- KJ Apa
- Griffin
- Maia Mitchell
- Phoebe
- Norman Johnson Jr.
- Mason
- Jacob Latimore
- Alec
- Wolfgang Novogratz
- Foster
- Sosie Bacon
- Audrey
- Mario Revolori
- Reece
- Jacob McCarthy
- Chad
- Halston Sage
- Erin
- Tyler Posey
- Ricky
- Gage Golightly
- Paige
- Nicole Forester
- Margaux
- Audrey Grace Marshall
- Lilah
- Valerie Jane Parker
- Claire
- Sameera Rock
- Janet
- Ed Quinn
- Griffin's Dad
- Gabrielle Anwar
- Griffin's Mom
- Heidi Johanningmeier
- Phoebe's Mom
- Jackie Sandler
- Tracey
- Brenna Sherman
- Sierra
- Greer Grammer
- Christine Purdy
- Jamison Belushi
- Promise Ring Girl
- Dylan Doornbos Hayes
- Promise Ring Boy
- Collin Grubbs
- Brother
- Amy Cates
- Mrs. Robinson
- Christopher Mele
- Older Trader Jerry
- Michael May
- Mr. Edmonds
- Jeffrey Grover
- Paige's Dad
- Layla Cushman
- Paige's Stepmom
- Dionnae Maree Ford
- Ricky's Ex
- Ryan Edward Hill
- Tyler
- Julia Kelly
- Jordan
- Addyson Raley
- Soccer Girl
- Boden Bindley
- Young Ricky Fan
- Ashleigh Morghan
- Warehouse Party Girl
- Brianna Burke
- Brenda Bonner
- Robert Ellis
- Brenda's Dad
- Cameron Woods
- Executive 1
- Will Bindley
- Executive 2
- Tino Roncone
- Executive 3
- Dylan Karz
- Cubs' Bat Boy
- Grace Bindley
- Beer Throwing Girl
- Scotty Conley
- Skateboard Announcer
- Gabriel Vigliotti
- Zachary
- Ian Pack
- Firecracker Guy #1
- Lyric Baker
- Volleyball Player
- Gloria Bishop
- Skate Park Competition Fan
- Steve Boress
- Baseball Fan
- Brooke Bowen
- Skateboard Fan
- Travis Bowen
- Broker
- Brian Briggs
- Erin's Dad
- Brielle Brown
- Yogurt Shop Twin
- Jeffrey Cain
- Stock Broker / Waiter / Pedestrian (uncredited)
- Cleveland Clark
- Cubs Baseball Player
- Lexi Cowan
- Christine Purdy's Sister
- Rick Dremann
- Commuter
- Gary Flamik
- Skateboard Fan
- Liliana Florea
- Baseball Fan
- Victoria Floyd
- Coffee Shop Customer / Partier (uncredited)
- Ed Frame
- Coffee Shop Patron
- Alvin J. Frazier II
- Bar Patron / Skate Park Fan (uncredited)
- Bryan Geary
- Guitar Shop Pedestrian
- Q Hasan
- Partier / Skate Park Fan (uncredited)
- Casey Hendershot
- Pedestrian
- Jake Herron
- Skate Park Fan / Windy City Bar Patron (uncredited)
- Rachel Fay Huffman
- Pedestrian / Train Passenger (uncredited)
- Amanda Hunter
- Partier
- Jenna Jaworski
- Jogger / Partier / Roller Rink Patron (uncredited)
- Cassandra Keegan
- Party Girl
- Cole Kornell
- Beach Partier & Downtown Pedestrian
- Daniel Lamont
- Stockbroker
- Angel Lane
- Grad Party Attendee
- Doug Meacham
- Skater / Skate Park Fan (uncredited)
- Nicole Merritt
- Party Girl
- Joe Morales
- Cafe Patron
- Emebet O'Connor
- Cubs Fan
- Roger Petan
- Coffee Shop Patron
- Evie Piekarski
- Audition Kid
- Ryan Polk
- Guy in Movie Theater / Dinner Party Guest (uncredited)
- Bobby Rodriguez
- Street Guy
- Edlyn Sabrina
- Train Passenger
- Melissa Santiago
- Waitress
- Audra Schildhouse
- Partier
- Kevin Slone
- Bar Patron
- Hannah Stoessner
- High School Graduate / Friend / Partier (uncredited)
- Ashland Thomas
- Cubs Fan
- Ming Wang
- Windy City Bar Patron
- Tiana Ware
- Skateboard Fan
- Maxwell Warner
- High School Graduate / Partier / Pedestrian (uncredited)
- Lloyd Weema
- Pedestrian Couple
- Abby Weissberg
- Guitar Student
- Felicia Worthington
- Waitress
- Christopher T. Yates
- Skate Finals Attendee
- Alex Zelenka
- Baseball Fan
- Nathaniel Zoffel
- Partier
