Recorded in Maryland, Chesapeake is Yamagata's first studio album since 2008’s Elephants...Teeth Sinking into Heart. She utilized the fan-funded music platform PledgeMusic to fund the album. She parted ways from her record label, and released it through her own label called Frankenfish Records. She told Steve Baltin of Rolling Stone, "It was really gratifying in that sense because I don’t have the pressures of a major label anymore. In a funny way, I think this might be a more commercial record for me in terms of reaching a broader audience because there was no attempt or requirement to be anything but what we felt like doing in the room."  She reunited with John Alagia, the producer of her debut album, Happenstance, to help produce the album.
James Christopher Monger of AllMusic said, "by far Yamagata's most laid-back release to date, offering up ten tracks that run the gamut from lush and languid (“Saturday Morning,” “Even If I Don’t”) to sultry and spooky (“Starlight”) and back again with the easy confidence of an artist on her home turf."