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Bernie's in Chicago
Photograph: Meghan Leigh PhotographyBernie's in Chicago

The 15 best happy hours in Chicago

Looking for the ultimate post-work drinks? We've rounded up some of our favorite happy hour deals throughout the city.

John Bills
Allison Yates
Edited by
John Bills
Written by
Allison Yates
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Society may have revised what post-pandemic work looks like, but post-work drinks? That’s a staple that won’t go away anytime soon. Leave it to Chicago’s best cocktail bars and restaurants to offer enticing happy hour drinks and food pairings, from yuquita fries and lavender-infused vodka cocktails to oysters and martinis. Whether you’ve been hard-pressed to get a reservation at a popular restaurant, want to kick back with coworkers and a few pitchers of sangria, or impress a date with your board game skills, the best happy hours in Chicago offer plenty of entertainment—4pm karaoke, anyone?—and atmosphere to spice up any day of the week. 

Time Out Market Chicago
  • Restaurants
  • West Loop

In addition to 18 kitchens that host some of the best chefs in Chicago, Time Out Market Chicago also boasts a killer happy hour deal. Monday through Friday from 4–7pm, anyone who makes a $15 food purchase can present their receipt at any Time Out Market bar and enjoy $5 beers, $7 wine and select $9 cocktails. Go ahead, have a drink with dinner!

Best happy hours in Chicago

  • Restaurants
  • Mexican
  • Lower West Side

You don’t need an excuse to celebrate taco Tuesdays, but the $3 tacos offered during La Luna’s happy hour offer a great reason to indulge. Head to this colorful Pilsen restaurant for your midweek pick-me-up and top off your meal with the $5 shot of the day. Sit inside below full-wall murals and when it’s warm, grab outdoor seating and take in the sights of 18th Street. Tuesday through Thursday, 5-7pm. 

  • Restaurants
  • Spanish
  • Lincoln Park
  • price 1 of 4

This beloved Lincoln Park tapas bar offers daily happy hour specials at the bar and lounge area. Grab some friends and indulge in a pitcher of $20 sangria, share $1.50 pintxos accompanied by $2.50–3.50 tapas such as patatas bravas, Jamon Iberico or meatballs with sherry tomato sauce. Daily at the bar, 4-6pm

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  • Restaurants
  • American
  • West Loop

While dining at the award-winning restaurant El Che is normally a splurge, you can snag great discounts during happy hour. The Argentine-influenced steakhouse offers $3 beef picadillo or kale florentine empanadas, $11 bone marrow and $8 glasses of house red wine. Tuesday through Friday, 5-6pm.

  • Bars
  • Lounges
  • Loop
  • price 1 of 4

Celebrate any occasion–even if that’s just the end of a long Tuesday–at this South Loop karaoke bar. Liquid courage for singing comes in the form of $5 Old Fashioneds, Moscow mules, and Palomas. If you’re looking for a more low-key experience, there’s another room for conversation and drinks without the off-pitch renditions. 5-7pm daily.

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  • Bars
  • Breweries
  • Logan Square

This Logan Square brewery, bakery, winery, and pizzeria offers a seemingly endless selection of yeast-based creations. The all-day neighborhood spot is worth traveling to—especially during happy hour. Deals include $5 beers and house-made natural wines as well as half-price pizzas. Wednesday through Friday, 3:30-6pm.

  • Bars
  • Cocktail bars
  • Rush & Division
  • price 3 of 4

Yes, frog legs are on the menu at this old-school seafood joint in the Gold Coast. The best deals at Hugo’s Frog Bar & Fish House arrive during happy hour when you can pair a $6 martini with as many $1 oysters as you fancy. Seafood is flown in daily, so stick around after happy hour for your fresh fish fix. Sunday through Thursday, 3-6pm

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  • Shopping
  • Bookstores
  • Lincoln Park
  • price 1 of 4

More than just a place to drink, this mission-driven Lincoln Park bar sells used books, offers board games, and hosts lectures—all in the hopes of inspiring face-to-face, intellectual interactions in a low-tech atmosphere. Get a seat here during happy hour for a discounted selection of rotating beers and wines (usually $5) and relish the conversation that cheap libations can spur. Wednesday and Thursday, 4-6pm.

  • Bars
  • Albany Park

This intimate Albany Park bar specializes in seasonally-rotating cocktails served in a sultry, dimly-lit space. Happy hour features select craft cocktails—the Maple Pecan O.F. with bourbon and Ango soda, the Shutter Speed with gin and sage and the Winter Punsch with rum and house punch—for $6, as well as $2 Old Style tallboys and $5 rose or pinot noir. Sunday through Thursday, 5-6pm and 11pm-12am.

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  • Restaurants
  • River West/West Town

Quirky taxidermy mixed with traditional decor—think cuckoo clocks and steins—sets the tone for Chef Mark Steuer’s reimagined German cuisine. The Michelin Bib Gourmand-awarded restaurant in West Town serves a special menu of “happy eats” and “happy drinks,” including a $25 piggy plate (a charcuterie board filled with pork products), a $6 garlicky pretzel and $6 schnitzengiggle beer. Tuesday through Sunday from 5-7pm.

  • Bars
  • Cocktail bars
  • Ukrainian Village
  • price 2 of 4

Wicker Park cocktail tavern Queen Mary serves food and drink with British maritime flair, so it’s no surprise the spot’s happy hour specials include $1 oysters and $6 martinis. Be sure to plan ahead—seating is first come, first served, and oysters are only available during this limited time. Sunday 3-7pm and Monday 5-7pm.

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  • Restaurants
  • Italian
  • River North

If you can make it past the temptations of the first-floor dessert counter and grocery storehouses inside this Italian mega-market, make your way to the second-floor restaurant La Piazza for an aperitivo. Taking inspiration from the traditional squares of Italian cities, this eatery offers $7 glasses of wine and half-price salumi e formaggi boards, ranging from $16–$36. Monday through Thursday, 4-6pm.

  • Restaurants
  • Peruvian
  • River North
  • price 2 of 4

Cozy up at the bar of this sleek Peruvian restaurant in River North for weekday deals. Skip the usual post-work fries and opt for $5 yuquita fries with Huancaina or $9 ceviche. Craft cocktails—including El Cholito, a mix of pisco, cucumber, jalapeno, vermouth, ginger, and tajin, and El Chingon with jalapeno-infused tequila, mezcal, lime, and simple syrup—are just $10. Monday through Friday at the bar, 5-7pm.

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  • Bars
  • Cocktail bars
  • Ukrainian Village

In the heart of Humboldt Park’s Paseo Boricua, this tiki-inspired Caribbean bar provides discounted classic cocktails as part of its daily happy hour special. Fantasize about warmer climates in the bar’s tropical decor and when summer arrives, soak in the afternoon sun on the patio as you sip a refreshing Moscow mule or margarita. 5-7pm daily.

  • Restaurants
  • American
  • River North

This River North eatery is a popular post-work hangout, serving elevated European-inspired pub grub. The casual vibe of the rooftop is a welcome change of pace—especially in an area best-known for its clubs and sports bars. Specials include $5 draft beers,$7 glasses of sangria, $5 fries, or $11 cheeseburgers. Monday through Friday, 5-7pm, Saturday and Sunday, 4-6pm.

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  • Restaurants
  • American
  • River North
  • price 2 of 4

The soft, golden hues of Gilt Bar’s interior are a warm retreat on chilly or rainy days—and a perfect place for a cheap (but romantic) date in the early afternoon. Happy hour is served daily until 5pm, following the pattern of five: $5 draft beers, $5 Old Fashioned cocktails and $5 small plates like sliders or fried calamari. Daily until 5pm.

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