Created April 13, 2008

© The Chicago Bar Project
Written by Sean Parnell


Swingers Night Chicago
Last Updated: May 4, 2008

This may be your last night with the bachelor as a "free man." Strap on your finest cocktail attire, board your Chicago Trolley and let the Chicago Bar Project be your guide to the following swanky hotspots:

Lounge
Address
The Hook
Directions to the Next Place
Suggested Timing
Club Lucky 1824 W. Wabansia Any experienced lounge lizard knows that a proper meal is the only foundation upon which to build a night out, unless you want a quick one. Start out at this 1940s-era cocktail lounge and family-style Italian restaurant, where I have personally seen Vince Vaughan himself. After Club Lucky, meet and board your Chicago Trolley, and have the driver go north (right) on Damen, and then east (right) on Irving Park until Sheridan. 7:00-8:30

Holiday Club 4000 N. Sheridan

Not a club in the traditional "nightclub" sense but rather in a retro, Las Vegas kind of way. "Swinger's Mecca" is now in its second location and is a far cry from the soup kitchen that used to be located here, especially with tiki on Sunday nights.

 South on Sheridan, take a spin around Wrigley Field once your reach Addison, and then continue south until Belmont, then head west (right) just past the six-corner Belmont, Lincoln & Ashland intersection. 9:00-10:00
Bungalow 1622 W. Belmont

Frank Lloyd Wright would be proud with an interior inspired by his work. More works of art are produced by well-skilled bartenders with new cocktails created monthly by Bungalow's resident mixologist.

 South down Ashland, east (left) down Chicago, then north (left) on Kingsbury just off the corner. 10:15-11:15
Motel Bar 600 W. Chicago

Swanky lounge draws the occasional celebrity and athlete with Japonais also being located in the landmark Montgomery Ward building, just around the corner. The specialty here are classic cocktails brought back to life from recipes thought to be lost.

 Directions: East on Chicago until Lake Shore Drive with its superb views of Lake Michigan, then north (left) to Lawrence, and east (left) to Broadway, past the historic Aragon Ballroom. 11:30-12:30
Green Mill 4802 N. Broadway The best jazz club in the known universe is surprisingly accessible with a cover in the single digits and a vibe that dates back to when the joint was owned by "Machine Gun" Jack McGurn and frequented by his boss, Al Capone. 1:00-4:00 (5:00 Sat)

~ Got a better idea for a Swingers trolley tour? E-mail me. ~

~ Have a good story relating to a bachelor party? E-mail me. ~

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– written by Sean Parnell