Kathy Osterman Beach, AKA Hollywood Beach, offers a little something different from our downtown locations. This quieter Uptown spot features a bit slower pace and less hustle and bustle then North Avenue or Ohio Street Beaches, especially on weekends. This locale offers Rentals, Lessons, Storage, and off-peak access with our 10hour and Season Pass options below. This location also has less boat traffic than the other two locations, which can often lead to flatter water. It is a good option during those mid-day weekends if you are looking to escape the downtown crowds.

Please note: The times for Osterman vary from our other locations and all weekday bookings must be pre-reserved ahead of time, please note the booking process and parameters below:

Reservations must be made by 11pm the night prior to paddle the next morning.

Reservations must me be made by 11am the morning of to paddle in the afternoon.


9a-5p, last boards on water by 4p

Pass and storage options allow you to use your code to access the equipment at your leisure at anytime sun up to sundown! (weather permitting)


Reservation start times:

  • Block 1 (7a/8a/9a)

  • Block 2 (3p/4p/)

    *This location only offers Rentals on Weekdays, please visit another location for Lessons

  • *If you have a group of rentals/lessons of 3 or more that wants to SUP outside of these designated time slots please contact us to reserve. 

  • Minimum 2 people must be signed up in a given time block. 

  • If you plan to SUP solo, please check number of available spots left in a given time slot, if it's less than 20 spots remaining it means other people have booked during that time slot and you're good to go. If you sign up solo for a slot/ block you run a risk it won't happen. Thus double check the slots in the block around your intended outing and ensure you're joining a time spot or block that has the minimum amount of bookings required. 

  • In the event the block minimum is not met or due to inclement weather, we will contact you ASAP to make arrangements

*If you have a group of 3 or more that wishes to paddle outside of these designated blocks of time, please contact us to reserve. 

If you wish to paddle outside of these designated hours consider one of our pass options below


5hour Rental Pass: $150

10hour Rental Pass: $250

Unlimited Season Pass: $500

Storage: $500

Off Peak Access: (Eligible with 10hour and Season Passes)

Access to boards daily 5a-9p during daylight hours, outside of regular business hours, weather permitting.

**Pass purchase does not guarantee you off-peak access privileges**

All pass holders seeking off-peak access privileges need to demonstrate an ability to paddle in a safe manner and a proficiency in the equipment handling process prior to being granted the privilege to access equipment at their discretion. A Chicago SUP Team member will personally assess each individuals ability to demonstrate the necessary requirements to access the equipment. A one-time $50 non-refundable fee will be required to conduct assessment for the privilege to access equipment. Once granted access, customers will be able to access the equipment 7 days/ week, 5a-9p, during day light hours, via fingerprint ID. Chicago SUP does not allow access to equipment during night/ adverse conditions. All patrons will be required to sign agreement and adhere to terms and conditions in order to receive and maintain access. For Off-Peak privileges at different locations there is an additional fee of $25 per location to be trained in that locations process.