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Chicago

· Chicago, IL

Why you should go…

Chicago is Illinois' largest city, built along the Lake Michigan shoreline around the Loop and Michigan Avenue's Magnificent Mile. Visitors come for architecture river cruises, lakefront parks, world-class museums, and a dining and live-music scene spanning dozens of neighborhoods.

  • #chicago
  • #lakefront
  • #architecture
  • #museums
  • #dining

Good to know

General sightseeing guidance

Habits that pay off across this whole category, not rules for this one venue. Always check the official site for the specifics.

  • The forecast is part of the ticket

    Haze, low cloud, and rain flatten a view. Clear-day visits are worth rearranging your plans for.

  • Golden hour sells out first

    Sunset slots at observation decks and cruises are the first to go, so book those further ahead.

  • Dress a layer warmer

    It is always breezier up high and out on the water than it feels at street level.

  • Timed entry is common

    Plenty of landmarks release tickets in windows rather than at the door, so check before you walk over.

What's around here?

The closest stops to Chicago, ordered by straight-line distance. A few more like it, plus some different kinds of fun so you can build a full day.

  • Shopping
    Iconic

    The Magnificent Mile

    Free

    Chicago's iconic stretch of Michigan Avenue: 400+ stores, landmark towers, and the historic Water Tower, river to Oak Street.

    0.6 mi awaySwitch it up: Shopping

  • Tours
    Quirky Fun

    Chicago Crime Tours

    $25–$50

    Guided bus tours through Chicago's Prohibition-era mob history and notorious crime landmarks.

    0.6 mi awaySwitch it up: Tours

  • Sightseeing
    Date Night

    360 CHICAGO Observation Deck

    $25–$50

    Lake-and-skyline views from 1,000 feet up, plus TILT, the glass ledge that leans you over Michigan Avenue.

    0.7 mi awayMore like this

  • Sightseeing
    Local Gem

    Chicago Riverwalk

    Free

    A 1.25-mile waterfront promenade of patios, wine bars, and skyline views along the Chicago River.

    0.7 mi awayMore like this

  • Tours
    Local Gem

    Wendella Sightseeing Boats

    $25–$50

    Family-run since 1935, classic river and lakefront cruises from the Michigan Avenue dock.

    0.7 mi awaySwitch it up: Tours

  • Sightseeing
    Iconic

    Buckingham Fountain

    Free

    Grant Park's grand 1927 fountain fires its center jet skyward every hour, with music-and-lights shows after dusk.

    1.6 mi awayMore like this