Explore Chicago with Debra – in June


What’s so special about June? For me, June brings peonies (mine are just about to bloom in my tiny sliver of a garden) and my daughter’s birthday (Kat turned 18 on the 1st). For us Chicagoans, June 1 is opening day for our glorious summer season. So get out there and enjoy what may be one of the best months of the year! Channel your inner greek; kick it into gear with yoga, pilates, zumba or tai chi – all on McDonald’s dime; sing the blues; power the band; and race a dragon float.

Explore Chicago with my top picks for the month of June!


June 5-7
Friday: 5pm to 11pm; Saturday: Noon to 11pm; Sunday: Noon to 10 pm

On Sheffield between Diversey & Schubert

Lincoln Park Greek Fest will again bring the aromas, sounds, tastes and traditions of Greece to all Chicagoans in June. This popular annual cultural celebration on the grounds of St. George Greek Orthodox Church will serve up an authentic dose of “filoxenia” (Greek hospitality and generosity of spirit) along with flavorful food, great music, dancing and pure fun. Whether one is Greek or not, this fest promises that everyone will be proudly Hellenic for at least a day. Opa! 


June 6 – September 5, 2015
Wednesdays and Saturdays

Millennium Park

Millennium Park will once again offer FREE Summer Workouts on the Great Lawn funded by McDonald’s. These free workout sessions will be held from 7 am to 11 am. Workouts are 45 minutes long with classes in Tai Chi, Yoga, Pilates and Zumba®. 


June 12 – 14, 2015
various locations

The Chicago Blues Festival is the largest free blues festival in the world and remains the largest of Chicago’s Music Festivals. During three days on five stages, more than 500,000 blues fans prove that Chicago is the “Blues Capital of the World.”

FRIDAY: Zora Young, Clarence Carter, Syl Johnson and more.

SATURDAY: Buddy Guy headlines the festival on Saturday, other headliners include Taj Mahal Trio and Toronzo Cannon.

SUNDAY: The festival closes on Sunday with Centennial Tributes to Willie Dixon and Muddy Waters.


Saturday June 20 – Sunday June 21
Damen Ave between North Ave and Schiller St

This environmentally conscious Wicker Park festival takes over Damen Ave, bringing green vendors, food and biodiesel- and bicycle-powered live music to the neighborhood for two nights. The south stage is powered by seven stationary bicycles! Lacking backup power, it is truly up to the audience to ensure that the band’s music can be heard throughout the day.
Folksy duo Shovels & Rope, West Coast garage rocker Mikael Cronin and alt-country singer-songwriter Lydia Loveless headline this year’s music lineup.


June 25th – July 26th
Oil Lamp Theater

Theater play by Bill Jepsen. This delightful love story had its Jeff Award-winning world premier at the Polarity Ensemble Theater in Chicago just two years ago. Oil Lamp’s Executive and Artistic Director Keith Gerth will direct this hilarious and poignant look at the many dimensions of modern romance.

Maria and Anthony are twins who’ve been damaged by love. Widowed once and divorced twice, Maria longs for a relationship but feels the stigma of a “three-time loser.” Dumped by his fiancé four years earlier, Anthony hasn’t dated since. Each has a lot to say about the other’s love life, but both are floundering in their own—while preparing for the 40th anniversary of their parents’ perfect marriage. 


June 27, 2015
8:00 am – 5:00 pm

Ping Tom Memorial Park, 300 West 19th Street

The Chinese Dragon Boat Race dates back to over 2,000 years and is a popular sport amongst Chinese and Asian communities all over the world. Started in 2000, the Chicago Dragon Boat Race is a family-fun activity enjoyed by the residents of Chinatown and the surrounding neighborhoods. Over 10,000 people will watch and participate in the activities. Proceeds from this year’s race will be donated to support and promote local literacy, cultural, and diversity programs. In addition to the boat tournament, this year’s event will feature other on-land spectacles such as live musical and dance performances, children’s activities and much more.