1. Magnificent Mile Lights Festival

#1 Parade & Holiday Event
One of the largest holiday events in the country will celebrate its 27th annual run this year. Presented by BMO Harris Bank, the weekend event kicks off with family-friendly activities, including the parade and tree lighting ceremony illuminating one million lights that concludes with fireworks overlooking the Chicago River. Next: November 16-17 2018
One of the largest holiday events in the country will celebrate its 27th annual run this year. Presented by BMO Harris Bank, the weekend event kicks off with family-friendly activities, including the parade and tree lighting ceremony illuminating one million lights that concludes with fireworks overlooking the Chicago River. Next: November 16-17 2018
Photo: Courtesy of the Magnificent Mile Association
2. St. Patrick's Day Parade

#2 Parade & Holiday Event
Chicago is serious when it comes to celebrating St. Patrick’s Day. Not only is the river dyed green, but thousands of people come out to view the parade that features bagpipers, Irish step dancers, floats, and marching bands. Next: March 2019
Chicago is serious when it comes to celebrating St. Patrick’s Day. Not only is the river dyed green, but thousands of people come out to view the parade that features bagpipers, Irish step dancers, floats, and marching bands. Next: March 2019
Photo: Patrick L. Pyszka/City of Chicago
3. McDondald's Thanksgiving Parade

#3 Parade & Holiday Event
The high-energy parade is a family tradition and well-known as the second largest in the country. The route kicks off on State Street from Congress to Randolph in downtown Chicago. It’s broadcasted nationally, which puts a major spotlight on the city and kicks off the holiday season. Next: November 22, 2018
The high-energy parade is a family tradition and well-known as the second largest in the country. The route kicks off on State Street from Congress to Randolph in downtown Chicago. It’s broadcasted nationally, which puts a major spotlight on the city and kicks off the holiday season. Next: November 22, 2018
Photo: Courtesy of McDonald's Thanksgiving Parade
4. Bud Billiken Parade & Picnic

#4 Parade & Holiday Event
Launched in 1929, the largest African-American parade in the country welcomes massive spectators to Bronzeville and Washington Park on Chicago’s South Side. For the 89th annual parade, Chicago actor/comedian Dean Cole, noted for his role on Black-ish, and rapper Vic Mensa were the grand marshals this year. Past grand marshals have included President Barack Obama, Oprah Winfrey, and, last year, Chance the Rapper. Next: August 2019
Launched in 1929, the largest African-American parade in the country welcomes massive spectators to Bronzeville and Washington Park on Chicago’s South Side. For the 89th annual parade, Chicago actor/comedian Dean Cole, noted for his role on Black-ish, and rapper Vic Mensa were the grand marshals this year. Past grand marshals have included President Barack Obama, Oprah Winfrey, and, last year, Chance the Rapper. Next: August 2019
Photo: Courtesy of Bud Billiken Parade & Picnic
5. Chicago Pride Parade

#5 Parade & Holiday Event (up from #6)
The 49th annual celebration welcomed some 750,000 supporters. Held at the end of Pride Month, the parade commemorated the anniversary of New York’s Stonewall Riots, a watershed moment for gay rights in the United States. Orlando El Fenomeno Cruz, who won the World Boxing Organizational featherweight title in 2016 and is the first openly gay active professional boxer, was grand marshal. Next: June 2019
The 49th annual celebration welcomed some 750,000 supporters. Held at the end of Pride Month, the parade commemorated the anniversary of New York’s Stonewall Riots, a watershed moment for gay rights in the United States. Orlando El Fenomeno Cruz, who won the World Boxing Organizational featherweight title in 2016 and is the first openly gay active professional boxer, was grand marshal. Next: June 2019
Photo: André Lage Freitas
6. Christkindlmarket

#6 Parade & Holiday Event
A Christmas market that started in Nuremberg, Germany, in 1545 has become the inspiration for what has become a cherished Chicago tradition. The city’s largest open-air market for gifts, roasted nuts, and mulled wine, has been held at Daley Plaza each holiday season. It has become so popular that the market has opened two more locations, including Naper Settlement in 2016 and the Park at Wrigley in 2017. Next: November 16-December 24, 2018
A Christmas market that started in Nuremberg, Germany, in 1545 has become the inspiration for what has become a cherished Chicago tradition. The city’s largest open-air market for gifts, roasted nuts, and mulled wine, has been held at Daley Plaza each holiday season. It has become so popular that the market has opened two more locations, including Naper Settlement in 2016 and the Park at Wrigley in 2017. Next: November 16-December 24, 2018
Photo: Courtesy of Christkindlmarket
7. Memorial Day Parade

#7 Parade & Holiday Event
The annual parade honors the military and begins in Daley Plaza with a wreath-laying ceremony. The procession then travels down State Street from Lake to Van Buren and features marching bands, veteran groups, floats, and some 6,000 junior ROTC cadets. This year’s grand marshal was Army Major General Charles W. Whittington Jr. Next: May 25, 2019
The annual parade honors the military and begins in Daley Plaza with a wreath-laying ceremony. The procession then travels down State Street from Lake to Van Buren and features marching bands, veteran groups, floats, and some 6,000 junior ROTC cadets. This year’s grand marshal was Army Major General Charles W. Whittington Jr. Next: May 25, 2019
Photo: Courtesy of the City of Chicago
8. 26th Street Mexican Independence Day Parade

#8 Parade & Holiday Event
Held in September, the year’s 49th Annual Mexican Independence Day Parade featured Illinois State Comptroller Susana Mendoza. Dubbed “the most colorful parade in Chicago,” the celebration encompasses floats, mariachi bands, and dancing in the streets. Next: September 2019
Held in September, the year’s 49th Annual Mexican Independence Day Parade featured Illinois State Comptroller Susana Mendoza. Dubbed “the most colorful parade in Chicago,” the celebration encompasses floats, mariachi bands, and dancing in the streets. Next: September 2019
Photo: Courtesy of the 26th Street Mexican Independence Day Parade
9. Columbus Day Parade

#9 Parade & Holiday Event
This year’s parade marked its 65th anniversary. Sponsored by the Joint Civic Committee of Italian Americans, the festivities began with a mass at the Shrine of Our Lady of Pompeii and a wreath-laying ceremony in Arrigo Park. The parade followed on State Street featuring 150 units that include bands, floats, and marchers. Next: October 14, 2019
This year’s parade marked its 65th anniversary. Sponsored by the Joint Civic Committee of Italian Americans, the festivities began with a mass at the Shrine of Our Lady of Pompeii and a wreath-laying ceremony in Arrigo Park. The parade followed on State Street featuring 150 units that include bands, floats, and marchers. Next: October 14, 2019
Photo: Courtesy of the Columbus Day Parade
10. Chicagoland Toys for Tots Motorcycle Parade

#10 Parade & Holiday Event
Billed as “The World's Greatest Motorcycle Parade,” this annual tradition helps donated toys reach needy children. As many as 50,000 motorcycle riders participate in the event each year; in 2017, the event marked its 40th anniversary. Next: December 2, 2018
Billed as “The World's Greatest Motorcycle Parade,” this annual tradition helps donated toys reach needy children. As many as 50,000 motorcycle riders participate in the event each year; in 2017, the event marked its 40th anniversary. Next: December 2, 2018
Photo: Jack Voss
11. Eve of the Eve

#11 Parade & Holiday Event
The annual party takes place the night before New Year’s Eve at the Merchandise Mart and features an open bar, a buffet of heavy hors d’oeuvres, a raffle, live music, a DJ, and dancing. Some 2,000 guests typically attend the evening that benefits HighSight's scholarship program. Next: December 30, 2018
The annual party takes place the night before New Year’s Eve at the Merchandise Mart and features an open bar, a buffet of heavy hors d’oeuvres, a raffle, live music, a DJ, and dancing. Some 2,000 guests typically attend the evening that benefits HighSight's scholarship program. Next: December 30, 2018
Photo: Courtesy of Eve of the Eve
12. AIDS Foundation of Chicago's World of Chocolate

#12 Parade & Holiday Event
More than 1,000 supporters kicked off the holiday season for the AIDS Foundation of Chicago’s annual event, raising $100,000. Guests sampled chocolate creations from 19 area chocolatiers; awards given in six categories included London House winning the People’s Choice and Best Savory. In 2018, the event will return to Revel Fulton Market. Next: November 30, 2018
More than 1,000 supporters kicked off the holiday season for the AIDS Foundation of Chicago’s annual event, raising $100,000. Guests sampled chocolate creations from 19 area chocolatiers; awards given in six categories included London House winning the People’s Choice and Best Savory. In 2018, the event will return to Revel Fulton Market. Next: November 30, 2018
Photo: Courtesy of AIDS Foundation of Chicago