Transformations on the South Side Bus Tour

Examine the dramatic changes in several prominent South Side neighborhoods.
Upgrade to include a soul food meal in Chicago's oldest restaurant.

This private South Side bus tour explores the historic architecture and new developments in Hyde Park, Washington Park, Kenwood, South Shore and Woodlawn. Additionally, we will see how the University of Chicago is developing its campus and expanding its reach into these surrounding communities. The tour can be upgraded to include a soul food meal at Daley’s, the oldest operating restaurant in the city.

We start and end this private tour at the Currency Exchange Café in Washington Park. This community-oriented café is part of the UChicago Arts Incubator. The tour concludes with a visit to the various spaces inside this innovative building, which is the brainchild of Theaster Gates, an acclaimed artist, community builder and UChicago professor.

Our coach bus will loop around the neighborhoods which surround the University of Chicago campus. Highlights include the wide green spaces of historic Washington Park, the Obamas’ home in Kenwood, new campus architecture, historic homes in Jackson Park Highlands, commercial developments on 53rd Street, and new construction on 63rd Street in Woodlawn.

Your tour guide will delve into the rich history and contentious future of Jackson Park. Home to the famous “White City” of the 1893 World’s Columbian Exposition, it is also the planned site for the Obama Presidential Center and a new Tiger Woods-designed professional golf course.

We also visit Woodlawn, which was one of Chicago’s busiest and most populous neighborhoods at the time of the 1893 World’s Fair. Decades of population shifts, disinvestment, and an often adversarial relationship with the university changed the neighborhood. Now the University and other powerful groups are investing heavily in the Woodlawn neighborhood. We’ll go by some of the new affordable housing developments and commercial redevelopment at the end of the CTA’s Green Line.

It’s here in Woodlawn where you can choose to stop at Daley’s Restaurant, now the oldest operating restaurant in the city, for a soul food meal for your group. With the food upgrade to this South Side bus tour, you get a massive meal of home-made soup, your choice of meatloaf with mashed potatoes or catfish with mac & cheese (no substitutions), and sweet potato pie for dessert. Prepare to be stuffed! Vegetarian option available.

This tour examines the history of the South Side, with an in-depth look at how social policies and developments have major impacts on Chicago’s diverse neighborhoods.


2-3 hours


Minimal walking


  • The Arts Incubator, Currency Exchange Café, and Stony Island Arts Bank
  • New towers by cutting-edge architects like Jeanne Gang
  • Historic and brand-new academic structures on the UChicago campus
  • Jackson Park - site of the 1893 World's Columbian Expo and planned Obama Center
  • New schools and developments in Woodlawn
  • Upgrade for soul food meal at Daley's Restaurant

Stories & Ideas

  • How spaces for creativity and art can help rebuild community
  • The effects of redlining and racial segregation
  • Historic and contemporary urban renewal projects in Hyde Park
  • Battle between past and future in historic Jackson Park
  • The University's influence on neighboring communities
  • The spectacle of the World's Columbian Exposition

Tour Includes

  • Transportation via 37-passenger coach bus
  • Engaging tour guide commentary
  • Optional upgrade for meal with dessert and beverage (see details above)
  • Tour of the UChicago Arts Incubator
  • All taxes and server gratuities
  • Special gifts

Tour Meeting Spot

The tour begins and ends at Currency Exchange Café, 53 E. Garfield Blvd.

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