Insider's Guide to Chicago

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Tour code: 3173HS

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Explore the Loop's famous architecture during this 2-hour walking tour with an expert guide from the Chicago Architecture Foundation. Discover the beginnings of the Chicago School of Architecture through visits to some of the city's oldest skyscrapers, dating from the late 19th and early 20th centuries. This sophisticated, informative tour is a must-do for history and architecture buffs. 


  • Historic Chicago Loop Skyscrapers
  • See Chicago architecture
  • Guided walking tour through historic Chicago - see the earliest skyscrapers, built between the 1870s and the 1930s
  • Learn about the architects who influenced the city's architecture

Recent Photos of This Tour

What You Can Expect

Chicago Walking Tour: Historic Skyscrapers

Historic Loop Skyscrapers

Meet your expert guide at the Chicago Architecture Foundation, located on Michigan Avenue across from the Art Institute. (See Itinerary section below for detailed directions). Stroll through the Loop area, stopping at multiple buildings and listening to engaging commentary from your guide. You'll see some of the city's earliest skyscrapers, dating from the 1870s to the 1930s. Learn about the architects who influenced the city's aesthetics and how the buildings shaped the city's culture. 

Visit the following buildings, among others:
  • The Rookery, a National Historic Landmark
  • The Auditorium Building, a Louis Sullivan masterpiece
  • Chicago Board of Trade Building, one of the city's finest examples of Art Deco architecture
Your tour ends back at its departure point after 2 hours. 


224 South Michigan Avenue in the Shop & Tour Center across from the Art Institute on the northwest corner of Jackson Boulevard at Michigan Avenue.

By Car:

  • Chicago's major expressways converge just west of the Loop. Exit at Congress Avenue and proceed east (this is also the eastbound extension of I-290)
  • Lakeshore Drive, from Hollywood in the north to Jackson Park in the south, follows the shoreline and

CTA rapid transit stations: (walking distance from the following)

  • Adams/Wabash station for the Brown, Green, Orange and Purple Lines
  • Jackson/State Station for the Red Line
  • Jackson/Dearborn Station for the Blue Line

Walk east on Adams or Jackson to Michigan Avenue. At Adams, turn right (south) on Michigan Avenue.

CTA Bus Lines:

  • Take any CTA bus that travels downtown and intersects with (starting from the south) Van Buren, Jackson, Adams, Monroe, Madison, Washington or Randolph. Walk (or connect on a CTA bus) east to Michigan Avenue.
  • Free downtown trolley service is provided by the City of Chicago and serves most of Michigan Avenue, the Museum Campus, and Navy Pier and also connects to the train stations. Schedules vary by season.

Commuter Trains: Metra operates 11 suburban commuter lines serving downtown Chicago.

  • Ending at Union Station just west of the Loop and south of the Ogilvy Transportation Center: Heritage Corridor Line, North Central Service, Southwest Service, Burlington Northern Santa Fe, Milwaukee District North&West Lines.
  • Ending at the Ogilvy Transportation Center (formerly the Northwestern Train Station) just west of the Loop and north of Union Station: Union Pacific North Line, Northwest Line and West Line. From these two stations it is a 20 minute walk east to Michigan Ave, or take a #20 or #56 eastbound CTA bus on Jackson Boulevard, or connect with the free trolley shuttle.
  • Ending at the LaSalle Street Station: The Rock Island District Line. Walk east on Van Buren to Michigan and then north on Michigan to Jackson
  • Ending at the Randolph Street Station: The Metra Electric Line and the Northern Indiana Commuter Transportation District (South Shore Line). Get off at the Van Buren/Jackson Station (the stop before the end). From here, walk one block north on Michigan Avenue to Jackson.

Customer Reviews

Brian R

5 star rating: Highly Recommended January 2016

Very informative tour.

Mathilde B

5 star rating: Highly Recommended December 2015

Very good tour, very interesting and the tour guide did a perfect job explaining everything !

Amy J

5 star rating: Highly Recommended October 2015

This was without a doubt my favourite tour in Chicago. As an architect I found our guide very informative and the buildings themselves awe inspiring. I would definitely recommend this tour for those looking for an incredible insight into the designs of the Chicago School architects.

Nancy L

5 star rating: Highly Recommended July 2015

Very informative but not too heady!


5 star rating: Highly Recommended June 2015

Terrific! Our tour Gide was fabulous and we learned tons!

Frederick G

5 star rating: Highly Recommended December 2014

This was a great tour of south loop Architecture. The tour guide was well informed and answered our questions.

Steve A

5 star rating: Highly Recommended July 2014

Despite late rain great experience

Bruce X

5 star rating: Highly Recommended February 2014

Great tour even though it was a cold snowy day.

John W

5 star rating: Highly Recommended December 2013

In spite of the inclement weather the tour was both informative and entertaining. First class!!!

Roberta S

5 star rating: Highly Recommended December 2013

Excellent! Our guide was awesome. The history was so interesting.

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