The Caleb & Jenna Travel Chronicles: Chicago Edition

by and

In the first of this three-part traveling playlist series, Caleb and Jenna explore the Windy City and all its glory

Featuring artists like: • Frank Sinatra • The Doobie Brothers • Chicago • James Brown • Sufjan Stevens • Johnny Rivers • ZZ Top • Wilco

Latest Collaborative Playlists from Musicto

AndrewJenna B

Songs That Would Be In A Villain’s Playlist
a playlist by Andrew and Jenna B

3 November 2026

Andie De GuzmanJenna B

Songs That Belong In A Horror Movie
a playlist by Andie De Guzman and Jenna B

19 October 2026

Ariana PizzutoAndrew

Artists That Feel Like Fall
a playlist by Ariana Pizzuto and Andrew

10 October 2026

Jenna BAndie De Guzman

Songs That Sound Better At Night
a playlist by Jenna B and Andie De Guzman

25 September 2026