Summer Festival Guide

Events, Things to Do — By adimarcial on April 5, 2010 at 1:17 am

The crocuses have begun to sprout, the trees have buds, and those birds are chirping like crazy. Winter may finally be behind us, and this means Chicago has come alive! Before you know it summer will be in full swing, but before you make any major plans check out the Chicago summer festival line up. Every weekend features a neighborhood festival, but it is the big ones you will not want to miss. This is the best time to catch live music and Chicago’s best food and artisans, all while enjoying the lovely sunshine. There are an overwhelming amount to choose from, but below is truly the best of the best, so mark your calendars!


Chicago Blues Festival: June 11th-13th, FREE

The annual Chicago Blues Festival draws music lovers from all over the country to Grant Park every summer. This year the festival will have six stages and 60 performances, featuring world-renowned artists like Jimmy Dawkins and Bobby Rush, among many others. This festival is lively, family-friendly, and a great cultural experience at absolutely no cost!  A great way to kick off the summer.

Chicago Pride Fest: June 25th-26th

Get ready for wild and colorful good time in the heart of Boystown at the annual Pride Fest. Celebrating the gay and lesbian community, the festival features two stages of entertainment, food, and arts & crafts vendors. The main attraction is the rowdy and raucous Pride Parade on Sunday, featuring local community members, businesses, and organizations who are supporters of community. It is a crazy early summer party where all are accepted and scantily-clad is the norm.

Courtesy of Brandon Cirillo

Taste of Chicago: June 25th – July 5th

Not only is this Chicago’s biggest event of the year, it is the world’s largest outdoor food festival, with over 70 vendors. Held in the picturesque Grant Park, the festival attracts close to 3 million visitors each year. The best of Chicago cuisine can be tested over the 10 days, so get ready to eat! Besides the delicious food, the festival features free music concerts, completely open to the public. Drawing big names in the music industry, these outdoor concerts are certainly not to be missed.


African-Caribbean International Festival of Life: July 2nd-5th

Held in the beautiful Washington Park in Hyde Park, this annual festival draws about 150,000 people to experience calypso and reggae music, as well as food, arts and crafts and exhibits. The cool vibe has attracted more people every year that this year another day was added for even more entertainment. A great cultural experience for the whole family.

Pitchfork: July 16th – 18th

This Chicago Indie music festival features over 40 bands across three stages in Union Park. Enjoy some of today’s best bands in what is known for being an unpretentious and easy-going outdoor festival, at a very reasonable price. This years line-up includes Broken Social Scene, Modest Mouse, Panda Bear of Animal Collective, and many more. This is the perfect warm-up for Lollapalooza later in the summer.

Courtesy of jcbehm

Sheffield Garden Walk: July 17-18

Chicago is in full bloom by this point in the summer, and the Sheffield Garden Walk sets up over 90 self-guided tours of some of Chicago’s best gardens. Festival goers will also enjoy vendors, food, and live entertainment by internationally recognized bands, including Rusted Root.


Lollapalooza: August 6th-8th

No music festival can surpass Perry Ferrell’s monster festival, featuring over 100 acts. With so many performances that take over Grant Park each summer, there is simply something for everybody. The rumored main stage performances (i.e. Soundgarden, the Strokes, Green Day, Lady Gaga) are enough to see how big this thing actually is, but the small stages bring some of music’s best smaller acts in all genres of music. This year will also feature a new food experience, with our very own Graham Elliot Bowles¬† hoping to bring a more local flair. This festival is nothing short of a true down n’ dirty music experience that will leave you amazed and full of stories.

Courtesy of J. Longstreet

Chicago Air & Water Show: August 14-15, FREE

This annual event is great for the whole family, and has grown tremendously from its beginning, now drawing several million people over the course of two days. Take a picnic and blanket down to North Avenue or Oak Street Beach to watch planes and boats perform incredible stunts and displays. It is a great way to spend a late summer afternoon.


Chicago Jazz Festival: September 4th-5th, FREE

This is the longest running music festival held on the Chicago lakefront. The festival features the best of Chicago’s jazz performers, as well as internationally acclaimed artists. The festival is perfect for a picnic and wine during those final days of summer, and is completely free of charge.

Courtesy of karaian

Festival de La Villita: September 10th-12th

Set in Little Village, this remarkable festival celebrates Mexican Independence Day, drawing thousands of visitors for performances, authentic Mexican food, unique artisans, a dance pavilion, and the 26th Street Parade. The famous parade is the city’s second largest parade and the largest Hispanic cultural celebration. The festival is great for children and families.

Tags: Chicago, festivals, music, summer