HangScout
Toronto
All Chicago plans
Weekend plan

Chicago for First-Timers — The Greatest Hits

Iconic landmarks, the food you fly in for, skyline shots and the must-do experiences.

Build your own

Friday

  1. 7:30 PM

    Bongo Room

    Brunch · $$ · Wicker Park

    Iconic kickoff — Red velvet pancakes — Chicago brunch institution, queue out the door.

    Open in Maps
    Why this pick
    • ·An iconic must-do for a first visit
    • ·Keeps you in Wicker Park — short walk from your other stops
    • ·A fall-perfect atmosphere

Saturday

  1. 10:00 AM
    Chicago Riverwalk
    Outdoors · Loop

    Walk or kayak past the city's famous architecture on river level.

    Open in Maps
    Why this pick
    • ·An iconic must-do for a first visit
    • ·Keeps you in Loop — short walk from your other stops
    • ·A fall-perfect atmosphere
  2. 1:00 PM
    Chicago French Market
    Food & Drink · West Loop

    Indoor market with local food vendors, coffee and sweets — an easy weekday lunch spot for locals.

    Open in Maps
    Why this pick
    • ·An iconic must-do for a first visit
    • ·Keeps you in West Loop — short walk from your other stops
    • ·A fall-perfect atmosphere
  3. 3:30 PM
    Intuit Center for Intuitive and Outsider Art
    Culture · Near West Side

    Small but world-class gallery of self-taught art — an overlooked gem for curious solo culture-seekers.

    Open in Maps
    Why this pick
    • ·An iconic must-do for a first visit
    • ·Keeps you in Near West Side — short walk from your other stops
    • ·A fall-perfect atmosphere
  4. 7:00 PM
    North Avenue Beach
    Family · Lincoln Park

    Boathouse-shaped beach pavilion and skyline-backed swims.

    Open in Maps
    Why this pick
    • ·An iconic must-do for a first visit
    • ·Keeps you in Lincoln Park — short walk from your other stops
    • ·A fall-perfect atmosphere
  5. 9:00 PM

    Pequod's Pizza

    Deep-dish · $$ · Lincoln Park

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

    Open in Maps
    Why this pick
    • ·An iconic must-do for a first visit
    • ·Keeps you in Lincoln Park — short walk from your other stops
    • ·A fall-perfect atmosphere

Sunday

  1. 11:00 AM

    Lula Cafe

    Brunch · $$$ · Logan Square

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

    Open in Maps
    Why this pick
    • ·An iconic must-do for a first visit
    • ·Keeps you in Logan Square — short walk from your other stops
    • ·A fall-perfect atmosphere
  2. 2:00 PM
    Smartbar
    Nightlife · Lakeview

    Club — Underneath Metro — house & techno since 1982.

    Open in Maps
    Why this pick
    • ·An iconic must-do for a first visit
    • ·Keeps you in Lakeview — 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.