Wave 1 City · Now Live

Chicago

A 19th-century tobacconist, a Gold Coast mansion, and Old Town smoke.

Chicago's cigar story is the country's oldest: Iwan Ries has been trading on Wabash since 1857, the Biggs Mansion pours in an 1874 Gold Coast landmark, and Up Down Cigar has anchored Old Town for generations. Jazz history, architecture, and a proper winter lounge season — the family will feel at home.

12Lounges

5Black-Owned

11Areas

2PIPS Events

Lounge Map

Tap a gold pin to see the lounge and jump to its card below.

Featured Lounge

This month's family spotlight

Biggs Mansion

An 1874 Gold Coast mansion turned cigar sanctuary — fireplaces, leather, and rooms that remember the Gilded Age. Day passes open the door; the experience keeps you coming back.

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Upcoming in Chicago

TBAOct

PIPS Chicago Meetup — Gold Coast

The family's first Chicago night, before the cold sets in.

Details

19Sep

Party in Palm Springs — Cigar Family Weekend

Destination weekend & Wave 1 celebration. Travel packages for members.

Details

Plan Your Visit

Where to Stay

The Loop — steps from Iwan Ries and the El.
Gold Coast / Old Town — one neighborhood, two lounges — walk between them.
River North — central to all three.
Hotel partner links go here — a natural sponsorship slot.

Getting Around

Flying in: O'Hare or Midway — the Blue and Orange Lines run downtown.
The El puts all three lounges within a short ride.
Walk it: Biggs and Up Down are 10 minutes apart on foot.
Winter tip: this is the best indoor-lounge town in America.

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Chicago is live.

Chicago is live — from an 1857 tobacconist to a Gilded Age mansion. The Midwest chapter starts here.