10 Chicago Festivals and Events to Attend this Year

10 Chicago Festivals and Events to Attend this Year

Written by; Erica Zazo

It’s that time of year again: Festival season in the city.

Outdoor festivals, fairs and pop-ups, and community-oriented events are arguably one of Sandhill Coffee’s favorite ways to spend time in Chicago. Because, really, what’s better than pulling up to a street festival with great music, local vendors, delicious food – and of course, good coffee?
Last year, we shared a number of outdoor events around the Midwest, and this year, we’re showcasing the best of Chicago-specific events. We hope this list of outdoor music festivals, art fairs, and food truck-filled street festivals makes it that much easier to get outside and enjoy your summer and fall.
Here are our favorite events happening in and around Chicago in 2022.

Psst…This season marks our second summer with the Sandhill Mobile Cafe! Events marked with ** below are events the mobile cafe will make an appearance at this summer.



  • **Batavia Farmer’s Market
  • Batavia – Saturday, May 28 - October

    Food and drink vendors, artists, and local community organizations gather in Batavia for the Farmer’s Market every Saturday of the Summer. On North River Street between Wilson Street and Spring Street, enjoy views of the Fox River while exploring makers’ booths, visiting local shops, or simply enjoying a stroll through downtown Batavia.

  • **Lemont Legends Cruise Nights
  • Lemont – Wednesday nights, June 1 - 31

    Classic, vintage, and specialty cars take over the streets of downtown Lemont at the month-long Lemont Legends Cruise Nights – each Wednesday in June. From exotic cars and motorcycles to farm tractors and 4x4s, car enthusiasts have the chance to see it all. 

  • Taste of Chicago – Neighborhood Pop-ups
  • Citywide – Saturdays, June 11, 18 & 25

    Price: Free

    Love food trucks? Then this is your event. Taste of Chicago’s neighborhood pop-ups is a micro-fest series that gathers food trucks from around the city in various neighborhoods – giving Chicagoans a bite-sized taste of the classic lakefront fest in their own backyards.

  • Blues Fest
  • Citywide and in Millennium Park – June 9 - June 12

    Price: Free

    Hear the best blues music in the heart of Chicago. The multi-neighborhood and citywide festival feature all types of genres of blues including soul, R&B, gospel, hip hop, rock, and more. The diverse and vibrant music festival is a Chicago classic, and, in our opinion, one that every true Chicagoan should experience in their lifetime.

  • Ravenswood On Tap
  • Ravenswood neighborhood – June 11 - 12

    Price: $10 suggested donation, per person, with beer tickets available for sale

    Malt Row in the Ravenswood neighborhood of Chicago is one of the country’s best craft brewing communities you’ll find. Sip some of the cultural ferment with Ravenswood On Tap, At the two-day outdoor festival, enjoy brews from favorites like Dovetail, Begyle, and Spiteful Brewing, cocktails from KOVAL Distillery, and many others. Plus, there’s axe throwing, live music, local vendors, and eats from popular food vendors.

  • Gold Coast Art Fair
  • Gold Coast neighborhood – June 18 - June 19

    Price: $10 admission per person, per day, will benefit Chicago Furniture Bank

    See and shop the creative works of over 200 local artists at the Gold Coast Art Fair. From paintings and jewelry to ceramics and textiles, the festival is one of the largest art fairs in the city. You’ll also find live music stages, beer tents, food vendors, and other festival entertainment at the two-day event. 

  • Taste of Chicago
  • Grant Park – July 8 - 10

    Price: Free

    Chances are if you live in Chicago, you love food. If so, you have to take advantage of The Taste of Chicago – the world’s largest free-admission outdoor food festival. Over the three-day festival, 30–40 eateries and food trucks feature the best notable and emerging chefs from around the city in one central location at Grant Park – making it easy to take a bite of local favorites without the hassle of running around town. 

  • Roscoe Village Burger Fest
  • Roscoe Village neighborhood – July 15 - 17

    Price: $10 suggested donation, per person, per day, will benefit the Lakeview Roscoe Village Chamber of Commerce

    Get ready for the smell of charcoal grills and greasy burgers. This street fest features the best burgers you can find in the city – all on one street. In addition to the classic Midwest grill-out, this fest features drinks, live music, and activities for kids all day long.

  • Bike The Drive
  • Lakeshore Drive – September 4

    Price: $18 for youth; $48 for adults; $70 for day-of admission

    Love to bike? Consider signing up for this lake-side bike ride benefitting the Active Transportation Alliance, a non-profit advocacy organization working to improve conditions for walking, biking, and public transit throughout Chicagoland. 16,000+ riders take over Lakeshore drive for a 30-mile scenic ride along Lake Michigan. An afterparty with vendors, drinks, food, and music greets riders at the finish line. 

  • Chicago Beer Festival
  • Field Museum – October (date TBD)

    Price: Early admission is $65; General admission is $50

    Grab a beer among dinosaurs and friends at The Chicago Beer Festival – the biggest citywide brewery gathering in Chicago. At the iconic Field Museum, sample rare, unique, and classic beers from over 65 breweries. Tickets for the event grant attendees access to the Field Museum exhibits as well.

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