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Food and drink at Tanta happy hour
Photograph: Mistey Nguyen

10 top-notch rooftop happy hour deals in Chicago

For drink deals and gorgeous views, look to some of Chicago’s hottest rooftop bars.

Written by
Shanti Chu
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Chicago has an alluring rooftop bar scene and dynamic happy hour options, but what if you want to have happy hour on a rooftop? Whether you’re having a Sunday funday or trying to relax after a stressful day at work, these Chicago rooftop bars have you covered. Some of the best bars in Chicago are whipping up creative cocktails and delicious bites for happy hour atop their gorgeous rooftop spaces, offering everything from pisco sours and frosé specials to incredible deals on appetizers—and best of all, the views are always free. Gaze at the dazzling skyline or retreat to a cozy, intimate space away from the hustle and bustle of Chicago’s busy streets with these rooftop happy hour specials throughout the city.

RECOMMENDED: The best rooftop restaurants in Chicago

The best rooftop happy hours in Chicago

  • Restaurants
  • Logan Square

Rooftop happy hour dreams come true in Logan Square at this vibey-yet-casual Tex-Mex taco gem with craft cocktails and plentiful vegan/vegetarian options. For their happy hour, sip $6 frozen raspberry margaritas made with mezcal, Curacao, lime and raspberry, or snag a Lone Star beer for a cool $2. Fuel up on food options like the dips and chips platter, which includes mini queso, mini street corn and an assortment of salsas for $8. With deals this good, you might end up staying past happy hour and can check out their sultry, subterranean bar, Golden Teardrop, after the sun sets. Sunday through Thursday from 3-6pm.

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

Sip a delightful $10 pisco sour on this charming rooftop bar while sampling mouthwatering Peruvian snacks. Tanta’s rooftop happy hour offers distinctive cocktails with ingredients like elderflower, mezcal, jalapeno, lavender-infused gin and other interesting ingredients as well as wines by the glass for $10 and beer for $6. For a tasty happy hour snack, try the seafood-centric Small Cebiche Mixto with octopus, shrimp, calamari, sweet potato and corn nuts. Happy hour is only at the bar and it’s first-come, first-served, so be sure to get there before the happy hour rush. Monday through Tuesday from 5-7pm and Wednesday through Friday from 4-6pm.

 

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  • Restaurants
  • American
  • River North

Sample $10 craft cocktails, wine and light bites while appreciating the Art Deco-inspired design of Upstairs at the Gwen. Entice your palate with a Creole Maple Old Fashioned with dickel rye, clement rhum, maple, angostura and orange bitters, then try some crispy falafel served with a dill-fennel salad, tzatziki and peanutsMonday through Thursday from 4-5:30pm.

  • Bars
  • Pubs
  • Wicker Park

For a more casual happy hour, Whiskey Business has you covered with $5 Miller Lites, $7 Jim Beam Highballs and $8 Wagyu Smash burgers. If you end up staying past happy hour, you might catch a Monday movie night, Taco Tuesday or a Thankful Thursday when teachers and nurses can get 25 percent off their total. Immerse yourself in 80’s/90’s nostalgia on this colorful and playful rooftop as an escape from the chaos of Division Street. Monday through Friday from 4-6pm.

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  • Restaurants
  • Mediterranean
  • West Loop

End your weekend or workday with an escape to the Mediterranean on Aba’s lush, plant-filled rooftop. The restaurant’s happy hour not only has drink specials (sommelier-selected $7 wine pours and $5 locally brewed beers) but also delicious vegetarian mezze for $15.95 that includes a spread of whipped feta, charred eggplant and classic hummus. Still hungry? Try the Date flatbread or Turkish flatbread for $9.95. Sunday through Thursday from 4-6pm.

  • Restaurants
  • Argentinian
  • Loop

This vibrant Peruvian street food spot offers a sunny, beautiful lounge with a retractable rooftop inside of the Kimpton Gray Hotel. You can get an herbaceous Fernet and Cola for $10 or their wine/beer of the day for $6-8. While catching up with friends over happy hour, share some Yaquitas (yucca fries) for $4 or Hongos (sautéed mushrooms) for $8. Diners can hang out at the bar or sit on comfy lounge chairs after a long workday. Wednesday through Saturday from 5-6pm.

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  • Bars
  • Lounges
  • River North

Luxurious views go hand-in-hand with tasty snack and drink options at this indoor/outdoor rooftop located in the Godfrey Hotel Chicago. A variety of appetizer options—such as blistered shishito peppers, black truffle fries and creamy avocado toast—are half off. For those sweltering summer afternoons, try frosé by the glass for $8 or opt for a $28 bottle of wine if you’re angling for a longer happy hour that turns into a debaucherous night out. Monday through Friday from 2-5pm. 

  • Bars
  • River West/West Town

Immerse yourself in a golden happy hour away from the Loop at the Hyatt Place in Wicker Park, where you’ll discover abundant seating and panoramic cityscape views. While the outdoor views are breathtaking, the bar also boasts an indoor lounge option if you’re craving some time away from the sun. Forget about the chaos of work with selected $7 glasses of wine and $10 cocktails—try a refreshing 818 Tequila Mule featuring 818 Blanco tequila, lime and Q Ginger Beer with a sprig of mint, or go for something simpler like a $5 domestic beer. Monday through Friday from 4-6pm.

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  • Bars
  • Lounges
  • Loop
  • price 3 of 4

Located on the 27th floor of theWit hotel, this trendy rooftop will keep you entertained and satiated as you’re looking to relax after a long work day. While some happy hours focus on drink deals, hungry diners can bask in their food-friendly happy hour with 20 percent off the bar’s Neapolitan pizzas. Sip house white, rosé or red wines for $10 on couches as you’re taking in breathtaking city views under a retractable glass roof that can be experienced rain or shine. Beer drinkers and cocktail fans have options, too, so everyone is satisfied. Try a Jim Beam seltzer for $8 if you’re looking for a lighter way of drinking bourbon. Wednesday through Friday from 4-6pm.

  • Bars
  • Cocktail bars
  • Streeterville

Happy hour can also be at lunchtime if you’re at Offshore Rooftop—the world’s largest rooftop, according to Guinness World Records—which features 36,000 square feet of indoor and outdoor space and stunning vistas to boot. Take advantage of the unobstructed views of Lake Michigan and the city skyline while you’re taking a break from the Navy Pier crowds, and relax with a $12 cocktail like their Whiskey Smash (Jameson orange whiskey, St. Germain, lime and mint). If you’re there closer to lunchtime, get a Bloody Maria made with Casamigos Reposado Tequila and appreciate the savory tomato flavors with your booze. Monday through Friday from 11am-3pm.

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