Arts/Neighborhood Fests & Events + Chicago= Family Fun for All!

Throughout Chicagoland, the one thing that can be guaranteed are the fests, and family fun!  You are sure to find something that you will enjoy!  In this blog, we will explore some of the many upcoming and ‘artsy’ & neighborhood fests, and other events coming up in and around Chicago.  Later blogs will focus on food and music fests.  We’re in for another exciting summer!


Now through Oct/Nov: Farmers’ Street Markets 

From Lincoln Square, to Andersonville, to Austin and Garfield Park markets, there are several to choose from! 


Shop locally grown produce, artisanal goods, ready-to-eat foods, and more at these neighborhood farmers markets.  Click HERE for more information. 


May 25-26: Randolph Street Market – West Loop (Fulton Market) 

For the vintage lovers, this is for you!  This festival features 200 top independent vendors, makers, dealers, and designers across America. Randolph Street Market features a high-quality selection of antiques and modern goods ranging from fashion to art, jewelry, décor, retro home furnishings, and more. Click HERE for more information.


May 31, June 1-2: Do Division Street Fest

Where: Division Street, between Damen Avenue and Leavitt Street, Chicago.

This Wicker Park street festival has events planned for all ages.  Local food and retail vendors will be featured, along with music performances and a fashion show. “Family Fun Fest” is a part of the festivities, focused on children’s entertainment.  There will be a petting zoo, an inflatable slide and kids’ music. Click HERE for more information about the fest.

June – September:  Summer Workouts – Millennium Park 

Millennium Park provides a unique outdoor studio where Chicagoans and visitors alike can be energized in the form of Summer Workouts.  On most Saturdays, guests can enjoy free 45-minute classes on the Great Lawn, including yoga, strength training, Pilates, and Zumba®.  Click HERE for class schedules and more information. 


June 6-9: Puerto Rican Fest – Humboldt Park

Puerto Rican Fest, or Fiestas Patronales Puertorriqueñas is an annual cultural celebration, complete with carnival rides, music, food favorites, a parade, and more.  Click HERE for details and tickets. 

June 7-9: Andersonville Midsommarfest 

Where:  Clark Street, from Foster Avenue to Gregory Street

This community event is an annual celebration of Andersonville.  Local vendors, food and music will take over the streets. For more information, click HERE.


June 8-9: Old Town Art Fair

Where:  1763 N. North Park Ave, Chicago 

On this June weekend, the Old Town Triangle Historical District transforms into a fine art wonderland, featuring more than 200 artists from around the country, there to sell and display their art. Get the details, HERE.


June 8-9: Wells Street Art Fest 

Where:  Wells Street, between North Avenue and Division Street, Chicago

Art lovers can venture down into Old Town and shop from artists from around the continent. The festival features food and drink vendors, music, entertainment, and a children’s play area. Find out more information about the event HERE.


June 15: Juneteenth Village Fest – North Lawndale 

Where:  (Anna and Fredrick) Douglass Park, 1401 S Sacramento, Chicago 

Juneteenth Village Fest highlights Black communities’ resilience, solidarity, culture, and progress in Chicago and around the U.S. The Fest features musical performances, food vendors, a Ferris wheel, carnival rides, and community-based organizations.  Find out all about this year’s celebration, HERE


June 22-23: Chicago Pride Fest 

Where: Northalsted on Halsted Street from Addison to Grace St.

This legendary Chicago street festival is celebrated by thousands to celebrate LGBTQ+ during Pride Month.  Held in Lakeview annually, it features live music at three stages, food and drinks, art vendors, giveaways, and so much more. Find out more information by clicking HERE



July 6-7: NASCAR Street Races 

Where:  Grant Park, Chicago

The Chicago Street Race is a unique two-day sports and entertainment even with a festival-like atmosphere.  This year’s headliners include Keith Urban, The Chainsmokers, The Black Keys and Lauren Alaina.  Visit for all you need to know about the upcoming races. 

August 7, 2024: Chicago Ducky Derby

people lined up along the Chicago Riverwalk watching Chicago's annual summer Ducky Derby eventPhoto: Shutterstock

Where:  401 N Michigan Ave, Chicago 

As with every summer, tens of thousands of yellow ducks will splash into the Chicago River in a nail-biting race to the finish line.  This special and fun event is held to raise money for the Special Olympics. Many line up on bridges and along the riverwalk to witness the spectacle, with many adopting several ducks, hoping to win big and enjoy supporting the Special Olympics. Find out more HERE.

Parking headaches. Traffic navigation. There is nothing better than the convenience of having your own relaxing transportation to and from any of these fests and events, with door-to-door service for you and your family.  Click HERE to make your transportation reservation with Fellowship Fleet Limousine and Bus Company!

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