Ranar 2 ga watan Maris, 2015, Sabres sun yi musayar Flynn zuwa Montreal Canadiens a shekara ta 2016
zagaye na biyar. A ranar 15 ga Afrilu, 2015, ya buga wasansa na farko a wasan karshe kuma ya zira kwallaye a wasan da Ottawa Senators suka yi a wasan farko na wasan kusa da na karshe na Gabas. Bayan kammalawa na kakar 2014-15, Flynn ya sake sanya hannu kan yarjejeniyar tsawaita shekaru biyu tare da Canadiens a ranar 1 ga Yuli, 2015.