1. On December 19, 1848, the Illinois and Michigan Canal was completed, linking the Great Lakes and the Mississippi River. This canal was crucial for transportation and shipping in the Midwest region, and helped Chicago become a major center for commerce.

2. In 1865, the state of Illinois adopted a new constitution which abolished slavery and established equal rights for all citizens regardless of race.

3. On December 19, 1958, the first phase of the Illinois Tollway was opened for business. This tollway system, which now spans over 290 miles, helped transform the state into one of the busiest transportation hubs in the country.

4. In 1972, Chicago's Sears Tower – now known as the Willis Tower – became the tallest building in the world, surpassing the World Trade Center in New York. It held the title until the completion of the Petronas Towers in Kuala Lumpur in 1998.

5. On December 19, 1986, the first Heartland Cafe opened in Chicago's Rogers Park neighborhood. The restaurant and music venue has since become an iconic part of the city's cultural scene, known for its commitment to local and organic food, and its support of progressive social causes.