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Transformations on the South Side Bus Tour

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

This three-hour-long neighborhood bus tour explores the historic architecture and new developments in Hyde Park, Washington Park, Grand Boulevard, Kenwood, South Shore and Woodlawn. Upgrade to include a stop for a big soul food lunch at Daley’s Restaurant, currently the oldest operating restaurant in the city.

Your private group tour guests will learn about neighborhood change. We can start the tour downtown. On our way to the South Side, your tour guide will share background and complexities of the history of its industrial rise and fall. Your group will see the beauty of the Chicago lakefront along Lake Shore Drive, and the landscaped grounds of the neo-classical Museum of Science and Industry.

We will weave through the University of Chicago campus to get a foundation on how this acclaimed institution is expanding its reach into some of the surrounding neighborhoods that we visit. We’ll see ornate Neo-Gothic buildings, contemporary architecture, and “the hospital of the future.”

The bus will weave through the gorgeous Washington Park, originally designed by Frederick Law Olmsted. In the eponymous neighborhood, your group will see the recently renovated ‘L station from 1893. This original train station, built for the 1893 World’s Columbian Exposition, will now be a welcome center for the University of Chicago Arts Block. A multitude of cultural programming abounds in these buildings, many of which are open to the community.

Bus tour 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 in Woodlawn. We’ll talk about bigger ideas for these neighborhood changes, including segregation and inequality, and positive forces in economic redevelopment.

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 PGA 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 at times adversarial relationship with the University of Chicago, changed all of that dramatically. Now, after decades of seeing the Midway as an invisible wall, the University (and other powerful groups) are investing heavily. It’s here in Woodlawn where your group may stop at Daley’s Restaurant, now the oldest operating restaurant in the city, for a hearty soul food meal.

Food options include home-made soup and choice of either meatloaf with mashed potatoes or catfish with mac & cheese. Sweet potato pie makes for a delicious dessert. Food options all come with corn bread. Prepare to be stuffed! Vegetarian option is mushroom burger with soup.

As you decide on a private group tour of Chicago, this quick guide may help you understand if Chicago Detours is the right tour company for your special event.


2-3 hours


Minimal walking


$43 per person


  • 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
  • The exterior of the Stony Island Arts Bank
  • Upgrade option for soul food meal at Daley's Restaurant

Stories & Ideas

  • The University of Chicago’s influence on neighboring communities
  • Urban renewal and gentrification
  • Racial segregation and integration
  • The spectacle of the World’s Columbian Exposition
  • Creative redevelopment of neighborhoods

Tour Includes

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

Tour Location

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Call: 312.350.1131
E-Mail: [email protected]