For an authentic Chicago neighborhood experience, there's no better place than Sheffield's in Lakeview. The large, outdoor patio complete with picnic tables is the perfect place for casual conversation or an impromptu bar game. Whether it's for an after work happy hour amongst locals or getting the weekend party started, the best people watching in Chicago is at the Cedar Hotel. The trendy, Near North Side establishment has a large outdoor courtyard overlooking the festivities on Rush Street.

For those who prefer to sip their drinks with a view, there's LandShark Beer Garden. Located on the east end of Navy Pier, the garden overlooks the Chicago skyline and is perfect for groups of any size. Going to a Cubs game? Stop by Vines on Clark which is located a few steps from the front gate of Wrigley Field. Vines enormous dining space is perfect for a pregame meal or celebratory cocktails after a Cubs victory.


Fresh food is made all that much better when combined with fresh air, which is we love our al fresco eateries. For a lively meal atop a stylish rooftop, visit ZED451. Chefs serve specially prepared dishes tableside and the bar features seasonally inspired, house infused cocktails. Sit along Kinzie Street, just blocks away from Chicago's famed The Magnificent Mile at Harry Caray's Italian Steakhouse. Dine on one of two outdoor patios at this Chicago staple, which serves some of the finest prime, aged steaks around. Grab a seat at the cool kids table with a trip to the trendy rooftop restaurant at ROOF On The Wit. The outdoor dining area features 7,000 square feet of fire pits and unparalleled views. Bring a big group. The space can accommodate up to 150 guests.


Deee-Lite once sang that the "groove is in the heart" but, as any cardiologist can tell you, you're much more likely to find "groove" in a dance club. Thankfully, Chicago has an unparalleled nightlife with no shortage of places for girls (or guys) who just want to have fun. For a taste of French culture in River North, visit Paris Club. The high energy lounge boasts great music, sophisticated décor and some of Chicago's most beautiful people. For a truly subversive experience stop by The Underground, this downtown hangout is decorated like a top-secret, military hideaway complete with artillery cases as cocktail tables. Get lost at the Hangge Uppe which holds five bars and three dance floors with a song mix as diverse as your group. Jam to classic rock favorites and guilty pleasures from the 80's on the lower floor. Then, make your way upstairs for a more modern playlist.


From Nat King Cole to Buddy Guy, the band Chicago and Kanye West, no trip to Chicago is complete without a little live music. For over 30 years Metro has provided a stage for nationally emerging artists and celebrated local acts. Legendary musicians like James Brown, Bob Dylan, and Prince have all performed for the lively Metro crowd. For a more intimate venue, try The Double Door which holds fewer than 500 people. Small in size but big in performers, the Wicker Park concert hall has hosted The Smashing Pumpkins, Cheap Trick, and even the Rolling Stones.

Blues Brothers would have been gift enough, but Dan Aykroyd really spoiled our city by opening up the House of Blues Chicago. Since 1996, the venue has hosted some of the music world's biggest acts. The Park West is perhaps Chicago's most seasoned venue, but your group will need advanced tickets to enter. Having been around for nearly a century, the Lincoln Park music hall hosts rock bands and special events, but was once a movie theater and, briefly, hosted live burlesque shows in the 1960's. Chicago and the blues go together like BB King and Lucille, so you'll have to take your group to national names and locat acts at Buddy Guy's Legends, which hosts nightly live music events.


One of Frank Sinatra's most celebrated singles is "My Kind of Town (Chicago Is)." If a member of the Rat Pack's crooning about a city, best believe that city knows a thing or two about mixing a drink. Chicago has a deeply-rooted, distinguished place in the cocktail culture with some prized establishments to prove our worth. For a fresh take on classic drinks, stop by The Bedford where spirits are flawlessly complimented with homemade bitters and fresh juices in this 1920s bank turned bar. If you're looking for a first-class drink free of pretentions, visit The Whistler and their ever changing menu of award-winning cocktails. For an experience as visually stunning as it is tasty, grab a seat at The Violet Hour. The French salon-inspired, modern lounge is as elegant as it is comfortable with high wing back furniture and small rooms to encourage conversation.

Related Listings

The Underground
56 W. Illinois St.
Chicago, IL 60654
(312) 943-7600

ROOF on theWit
201 N. State St.
Chicago, IL 60601
(312) 239-9502

Park West
322 W. Armitage
Chicago, IL 60614
(312) 440-9191