If you plan to book flights to Chicago to visit the Windy City, you’re sure to get blown off your feet by some amazing places to imbibe to your heart’s content. Whether it’s charming neighborhood dive bars, fancy cocktail lounges, or sports bars that entertain the raucous masses, you’ll find the perfect solution to your mood and budget. Here are just a few places you should visit to get your tipple on.

When You’re Thirsty for a Few Good Brews…

Revolution Brewing

Probably one of Chicago’s most famous watering holes, this Logan Square gem is a brewpub you shouldn’t miss out on. In addition to their amazing brews, you get a simple but delicious menu. We’re big fans of their Anti-Hero IPA, and you will be too after just a few sips!

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Hopleaf Bar

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This gastropub serves well over 20 beers on tap as well as a wide range of bottled brews. Its menu also boasts hearty and satisfying dishes, with standouts being their pomme frites, chicken wings, mussels, and duck reuben.

The Map Room

Often rated as one of the best beer bars in the country, this colorfully decorated bar — with tons of magazines and flags lining the walls — creates the perfect atmosphere for sampling light IPAs to full-blooded Imperial Stouts, and everything in between. Just ask their very knowledgeable bartenders for suggestions.

When You’re in the Mood for a Really Good Cocktail…

Green Mill Cocktail Lounge

Who wouldn’t want to drink like a gangster? You can do exactly that at Al Capone’s favorite drinking spot. This bar has an old-school jazz and blues club vibe that attracts patrons from far and wide. So go ahead sip on one of their excellent cocktails, tap your fingers to the swingin’ tunes, and lounge like a badass.

Lost Lake

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This tiki bar produces some amazing drinks that are generously garnished and expertly mixed. All you have to do is try their Bunny’s Banana Daiquiri or their Tic-Tac Taxi to know exactly why this establishment is so highly rated by cocktail lovers from all across the country.


This dimly-lit, intimate establishment serves up trendy bar food (and even has a great brunch menu) and a great seasonally-changing drinks menu that leans heavily towards gin.

When You’ve Got to Root for the Cubs…

Murphy’s Bleachers

You can’t beat Murphy’s Bleachers for the quintessential game-day booze up. Just across the street from Wrigley Field, this legendary little bar offers up quite the raw, energetic experience, especially if you visit during a Cubs game.


Sports fans can’t get enough of this bar, thanks to its great food, solid drinks, and a large number of TVs showing almost any sport you would want to watch. Order some tater tots and their delicious pulled pork sandwiches, along with a cold beverage of your choice, and you’re all set for that nail-biting finish.

First Draft

Craft beer fans will delight at the more than 40 tap options available at this spacious sports bar. You can catch all the games while downing a few Zombie Dusts and digging into their succulent burgers — it’s a win-win regardless of your team making it through at the end of the night.

Honorable Mentions: Drop by for a Drink at These Bars…

Old Town Ale House

Basic drinks are the cornerstone of this legendary dive bar. Whether it’s the crass interpretations of Chicago history that adorn its walls or the eclectic group of people who frequent it, you’re sure to find something uniquely Chicagoan right here.

Kingston Mines

Dig some good live music? If so, you’re certainly going find some cheap flights to Chicago! You can’t miss out on the talented jazz and blues artists that keep it real on the stage at Kingston Mines. Cheap beer and southern comfort food are the staples here, so you have all you need to make it a night to remember.

Got any favorite bars in Chicago? Tell us about them in the comments.

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About The Author

Dhinesh Manuel

Socialite, philanthropist, costumed crime fighter by night...no wait...that's Batman...my bad ... Musician, writer, travel junkie, dog lover, and database of useless information. I love to learn about new cultures, experience new cuisines, meet new people, and have a few laughs along the way!