Windy City Cowboys

08/13/2026

Second City Outlaws SWAY with Kameron Ross at Northalsted Market Days

08/13/2026

Second City Outlaws having a GOOD TIME dancing to NEW MUSIC from Kameron Ross!!

08/10/2026

Get a look at how the Second City Outlaws get on stage and SWAY with Kameron Ross at Northalsted Market Days!

08/10/2026

The Second City Outlaws giving the BEST IN COUNTRY DANCING FUN AND ENTERTAINMENT with the amazing Kameron Ross!

07/01/2026

Year after year the Second City Outlaws can be counted on to bring the BEST IN COUNTRY DANCING FUN AND ENTERTAINMENT to the Chicago Pride Parade!

06/29/2026

Look at the Second City Outlaws doing what they do BEST in the Chicago Pride Parade!!!

06/28/2026

TODAY is the BIG DAY to catch the Second City Outlaws in action at the Chicago Pride Parade and Back Lot Bash

06/26/2026

It's not the Chicago Pride Parade without Second City Outlaws!!! Celebrate Pride ALL DAY on Sunday with the festivities ending up at the Back Lot Bash

Celebrate PRIDE with us ALL DAY - Sunday June 28th with the BEST IN COUNTRY DANCING FUN AND ENTERTAINMENT!

The Chicago Pride Parade kicks off at 11AM. We are #71 in the line-up. Chicago Pride Parade 2026

Then we head over to the Back Lot Bash to teach fun and easy line dance lessons and give our performance! Second City Outlaws at Back Lot Bash

Second City Outlaws takes great PRIDE in being a mainstream Country Dancing Performing Group that is OPEN and inclusive to ALL country dancers regardless of age, race or gender identity.
For more information about us including how to join, send an email to: [email protected]. And remember, participation with the Second City Outlaws is completely FREE - there's NO MEMBERSHIP FEE thanks to the support of our amazing sponsors!

UNIFORMS PROVIDED BY Alcala's Western Wear