The Gallery Cabaret, 2020 North Oakley (near Western and Armitage), is a little Bucktown bar with an eclectic schedule of entertainment, but the 74-yr-old owner LOVES Big Bands and has a dynamite pair of Big Bands playing on the first Monday of every month. For FREE!
At 6:30 - The Heisenberg Uncertainty Players, led by John Dorhauer, is a new Chicago-area big band, playing only original compositions and arrangements from the members of the group. They feature some of the finest writing and performing talent Chicago has to offer.
At 10:00 - Big Band Boom ("Serious Fun, Big Band Style") salutes The Great American Songbook and plays original arrangements by band members. In November, they will be joined by vocalist Kimberly Gordon.
Stop in early or late - both bands are outstanding!
Listed on several Meetups.
For a schedule of Big Band Jazz in the Chicago area provided by the Chicagoland Big Band Jazz Society (Join CBBJS for $10/yr.):