[2][3] As a teenager, he published a blog entitled "Verbal Diarrhea" and played the role-playing game Ragnarok Online.

[6][7] Chayka was the first staff writer of the arts magazine Hyperallergic, becoming a senior editor for the publication in 2012.

In a 2016 essay for The Verge, he coined the term "AirSpace" to describe the prevalence of "sameness" across cafes and offices around the world.

[11] In 2021, he became a staff writer for The New Yorker, where he writes the "Infinite Scroll" column on digital culture.

[1] Chayka is married to The New York Times politics reporter Jess Bidgood, whom he met at Tufts.