Prosper

Happy New Year from the Prosper family. Big plans ahead for 2026. Appreciate everyone who continues to support — more coming soon.

Merry Christmas & Happy Holidays from the Prosper family.

New Old English Holiday Colors

- T-Shirt: $25 | Hoodie: $45 — Sizes S–5XL
- Ships in 3–5 business days — Link in bio

Prosper Milagro hoodies available online now

- $45 - Sizes S-5XL
- Available in white, sand, heather grey, and maroon
- Ships in 3-5 business days - Link in bio

Happy Thanksgiving from the Prosper family

Prosper Raffle Update

-1st Place: Prosper Marlboro Skate Box
- 2nd Place: $50 Gift Card
- 3rd Place: $25 Gift Card

Raffle ends: Friday, October 3rd at 7PM
- Tickets: $5 each, available on our website
- Multiple entries allowed

*Local pick up only

Prosper Raffle
We’re raffling off the Prosper Marlboro Skate Box.

Tickets are online now, $5 each, and you can purchase multiple entries to increase your chances.

Winner will be announced Wednesday, October 1st at 7 PM.

thank you chicago skateboarding for holding us down for so many years after 14 years of serving the southside skate community this week 9/2 - 9/6 will be our last open week we’ve done everything we could to keep prosper skateshop alive as long as possible and saying this out loud is heartbreaking

to everyone who ever stopped by grabbed a board chilled at the shop or just came through to talk you’ve made this place what it is the people who walked through these doors mean more to us than we could ever put into words this shop was never just a store it was a home a safe space and a family

we’ll be here Tuesday through friday 12–7 so please stop by hang out with us and help us close this chapter right

thank you for every ounce of love and support over these years we wouldn’t have made it this far without all of you and remember “without labor nothing prospers”

Prosper “South Side Crew”
- Tee: $30 (sizes S–5XL)
- Tote Bag: $20
- Available online now
- Ships in 3–5 business days

“Southside Crew” Tees & Totes are available now, Sizes S–5XL. This is an online exclusive!! Orders ship in 3–5 business days, so don’t wait.