Chicago Summer Street Festival Guide 2019

When it comes to summer festivals, Chicago is the place to be. Whether you’re a self-proclaimed foodie, an ardent music lover, or someone who just likes to explore all that Chicago has to offer during the summer months, there are street fairs, events, and fests perfect for you, on practically every weekend of the summer.

Of course, with so many amazing events on your radar, it can be hard to keep track of them all. To help, Real Group RE has compiled a list of local favorites and new additions for the year.

Looking to plan your summer of fun? Here’s our handy guide to the best festivals in the city...

Our Favorite Summer Festivals, 2019


Grant Park Music Festival | June 12 – August 17 | Grant Park

With performances of Mozart, Brahms, and Haydn, this year’s Grant Park Music Festival is a must visit for anyone with an interest in classical music.


Taste of Randolph | June 14 – 16 | West Loop

Visitors can explore the “foodie row” of Chicago and enjoy live music and good eats from some of the city’s best food options.


Chicago Pride Fest & Parade | June 22 – 23, June 30 | Boystown

The month of June is LGBTQ Pride Month! A two-day street festival is held the weekend before the parade, both of which celebrate LGBTQ life, culture, and community.


Ravenswood On Tap | June 22 – 23 | Ravenswood & Berteau

Home to Malt Row, Ravenswood has one of the best craft brewing communities in the country, and they celebrate each summer with Ravenswood on Tap.


Chicago Food Truck Festival | June 22 – 23 | South Loop

Whether you’re looking for delicious tacos or a buttery lobster roll, the Chicago Food Truck Festival is the largest in the state and offers a number of crave-worthy options.  


Millennium Art Festival | June 28 – 30 | Millennium Park

Bringing the “art of happiness to the heart of downtown Chicago”, Millennium Art Festival brings over 100 artists to the park, alongside food and live performance for the ultimate art filled experience.



Fourth of July Fireworks at Navy Pier | July 4 | Navy Pier

What better way to celebrate America’s founding than by hanging out with friends and family on Navy Pier, watching the skyline and the fireworks?


Taste of Chicago | July 10 – 14 | Grant Park

Always wanted to try a little bit of all the food Chicago has to offer? Taste of Chicago’s outdoor food festival will leave you licking your fingers and wanting to go back for more.


Irish American Heritage Festival | July 12 – 14 | Irish American Heritage Center

Feeling the luck of the Irish? The Irish American Heritage Festival brings local and international Irish culture, food, and fun to Chicago.


Windy City Smokeout | July 12 –14 | River West

Bringing some of the best pitmasters in the country to the city of Chicago, Windy City Smokeout highlights all things good about barbecue, including the food, the drinks, and the music.


Southport Art Fest | July 13-14 | Wrigleyville

Southport Art Fest highlights artwork from many different media, with over 100 of the city’s most diverse artists making appearances during this two-day festival.


Roscoe Village Burger Fest | July 13 – 14 | Roscoe Village

Whether you like them thick and juicy, or thin and crispy, Roscoe Village’s Burger fest is perfect for those wanting to taste some of the best burgers in all of Chicago.


Pitchfork Music Festival | July 19 – 21 | Union Park

With big names like HAIM, Robyn, and the Isley Brothers headlining, and even Stereolab making an appearance, Union Park’s three day music fest isn’t one you’ll want to miss.


Taste of River North | July 19 – 21 | Ward Park

All things River North come together for this three-day festival, including fun, food, and music for all ages.


Chicago Yacht Club Race to Mackinac | July 13| Navy Pier, Chicago Lighthouse

In its 111th year, the race to Mackinac Island is one of the biggest boating days of the year. Want to watch? Head to any beach or hang out at Navy Pier to see them set sail.


Sheffield Music Fest & Garden Walk | July 19– 21 | Sheffield & Webster

Sheffield Music Fest & Garden walk features over 80 gardens sure to inspire and impress, complete with tours and architecture that even those without green thumbs are sure to love.


Chicago Craft Beer Festival | July 20 – 21 | Lincoln Park

Whether you prefer a stout or an IPA, Chicago’s Craft Beer Festival has a taste of everything, with daily samplings, great food vendors, and over 70 specialty beers on hand.


Wicker Park Fest | July 26 – 28 | Wicker Park

Reflecting this community’s musical heritage and eclectic nightlife, Wicker Park Fest brings over 50 bands to four stages, ensuring that everyone who comes will be dancing the day away.


Taste of Lincoln Avenue | July 27 – 26 | Lincoln & Fullerton

Spanning over six city blocks, Taste of Lincoln Avenue celebrates 36 years of music, food, and crafts for all Chicagoans to enjoy.



Lollapalooza | August 1 – 4 | Grant Park

For the fourth year in a row, Lollapalooza will be four-day festival with headliners including Ariana Grande, Childish Gambino, and more.

Jeff Fest | August 2 – 4 | Jefferson Memorial Park

Dubbing themselves as having “something for everyone, every genre”, Jefferson Park Fest has become one of the most anticipated music festivals in all of Chicagoland.


Retro on Roscoe | August 9 – 11 | Roscoe Village

If you’re ready to step back in time, then come to Retro on Roscoe! With over 50 antique cars and antique vendors, the entire family can feel like time travelers.


Tastemaker Chicago | August 16 – 18 | Revel Space at Fulton Market

Top chefs from Chicago and Toronto have to come together to bring off-menu items to the West Loop in one of the most intimate summer festivals in Chicago.


Chicago Air & Water Show | August 17 – 18 | North Avenue Beach

The Chicago Air & Water show brings daredevil air tricks to the city’s beach and skyline. You’ll see the best views along Chicago’s Lakefront, with North Avenue Beach being the focal point.


Chicago Jazz Festival | August 23 – September 1 | Millennium Park

No matter if you’re a John Coltrane fan, or a Duke Ellington fanatic, Chicago’s Jazz Festival brings everything jazz to the masses for one week in August.


Great American Lobster Fest | August 30 – September 1 | Navy Pier

All the way from the cold waters of the Atlantic comes a smorgasbord of fresh seafood just waiting to be eaten at the Great American Lobster Fest.


African Festival of the Arts | August 30 – September 2 | Washington Park

Visitors will be taken across the Diaspora over Labor Day weekend, where a simulated African village is built – complete with drumming, hand-woven fabrics, and collectible artifacts.



Riot Fest | September 13 – 15 | Douglas Park

Celebrate Riot Fest’s 15th anniversary with headliners including Blink-182, Bikini Kill, the Raconteurs and more over their three-day lineup.


Lakeview Festival of the Arts | September 14 – 15 | Lakeview

You’ll be able to check out the work of over 150 artists at the Lakeview Festival of the Arts, which includes painting, sculpture, furniture, jewelry, and more.


Chicago Bourbon and Barbecue Fest | September 14 – 15 | Roscoe Village

For two days you can indulge in some of the city’s best spirits and barbecue at the third annual Chicago Bourbon and Barbecue Fest.


Bon Appetit’s Chicago Gourmet | September 27 – 29 | Loop

Chicago Gourmet offers visitors culinary demos from tops chefs around the country and tents with small dishes and beverages, making it a must-see for any true foodie.


Discover Something New This Summer

Ready to get your summer on? Or ready to move closer to your favorite summer festival so you can experience all the great things of your favorite neighborhood year round? Reach out to Real Group RE – with tons of expertise and connections, Real Group can ensure that you’re living your best summer life every day of the year.

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