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Best Bars in Chicago to Check Out On Your Next Visit

by Jacqueline Hanikeh 5 years ago in bars
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Living in Chicago or taking a trip to the Second City, but don't know which bars are the best? See our list of the best bars in Chicago and consider any of these places for your next hang out.

Chicago is a fantastic city to live or even to tour in. There's so much opportunities to partake in and a lot of history in the city. Not to mention Chicago is known for their mouthwatering deep dish pizzas. There are tons of restaurants that serve deep dish pizza in Chicago — almost on every corner. But know what else Chicago is special for? Their bars!

Yes, if you love bars in New York City, you'll love bars in Chicago just as much. Chicago is home to some of the most creative and eye-catching bars across the country. Not only are their drinks and cocktails remarkable, but just the atmosphere says a lot. So, if you're in Chicago or visiting the place sometime soon and want to check out a few bars down there, see which bars are the best bars in Chicago. Trust me, you won't be disappointed.

The Rabbit Hole

Starting off the list of the best bars in Chicago, this one is unforgettable.

Step inside this magical bar called The Rabbit Hole and you’ll be falling straight through the hole and into Alice in Wonderland. This Wonderland-themed bar does not only have a portrait of the White Rabbit propped up on one of the bar’s walls, but there are board games scattered around the room like Pictionary and Jenga. So, you and your friends can engage in games while indulging in great drinks. Also, the more you drink, the more fun these boardgames will be — of course.

Aside from the drinks, they have a small variety of delicious foods such as wings, a “1951” burger, a “Queen of Hearts” salad, and “Jabberwock” Angus sliders.

If you want somewhere to watch the big game with your friends, this place has ten flatscreen TVs. Yes, ten! So, it’ll be nearly impossible to miss a play.


Estereo is a cool-vibe bar and the type to allow in a lot of fresh air… a lot. Don’t know what I mean? This bar is very open and spacious — one section of the place is made up of garage doors. When those garage doors open up, half of the bar is exposed to fresh air and a nice breeze — ideal during warmer weather seasons, and making this place one of the best bars in Chicago.

This triangle-shaped chill bar includes DJs messing with vinyls and even Latin-inspired unique cocktails. Not to mention that there’s a cocktail named “Breezy” to really let the breeze get you.

The Sixth

The Sixth is easily one of the coolest best bars in Chicago.

This fancy modern-styled bar has some of the coolest features like yellow cushioned chairs, funky mirrors on the walls, and it’s a comfortable atmosphere.

Your drinks can be served in unique mini-fishtanks (not used fishtanks) and gold metal pineapples. And if you order the Silly Rabbit cocktail, it’s a gin mixed drink poured over flavored ice cubes with the Weston combines bourbon with Dark Matter’s famous Unicorn Blood coffee and pipe tobacco — bizarre but exotic.

You can also ask for the “Dealer’s Choice” cocktail and the bartender will surprise you with his/her choice of drink.


Tapster is literally Froyo, but with alcohol. Just like how you have about 12 options of frozen yogurt to choose from, you have 62 wall taps dispensing beer, craft cocktails, wine, craft sodas, and even coffee and kombucha all around you! It’s actually heaven on earth.

All you have to do is buy a tap card from the hostess stand and then let loose pouring yourself anything your heart desires.

The setting at this exposed-brick bar is really cool, too. There’s even an upstairs lounge with leather sofas and live music playing.

If you’re hungry, there’s a deli counter in the back where they serve everything from popcorn to sandwiches and even waffles and fondue — a great variety.

But wait, there’s a swing set — bringing back childhood memories, but with alcohol in your hand.


Nature isn’t only outside when it comes to Quiote. This bar has exotic and vibrant plants all around you. So if you don’t like nature, this bar can help ease down your hate — because you’ll be drinking around them. There’s also lightbulbs scattered across the ceiling — coming off as the night sky, so it really feels like you’re outdoors.

Also, the drinks and food here are pretty cheap. Bars with affordable drinks make the list of best bars in Chicago, right?

Vol. 39

This is easily my favorite type of bar out of this list of best bars in Chicago — easily!

Vol. 39 is a really classy bar, ideal to lounge in with a date. It’s right off the lobby of the Kimpton Gray Hotel.

The romantic scene sets perfectly in this place with dimmed lights, and mahogany shelves casing rows and rows of books!

The servers here are dressed in white coats and even stroll silver carts back and forth, offering you finger foods like oysters and caviar — talk about living the high-class life.

Money Gun

This is certainly a retro, speakeasy-vibe bar to enjoy drinks and cocktails at. The Money Gun bar is considered one of the best bars in Chicago.

A uniquely designed bar, you can binge on drinks while settling into a booth beneath the mirror-paneled cocktails and eat a few of the place’s specialties, like their salt cod fritters or their soy pickled eggs — it’s better than it sounds.

Not to mention this bar plays the best throwback songs out there and you’ll find yourself jamming hard with your buddies.

The Flamingo Rum Club

If you’re looking for a more tropical-themed bar to take your friends or your date to, consider The Flamingo Rum Club. This place just oozes tropical, from the palm trees on the walls to the staff wearing island-chic outfits — also, a lot of bright pink flamingos.

The Cuban-inspired bar and lounge provides one of the best rum selections out there. But wait, they host live burlesque and cabaret shows! So, you’ll be enjoying a drink and a bite while watching these fantastic shows with your date or a friend.

Come here even during the winter and make the night a summery one.

Lost Lake

Just like the previous bar, this one also gives off that summery feel. The Lost Lake in one of the coolest best bars in Chicago.

This tiki bar serves up the greatest cocktail drinks under wooden basket-like ceiling lights and mellow-vibe tunes playing around you.

And if you’re a sucker for fruity cocktails, the Lost Lake is the right place for you

The Whistler

The Whistler is seen to be one of the best bars in Chicago to this day. Why? Because of the amazing live music that occurs all seven nights of the week. The bar doesn’t only host live music, but it also showcases art in their gallery.

Their always-changing menu features award-winning cocktails and great, cheap beer.

Their live music ranges from a mix of jazz, rock, electric, country, and even soul. In addition, they host film screenings, readings, and other artistic endeavors.


About the author

Jacqueline Hanikeh

Reading good literature plays a huge role in my life — and so does online shopping and wine.

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