[2] American Songwriter's Lee Zimmerman wrote that Crowell's "skills are, naturally, apparent as always, and given his decision to put Jeff Tweedy in the producer's chair, another exceptional album is all but assured", elaborating that he is "in prime form, and the ten songs that make up the set list hold to the high standard he's known for".

[1] Paste's Eric R. Danton described it as "the work of a singer and songwriter with nothing left to prove, which means that Crowell can simply enjoy himself" as he "has no thematic agenda with these songs".

[5] Reviewing the album for PopMatters, Michael Elliott also acclaimed Tweedy's approach to production, saying that Crowell sounds "comfortable, confident, and at ease throughout The Chicago Sessions while gifting us some of his best material in years" and concluded "that both his pen and voice are still as vital as ever".

[6] Jeremy Winograd of Slant Magazine opined that Tweedy "wields a light touch as producer and accompanist, mostly keeping Crowell within his acoustic country-folk and boogie-based wheelhouse, abetted by simple, crisply recorded arrangements".

[8] Mojo stated that "beneath Tweedy's twinkling lights, Crowell wears each look like a favourite old coat – familiar, easy, and pocked by stains and rips that remind him of all he's seen".