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The Phenomenal Bars in Downtown Chicago

From Gold Coast to Wicker Park to Logan Square, the Windy City is brimming with fine drinking establishments, so it’s not surprising that you’ll find some of the city’s best bars in downtown Chicago.

Some of Our Favorite Downtown Chicago Bars

  • ROOF on theWit: One of the best rooftop bars downtown Chicago has to offer, this establishment offers stunning skyline views of the city, craft cocktails from brilliant mixologists, and rare spirits to satisfy the most sophisticated palette. This summer hotspot also offers refined fare from award-winning Executive Chef Nathan Sears.
  • Three Dots and a Dash: Luau bites and over 200 rums are highlights of this tiki speakeasy in River North. Their cocktails are served in tiki mugs of varying designs, allowing you to fully embrace the bar’s theme. Reservations are accepted, though walk-ins are always welcome.
  • The Gage: This gastropub combines rustic American fare created by Executive Chef Christopher Gawronski with stunning views of Millennium Park. With a combination of craft beers and innovative cocktails, there are also plenty of interesting libations to enjoy.
  • Brando’s Speakeasy: Billing itself as “Chicago’s Best Karaoke Lounge,” this vintage Chicago tavern is great for parties and other events as well as for spontaneous nights out with friends. Cocktails, beer, champagne, and snacks are all on the menu.

Enjoy Downtown’s Bars Even More with a Chauffeured Service

It’s important to drink responsibly — and is much easier to do if you don’t have to worry about driving. Signature Transportation Group offers chauffeured services throughout the city, and our fleet is replete with vehicles for parties large and small.

Sedans and SUVs

  • Lincoln Continental
  • Mercedes-Benz S-Class
  • Cadillac Escalade
  • Chevy Suburban
  • Cadillac XTS


  • Limousine-Style Mercedes-Benz Sprinter
  • Turtle Top
  • Executive-Style Mercedes-Benz Sprinter

Executive Buses

  • 24-Passenger Executive Bus
  • 39- to 43-Passenger Executive Bus
  • 55-Passenger Motor Coach

Special Occasion Vehicles

  • 30-Passenger Trolley
  • 36-Passenger Limousine Style Party Bus

Get a Ride With Signature Transportation Group

Enjoy a worry-free night bar-hopping in downtown Chicago when you ride with Signature Transportation Group. Contact us to learn more about Chicago, such as upcoming summer concerts, best restaurants in Hyde Park, our guide on O’Hare transportation options, or to discuss our rates!