Swingers Night Chicago

Swingers Bachelor Party Pub Crawl Chicago

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.


The Hook

Directions to the Next Place

Chicago Trolley

Starting Point:

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.

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.

Book Chicago Trolley for Your Swingers Bachelor Party

To book a trolley, contact Chicago Trolley for pricing & availability:

Chicago Trolley & Double Decker Co.
(773) 648-5000

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.

Book Chicago Trolley for Your Swingers Bachelor Party

1st Stop:

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.

West on Irving Park until just after Ashland on the north (right) side of the street.

2nd Stop:

Long Room

1612 W. Irving Park


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.

3rd Stop:

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.

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)

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.