August 27, 2021 – Summer is not over yet. Grab your friends, head out, and say cheers!

Race down the river

Color and pageantry await you at the annual Chicago Dragon Boat Race for Literacy, sponsored by the Chinatown Chamber of Commerce. This annual event is a family-fun activity in which 30-plus teams of brightly decorated dragon boats paddle the Chicago River to raise funds for local schools and literacy organizations.

Entertainment includes Sally Marvel (above), one of approximately 50 known female sword swallowers in the world. Activities for children, too.

Races begin at 8:00 a.m. Opening ceremony starts with a Lion Dance at 9:00 a.m. Enjoy a free Chinatown Trolley from the park and loop around Chinatown during the event from 9:00 a.m. to 4:00 p.m. Free admission.

Saturday, August 28

8:00 a.m. – 5:00 p.m.

Ping Tom Memorial Park, 300 West 19th Street

 More info: Chicago Chinatown Chamber of Commerce

It’s all Greek to me! Get your fill of savory Greek food at the 31st annual Taste of Greektown as you chow down on gyros, souvlaki, and baklava.

Celebrate Hellenic pride with traditional music and entertainment, including Greek bands, as well as games for kids and families. Dine divine with delicious fare from Artopolis, Athena, Mr. Greek Gyros, and more. There’s even a Gyros Eating Contest. Free admission. Opa!

August 27-29

Friday: 4:00 p.m. to 11:00 p.m.

Saturday-Sunday: Noon to 10:00 p.m.

400 South Halsted Street, Van Buren Street north to Adams Street

 More info: Greektown Chicago

Hey, Margarita! Bring your pals to Navy Pier and tempt your tastebuds at the Chicago Margarita Festival. Sip your favorite margaritas made from top-shelf ingredients, while dancing to live Latin and island sounds.

There’s no better way to spend the day than lounging with friends and listening to music, all overlooking the lake. $20 general admission. Drink tickets sold separately.

Saturday, August 28

10:00 a.m. – 11:00 p.m.

Navy Pier, 600 East Grand Avenue

 More info: Chicago Margarita Festival

Take the family cruising Cruise down the Chicago River on a 75-minute boat ride aboard the Island Time (right). See Chicago’s architectural wonders, take in the exquisite views, and enjoy a refreshing beverage.

Due to COVID-19 restrictions, only a limited number of tickets will be sold.

Sunday, August 29

12:00 p.m. – 1:15 p.m.

Island Party Hut, 355 Chicago Riverwalk, between Columbus Drive and Lake Shore Drive

 More info: Chicago Party Boat

Bring the house down Discover the beat at the two-day House Music Festival with Chicago’s most popular DJs and dancing crowds.

Sponsored by RE/MAX Loyalty, this fifth annual music-to-the-max fest raises funds for local charities in the Pilsen neighborhood. Enjoy music, live art, food trucks, and local vendors.

Saturday, August 28 – Sunday, August 29

Noon – 10:00 p.m.

Harrison Park, 1824 South Wood Street

 More info: My House Music Festival

Photo provided by My House Music Festival

Get art smart The Edgewater Arts Festival returns with a flagship fair featuring 80 artists from the local community in Chicago’s Edgewater neighborhood.

Sponsored by Edgewater Artists in Motion, the festival features an impressive multi-cultural and multi-generational lineup of artists. This year’s program includes juried artists, live music, craft beer, children’s activities, and more!

Saturday, August 28 – Sunday, August 29

11:00 a.m. – 7:00 p.m.

1140 West Granville Avenue

 More info: Edgewater Artists in Motion

Celebrate the King of Pop A food truck fest and Michael Jackson tribute is a real thriller. Head to Daley Plaza for the 2021 Food Truck Fest.

Chicago’s own Rico Hampton will honor Michael Jackson and perform some of his greatest hits from noon to 1:00 pm on Daley Plaza.

August 27

10:00 a.m. – 3:00 p.m.

Daley Plaza, 50 West Washington Street

 More info: Chicago Food Truck Fest

Rock it out of the park

Adam Levine and Maroon 5 take the stage at Wrigley Field. Maroon 5 has sold more than 120 million records, making them one of the biggest musical artists on the planet.

August 30

7:00 p.m.

Wrigley Field, 1060 West Addison Street

 More info: Wrigley Field Tickets Office