Summer Festival Calendar: A Guide to Chicago’s Popular Street Fests for 2014

The first sign of summer in Chicago has arrived with the Summer Festival Calendar busting out all over.  Here’s the skinny on some of the best of the fests…with more to come.

Click here for Show Me Chicago's annual list of more than 100 summer festivals and events for 2014.

Do-Division
May 30 - June 1, Division St from Ashland to Leavitt,: Fri, 5 p.m. to 10 p.m.; Sat & Sun, noon to 10 p.m., $5 donation.
fest1dodivPhoto credi: REP3.com

Do-Division Street Fest & Sidewalk Sale, with an estimated 70,000-plus fest-goers expected, kicks off Chicago's 2014 festival season. The annual street fest has it all with shopping, live music and family entertainment.  Spanning 10-city blocks, there's room to roam and take-in the great mix of live music (band lineups TBA), the Family Fun Fest, the Do-Fashion section, shopping, and, of course, food, crafts and art.  

Bottom line: Do-Division Street Fest is a great place to experience what Chicago street fests are all about and taste of what makes West Division (aka, "Do-Division") one of the hottest destination corridors in Chicago. Expect a heavy influx of millenniums, mixed with families and artsy types.

Wicker Park’s Green Music Fest
June 21-22,  Damen Ave b/w North and Schiller, noon to 10 p.m. both days, $5 donation. fest2greenPhoto credi: REP3.com

Go green at the environmentally-conscious Wicker Park's Green Music Fest  that sets itself apart from other fests by mixing great bands (lineups TBA) with environmentally-friendly production, eco-minded vendors and services, sustainability demonstrations, green arts and crafts.

Bottom line: Wicker Park's Green Music Fest celebrates the neighborhood's cultural roots featuring great music combined with a conscious eye toward the environment. Expect a hipster crowd from the neighborhood, lots of gen yer's along with like-minded fest lovers and a lack of pretense in the 'hood that's been home to the likes of Wilco, The Jesus Lizard and Trenchmouth.

West Fest
July 12-13,  Chicago Ave b/w Damen and Wood, noon to 10 p.m. both days, $5 donation.fest3westPhoto credi: REP3.com

The eclectic persona of the West Town neighborhood is alive and well at the West Fest, street fair. Named one of the "best" overall summer fests in Chicago by the Chicago Tribune with a "thumbs up" from music critic Greg Kot for the music line-ups, the annual fest is the place to go for music fans.  The fest also offers a Kid Fest and Pup Fest plus vendor booths from neighborhood retailers, restaurants, and artists.

Bottom line: The fest has a local vibe welcoming singles, dogs and families in the hot West Town 'hood that consists of several demographic areas including East Village, Wicker Park, Bucktown and Ukrainian Village. Daytime offers family fun with the evening heating up with more local cutting edge bands along with national touring acts on three stages (lineups TBA) followed by late into the night after-parties at Empty Bottle.

Taste of River North
July 18-20, Ward Park (Kingsbury & Erie), Fri, 5 p.m, to 10 p.m.; Sat, noon to 10 p.m.; Sun, 11 a.m. to 8 p.m., $5 donation. fest4tasterivernorthPhoto credit: Taste of River North.

The Taste of River North gets more popular each year, with a record 40,000-plus attending in 2013.  Now in its 13th season, ToRN  takes place in the picturesque riverfront setting of Ward Park.  A selection of popular restaurants (partial lineups posted on their website) is the big draw along with world-class galleries, non-stop live music, from Chicago party bands like Second Hand Smoke (Sublime tribute), Funky Monks (Red Hot Chili Peppers tribute) and Sixteen Candles (80s tribute) with more of this year's lineup  posted on their website).

Bottom line: ToRN offers a fun, somewhat refined, perhaps more upscale, alternative to Taste of Chicago (July 9-13).

Wicker Park Fest,  July 26 - 27, Milwaukee Ave b/w North and Paulina, noon to 10 p.m. both days, $5 donation. fest5wickerparkfestPhoto credit: Wicker Park Fest

If Lollapalooza or Pitchfork aren't in your budget, Wicker Park Fest is a great alternative. Described as the "best street fest all summer" by Chicago Magazine in 2013, Wicker Park Fest is expecting to host over 70,000 this year as word of mouth spreads the buzz on their stellar live music bill that encompasses three stages and a kid's stage (lineups TBA).  If that's not enough Wicker Park Fest Arts area and Wicker Park Fest Kids are happening fests-within the Wicker Part Fest.

Bottom line: Historic yet hip, Chicago's Wicker Park and Bucktown district is the backdrop for diverse art, trendy restaurants, family activities and a cutting-edge fashion scene - all represented front and center at the fest.

Chicago Food Social, August 23 - 24, Kendall College (parking lot), 900 Branch Street, 11 a.m. to 10 p.m. $5 admission.
fest6chicagofoodsocialPhoto credit: REP3.com

Chicago Food Social  is the re-visioned version the popular Food Truck Social (2011 and 2012) that featured Chicago's most popular food trucks.  The renamed fest has added a curated group of notable chef-driven local restaurant vendors and chef demonstrations with prominent guest celebrity chefs along with the food trucks. This year's Top Chef finalist and Michelin Star-awarded Carlos Gaytan, chef-owner of Mexique in West Town, is just one of the chefs that will be on-hand.

Bottom line: Communal dining, hands-on culinary activities for adults and kids, and a live music stage set the scene.  Plus it's for a good cause with proceeds benefiting Share Our Strength's Cooking Matters, a national non-profit attempting to end childhood hunger in America.

Chicago Fashion Fest, August 23 and 24. Division Street from Wolcott to Paulina, noon to 10 p.m., $5 donation.

fest7chicagofashionfestPhoto credit: Chicago Fashion Fest

On the same weekend as Chicago Social Fest, Chicago dons its passion for fashion with Chicago Fashion Fest—a  two-day fashion extravaganza showcasing the best of Chicago's designers, boutiques and trends.  The fest features a bleachered-in runway stage where bands and DJs set the tone as models tout what's trending for the end of summer and fall 2014.  Over 20 unique fashion runway shows will include: vintage, kids, teen, back-to-school, curvaceous, bridal, 'Do-Fashion' (with only Division Street boutiques) and more.  Plus, each night, starting at 8 p.m., Wicker Park after Dark--a charity-hosted red carpet extravaganza is expected to bring out the paparazzi, VIPs and celebs.

Bottom line: Perfect for shoppers and fashion fans offering, in addition to the runaway, an on-site "Shopper's Row" featuring an expected 50 exclusive booths of local fashion designers, boutiques, and salons, plus food, drink and a dedicated kids area.

 Design Harvest, September 20 - 21, Grand Ave b/w Damen & Wood, 11 a.m. to 6 p.m. both days, $5 donation.
fest8designharvest
Photo credit: REP3.com

Check out the best of contemporary and sustainable design at Design Harvest in Grand Avenue's Design District, where you'll find local makers and collectors of design objects in a pop-up shop marketplace setting that showcases both home and garden.  You'll find vintage and antique objects from the past mixed with environmentally-friendly and modern goods handcrafted by Chicago designers.

Bottom line: Expect a laid-back atmosphere at this one-of-a-kind street fest where you can sip wine, go for a hay ride and listen to music.

West Town Art Walk, October, 3 - 4
Chicago Avenue between Leavitt and Ogden / Milwaukee, Fri, 5 p.m. to 10 p.m.; Sat, 11 a.m. to 10 p.m.
fest9westtownartwalk

Photo credit: REP3.com

This gallery art walk pops up in dozens of West Town's storefronts showcasing visual art, performance art, music, culinary arts and fashion along the Chicago Avenue corridor. West Town's fourth annual, West Town Art Walk will also feature a "party central" tented location with beer and wine, along with a designer "lounge" area, and DJs.  Plus, there's still more with trolleys, bike rickshaws and an after-party.

Bottom line: Not too hot, and not too cold. As fall envelops the city, it's the perfect time of the year to get out and enjoy a leisurely art walk and experience this vibrant arts community.  A G-rated all-ages fest offering good times for families, artsy types, fashionistas and almost anyone.

Click here for more festivals and events for May through September 2014.

Subscribe to Show Me Chicago by email

If you would like to keep in touch with what's happening in Chicago, like us on Facebook or subscribe to Show Me Chicago by email. To subscribe, type your email address in the box below and click the "create subscription" button. Our list is completely spam free, and you can opt out at any time.

Leave a comment

  • ChicagoNow is full of win

    Welcome to ChicagoNow.

    Meet our bloggers,
    post comments, or
    pitch your blog idea.

  • Advertisement:
  • Meet The Blogger

    Carole Kuhrt Brewer

    Arts and Entertainment Reporter for media since 1997.

  • Recent posts

  • Categories

  • Tags

  • Monthly Archives

  • Latest on ChicagoNow

  • Advertisement:
  • Fresh Chicago News