HangScout
Toronto
All Chicago plans
Weekend plan

Outdoor Adventure in Chicago — Parks, Trails, Water

Trails, waterfronts, viewpoints and patios — outside from sunrise to sundown.

Build your own

Friday

  1. 7:00 PM

    Big Star

    Brunch · $$ · Wicker Park

    Patio kickoff — Breakfast tacos & bloody marys — Patio brunch with Mexican leanings.

    Open in Maps
    Why this pick
    • ·Outdoor pick — built for fresh-air time
    • ·Keeps you in Wicker Park — short walk from your other stops
    • ·A fall-perfect atmosphere
  2. 8:30 PM
    Chicago Riverwalk Summer Patios
    Outdoors · Loop

    Waterfront bars and restaurants along the river — the city's liveliest warm-weather outdoor hangout.

    Open in Maps
    Why this pick
    • ·Outdoor pick — built for fresh-air time
    • ·Keeps you in Loop — short walk from your other stops
    • ·A fall-perfect atmosphere

Saturday

  1. 9:00 AM
    Millennium Park
    Outdoors · Loop

    Anish Kapoor's Bean (Cloud Gate), free concerts at Pritzker Pavilion.

    Open in Maps
    Why this pick
    • ·Outdoor pick — built for fresh-air time
    • ·Keeps you in Loop — short walk from your other stops
    • ·A fall-perfect atmosphere
  2. 1:00 PM

    Lula Cafe

    Brunch · $$$ · Logan Square

    Outdoor lunch — Farm brunch tasting — Seasonal brunch icon, James Beard-nominated.

    Open in Maps
    Why this pick
    • ·Outdoor pick — built for fresh-air time
    • ·Keeps you in Logan Square — short walk from your other stops
    • ·A fall-perfect atmosphere
  3. 3:00 PM
    Promontory Point sunset
    Outdoors · Hyde Park

    Walk — Lake Michigan stone amphitheatre at golden hour.

    Open in Maps
    Why this pick
    • ·Outdoor pick — built for fresh-air time
    • ·Keeps you in Hyde Park — short walk from your other stops
    • ·A fall-perfect atmosphere
  4. 6:00 PM
    360 Chicago
    Outdoors · Streeterville

    View — 94th-floor TILT over Magnificent Mile.

    Open in Maps
    Why this pick
    • ·Outdoor pick — built for fresh-air time
    • ·Keeps you in Streeterville — short walk from your other stops
    • ·A fall-perfect atmosphere
  5. 8:00 PM

    Pequod's Pizza

    Deep-dish · $$ · Lincoln Park

    Caramelized cheese crust — the locals' deep-dish pick.

    Open in Maps
    Why this pick
    • ·Outdoor pick — built for fresh-air time
    • ·Keeps you in Lincoln Park — short walk from your other stops
    • ·A fall-perfect atmosphere

Sunday

  1. 9:00 AM
    Kayak / Paddleboard Rental
    Outdoors · Waterfront

    Hop on the water for an hour — beginner-friendly, great with a friend or date.

    Open in Maps
    Why this pick
    • ·Outdoor pick — built for fresh-air time
    • ·Keeps you in Waterfront — short walk from your other stops
    • ·A fall-perfect atmosphere
  2. 1:00 PM

    Girl & The Goat

    Modern American · $$$ · West Loop

    Stephanie Izard's wood-fired plates, share everything.

    Open in Maps
    Why this pick
    • ·Outdoor pick — built for fresh-air time
    • ·Keeps you in West Loop — short walk from your other stops
    • ·A fall-perfect atmosphere

Remix

Want a different vibe?

Every plan below is freshly built from Chicago's top curated picks.