairs, which is busier and louder than the second-floor dining room. So, also more fun.
When: 4:30-6:30pm The Deal: $7 Wine, $5-$9 Beer And Cocktails, $6-$12 Food Specials
River North has a lot of loud and crowded spots, and that makes us really appreciate hanging out at the very relaxed Bernie’s Lunch & Supper. The seats are far enough apart to make it feel spacious, and you’ll be able to get a seat at the large outdoor bar if you’re just having a drink and some snacks after work. If you’re doing that, consider using the money you’re saving to get the excellent burger - it’s number 15 on our Burger Power Rankings.
When: Mon-Fri 5-6pm The Deal: $6 Old Fashioneds, $11 Chef’s Cocktail, $6 Shot And Beer, $10 Snack And Drink Combo
This Chinese spot from the Giant team is just as much a fun bar as it is a restaurant. Expect it to be crowded and full of loud people who seem like they’ve been at Happy “Hour” for days. We like the fact that they have a $10 combo special, where you can pair drinks like gin and tonics and Old Fashioneds with good drinking food like fried rice and egg rolls.
When: Mon-Fri 3-5pm The Drink: $5 Wine And $5 Assorted Mezze Plates
We like hanging out at Ema’s bar if we’re having a rough day. It’s bright and has lots of plants, and is chill (by River North standards) without feeling eerily deserted. This Mediterranean spot has great wines for Happy Hour, and their mezze plates (including hummus and labneh) are always delicious. After both of those, you’ll forget all about that email you just got from you boss before you left the office.
When: Mon-Fri 5-7pm The Deal: $5 Beers, $7 Wine, $10 Drinks, And $8 Select Bites Vajra is an Indian and Nepalese restaurant in West Town that has great food and fantastic cocktails. You can get things like chicken or chili paneer, and drinks like “The Dwarf of Casterly Rock.” If you don’t want to order that after a long day at work, you need to take a good look in the mirror.
When Mon-Fri 3-6pm The Deal $7 Wine And Aperol Spritzers, $7 For 7 Oysters And/Or Other Snacks
Nico Osteria might be obsessed with the number “7” because you can get $7 glasses of wine, $7 aperol spritzers, $7 random snacks, and 7 oysters for $7 during Happy Hour. It’s probably related to some sort of gambling problem, but we don’t care - the Gold Coast is expensive, and wine and oysters are delicious. Plus, we like this Happy Hour for low-level people watching - the bar area is always filled with people who work in the area, and tourists pre-gaming before heading out into the city.
When Mon-Fri 4-6pm The Deal $6 Beer, $7 Cocktails, $8 Wine, And $5 “Happy Hour Food”
Everyone needs a go-to sports bar in their life, and Jake Melnick’s can be yours. This large spot in River North is known mainly for its fantastic wings, perfectly fine bar food, and having plenty of flatscreens playing every Chicago team all the time. Come here to meet up with a group of friends after work and yell at the TV.
When: Mon-Thu 5-6:30pm The Deal: $1 Oysters, $15 Bottomless Carafes (House Wine And Etta-ritas)
If you want Happy Hour to capture the sh*tshow magic of a fun bottomless brunch, go to Etta in Wicker Park. The first thing that hits you when you walk in is the fact that it’s crowded - it’s a loud, busy spot. There are two large bars here, one on the first floor and one upstairs, and both are great for hanging out. Wherever you sit, you’ll be able to get $1 oysters, and (most importantly) $15 bottomless carafes of wine and something they call “Etta-ritas.” You have 90 minutes to find out exactly what they are, so you better hurry.
When: Mon-Thu 4-6pm The Deal: $5-$8 Wine And Cocktails, $5-$8 Small Plates, $80 “Bubbles And Pork Shank”
We’re flat-out impressed with the Happy Hour at Cabra. This Peruvian-inspired spot from the Girl & the Goat team is on the roof of the Hoxton Hotel and has a fantastic view of the West Loop skyline. But great space aside, this place has an extensive Happy Hour menu with lots of food and drink deals to choose from - including their “bubbles and pork shank,” where you get a bottle of sparkling wine and the excellent chicharron del puerco.
When Mon-Thu 3-6pm The Deal $6 Beer And Wine, $10 Cocktails, $9 Bar Bites
The Magnificent Mile isn’t known for being affordable, and neither is the Saks Fifth Avenue that’s on it - which is where you’ll find this upscale vegan restaurant (it’s on the seventh floor). But even if you eat meat and dairy, you should come here for Happy Hour. You can get deals on drinks, plus $9 bites like smoked hummus and a flatbread pizza made with cashew ricotta. You’ll appreciate the savings after spending all that money on makeup and John Varvatos pullovers.
When: Daily 5-6:30pm The Deal: $6 Wine, Half-Off Appetizers And Meatballs
Head to Bar Roma in Andersonville for great Italian food, and to drink $6 glasses of wine in what feels like a Pinterest board for “Rustic Italian Countryside Bar.” The space has a lot of wood and distressed furniture, plus bags of flour lying around to remind you that they make all their pastas in-house. There’s an entire menu section dedicated to meatballs, and they’re half-off during Happy Hour (which is every day of the week).
