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:
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If you buy a copy of our book Historic Bars of Chicago ($12), you can get a Chicago Trolley $45 coupon that is more than 10% off for most rentals.
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Lounge |
The Hook |
Directions to the Next Place |
Chicago Trolley |
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Starting Point: 1824 W. Wabansia 7:00-8:30 |
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. 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: 4000 N. Sheridan 9:00-10:00 |
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. |
West on Irving Park until just after Ashland on the north (right) side of the street. |
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2nd Stop: 1612 W. Irving Park 10:15-11:15 |
In our less-than-humble opinion, Long Room is the best cocktail lounge in Lakeview and a good place to try out your moves. However, it won’t be easy: the ladies here are savvy and have acute b.s. radar, so bring your A-game. |
East on Irving park, south (left) on Ashland, east (left) on Chicago, then north (left) on Kingsbury just off the corner. |
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3rd Stop: 600 W. Chicago 11:30-12:30 |
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. |
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. |
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Final Stop: 4802 N. Broadway 1:00-4:00 (5:00 Sat) |
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. |
If you buy a copy of our book Historic Bars of Chicago ($12), you can get a Chicago Trolley $45 coupon that is more than 10% off for most rentals.