The 6 Best Happy Hours in Streeterville

There is so much to do in Streeterville, the gateway to Navy Pier. Next time you’re in the area, make sure to stop at one of our favorite happy hour spots. 

One of the top tourist attractions in the world, the area attracts a number of tourists yearly that come for the spectacular views of the lake. After a long day of work or touring, unwind by grabbing a drink at some of the best happy hours in Streeterville.


201 E Delaware Pl

This sexy rooftop cocktail lounge (located on the 18th floor of the Raffaello Hotel) offers some of the most limited selection of wines and spirits, which you can sip inside their Mad Men-inspired lounge or on their chic outdoor patio. Current cocktail selections by beverage director Whitney Morrow are travel-themed, with cocktails named after favorite summer haunts. Happy hours run during prime drinking hours (8-10pm), where you can partake in $5 beers and $8 frose, wines and cocktails.

Three Dots and a Dash

435 N Clark St

This Polynesian-inspired lounge is an underground hidden gem that serves both classic and modern tiki cocktails made with fresh juices and syrups, matched with a selection of over 200 distinctive rums. Once you get past the glasses shaped like skulls and treasure chests, you’ll find yourself wanting more of the drinks, inspired by several cultures around the world. Cocktail experts Julian Cox and Kevin Beary, the men behind the bar named one of the World’s 50 Best Bars by Drinks International, created over 250 different drinks to choose from! Happy hour is available from 5pm-2am.

If we played the name game, this drink would win. 🍍🌱Aloha Felicia: Rum, dark Jamaican rum, coconut, pineapple & Thai basil.

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Miller Lite Beer Garden

600 E Grand Ave

For popular tourist spots like Navy Pier, everything runs a bit expensive. But, if you want a drink and you’re stuck right smack in the middle of it all, you don’t have to worry about breaking the bank. The Miller Lite Beer Garden offers some pretty good happy hour deals, like $3 Miller Lite and Coors Light draft pours, $5 Henry Hard Ginger Ale and $6 nachos, all available from 4-6pm daily.

It's gonna be a hot one today! Come hang with us and a refreshing 🍺 #MLBGChi 📸: @yeaitscaleb

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Safehouse Chicago

60 E Ontario St

Themed restaurants don’t usually have the best food, but this spy-themed restaurant begs to differ. Other than an amazing selection of burgers (named one of the best spots for this beefy favorite in Chicago!), Safehouse Chicago also challenges patrons to solve puzzles and games, even making one out of their happy hours, available from 4-6pm, Monday to Thursday. Drinks and food like nachos, cheese curds and wings are available between $4-6 each, but be sure to let the waitstaff know you’re in on the secret.

Is it really an impossible mission if you believe you can do it? #SpyStuff

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The Purple Pig

500 N Michigan Ave

Wildly popular, Michelin-starred Chicago restaurant The Purple Pig serves up a 5-star experience featuring their Mediterranean cuisine, but also offers some amazing wine, swine and cheese pairings for their happy hours.

Rosé sangria for the win. 🍷🌺 Such a beautiful mix of flavors. Have you tried it yet?

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671 N St Clair

Because Beatrix offers one of the best brunches in the city, you can rest assured that they also have some of the the top libations on shelf, available all day at the bar. Wines that start at $12 become $5 come weekdays, from 3-6pm. If wines aren’t your thing, enjoy spiked fresh juices at the eclectic eatery/coffee shop/bakery/cafe during your afternoon break.

Which of the best happy hours in Streeterville have you checked out? Tell us in the comments!

Author: Maddy Osman, an SEO Content Strategist who has a passion for blogging. Her lifestyle blog, ChicagoCheapAss, shows young adults how to find the best deals and values in Chicago!