When Stan accidently orders too many tickets when trying to get himself one, Jessie's old babysitter Ellen Jennings invites her, the Rosses, Bertram, and even Mrs. Kipling to go to Shake It Up! Chicago with them.
The Ross children and Mrs. Kipling are in the screening room watching Shake It Up! Chicago. After they talk about how cool the dancers are, Jessie walks in and tells them that her old babysitter Ellen invited them all to come watch Shake It Up! Chicago live. Once getting permission from Morgan and Christina, Jessie gets their flights scheduled. They decide to meet up with the James-Jennings family in Denver, but Jessie scheduled the wrong flight, and they end up in Miami. Fortunately, Austin is performing on Shake It Up!, so he gets them a flight to Denver, where they meet up with the James-Jennings and even run into the Duncans, who are also performing. They fly to Chicago together, but with plenty of time before the performance, decide to go to the mall. However, while Avery and Ravi are trying to help tie Charlie's shoe, they get left behind and are lost in a crowd of ANTs.
- Debby Ryan as Jessie Prescott (JESSIE)
- Peyton List as Emma Ross (JESSIE)
- Cameron Boyce as Luke Ross (JESSIE)
- Karan Brar as Ravi Ross (JESSIE)
- Skai Jackson as Zuri Ross (JESSIE)
- Kevin Chamberlin as Bertram Winkle (JESSIE)
- Frank the Lizard as Mrs. Kipling (JESSIE)
- G. Hannelius as Avery Jennings (Dog with a Blog)
- Blake Micheal as Tyler James (Dog with a Blog)
- Francesca Capaldi as Chloe James (Dog with a Blog)
- Stephen Full as Stan (voice) (Dog with a Blog)
- Regan Burns as Bennett James (Dog with a Blog)
- Beth Littleford as Ellen Jennings (Dog with a Blog)
- Zendaya as Rocky Blue (Shake It Up)
- Bella Thorne as Cece Jones (Shake It Up)
- Caroline Sunshine as Tinka Hessenheffer (Shake It Up)
- China Anne McClain as Chyna Parks (ANT Farm)
- Sierra McCormick as Olive Doyle (ANT Farm)
- Jake Short as Fletcher Quimby (ANT Farm)
- Stefanie Scott as Lexi Reed (ANT Farm)
- Carlon Jeffrey as Cameron Parks (ANT Farm)
- Ross Lynch as Austin Moon (Austin & Ally)
- Laura Marano as Ally Dawson (Austin & Ally)
- Bridgit Mendler as Teddy Duncan (Good Luck Charlie)
- Leigh-Allyn Baker as Amy Duncan (Good Luck Charlie)
- Bradley Steven Perry as Gabe Duncan (Good Luck Charlie)
- Mia Talerico as Charlie Duncan (Good Luck Charlie)
- Eric Allan Kramer as Bob Duncan (Good Luck Charlie)
- Jason Dolley as PJ Duncan (Good Luck Charlie)
- Zach Steel as Gibson (ANT Farm)
- Aedin Mincks as Angus (ANT Farm)
- R. Brandon Johnson as Gary Wilde (Shake It Up)
- Jake Cinoa as Toby Duncan (Good Luck Charlie)
- Davis Cleaveland as Flynn Jones (Shake It Up)
- Roshon Fegan as Ty Blue (Shake It Up)
- Adam Irigoyen as Deuce Martinez (Shake It Up)
- Raini Rodriguez as Trish de la Rosa (Austin & Ally)
- Calum Worthy as Dez (Austin & Ally)
- Despite the fact that it is only a cameo, Rocky, Cece, and Tinka are the only main Shake It Up cast to appear in this episode.
- On the same note, Austin Moon and Ally Dawso also cameoed without Dez and Trish.
- All of the extra characters except Jimmy Starr appeared in this episode, though Angus and Gibson were just cameos.
- Gabe: Do I know you?
Avery: I don't know, were you in my art class?
Gabe: ...No, never mind.