What are the top 11 bars in downtown Chicago to spend a night out at?

A night out on the town is often the best way to enjoy the city you are in and to experience something new and exciting. The nightlife scene in Chicago is undoubtedly a lively one, especially in the downtown area. With that in mind, we’ve put together a list of some of the top 11 bars to try in downtown Chicago. Some of these bars are worthy of any Instagram feed with breathtaking views, bar concepts with delicious food and cocktails that look incredible.

Monks Pub

Monks Pub has been operating in downtown Chicago for more than 40 years. The exterior of the pub resembles that of a medieval tavern with the interior being decorated with German and old English antiques, that range from vintage books to wooden barrels. The food menu offers pub friendly foods, such as burgers and sandwiches that will satisfy any palate. But, what sets this bar apart from the rest is its extensive beer menu which comprises of nearly 200 different beers. This includes 16 of their own craft beer that changes on a daily basis. This makes it one of the most popular bars in town so it’s best to get there early and enjoy a couple of rounds before the 5pm crowd starts to roll in.

Cindy’s

If you are looking for breathtaking views of the Chicago city skyline, Millennium Park and Lake Michigan, then your best bet is to visit Cindy’s. This rooftop restaurant and bar serves some of the most well balanced and beautiful looking cocktails in the US. If you are on vacation, or even a local, grab your friends and take them to enjoy the well-prepared and generously portioned meals on their menu and enjoy a couple of cocktails or two while gazing out at the skyline and surrounding area.

Roof on theWit

Located on the 27th floor of theWit - a DoubleTree by Hilton hotel, this rooftop bar showcases one of the most breathtaking views of downtown Chicago’s skyline. Most people spend up to 3 hours here sipping on cocktails and enjoying the incredible sunsets from 27 stories up from large floor to ceiling windows. ROOF’s skilled mixologists will elevate your drinking with craft cocktails and fine and rare spirits to please any connoisseur while keeping the champagne flowing.

City Winery Chicago at the Riverwalk

City Winery Chicago at the Riverwalk has some of the most incredible city views when compared to the other bars and restaurants. With its full menu of delicious food partnered with wines, beers and cocktails, you will probably end up sending an entire night here. The combination of food, drinks, and the view is wonderfully suited for an al-fresco dining experience of note. During the colder months of the year, City Winery offers a unique dining experience in the form of large plastic dome tents providing you with a small area all to yourself while still enjoying the breathtaking views of the city and its lights at night.

The Rec Room

In the mood for some nostalgic memories? The Rec Room’s entire atmosphere of décor and music will have you transported back in time dancing under a disco ball. You’ll be at ease and reminiscing of the days partying in your friend’s basement as soon as you enter. Apart from the partying and nostalgic feeling you get at the Rec Room, you can also enjoy a unique and fun concept created by the bar where you get to “Raid the Fridge” and select the food of your choice from a revolving island. The Rec Room is famous for its laid back vibe and extensive beverage program in River North that is second to none.

Buddy Guy’s Legends

Live music can easily change the atmosphere of any restaurant and bar, for the best live music performances Buddy Guy’s Legends is the only place that will deliver. The premier blues club is the residency of Chicago’s blues legend Buddy Guy, every January. The club has hosted some of the biggest names in music such as David Bowie. Headliners include both local and international touring musicians every night of the week. So sit back, order a cocktail and enjoy the music.

Brando's Speakeasy

If you’re someone that loves to sing, especially after knocking back a couple of beers and a few cocktails, Brando's Speakeasy is where you’ll be more than welcome to do so. Sing your heart out karaoke-style at this bar and lounge that will cater to your on the spot karaoke needs. They also have an extensive cocktail and beer menu that list the bars specialty drinks, and bites so that you can bleach out those melodies all night long.

The Game Room

Looking to do more than just hang back with a couple of drinks with friends? The Game Room, located on the second floor of the Chicago Athletic Association will surely give you that. The old Chicago-styled design with a billiard room vibe in mind. It will provide you with a new understanding of the different potential nightlife experience you can have. The atmosphere pairs cocktail culture, and classic bar food with that of billiards, shuffleboard, chess, checkers and a built-in bocce bay.

Milk Room

For a more intimate and cozy bar experience, the Milk Room that is located on the second floor of the Chicago Athletic Association will not disappoint. This exclusive bar only seats eight people at a time, and primarily focuses on classic, and spirit-forward cocktails with a twist of very rare, vintage spirits and hard to come by ingredients.

Three Dots and a Dash

Long overdue for a beach getaway where you’re sipping away on tiki cocktails? For a close second option, head on down to Three Dots and Dash in downtown Chicago after work. The cocktail focused tiki lounge is decked out in tropic inspired decor. The menu is primarily Asian fusion in regards to the food section, while drinks half of the menu features both classic and modern tiki cocktails with a selection of over 200 distinctive rums that are accompanied by fresh juices and syrups that are made daily in house.

SafeHouse Chicago

This bar is surely among one of the most unique and fun places in the Loop to grab a burger and some drinks at any time of the day. The spy-themed restaurant and bar is an experience in on itself into the world of espionage. To get into SafeHouse Chicago, you first need to find the hidden entrance, and in order to enter the establishment you’ll need to provide a password, but what happens if you don’t know it? Then prepare yourself to complete a fun clearance test. Once inside the fun doesn’t stop, the interior design is tailored and detailed to provide customers with the best experience possible. The menu is an extension of the ongoing espionage world the bar creates, through their food and signature drinks fit for any spy.

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