Who doesn't love enjoying drinks and their friends’ company on a night out in the city? Take a look at some of Chicago’s bars and restaurants to see where your next gathering will be!

  • Drumbar
  • Green Mill Cocktail Lounge
  • Tapster
  • EZ Inn
  • Vol. 39
  • Gilt Bar
  • Bordel
  • Signature Lounge
  • Flamingo Rum Club


Within walking distance of the Magnificent Mile, Drumbar is in Gold Coast. Drumbar is located on the 18th floor of the Raffaello Hotel, and even has a seasonal outdoor patio for those beautiful Chicago nights! Not to mention, Drumbar offers a wide selection of bourbon, cognac, scotch, and whisky. Many of the liquors are one-of-a-kind, and are only available for a limited time.

Drumbar focuses on their cocktail selection. One category is their cocktails from around the world. The Caribbean cocktail has a dark Pineapple Rum, making it taste like a beachy drink. If that is too sweet, try the cocktail based from Mexico. It will have a bit of a kick, since it contains a jalapeno based alcohol. Classic cocktails are made to perfection as well. Those include Daiquiri’s, Mint Juleps, and Side Cars. If cocktails are not your thing, be sure to check out their beer menu. They offer beers made in Illinois (12 of Never and Northwind and more) and Colorado (G-Knight and Modus Hoperandi to name a few). There is a great variety of alcoholic beverages at Drumbar.

Green Mill Cocktail Lounge:

Green Mill Cocktail Lounge is a Jazz bar that has live entertainment every night. Located in Uptown, the bar aims to maintain a 1940’s atmosphere by having a variety of nightly music and performances.

Every night a different band performs. Depending on the band playing, the cover charge to get in will differ. A popular performance is the Poetry Slam. You can watch these shows every Sunday. If you do not like poetry, be sure to stop in any other night to watch live jazz performances.


Tapster is the first self-serving bar in Chicago. Bartenders are available near the taps to give guidance on those who need it. There are 32 beers on tap and 8 wine taps. They even have 12 specialty craft cocktails on the menu. Do not feel left out if you do not drink alcohol. Tapster wanted non-alcoholic drinkers to feel just as welcomed, so they have 4 craft sodas and 2 cold-brew coffee drinks. There are many drink choices at Tapster!

For a main dish, Tapster’s grilled cheese comes with a variety of cheeses. Swiss, provolone, and chipotle cheddar cheese are grilled together on sourdough bread. Another sandwich that sounds packed with flavor is the Corned Beef Sliders. Corned beef is topped with Swiss cheese and creole mustard on a toasted pretzel buns. Now comes the fun part, getting your own drinks! Being able to get your own alcohol means you can try as many flavors as you want, with the amount you want to drink. There are countless taps you can try, so go ahead and visit this unique bar in Wicker Park.

EZ Inn:

This bar is very cozy, only seating about 70 people. It is located in the Ukrainian Village, and has been a popular hangout spot for many years. 14 tap beers from Chicago breweries, boozy sodas, and cocktails are served at this neighborhood tavern.

EZ Inn serves an assortment of drinks. Try one of their staple cocktails like #ClassyAF. Choose either Gin or Vodka, citrus, bitters, cava, and sidecar. Even their boozy sodas have fun names! The four you can pick from are Pisco Ginger Cream, Fernetaboutit, Mezcal Peach Cobbler, and Grapefruit Gin and Tonic. EZ Inn sells $3 bottles and cans of Miller High Life, Bud, and Coor’s Banquet or Old Style. Not a bad deal!

Vol. 39:

Located on the second floor of the Kimpton Gray Hotel, this bar redefines maturity. With shelves of books about law and silver carts to serve food, Vol. 39 looks like you are stepping into an episode of Mad Men. The main alcohol and food that is served fits the mood of this bar: very sophisticated. There is a wide range of wines and spirits to pick from, as well as fine food items.

The Vol. 39 Vintage Old Fashioned is a must try. It is comprised of a 30-year vintage Armagnac, barrel aged demerara sugar, and Angostura. This sophisticated drink is poured over hand carved ice. The food items are on the same level as their fine drinks, such as caviar and artisanal cheeses.

Gilt Bar:

This River North bar and restaurant serves a variety of contemporary American dishes and classic cocktails. The food is meant to be shared with the table, while the cocktail menu offers the classics, such as Mules and Old Fashions.

One of Gilt Bar’s popular dishes is the Tenderloin Steak Tartare. The steak is mixed with a combination of flavors, such as chile puree, parsley, and shallots. The dish is served with a side of dijonnaise and topped with egg yolk. Their house made bread is served on the side. This dish is served with an abundance of flavors. Another signature dish is the Truffle Pasta. It is a noodle pasta mixed with pecorino and truffled mushrooms.


Bordel is a hidden gem located in the Ukrainian Village. The theme of the bar comes from Chicago’s Prohibition Era and Paris’ Belle Époque. They offer nightly entertainment, including burlesque performances, magicians, and jazz musicians. Don’t forget to check out their craft cocktails when visiting.

An interesting cocktail to order is a Root Beer Manhattan. It contains Bourbon, Amaro, Vanilla Root Beer Cordial, and Cola Bitters. If you are going with a group of people, try a large cocktail. It serves 5-6 people. There are five cocktails you can pick from. One cocktail to try is the Brunch Crowd. It has Vodka, Peach Cordial, Sparkling Wine, Lychee, and Lemon. The sparkling wine will give this drink an extra fizz, making it a must try.

Signature Lounge:

Just imagine enjoying a drink overlooking Chicago. With the Signature Lounge located on the 96th floor of the Hancock Building, that can become a reality. The menu lists a variety of specialty cocktails, including rum, vodka, tequila, and many more. Look no further to see one of Chicago’s best views while drinking cocktails with friends and family.

The signature food item to order is the Raw Bar for two. Included is Maine lobster, oysters, shrimp, crab legs, and a seaweed salad. It is the perfect dish to share if you are a seafood lover. If not, try the Grilled Chicken Wrap. It has guacamole, bacon, tomatoes, lettuce, and cheese. Not to mention it comes with a side of kettle chips.

For drinks try the Skyscraper cocktail. It is a rum based cocktail with pineapple and cranberry juice. It has the perfect name for a drink overlooking the city from the 96th floor. They even have a drink called The Gold Coast. This drink has Gin, Aperol, Ginger Ale, fresh lemon sour, and lemon wheel. Why not sip a drink called the Gold Coast while in that part of Chicago.

Flamingo Rum Club:

The Flamingo Rum Club is a fun and lively place to enjoy a night out with friends as well as enjoy great food! The restaurant made itself known in the busy River North neighborhood in the fall of 2016, and with some help from its flamboyant flamingo decorated exterior it became a heavily visited spot.

Flamingo Rum Club is a bar, a restaurant, and a club all in one place and offers a truly unique and exciting experience with every visit. Its Cuban-inspired menu is filled with authentic, mouthwatering delectables that one can enjoy while tapping their feet to the riveting music that plays throughout the night.

A classic dish to order off the menu is The Tropicana Royale which features an abundance of delightful flavors and textures from the plantain and malanga chips, the shrimp ceviche, the pineapple relish, and the many other fresh ingredients that are guaranteed to keep your mouth as entertained as you are by the music.

Another amazing item to try on the Flamingo Rum Club menu is El Gran Havana, a hearty dish of saffron rice croquettes, pinche de pollo, and a ceviche of your choice. Good energy along with delicious authentic Latin food, drinks, and entertainment await guests at this venue. Be sure to put on your dancing shoes and head over to Flamingo Rum Club for a time to remember.

All of these Chicago bars and restaurants have different vibes, so check out the ones that appeal to your lifestyle! Let us know which bars you are most excited to try!