TieredTravel › North America › United States › Chicago › Walks › 3 hours › The river and the Loop in three hours

Mid-range · 3-hour walk · Chicago

The river and the Loop in three hours

The Tribune Tower's borrowed stones, the Riverwalk, the Rookery's lobby and the Skydeck.

On foot
2.1 km
Walking
28 min
At stops
130 min
Total
2h 38m
Stops
5

Chicago invented the skyscraper after the fire of 1871 cleared the city to build again, and the Loop is still the best place to read the story. This route follows the river from Michigan Avenue to the financial district, takes in a lobby Frank Lloyd Wright remodelled, and finishes 412 metres up.

  1. Tribune Tower

    The Gothic tower of 1925. Set into its walls at street level are stones from the Great Wall of China, the Parthenon, the Taj Mahal and more than a hundred other places.

    15 min here Walk here →
  2. Chicago Riverwalk

    The river was reversed in 1900 to flow away from the lake, and its south bank is now a walk of cafés, kayak rentals and boat-tour docks below street level.

    25 min here Walk here →
  3. The Rookery

    Burnham and Root's office block of 1888. Frank Lloyd Wright remodelled the light-court lobby in 1905 in white marble and gold. Free to walk in.

    20 min here Walk here →
  4. Willis Tower Skydeck

    The 103rd floor of the former Sears Tower, the tallest building in the world from 1973 to 1998. The Ledge is a glass box that sticks out from the side.

  5. Union Station

    The Great Hall of 1925 under its barrel-vaulted skylight. The staircase was the scene of the pram sequence in The Untouchables.

    10 min here Walk here →

Every walking route in Chicago, the full Chicago guide for where to stay and what a day costs, or walks in other cities.

Weekly destination guides, hidden gems, and tier breakdowns — straight to your inbox.