Walking Atlas
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Chicago itinerary for first-timers

The classic neighborhoods in an order that works, with a 4K street walk for every stop. Watch your trip before you take it.

How long is your trip?

Day 1: The Loop & the Riverwalk

Millennium Park and the Bean, State Street, LaSalle Street and the Willis Tower, and sunset on the Riverwalk.

  1. 1

    Morning

    Millennium Park & the Bean

    The park on Michigan Avenue at the edge of the Loop, home to Cloud Gate, the mirrored sculpture everyone calls the Bean, the Crown Fountain's video faces and the Art Institute of Chicago next door.

    • Cloud Gate (the Bean)
    • Crown Fountain
    • Art Institute of Chicago

    Go early in the morning to see the Bean without the crowds reflected in it.

    Chicago Lights Up: Sunset to Night Drive

    Video by Relaxing Scenes Driving on YouTube

    Jump to

    Walk west along Washington or Madison Street, about 5 min.

  2. 2

    Late morning

    State Street

    The Loop's historic shopping street under the elevated tracks, lined with landmark buildings: the old Marshall Field's department store, the glassy Reliance Building, the Sullivan Center's ironwork and the marquee of the Chicago Theatre.

    • Marshall Field's / Macy's
    • Reliance Building
    • Sullivan Center
    • Chicago Theatre

    [4K] State Street in Downtown Chicago Loop, Illinois USA Walking Tour

    Video by Wind Walk Travel Videos on YouTube

    Jump to

    Walk west through Daley Plaza to LaSalle Street, about 15 min.

  3. 3

    Afternoon

    Daley Plaza, LaSalle Street & the Willis Tower

    The Picasso sculpture in Daley Plaza, the canyon of bank towers along LaSalle Street, and the black Willis Tower, with its glass-floored Skydeck ledges on the 103rd floor.

    • Chicago Picasso
    • LaSalle Street
    • Willis Tower Skydeck

    Downtown Chicago Walking Tour

    Video by GWE on YouTube

    Jump to

    Walk north along Wacker Drive to the river, about 20 min.

  4. 4

    Sunset

    The Chicago Riverwalk

    A path along the south bank of the river below the towers, with steps to sit on, kayaks and tour boats passing, and the bridges lighting up at dusk.

    • River Theater
    • The Jetty
    • DuSable Bridge

    The architecture boat tours leave from the river here; they are one of the best ways to see the skyline.

    Sunset Ambiance at Chicago Riverwalk

    Video by GWE on YouTube

    Jump to

Travelling with someone?

Send them this 3-day Chicago plan, videos included.

Planning your first trip to Chicago

How many days?

Three days covers the Loop and the river, the Magnificent Mile with River North and the West Loop, and the neighbourhoods of Wicker Park and Lincoln Park. Two days is enough for the highlights.

Where to stay

The Loop is central for sightseeing; River North and the Magnificent Mile have the most hotels and restaurants; the West Loop is the dining district; Lincoln Park and Wicker Park are quieter neighbourhood bases. Compare areas →

Getting around

Walk downtown and take the 'L' trains or buses to the neighbourhoods; tap a contactless card or phone at the gates and on buses.

Chicago is built on a flat grid beside Lake Michigan, which makes it one of the easiest big American cities to walk. The Loop, ringed by the elevated trains, holds the early skyscrapers, State Street and Millennium Park; the Chicago River curls around its north and west sides, with the Riverwalk along its bank; and across the river River North, the Magnificent Mile and, further out, Lincoln Park and Wicker Park each have their own character.

Every stop comes with a walking video filmed on those streets, so you can see the towers, the river and the neighbourhoods before you arrive. Use the buttons under each video to jump to the landmark, or press Preview to watch a whole day in a row.

Chicago itinerary: common questions

How many days do you need in Chicago?

Three days is a good first visit: one for the Loop and the Riverwalk, one for the Magnificent Mile, River North and the West Loop, and one for the neighbourhoods and the lakefront. Two days covers the highlights.

Is Chicago a walkable city?

Yes. Downtown is flat and laid out on a grid, and the Loop, the Riverwalk and the Magnificent Mile are all within walking distance of each other. The 'L' trains and buses reach the neighbourhoods further out.

Is the Chicago architecture boat tour worth it?

For a first visit, yes. The tours run along the river through the Loop and explain the city's skyscrapers from the water; they run mainly from spring to autumn.

When is the best time to visit Chicago?

Late spring to early autumn is the walking season, with summer festivals and beaches on the lake. Winters are long, cold and windy, though the city stays busy and the holiday lights are a draw in December.

Travel times are approximate. Check opening days and any booking requirements before you go.

Where to stay in Chicago

6 areas compared, each with a street walk so you can see the neighborhood before you book.

Read the guide →

Keep exploring Chicago

More 4K walking videos, top sights, food markets and dishes to try.

Chicago city guide →