Stop comparing options and building your own itinerary. We have already done it, every pick includes the full plan, insider tips, reservation advice, maps, backups, and the exact order to do it in.
Every one runs start to finish, the spots, the timing, the order to do them in, plus reservations, maps, budgets, and a backup for each.
Beneath the Green Door Tavern, one of the only wooden buildings to survive the Great Chicago Fire, and a real Prohibition-era speakeasy in its day, a staircase leads down to The Drifter, a low, atmospheric basement…
There's no menu, cocktails come from a rotating deck of custom tarot cards, each card a different drink. You draw, or describe what you like and let the bartender deal you something.
Generally walk-in, which makes it the flexible one on this list, but weekend nights and show nights get busy, check their calendar and go earlier for a seat.
Step in for a set and you're standing in the city's speakeasy history, unchanged.
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We've done every one of these guides ourselves.
Some are where we celebrate birthdays. Some are where we take friends visiting Chicago. Some have just become our favorite “we don't even need to think about it” go-tos.
These are the guides we recommend to the people we care about most.
Now go enjoy it,
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