Things to Do in Uptown

Free beach, bird sanctuary, dog beach, kayak rentals. Less touristy than North Ave.

A wide, sandy beach on the North Side with a dog-friendly section (one of only a few in the city), a kayak/paddleboard launch, the Montrose Point Bird Sanctuary, and a seasonal beach house bar. Free to enter. Less crowded and more laid-back than North Avenue Beach. The bird sanctuary draws serious birders during migration.

4400 N Lake Shore Dr, Chicago, IL 60640 · Beach: Memorial Day-Labor Day 11am-7pm · outdoor

Al Capone's hangout. Jazz 7 nights. Cash only. No talking during sets.

Art Deco jazz club, former Prohibition speakeasy -- Al Capone's favorite hangout. Live jazz seven nights a week, small cover. Sunday night Uptown Poetry Slam has run since 1986 -- longest-running in the country. Cash only. They will shush you.

4802 N Broadway Ave, Chicago, IL 60640 · Daily 4pm-4am (5am on Sat) · indoor

50 years of original African American musicals — 2026 season includes Muddy Waters

A 50-year-old theater company in Uptown dedicated to telling African American stories through original musicals and biographical shows. The 2026 season includes an ode to Muddy Waters. The work here is unlike anything on the North Side commercial circuit -- rooted in community and history.

4450 N Clark St, Chicago, IL 60640 · Show times vary, check schedule · indoor

BYOB Lebanese with 880+ Yelp reviews and $12 combo plates. Bring wine, order the mixed grill, tip well.

Family-run Lebanese restaurant, BYOB since forever. The combo plates are $12-15 and enormous. Falafel, shawarma, kibbeh — all solid. Bring a bottle of arak or wine. No pretense, just consistently good food in Uptown. Cash preferred.

1509 W Foster Ave, Chicago, IL 60640 · Mon-Sat 11am-10pm, Sun 11am-9pm · indoor

Three acres of beach, your dog can swim in Lake Michigan, and it's free. Summer weekends hit 200+ dogs. Get the $5 DFA tag or you'll get fined.

Chicago's first legal off-leash beach — over 3 acres of sandy shoreline where dogs can swim, run, and dig. Fenced, with free waste bags, a dog wash station, and water fountains. Open year-round, sunrise to sunset. You need a Chicago DFA tag ($5/year). Summer weekends are a zoo — 200+ dogs easy.

601 W Montrose Ave, Chicago, IL 60613 · Sunrise to sunset, year-round · outdoor