Montrose Avenue is the largest urban beach in Chicago, situated on the city's north side at the southwestern tip of Lake Michigan. It's a designated surfing beach by the Park District, making it a go-to spot for local surfers. The spot tends to attract a decent crowd, especially in the fall when the conditions are usually best. The beach features a distinctive hook-shaped pier at its southeast end, which can offer some protection from wind and can help with wave formation.

This beach works well on medium swells and can handle swell directions from North to Northwest, and even as far as East if the waves are powerful enough. Generally, you can expect waist to shoulder-high waves (around 0.6 to 2.1 meters). The best surfing conditions are during autumn and winter. Winds from the Northwest to Southwest work best for Montrose, especially when they shift offshore. The waves can vary due to the shifting inner, middle, and outer sandbars, offering multi-sectioned waves. For more consistent rides, head to the area directly off the end of the beach walkway, where you’ll find the most regular takeoff spots. The waves here can break in both left and right directions over the sandy bottom, accommodating surfers of all skill levels from beginners to experts.

Getting to Montrose is pretty convenient as you can access it by bus, train, car, or even by biking along Chicago’s 18-mile Lakefront Trail. Be ready for a bit of a paddle, though; short-period waves and prevailing onshore winds can result in a washing machine effect, making it more challenging to get out. Check the conditions before you go, especially in the winter when you might encounter ice, but overall, the local surfing community is friendly and welcoming, so it's a good place to connect with fellow surfers.