Here is an updated list of places to play chess in Montreal (there may be others).
Note that Cafe Pi is no longer in business after almost 20 years.

1) Outdoor chess (under shelter) from May 21 to September 25.
Tuesdays from 4-8; weekends from 11-4
Daisy Peterson-Sweeney Park - Charlevoix at the canal.
Metro: Charlevoix or Lionel Groulx.

2) GIANT CHESSBOARDS
Giant Chessboards

MAY 4, 2021 TO MAY 29, 2022 (and probably other time periods throughout the summer).

Sainte-Catherine street, between de Bleury and Saint-Urbain street
Esplanade Tranquille. Metro Place des Arts.
FREE !

PRACTICAL INFORMATIONS
From Wednesday to Sunday
From Noon to 7 p.m.
Note that on May 19, 20 and 21, the Giant Chess Games will be temporarily closed

3) "La Bolduc" park (Berri & Rachel) - Nightly when weather permits (no shelter). Bring your equipment (and your beer). Metro: Mont-Royal or Sherbrooke.

4) Café "Kofi Crepe" (4483 St-Denis - corner of Mont-Royal). Nightly until 10 pm. Bring your equipment. Metro: Mont-Royal

5) After 10 pm: "Pastel" bar, 426 Rachel E. Next to the park.

If you can't find players in the park or at the cafe, they are probably at the bar.