Over the years, Sidetrack has grown from one room with less than 1000 square feet to a collection of spaces spanning more than 8 storefronts and multiple levels that can host more than 1000 people at a time.
- 1982 Open for business with beer cases as seating. Signless.
- 1984 First expansion doubles the size. New, signless white tile facade.
- 1988 Open first version of BackBar.
- 1994 Open CherryBar overlooking MainBar. Small sign on Halsted Street. Facade includes a window for the first time.
- 1998 Remodel and expand BackBar.
- 1999 Open GlassBar and Courtyard…now everyone can see inside. A kiosk with the Sidetrack Logo is featured.
- 2001 Expand CherryBar with CherryLounge.
- 2004 Open Rooftop and DeckBar.
- 2007 Expand CherryLounge.
- 2009 Open SideBar with access to Courtyard.
- 2013 Remodel Entryway and MainBar.
- 2017 Install state-of-the-art HD Video System bar-wide.
- 2020 Remodel CherryLounge to become NorthBar.
Named the Most Popular Bar in Illinois by Buzzfeed.com, the Most Visited Bar in Chicago by LYFT, the Best Gay Bar in Chicago by TimeOut and one of the 50 Top Gay Bars in the US. Yelp, 2017.