Annual Festivals/Fairs » Chicago, IL

Annual Festivals/Fairs in Chicago, IL

Hot summer days and nights make the perfect backdrop for festival season in Chicago. Chicagoans young and old look forward to the warmer months when festivals and fairs are in peak season. Here's an insiders look on the top, can't-miss festivals for you to check out while in the Windy City.
Max 5 stars
My Rating
Rollover to rate this

Chicago Blues Festival

This legendary music festival is an annual summer staple on the Chicago festival scene that won't have you singin' the blues, we promise! Each year a different blues legend is showcased during this three-day musical event. Even if you're not a jazz aficionado the crowd energy is contagious and you'll be humming along before you know it. Chicagoans get into the spirit for this, amazingly, free public show. The festival runs Friday and Saturday from 11 a.m.-9:30 p.m. and Sunday from 11 a.m.-9 p.m. If you're in the Windy City towards the end of July it's an absolute can't-miss.

Chicago Annual Pride Parade

The LGBT (lesbian, gay, bisexual and transgender) population is a vibrant one in the city of Chicago. Each year the Pride Parade is an event the whole city enjoys each summer. The Pride Parade is scheduled each year the last Sunday in June and is held in East Lakeview. The parade kicks off at noon and proceeds east on Montrose Avenue and ends on Diversey Parkway. Parade entrants have the option of using a theme or slogan of their own choice with awards given to the best entrants. More than 800,000 spectactors gather annually to take in this colorful and fun-filled parade.


Taste of Chicago

Taste of Chicago is a summer tradition in Chicago and attracts thousands of tourists and visitors each year. It is dubbed the nation's premier outdoor food festival while simultaneously featuring the diversity of Chicago dining. With hundreds of local food and drink vendors, live music and drink tents it's no wonder "The Taste", as the locals call it, is so popular. Don't miss out on an opportunity to sample all sorts of local flavor and sumptuous cuisine with gorgeous Lake Michigan as a backdrop behind you. While food is the name of the game at The Taste, the live entertainment is just as fantastic. Past musical guests include the Counting Crows, Jewel and Jennifer Hudson.


Chicago Air & Water Show

If you happen to be visiting Chicago in the end of August, you will have the privilege of enjoying this incredibly impressive display of aeronautics on the shores of Lake Michigan. Technically situated on the lakeshore, this dazzling showcase of planes is viewable in most areas of Chicago. It's a wonderful (and free!) event to take in with the entire family. Just take note, if you plan to watch the show from the beach, be sure to head there nice and early - prime viewing seats get reserved quite early. Alternately, many people take to the water and check out the show from their boats. If this is up your alley, research different boat chartering services in the area to view the show by sea.

Taste of Randolph

In a city known for fabulous restaurants and fine dining, Taste of Randolph takes place on Chicago's most well-known restaurant row. Situated in the city's West Loop neighborhood, Taste of Randolph attracts upwards of 100,000 each year. Chicagoans and tourists alike enjoy Taste of Randolph for it's healthy dose of local flavor and one-of-a-kind offerings. The festival takes place on the six-block stretch of Randolph Street from Peoria Street to Racine Avenue, where festival-goers can dive into the city's finest hand crafted goods and most delicious eats, of course! The Taste of Randolph also features two unique stages of crowd pumping live