City Digest: Chicago

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A curated list of activities, eateries and more in the Windy City, Chicago.


  • Near North Side: It's the northernmost and second largest of the four community areas that make up Downtown Chicago. The famous Magnificent Mile is here: an upscale section of Michigan Avenue filled with luxury boutiques, department stores, and posh hotels.
  • Loop: Located just to the south of Near North Side, this is Chicago's commercial core. Here you'll find Grant Park, the Art Institute of Chicago, Millennium Park, and Willis Tower.
  • Near South Side: Located just south of the Loop. Several sports venues are here, including Soldier Field, where the Chicago Bears play. The Gold Coast Historic District is also here.
  • West Loop: Known for its trendy dining scene, this area west of the Loop is packed with high-end restaurants and hip bars.
  • River North: Located directly to the west of the Near North Side, River North is known for its vibrant nightlife and dining scene. It is also home to many art galleries.
  • Lincoln Park: North of the Near North Side. It's famous for its big park, beautiful brownstone buildings, and the free-entry Lincoln Park Zoo.
  • Lakeview: Further north from Lincoln Park, Lakeview is home to Wrigley Field, where the Chicago Cubs play.
  • ⭐️ Wicker Park/Bucktown: Located to the northwest of downtown, this hip, vibrant neighborhood is known for its cool coffee shops, indie boutiques, and contemporary art scene.
  • Hyde Park: To the south, Hyde Park is known for its rich history, beautiful architecture, and the University of Chicago.
  • Chinatown: Located in the South Side, Chicago's Chinatown is a hub for Chinese culture, food, and shopping.


  • 3 Arts Club Cafe
  • 🇵🇭 Kasama

Lunch / Dinner

  • 🍕 Lou Malnati’s
  • 🍕 Giordano’s
  • 🥩 Bavette's Bar & Boeuf
  • 🍔 Au Cheval — Probably the best burger I’ve ever had! They also served chicken liver as appetizer.

Things To Do

  • 🖼️ Art Institute of Chicago
  • 🏞️ Millennium Park
  • 🏃 Run along the Chicago Lakefront Trail
  • 👣 Stroll through the Old Town neighbourhood
  • 🚶Hike along The 606 (an elevated park trail)
  • 🎨 Museum of Contemporary Art
  • 🛍️ Explore the boutiques and art galleries River North


  • Pendry Chicago