Stand-Up Paddleboarding on Lake Michigan | 4 Places to Go Next Summer

The first time I ever tried SUP was during a yoga class I found via Dabble. The class was held at Montrose Beach, and you meet at the Kayak Chicago paddleboard rental shop, where you can store your belongings. This class was $45 for an hour and a half. Of my three SUP experiences, this class was the most helpful in terms of teaching you how to paddle. As I wrote in my post, the teacher spent time in the beginning talking about how to maneuver on the board.

Another place to rent paddleboards is at Leone Beach in Rogers Park. Graham and I tried to rent paddleboards one day so he could try it, but sadly we didn’t realize that the Leone/Loyola Beach SUP company, which sets up outside the lifeguard office, is closed on Mondays and Tuesdays during the summer. I can’t speak to how well they set you up to paddleboard, but it’s a nice option if you are in the northern part of Chicago. It costs $20 per hour to rent a board here and they have two locations. Yoga classes and group outings are $35 for 90 minutes.

After our unsuccessful attempt at Leone Beach, Graham and I went to Chicago SUP at North Avenue Beach. Of the three times I paddled, this location had the best view of the Chicago skyline. It’s amazing at sunset! Graham and I rented boards for $30 an hour each, and we ended up paddleboarding with a large group. It was fun to chat with other random people we met on the water. The water on this day was a bit choppy, so I sat for most of the time. I was too sore from Orangetheory Fitness to want to stand. This paddleboard experience was the most challenging. Also, we got here kind of late and without reservations, so we almost couldn’t paddle. The guy ended up saying he had two boards left but we had to carry them to the water. (They can be heavy. Luckily Graham carried mine like a gentleman.) He didn’t provide any instruction whatsoever, because it wasn’t a class.

The last paddleboarding session I went on was via Chicago Paddle Company at Hollywood Beach in Edgewater. This was the trickiest social paddle to get to because Hollywood Beach doesn’t really have a parking lot. My friend and I had to find a parking spot in the neighborhood and then walk about half a mile to the beach. The paddle was called Chicks with Sticks and was held every Monday at 6:45 p.m. On this particular day it was raining, so we were worried the session would be canceled, but it wasn’t. Paddles happen rain or shine as long as the rain isn’t too heavy and there isn’t lightning or dangerous wind. This paddle was $35 but was part of a two-for-one paddle session deal. (I ended up not using the second class before the season ended.) I also didn’t stand the whole time during this session because it was a little choppy. And, as usual, I was sore from marathon training. This paddle was fun because we decided as a group how far we wanted to go, and we went farther from the starting point than the other paddleboarding classes/rental sessions I did this summer.

Have you ever tried SUP? What did you think? I suggest adding it to the itinerary next time you’re in Chicago in the summer!

** Some of these companies are now closed for the season but some are still offering rentals depending on the weather. Check on their websites or call them to make sure.