Chicago: Outdoor Events Summer 2011


City breaks aren’t everyone’s first choice for summer holidays, but for urban experience junkies, nothing could be better. Among big cities, Chicago is one of the very best for taking care of its citizens and visitors with a season packed full of outdoor events and many of them are absolutely free. Here are our picks for summer 2011…


Grant Park

Naturally, many of the city’s big summer draws happen in Chicago’s ‘front yard’, on the sprawling lakefront lawns of Grant Park, where free attractions dominate virtually every weekend of the season.



Chicago Blues Festival

Fittingly, the park’s free event calendar kicks off with the event that perhaps best defines the culture of the city, the Chicago Blues Festival. A weekend of world class acts on five stages (usually in the sunshine), the festival is simply the best way to enjoy the musical heritage of Chicago without paying the tourist trap blues bar prices.


When: June 10th – 12th

Front Porch stage at Chicago Blues Festival

Front Porch stage at Chicago Blues Festival © 2010 City of Chicago



Taste of Chicago

Next up the city tickles the taste buds with a Taste of Chicago, the world’s largest food festival. Fifty nine restaurants representing the culinary cultures of Chicago’s many diverse neighbourhoods come to one place to share their wares with six $2 sample dishes. If you can move around after filling your face with an endless array of local delicacies, there are chef demonstrations and plenty of musical entertainment to keep you occupied. Possibly thebest week-and-a-half to visit the Windy City.


When: June 24th – July 3rd

Taste of Chicago welcome sign by jstuppy on Flickr

Taste of Chicago welcome sign by jstuppy on Flickr



Grant Park Music Festival

Spread out among many other events over two months, the Grant Park Music Festival brings classical music to the people in the auspicious environs of the Frank Gehry-designed Jay Pritzker Pavillion. Beginning with Berlioz and Ravel on the 15thJune, the park’s own orchestra will take on everything from Mahler to Broadway hits, opera to Latin orchestral works, during the course of the summer. If you have a packed evening’s schedule, open rehearsals can be seen on the days preceding most concerts.


When: various dates between June 15th and August 20th

Jay Pritzker Pavillion at night © Andrew Bowman

Jay Pritzker Pavillion at night by Andrew Bowman



Gold Coast Art Fair

Showcasing over 350 artists from around the world alongside 20 emerging talents from the School of the Art Institute of Chicago, the Gold Coast Art Fair is a prime opportunity to get hold of some original, high quality artwork. Pieces range from a mere $25 to a whopping $25,000, but if you get up early, you can bag a discount on many works between 9:00 and 10:00 AM. A speed painter and tons of kids activities (scavenger hunt, Make-A-Messterpiece) are also on site, making the event very family friendly.


When: July 9th and 10th

Chicago Jazz Festival

When the heat starts to die down, Grant Park spreads the cool vibes throughout Labor Day Weekend with the 33rd annual Chicago Jazz Festival. Though things kick off inside at the Chicago Cultural Center on the afternoon of the 1st, most of the festival takes place on various points around the park with all-day entertainment across four stages. Every colour of jazz spectrum is covered and every generation represented. The perfect end to a city summer.


When: September 1st – 4th

Chicago Jazz Festival audience in Grant Park by Andrew Bowman

Chicago Jazz Festival audience in Grant Park © Andrew Bowman



Elsewhere around the city…

This weekend, the nearby downtown area around Lake Street and Michigan Avenue plays host to the Eastside Millenium Art Festival, a kind of smaller warm-up act for Grant Park’s Gold Coast fair. Demonstrations, artist chats, and music make for a lively atmosphere in which to browse the art on display. A special showcase of artwork created by participants in Chicago’s Special Olympics will also be shown this year.


When: June 3rd – 5th

Hyde Park

Also this weekend, the 57th Street Art Fair takes place in the Hyde Park neighbourhood. The city’s oldest and friendliest juried art fair offers works in all kinds of mediums from painting to photography, glassware and sculpture to leatherwork and printmaking. For a guided tour with advice, sign up for the fair’s ‘Boot camp’ and learn a little about buying art to suit your own budget and surroundings.


When: June 4th – 5th

House in Hyde Park, Chicago by Sampete

House in Hyde Park, Chicago © Sampete |


Hyde Park also holds its own rather prestigious Jazz Festival at the very end of summer. Though much of it takes place inside at various venues, there’s outdoor action on the James Wagner Main Stage in the Midway Plaisance park.

When: September 24th – 25th Last year’s event:

Wicker Park

Not exactly free, but well worth it for the paltry $5 donation, Wicker Park Fest brings three stages of live bands and DJs to the streets of the city’s most perennially hip neighbourhood. With a line-up as diverse and distracting as the great restaurants and arty boutiques of the area there’s something for everyone and it’s a great place to discover new music.


When: July 23rd – 24th

Wicker Park mural by Andrew Bowman

Wicker Park mural © Andrew Bowman


A little later, at the beginning of September, the Renegade Craft Fair also comes to its natural home in Wicker Park. 300 indie artisans of handmade goods descend on Division Street for two full days of crafty fun. Jewellery, artwork, stationery, clothing and much more can be found against a backdrop of live music, street food and hands-on workshops.

When: September 10th – 11th

Renegade Craft Fair Chicago by dirty black chucks on Flickr

Renegade Craft Fair Chicago by dirty black chucks on Flickr


Thanks to Flickr photographers dirty black chucks and jstuppy. Header image by Andrew Bowman.

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