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Chicago Chicago Local Guides

(featured photo by Maddie Casey)

Your guide to August & September events has arrived! Keep for the second installment of our festival picks, sure to keep your calendar booked all season long. 

Revisit part 1 here.


Chicago Hot Dog Fest
August 5-7

Head down to Clark and LaSalle streets for hot dogs like you’ve never tasted before, along with live music. (Free)

South Loop Beer & Cider Fest
August 6

Cool off from the summer heat by grabbing your crew for an afternoon of cold craft beers, hard ciders, food and live music.  (Starting at $15)

We Are Hip Hop Festival
August 6

Celebrate all things hip hop with MCs, DJs, breakdancers and spoken word performers. (Free)

Wrigleyville Summerfest
August 6-7

Head to the home of the Chicago Cubs for some food, beer and live music. (Free, $5 donation suggested)

Festa Italiana
August 18-21

Little Italy Chicago is hosting a four day festival…and challenging you to see how many meatballs and cannoli’s you can eat. (Free)

Chicago Air and Water Show
August 20-21

Head to the beach to watch these air and water daredevils perform jaw dropping stunts. (Free)

Taste of Greektown
August 27-28

Opa! Halsted is the epicenter of Chicago’s Greek restaurant scene. Make your way to the festival for some traditional greek food and drinks.  (Free)

Randolph Street Market
August 27 – 28

Discover quality vintage finds at America’s largest urban antique market. (Admission prices vary)

Bucktown Arts Fest
August 27 – 28

Bucktown art scene is bumpin’. Head down for a two day festival of art, music, craft beer and food. (Free, donations accepted)


North Coast Music Festival
Sept. 2-4

End summer with a bang! Gather your friends for some sick beats from all music genres. ($211)

Chicago’s Best Summer Wingfest
Sept. 5

All the chicken wings you can image that will have your taste buds “wingin’ out” .  ($40)

Shock Top Oyster Fest
Sept. 9-10

Beer and oysters to kick off the unofficial start to autumn. Don’t be shellfish, there is enough oysters for your entire crew to enjoy. ($7 donation)

World Music Festival
Sept. 9-25

Get a flavor of traditional and modern jams from all around the world during this 11 day music festival. (Free)

Riot Fest Chicago
Sept. 16-18

Rock out with this killer lineup set to perform at this years festival at Douglas Park. (Prices vary)

Sam Adam’s Lakeview Taco Fest
Sept. 17-18

There is no better way to compliment specialty tacos then with cold beers, music and lucha libre (Mexican wrestlers). (Free, $7 donation)

West Loop Art Fest
Sept. 17-18

Head to one of the hippest hoods in Chicago for all things art, music and food. ($10 donation)

City Made Fest
Sept. 18-19

Party hard with the locals and celebrate the city with craft beers, music, food and artists. (Free, $5 donation)

Oktoberfest Chicago
Sept. 23- 25

Oktoberfest in September! Head to Lakeview for beer, music and food. ($5)

West Town Food Truck Social
Sept. 24-25

While jamming out to local DJ spinning tunes; sample food from the best food trucks in Chicago. ($5 donation)