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

Click here if you need to book a private party room
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Lounge
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The Hook
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Directions to the Next Place
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Chicago Trolley |
| Starting Point:
Club Lucky
1824 W. Wabansia
7:00-8:30
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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.
Alternate: book Bluelight if you're hosting "entertainment" before you head out for the night. |
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. |
To book a trolley, contact Chicago Trolley for pricing & availability:
Chicago Trolley & Double Decker Co.
(773) 648-5000
chicagotrolley-charter@coachusa.com
Your pub crawl agenda is completely up to you. If you'd like to hire a guide, please be sure to mention that when you contact Chicago Trolley.

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| 1st Stop:
Holiday Club
4000 N. Sheridan
9:00-10:00
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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.
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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. |
| 2nd Stop:
Bungalow
1622 W. Belmont
10:15-11:15
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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.
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South down Ashland, east (left) down Chicago, then north (left) on Kingsbury just off the corner. |
| 3rd Stop:
Motel Bar
600 W. Chicago
11:30-12:30
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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.
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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. |
| Final Stop:
Green Mill
4802 N. Broadway
1:00-4:00 (5:00 Sat)
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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. |
Time for a taxi, which you'll find out front. |
Click here if you need to book a private party room
~ Got a better idea for a Swingers pub crawl? Email us. ~
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