Chicago, Illinois

Le Colonial isn't only a refined dining establishment, but also a lounge featuring a chic bar popular with the young, clubby set. It is located upstairs from the restaurant of the same name. The staff serve tasty cocktails in a comfortable and romantic setting.

Jazz Showcase is a famous venue for live Chicago jazz since 1947, showcasing local and international talent. Matinees with special discounts for students, seniors, and musicians on Sundays.

The Green Mill Cocktail Lounge is a legendary live music venue with different varieties of jazz in a 1940s-style lounge. They capture jazz from New York to New Orleans.

The Cubby Bear is located right across the street from Wrigley Field, and anyone hanging out in one of the club's private rooms has a view of the field. This is the place to be to catch all of the action after a Cubs game. Live bands perform regularly. Check the club's website for a list of performances. This late-night venue also serves lunch.

Gather around the piano and sing along to live music. The Redhead Piano Bar's intimate atmosphere is conducive to connecting with old and new friends over a drink and a song. Business casual attire is required.

Owner of Three Dots and a Dash Paul McGee is one of Chicago's favorite mixologist. His newest Polynesian-island themed bar centers around a 16 drink menu, focusing on eight classics and eight new creations, and has a Hawaiian tiki bar feel. Make sure to try the famous Painkiller No. 3 and enjoy some snacks. It's a great place to mingle with Chicagoans.

When mixologist Alex Bachman and Yusho eatery chef Matthias Merges joined forces, they created Billy Sunday, a cozy, high concept antique-accented cocktail bar. Their drink menu features unique ingredients such as quince, grenadine, and ambergris-laced palm sugar; their food menu has items like pig ears and a chicken liver spread. Each of their 10 signature drinks feature different spirits. If you prefer more straight up beverages, they are able to accommodate all tastes.

Located in the Acme Hotel, the Berkshire Room is a popular night spot for Chicagoans. Benjamin Schiller’s Blue Collar Lagers menu has become famous for its variety and delicious offers. Executive Chef Chris Curren offers delicious food to complement the fantastic drink menu. Try the Dealer’s Choice: you choose the liquor, flavor, and glassware, and the bartender crafts your drink from there.