Chicago on the Cheap

Deals, discounts and free events in Chicago

Expired

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

Posted by Living on the Cheap Filed Under: Expired

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

Chicago Pride Parade

The Chicago Pride Parade is one of the oldest and largest pride parades in the country. Filled with floats, music, local celebrities and performers, Chicago's Pride Parade is one of the most anticipated events in Pride Month. The 55th annual Chicago Pride Parade kicks off on June 28, … [Read more...] about Chicago Pride Parade

Taste of Randolph Street

Over 16 restaurants and two stages of live acts will commemorate the 28th anniversary of the Taste of Randolph on June 19-21, 2026. The highly anticipated festival features some of the best bites in the West Loop neighborhood. Expect to eat and dance your way through three days of events, … [Read more...] about Taste of Randolph Street

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

Memorial Day Weekend freebies and deals 2026

Memorial Day is a day for parades and remembrance, picnics and barbecues — and lots of deals! Many restaurants and retailers are offering discounts and freebies over the Memorial Day weekend. Some of the deals are only for military personnel or veterans, while others are available to all. Some of … [Read more...] about Memorial Day Weekend freebies and deals 2026

Posted by Living on the Cheap Filed Under: Expired

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

Member of the Living on the Cheap Network

Chicago on the Cheap is a member of Living on the Cheap, a network of websites published by frugalistas, journalists and consumer advocates. Find practical advice on saving money on groceries, travel and shopping, plus tips from our experts on how to live the good life for less at Living on the Cheap.

Living on the Cheap in the media