On Father’s Day, many restaurants and retailers are offering discounts and freebies to make celebrating with Dad a little easier on the wallet. Whether your dad is a steak guy or has a passion for Mexican or Italian food, you’ll be able to treat him right without worrying about your … [Read more...] about Best Father’s Day deals and freebies 2026
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1865 Fest Juneteenth Celebration
The annual 1865 Fest brings cultural family activities, live music, educational workshops, food and fun to Garfield Park for two days, June 19-20, 2026. Honoring the Juneteenth holiday that brought freedom to enslaved Americans two years after official emancipation in 1865, the free events connect … [Read more...] about 1865 Fest Juneteenth Celebration
Jamba celebrates National Smoothie Day with $1 smoothies
Sip on savings at Jamba! Summer and smoothies are the perfect pairing for a refreshing break. With so many fruitful options on the menu, Jamba is the perfect stop on a hot summer day to chill out and enjoy a delicious smoothie. And the popular smoothie shop is celebrating National Smoothie Day … [Read more...] about Jamba celebrates National Smoothie Day with $1 smoothies
DuSable Museum Juneteenth Celebration
DuSable Black History Museum and Education Center celebrates Juneteenth, the oldest nationally recognized commemoration of the ending of slavery in the U.S., with an all-day Juneteenth Celebration on Friday, June 19, 2026. Yoga, horseback riding, a farmers' market and special … [Read more...] about DuSable Museum Juneteenth Celebration
57th Street Art Fair
For art lovers, the Chicago summer season officially kicks off with Hyde Park's beloved 57th Street Art Fair. The 78th annual 57th Street Art Fair is the first major art fair of the season. It opens on June 6-7, 2026. Stroll through Hyde Park's tree-lined thoroughfares and browse a … [Read more...] about 57th Street Art Fair
Chicago Pride Fest
Chicago is home to the nation's first recognized LGBTQ community and the annual Chicago Pride Fest is one of its most anticipated community events. The fest returns on June 20-21, 2026, with three stages of music, vendors, food, drinks and fun. Kicking off the weekend before the Chicago Pride … [Read more...] about Chicago Pride Fest
Old Town Art Fair
Kick off your summer at one of the first art fairs in the country. Old Town Art Fair supplies art, music, food, a children's corner and a garden walk in the historic Old Town Triangle Historic District on June 13 and 14, 2026. Roam through the charming streets of Old Town and view the work of … [Read more...] about Old Town Art Fair
Puerto Rican Festival
The Humboldt Park neighborhood will celebrate 45 years of Puerto Rican history, culture and art with the annual Puerto Rican Festival on June 11-14, 2026. The four-day fest will fill Division Street with the sights and sounds of Puerto Rico. The music, dance, art and food of Puerto Rico … [Read more...] about Puerto Rican Festival
Chicago Blues Festival
Chicago is home to the largest free blues festival in the world and this much-anticipated event draws fans from all over the world to experience the influential art form that was nurtured in the city. The Chicago Blues Festival returns to Millennium Park from June 5-7, 2026. This free … [Read more...] about Chicago Blues Festival
Do Division Street Fest
Division Street in West Town comes alive with live music, food, boutique sales, fashion shows and family fun with the annual Do Division Street Fest on May 29-31, 2026. One of the most anticipated summer music fests, Do Division Street Fest serves up an astonishing selection of local … [Read more...] about Do Division Street Fest
Celebrate German Culture at Chicago Maifest
Welcome spring at the traditional German celebration of the season, Maifest Chicago. The 26th annual festival runs from May 29 -31, 2026, in the heart of Chicago's German community in Lincoln Square. Chow down on lots of German food and witness a traditional keg tapping, maypole dancing … [Read more...] about Celebrate German Culture at Chicago Maifest
Andersonville Midsommarfest
One of the most beloved summer events is when the Andersonville neighborhood celebrates its Swedish heritage and culture with the 60th annual Andersonville Midsommarfest, from June 12 through June 14, 2026. One of Chicago's oldest and most anticipated street festivals, Andersonville … [Read more...] about Andersonville Midsommarfest
