The 22 Best Happy Hours In Chicago - Chicago - The Infatuation (2024)

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.

THE SPOTS

When: Tues-Sun The Deal: $10 co*cktails and Bites

This Wicker Park spot is always a good time, whether you’re hanging out in the small dimly lit space or on their sidewalk patio. And though Lilac Tiger has the loud music and lively energy of a dive bar, their drinks and excellent South Asian food are significantly better than your typical neighborhood bastion of Malört. It’s great for a casual dinner, but if you want to kick off date night earlier or swing by for a post-work hang, their $10 Happy Hour has tasty snacks and drinks like their spicy tandoori honey chicken nuggets and refreshing chai daiquiri.

When: Tues-Sat The Deal: $1 Oysters, $2 Limoncello Shots, $3-off Flatbreads, $4 Toasts, $5 Beer, $6 Wine on tap, $7 Spritzes, $8 Sangria

This Roscoe Village wine bar has one of the best secret patios in the city. It’s spacious, covered, and even has private cabanas where you can enjoy dishes from Volo's loosely French menu like flaky salmon with a cider gastrique for dinner. But we recommend coming a little earlier for their great Happy Hour deals from 4-6pm nightly. When you’re slurping oysters, drinking wine, and saving money, sitting on a cushioned bench in your own cabana feels even better.

When: Sun, Wed, Thurs 4-6pmThe Deal: $6 Snacks, $6 Beers, $6 Wine

The decision to go to Dell Rooster in West Town is always a good one. This isn’t just because this all-day Latin American restaurant has great food (and it really, really does) but because it works for all sorts of situations—date night, dining solo at the bar, or, most importantly, post-work drinks and snacks. Besides half-off bottles of wine on Wednesdays, their Happy Hour has papas bravas, corn empanadas, and seasonal beers, all at $6.

When: Wed-Thurs 4-6pm At The Bar The Deal: $7 Bites, co*cktails, and Wine

Upbeat funk and R&B jams, delicious food, a long wine list, and live music on their plant-filled sidewalk patio—four very valid reasons to hang out at Bronzeville Winery. A fifth is midweek Happy Hour. You can expect $7 glasses of wine and co*cktails, plus bar snacks that change regularly. All of the above makes the fact that there’s still a day (or two) left in the workweek a little better.

When: Thurs-Sun 3:30-6pm The Deal: $8 co*cktails, $4 Beers, $2-$4.50 Snacks and Tacos

Solazo is an upbeat Mexican spot in Gage Park from the owners of La Josie. The busy space is filled with friendly servers, small groups, lively Latin music, and it’s always a good time. Besides specials throughout the week like “Taco Tequila Tuesday” and “Raicilla Sunday,” Solazo’s Thursday and Friday Happy Hour includes $8 margaritas, plus discounted beer, tacos, and snacks. The food is fine, but the main reason to come here is to drink margaritas and/or catch up with friends on their large back patio—preferably both.

When: Mon-Thurs 5-6pm, Sun 3-5pm The Deal: $2-$6 Snacks, $6 Beers, $7-$10 Wine, $10 co*cktails

Bar Goa is a clubby co*cktail bar in River North from the folks behind Rooh. The food is Indian with Portuguese influences, with dishes like butter chicken croquettes, tapioca fritters, and fried coriander chicken wings that are all available as Happy Hour bites. They also have a co*cktail menu that includes $10 gimlets, daiquiris, and whiskey sours. Come here for drinks and a snack before going out in the neighborhood, or if you're in the mood for a club-lite kind of night.

When: Mon-Fri 4-6pm The Deal: $6 Bar Bites, $6 Sushi Handrolls, $6 Wine, $8 co*cktails, $14 Sake Cans

If you walked into Sunda right now, it’s likely to be filled primarily with out-of-towners who read an old copy of Time Out, or your friends who moved to Schaumburg. It’s a sceney Asian fusion spot in River North with consistently good food, and sure, it’s pricey, but that’s why the move is to come for discounted snacks before going out downtown. Besides $6 glasses of wine and deals on co*cktails and sake, the Happy Hour menu has four different types of sushi, plus bar food like nori fries, seoul wings, and adobo pork belly bites.

When: Mon-Fri 4-6pm The Deal: Half Off Selected Wine and Beer

This is exactly the kind of chill place you want to decompress after a work day that involved forgetting to turn your microphone off during a company-wide Zoom. This little bar and restaurant is hidden in the courtyard of a small office building, only has about 30 seats, and serves outstanding co*cktails and great Southern-inspired food. And if an excellent neo-soul soundtrack and a smooth Old Fashioned doesn’t help you forget about that 4pm Friday meeting request your boss just sent, well, we're sorry.

When: Daily 4-5:30pm The Deal: $6-$11 Snacks, $8 Old Fashioneds, $7 Highballs, $6 Teeny Martinis, $6 Wine and Beer

Like most restaurants from the team behind Bavette’s, Armitage Alehouse, and Trivoli Tavern, this place’s dim lighting, jazz playlist, and vintage decor seems like you just walked into a 1920s speakeasy. But unlike those restaurants, grabbing a seat at this upscale River North spot is easy—which is essential because time is of the essence when Happy Hour is literal. From meatball sliders to beer and co*cktails, you have plenty of $6 options. You can even make a light meal of a slider, mussels, and a drink for just $24—and then brainstorm all the ways to use the extra $5 you saved, because a full order of mussels is normally $29.

When: Sun-Thurs 3-6pm, Fri-Sat 2-5pm The Deal: $2 Oysters, $4 Tacos, $8-16 Snacks, $5 Beer, $8 Wine, $10-11 co*cktails

Given the proliferation of boozy taco spots a few blocks north on Randolph, it would be easy to write off Bocaditos. This quiet Mexican restaurant in the West Loop does have margaritas and tacos, but the food is solid, and you can enjoy catching up with a friend in a place that won’t cause the “Loud Environment” warning on your watch to constantly buzz. Sure, some of the chicken in the Happy Hour tacos may be a little dry, and the carne asada might be a little salty. But the tortillas are soft, the creative drinks are tasty, and there's also a ton of seafood options and entrees like enchiladas and poblano fettuccine if you decide to stick around for dinner.

When: Tues-Thurs 4-6pm The Deal: $1 Oysters, $8 Olives, $20 Charcuterie Board, $8 Old Fashioneds and Martinis, $10 Wine, $45 Dozen Oysters and Bottle of Sparkling Wine

The West Loop has plenty of loud party bars—but after an exhausting day, sometimes the last thing we want is a busy spot filled with untz-untz music. Luckily, the area is also home to The Press Room, a speakeasy-esque, basem*nt wine bar. And we like coming here for Happy Hour when we want a relaxing drink after impatiently waiting eight hours to set our Slack status to "Away." They only offer Happy Hour Tuesday through Thursday, but $8 Old Fashioneds and martinis plus $1 oysters are exactly the midweek pick-me-ups we need.

When: Mon-Fri 4-6pm The Deal: $5-$15 Tapas, $4-$8 Beer, $6-$10 Wine, $7 Vermouth, $8 Sangria, $8-$11 co*cktails

Happy Hour at River North's Jaleo is actually a fun experience, despite being surrounded by couples rambling on about "flying buttresses" after their architectural boat tour. Rather than being unbearable, this Spanish restaurant channels that touristy energy into a pleasant, lively atmosphere. But the real draw are the deals—stop by for $7 patatas bravas or chicken croquettes and wash it down with some sangria, wine, or draft beers which all cost around $8.

When: Mon-Thurs 5-6pm, Sunday 4-5pm The Deal: $6 co*cktails, $6-$7 Wine, $4-$10 Small Bites

Amaru is a small, casual Latin American spot in Wicker Park with upbeat energy that will keep you awake even though you had to get up at 6am this morning. And their Happy Hour deals will also motivate you to not just immediately head home after work to become one with your couch. They have dishes like ceviche, piononos with sweet plantains and chorizo wrapped in bacon, which cost $10 or less, plus some co*cktails and wines for $7 or less. And, as our ex-roommate who never paid rent on time used to say: "There’s no shame in crafting a full meal out of Happy Hour bites."

When: Tues-Thurs 4-6:00pm The Deal: $5-$7 Mini Sandwiches and Sliders, Half-Price Draft Beer, $10 co*cktails

Not only does this New Orleans-inspired Hyde Park spot have the best po’boys we’ve encountered in Chicago, but it’s also a blast for Happy Hour. The spacious counter-service restaurant has a full bar, live music, and makes boozy co*cktails that aren’t too sweet. Along with deals on drinks and the aforementioned po’boys (like fried shrimp), the Happy Hour menu has scaled-down sizes of things like their muffuletta sandwich and fried chicken sliders.

When: Mon-Fri 3-6pm The Deal: $5 Select Beer and Cider, $6 Wine, $7 co*cktails, $12 Burger (With Beverage)

Like a Tom Hanks movie from the '90s, 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, and tacos, and a solid burger that’s only $12 (with a beverage) during their Happy Hour. 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-Thurs 4-7pm The Deal: Half Off Draft Beer, $7 Select Wine

With its spacious back patio, laid-back atmosphere, and delicious co*cktails, Spilt Milk is one of our favorite bars in Logan Square. But we also like coming to this cozy, dimly lit spot for their Happy Hour, when select drafts and wines are half off. And since this deal lasts until 7pm, your Uber driver won’t have to break out any Lewis Hamilton-esque F1 driving skills in order to make it in time.

When: Daily 4-6pm At The Bar The Deal: $1.50 Select Pintxos, $3-$5 Select Tapas, $22 Pitcher of Sangria, $4-$5 Select Beers

If we’re talking solely about logistics, tapas are the perfect bar snack. Luckily, not only are the tapas at Lincoln Park’s Cafe Ba-Ba-Reeba good, but they also have a fantastic Happy Hour where you can order small plates like patatas bravas, bacon-wrapped dates, or ham croquettes—all for less than $4. Bring your friends, order a bunch of food, and also make sure to get a $22 pitcher (or two) of sangria to share.

When: Wed-Fri 5-6:30pm, Sat-Sun 3-6:30pm The Deal: $2 Oysters, $2 Shrimp, $5 Glasses of Cava

A long wine list and delicious food make Uvae a good spot for a casual dinner—especially if you get there a little earlier for their Happy Hour. The cozy, close seating and friendly staff gives this Andersonville restaurant the atmosphere of a neighborhood dinner party, where you can knock back $2 oysters and shrimp. When you need a break from seafood, they have $5 glasses of cava to help cleanse your palette.

When: Wed-Fri 4-6pm The Deal: Half Off Select Pizza, $5-$15 Beer and Wine

Middle Brow Bungalow’s light sourdough crust and delicious topping combinations (like soppressata with hot honey) make it one of our favorite pizza places in Chicago. And duringHappy Hour, you can grab one of their pies for half-off. Throw in a $5 beer or glass of wine and you have an affordable meal. Or you can just come to drink while embarrassing yourself in the game of bags they occasionally have set up on their patio.

When: Mon-Fri 5-7pm Only At The Bar The Deal: $6 Beer, $10 co*cktails and Wine, $7-$16 Snacks

Tanta in River North is an appealing alternative for when you just can’t with your coworker and their "beer and a slider" choice for the fourth Happy Hour in a row. It’s always a fun spot for dinner (thanks to clubby lighting and a pop playlist) but Tanta is also great for pisco-based drinks and Peruvian snacks like cebiches and empanadas. And since the deals run until 7pm, you can still enjoy a pisco sour and anticucho even if you got stuck on a 5pm call that could have been an email.

When: Daily 5-6pm The Deal: $6 Draft Beer, $9 Select co*cktails, $6-$11 Snacks

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 for $12, you can get a draft beer and a great drinking snack like an egg roll or spring roll. Or, if it’s really been a long day, spring for the $11 Combo of a shot, PBR, and an egg roll.

When: Wed-Fri 4-5:30pm Exclusively At The Bar The Deal: $4 Beer, $9 Wine, $10 co*cktails, $5-$13 Snacks

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 $9 glasses of wine, and share small plates like catfish sliders, and mac and cheese fritters.