Chicago Beach Restaurants & More: Season Opens for Summer 2025!

As warmer days arrive and Lake Michigan beckons, Vandalay Brands is thrilled to announce the openings of our Milwaukee and Chicago beach restaurants for the 2025 season!

• The Dock at Montrose Beach (Chicago, IL)

• Caffè Oliva at Ohio Street Beach (Chicago, IL)

• The Dock at Bradford Beach (Milwaukee, WI)

From citywind shortcuts to lakeside escapes, we bring you the best in food, drinks, and waterfront ambiance—whether you’re staying local or venturing north.

The Dock at Montrose Beach — a favorite Chicago Beach Restaurant & Live Music Spot

Set on expansive Montrose Beach, Chicago’s largest sand haven, The Dock at Montrose Beach delivers casual dining—burgers, tacos, fresh salads, beachy cocktails—and live music every single night. This vibrant spot is a longtime favorite for beachgoers, dog walkers, and city dwellers seeking good food beside their toes in the sand.

The Dock at Montrose Beach is located at 200 West Montrose Harbor Drive, Chicago, IL 60601

Caffè Oliva at Ohio Street Beach — Mediterranean Vibes & Live Music by the Lake

Just steps from Navy Pier, Caffè Oliva brings Mediterranean-inspired cuisine to Ohio Street Beach with fresh seafood, crisp salads, and handcrafted cocktails—all paired with sweeping skyline views. Weekend DJs and acoustic sets on Wednesdays and Fridays create the perfect soundtrack for lakefront dining, while private cabanas offer an upgraded experience for groups looking for a relaxing afternoon by the water. This combination of great food, live music, and beachside ambiance makes Caffè Oliva one of Chicago’s most inviting lakefront destinations.

Caffè Olivia at Ohio Street Beach is located at 550 E Grand Avenue, Chicago, IL 60611

The Dock at Bradford Beach — Milwaukee’s Tiki-Style Lakefront Hangout

Just north in Milwaukee, The Dock at Bradford Beach delivers tropical vibes on white sandy shores. Enjoy burgers, Baja tacos, wraps, frozen drinks, and cold drafts beneath tiki huts. With beach volleyball courts and a lively scene, it’s a go-to for anyone looking for a fun day at Milwaukee's best beach.

The Dock at Bradford Beach is located at 2400 North Lincoln Memorial Drive, Milwaukee, WI 53211

Why Vandalay Brands Beach Restaurants Shine

With prime lakefront locations, Vandalay’s beach restaurants offer something for everyone—from Chicago favorites at Montrose and Ohio Street to a lakeside escape at Milwaukee’s Bradford Beach. Each spot features beach-friendly menus with sliders, tacos, grilled seafood, frozen cocktails, and local beers, perfect for casual dining by the water. The experiences go beyond great food: Montrose comes alive with live music that sets the tone for sun-soaked days, Caffè Oliva pairs DJs on weekends and acoustic music midweek with private cabana rentals, and Bradford brings a playful vibe with beach volleyball and perfect views that keeps the energy high all summer long.