Hidden Gems_ 10 Must-Visit Local Spots Only Chicago Locals Know

1. Hidden Gems: 10 Must-Visit Local Spots Only Chicago Locals Know Chicago is famous for its iconic attractions—Millennium Park, Navy Pier, and the Magnificent Mile—but the city’s true charm lies in its lesser-known local haunts. If you're looking to experience Chicago like a true local, skip the tourist traps and explore these hidden gems instead. From secret gardens to off-the-radar eateries, here are 10 must-visit spots that only Chicago insiders know about. 1. The Secret Garden at Alfred Caldwell Lily Pool Tucked away in Lincoln Park, the Alfred Caldwell Lily Pool is a serene oasis that feels worlds away from the bustling city. This hidden garden features winding stone paths, cascading waterfalls, and native plants, making it the perfect escape for nature lovers. 2. The Last Stop Before the Suburbs: The Green Mill Cocktail Lounge A legendary jazz club with a Prohibition-era past, The Green Mill in Uptown is where Al Capone once held court. Today, it’s one of the best spots in the city for live jazz and a vintage Chicago vibe.

2. 3. The Best Dive Bar You’ve Never Heard Of: Rossi’s Liquors Located in River West, Rossi’s Liquors is a no-frills dive bar with cheap drinks, a jukebox, and an old-school Chicago feel. It’s the kind of place where locals go to unwind without the pretension of trendier spots. 4. A Hidden Beach: Osterman Beach (Hollywood Beach) While North Avenue Beach gets all the attention, Osterman Beach (known locally as Hollywood Beach) offers a quieter, more relaxed lakeside experience. It’s a favorite among locals who prefer a peaceful day by the water. 5. The Coziest Bookstore: The Book Cellar Nestled in Lincoln Square, The Book Cellar is an independent bookstore with a charming café where you can sip wine while browsing books. It’s a literary haven that feels like a well-kept secret. 6. The Best Late-Night Bite: The Wiener’s Circle If you’re out late in Lincoln Park, The Wiener’s Circle is a must-visit for its infamous char-dogs and no-nonsense attitude. Just be prepared for some playful (and often loud) banter with the staff.

3. 7. A Hidden Art Gallery: The Martin Located in a former garage in Pilsen, The Martin is an intimate art space showcasing emerging local artists. It’s a great spot to discover Chicago’s underground art scene. 8. The Best Hidden Music Venue: The Hideout This unassuming bar in Bucktown is one of Chicago’s best-kept secrets for live music. The Hideout has hosted everyone from local indie bands to surprise performances by big-name artists. 9. A Secret Rooftop: Cindy’s at the Chicago Athletic Association While not entirely unknown, Cindy’s Rooftop offers one of the best views of Millennium Park without the crowds of more touristy spots. It’s a chic place for cocktails with a breathtaking skyline backdrop. 10. The Ultimate Hidden Speakeasy: The Violet Hour This Wicker Park speakeasy is disguised behind an unmarked door and a rotating mural. Inside, The Violet Hour serves expertly crafted cocktails in a moody, intimate setting—perfect for a classy night out.

4. Why Explore Chicago’s Hidden Gems? While big attractions like the Big Ten races on the lakefront (read more here) and Alpine Energy Midwest Madness (check it out) draw crowds, Chicago’s real magic lies in its hidden corners. These local favorites offer a more authentic, intimate way to experience the city.