Chicago is always changing: the people, the food, the skyline. So with the Democratic National Convention coming to town (as you may have heard), how much has changed since the last time we hosted a convention in 1996? More than you might think.

In some ways, the 1990s marked a turning point from the old Chicago to the new — with the United Center (1994) replacing the Chicago Stadium, and a new Comiskey Park (1991) replacing the older one. There were plans for new parks and buildings, and huge swaths of public housing were demolished.

So in our “city on the make,” as author Nelson Algren called it, here is a little quiz to see if you remember what was going on in 1996 and if you have also kept up with the city’s changes since.

First, we’ll start with questions about about high-profile people and things that were making headlines in 1996. Then, we’ll move onto things from current times that weren’t around in 1996. (Answers are given below.)

From 1996 . . .

MJ and the Bulls

Mayor Richard M. Daley was several years into his record-long 22-years in office, but Michael Jordan owned the city. The Jordan-led Bulls electrified Chicago, and won six NBA championships in the decade.

The 1995-96 season was Jordan’s first after a premature retirement. The team set an NBA-best mark with its 72-10 record.

Jordan retired again (temporarily) after the 1998 season, and the team started a rebuilding that goes on to this day.

Question 1: So whom did the Bulls beat for the NBA title in 1996? Hint: That team no longer exists.

Oprah

Then-Chicago-based Oprah Winfrey premiered her famous book club in 1996. As producer and host of the most popular daytime talk show in American television history, Oprah’s selections regularly shot to the top of the best-seller lists.

Oprah’s show, which helped launch the careers of psychologist Phil McGraw, financial adviser Suze Orman, and Dr. Mehmet Oz, was shot in Chicago for its entire 25-year run. It ended in 2011 — the same year Daley left office.

Question 2: What was the first book Oprah chose for her book club?

That great street

The one-time center of Chicago’s shopping district, State Street, was turned primarily into a pedestrian mall in 1979. The nine-block stretch in the Loop was meant to compete with suburban malls, but it never achieved its intended vibe.

With wider sidewalks and less traffic, shoppers said it felt deserted, as one by one the department stores closed.

After it fell into further disuse, it was targeted for a major restoration, and the pedestrian mall concept was abandoned in 1996. The street reopened to traffic, but with planters to separate pedestrians from the street, and retro designs on lighting and subway entrances. An increase in other uses, including theater, office, and residential, helped spark a resurgence.

Question 3: What was one of the key features blamed for the failure of the State Street mall?

Cabrini-Green

Also in 1996, Daley announced a plan to redevelop the Cabrini-Green public housing complex.

But resident leaders were noticeably absent, and their attorney called the plan to tear down the mostly Black-occupied apartments “ethnic cleansing.’

By 2011, demolition began on the last high-rise, part of a program to tear down more than 17,000 units. Under a later court agreement, more than 480 new units are to be built on the site.

Tenant advocates said the city failed on promises to build new homes for those displaced. To settle a lawsuit, the Chicago Housing Authority has promised to continue developing scattered site and mixed-income housing, and improve its voucher program.

Question 4: For whom was the Cabrini-Green development named?

. . . to 2024

Millennium Park

Since opening in 2004, Millennium Park has attracted both tourists and residents with its curious combination of interactive sculpture, outdoor dining, ice skating, garden and concert venue.

The $475 million public-private project, led by Daley, is widely considered a key step in the city’s downtown revitalization.

The park celebrated its 20th anniversary this year with a free concert featuring Common, Jennifer Hudson, De La Soul, and the Grant Park Orchestra. Other special attractions include a new app-driven augmented reality art installation, Lyric Opera’s appearance on Aug. 25, and the Jazz Festival the last weekend of August.

Question 5: What simple observation helped lead to the city acquiring the land for Millennium Park?

Google it

Of course, a whole new world of technology has developed since 1996. The Internet expanded hugely, bringing with it advancements like ride-sharing, expanded home food delivery, social media, and the tech industry.

Perhaps nowhere is the effect of those tech giants more obvious than the former State of Illinois building, known as the Thompson Center. Google bought the glass-domed atrium from the state for $105 million and this spring began an extensive renovation to drop the red-white-and-blue exterior with new clear glass and make it more energy efficient.

The new home for Google is hoped to revitalize the Loop after pandemic shutdowns and record office vacancies, and to attract high-tech workers.

Question 6: What is unique about transit access at the new Google site?

NASCAR

NASCAR came to town in 2023 and again this year, stirring excitement among racing fans and begrudged by people who found their routes blocked by closed streets. Both runs of the Grant Park 165 were interrupted by rain and accidents, prompting fans to leave early, but city leaders considered them a success.

The first race cost the city $3.5 million in overtime and other costs to host, and brought in only $620,000 directly from NASCAR.  In contrast, the annual Lollapalooza music festival paid the city nearly $10 million in 2023.

But an economic impact report estimated total NASCAR revenue generated, including jobs, hotel rooms and restaurant tabs, cleared $100 million.

The race was an initiative of Mayor Lori Lightfoot, but Mayor Brandon Johnson hopes to continue to hold it next year.

Question 7: Who won the race this year?

Answers

Answer 1: The Seattle SuperSonics. The Bulls’ regular-season record was eclipsed by the 2015-16 Golden State Warriors, who finished 73-9.

Answer 2: “The Deep End of the Ocean,” by Jacquelyn Mitchard.

Answer 3: It also included a path for public transit, with fifteen bus routes roaring down the street, filling it with diesel fumes.

Answer 4: Mother Frances Cabrini, the first American citizen to be named a saint, and William Green, the former president of the American Federation of Labor.

Answer 5: Much of the land where Millennium Park sits used to hold only railroad tracks. People thought the area was owned by the Illinois Central Railroad.

But a park district attorney who noticed a huge gravel lot with a single boxcar, checked into it and discovered that the city owned much of the land. It sued and got back the land north of McCormick Place that was not being used by the railroads.

Answer 6: It’s the only place where six of Chicago’s elevated train lines converge. Now that’s old-school high tech!

Answer 7: Alex Bowman. It was his first win in two years after being sidelined by a concussion. After winning, he declared, “We’re going to drink so much damn bourbon tonight, it’s going to be a bad deal. I’m probably going to wake up naked on the bathroom floor again.”