Illinois, United States

Chicago

Chicago is known for its skyscrapers, riverwalk and lakefront parks, and its downtown Loop is one of the best places in the world to see modern architecture.

Chicago: Original Chicago Architecture Interiors Tour: Dazzling Interiors
Featured walk: Original Chicago Architecture Interiors Tour: Dazzling Interiors · Photo supplied by Viator

The city on foot

Chicago rebuilt itself after the Great Fire of 1871 and became the birthplace of the skyscraper. Its architecture is a draw in its own right.

Downtown is flat and laid out on a grid. The Riverwalk, Millennium Park and the lakefront trail make walking easy.

What makes Chicago distinctive

  • Skyscrapers and the Chicago River
  • Millennium Park and the Cloud Gate sculpture
  • Deep-dish pizza and hot dogs
  • Blues and jazz clubs

Walking tours in Chicago

Hand-picked guided walks in Chicago, each rated highly by travellers. Ratings and photos are from Viator; select a tour to see dates, prices and full details, and to book.

Advertising disclosure: tour links go to Viator. If you book through one, we may earn a commission at no extra cost to you. It does not affect the price you pay or which tours we choose.

Prices are Viator's lowest "from" price per person, converted to pounds and checked on 28 October 2026. The booking page shows the current price in your currency.

By theme: Food tours in Chicago · History walks in Chicago · Night and ghost tours in Chicago

Compare with other cities: Food tours · History walks · Night and ghost tours

More walking tours on GetYourGuide

GetYourGuide sells many of the same walks and some that Viator doesn't. Their list for Chicago is chosen and ranked by GetYourGuide, not by us.

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Main sights

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Neighbourhoods worth wandering

  • The Loop

    The downtown business district, ringed by elevated trains.

  • River North

    Galleries, restaurants and nightlife.

  • Lincoln Park

    A neighbourhood and lakefront park with a free zoo.

Free self-guided walk

Millennium Park and the Riverwalk

A free self-guided walk through downtown Chicago, from Cloud Gate in Millennium Park along Michigan Avenue to the Chicago Riverwalk.

2 km · 6 stops · map and directions

See the walk

Best areas to explore on foot

  1. Riverwalk

    Along the south bank of the river through downtown.

  2. Lakefront Trail

    An 18-mile path along Lake Michigan.

  3. Magnificent Mile

    Michigan Avenue's shopping street north of the river.

Practical walking notes

  • Terrain

    Flat throughout.

  • Wind

    Strong winds off the lake, especially in winter.

  • Winter

    Very cold and snowy from December to March.

When to visit

  • Summer

    Warm, with beaches, festivals and boat tours.

  • Spring and autumn

    Cool and good for walking.

  • Winter

    Bitterly cold.

Getting there and getting around

Arriving

  • By air

    O'Hare and Midway airports are both linked to the Loop by the 'L' trains.

Local transport

  • The 'L'

    Elevated and subway trains cover the city.

  • Water taxis

    Run along the river in the warmer months.

Questions travellers ask about Chicago

Should I take an architecture tour?

Yes. River cruises and walking tours explain the buildings and their history.

How many days do I need?

Three days covers downtown, a museum and a neighbourhood or two.

Where can I try deep-dish pizza?

Several historic pizzerias in River North serve it.

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Sources and review date

This guide was last updated on 2026-10-28. Opening hours, fares and services change; please confirm details with official sources before travelling.