The Haute Seeker

10 Food Festivals That Are A True Taste of Chicago

Growing up, my family would rave about the Taste of Chicago. They would leave my hometown of Dayton, Oh early in the day to drive the 4 hours into the city for a day-long adventure of eating what they deemed, “the best food in Chicago.” I had heard these stories so often that I had to make that one of my first Chicago experiences when I moved to the city five years ago. I wasn’t impressed. It was crowded and overpriced; the only thing that was remotely interesting was the musical acts. Safe to say that I did not like my first “taste” of Chicago.

Inspired by everyday conversations on food, festivals, and my own experiences, I decided to create a list of some of my favorite food and drink festivals—as well as celebrations that I plan on attending this year that provide an authentic taste of Chicago. This list consists of diverse food trucks, eateries, and restaurants that showcase got their start at many of these neighborhood food festivals first and have now expanded to the Taste of Chicago stage, representing an unmatched food community that draws an estimated 1.4 million people every year.

This list is no shade to the world’s largest food festival, as the Taste consistently exposes millions of visitors and drives revenue for fantastic local restaurants and eateries. This list is for those who are looking to venture outside of the festival and explore intimate, true to the neighborhood food events. Check out the list of these ten food festivals that take place annually in Chicago.

1. Little Italy Festa- Taylor St.

August | Ashland and Taylor St. | Free


Get a Taste of Italian cuisine rich in history and heavy red sauces. Taylor Street is one of the most historic neighborhoods in Chicago. The area was the hub for Italian immigrants from the late 1800s to the 1950s and soon became Chicago’s “Official” Little Italy. The annual street festival continues to celebrate the history of the neighborhood through food from award-winning area restaurants, music, and family-friendly entertainment. For more information on this festival be sure to visit the event website.

2. Chicago Food Truck Festival

June | Gallagher Way | 3637 N Clark St. | Free


Budweiser’s Get a Taste of food trucks that the locals know and love on a daily basis. Plus, some smaller businesses looking for their next big break! Taste of America Food Truck Festival, powered by the Chicago Food Truck Festival makes its way to Wrigleyville this summer for one of the biggest food truck celebrations of the summer. The festival will feature 45+ food trucks plus musical performances, interactive games, and more. For a complete list of food truck vendors be sure to visit Chicago Food Truck Fest. Fiesta del Sol

3. Tacos Y Tamale

August | 837 W 16th St. | Free


Get a Taste of some of the city’s best tacos and tamales. What makes it a winner is the tender loving care that goes into the homemade tortillas and freshly seasoned meat. Tacos and Tamales located in Pilsen is a street fair based on a traditional market known as Tianguis; where authenticity is at the forefront for food, drink, music, shopping, & more. Attendees can expect the best and most authentic tacos and tamales that Chicago has to offer, plus local art installations, merchant vendors, a Modelo Beer Garden plus much more. Donations toward this event will benefit the Frida Kahlo Community Organization. Get the most out of Tacos and Tamales and RSVP for a free ticket and receive exclusive updates on this event before anyone else.

4. Fiesta Del Sol

July | 1400 W Cermak Rd. | Free


Get a Taste of everything, from cheap and savory churros to full fledge meals featuring some of the city’s best South and West Side taquerias, restaurants, and local eateries. Fiesta del Sol is one of the biggest Mexican food festivals in the city of Chicago. One of my favorite food and cultural festivals in Chicago, the family-friendly event draws over 1 million visitors over the course of four days every year. Annually, it brings live entertainment, local art, a variety of food, carnival rides, a children’s area, educational resources, and much more. Learn more about the largest fest in the Midwest by visiting Fiesta del

5. Chicago Japanese Matsuri

September | NewCity plaza | Free


Get a Taste of Authentic Japanese cuisine from one of the city’s most well-known Ramen spot. The Chicago Japanese Matsuri hosted by Kizuki Ramen & Izakaya and Japanese Culture Center – 日本文化会館  hosts the annual Japanese summer festival in Lincoln Park. Guests of the fest will enjoy authentic Japanese festival foods, cultural performances of Taiko drumming, Shodo/large-scale calligraphy, Traditional Martial Arts, Sumi-e ink painting, Cosplay contests, interactive cultural booths, and much more. For more information on this event, visit the festival website here.

6. Sangria Festival

August | Humboldt Park | 3021 W Division St. | $25 – $100

Get a Taste of some of the best sangria the city has to offer. Sangria Festival in Humboldt Park is the perfect Sunday that pairs over 20 handcrafted sangria with local food bits and a variety of live entertainment that will take you to a Spaniard-inspired paradise. Guests receive drink tickets included with the purchase of the event entry ticket, plus a commemorative glass that will have you reminiscing on the location long after it is over. For more information and to purchase your tickets, visit the Sangria Festival Chicago website. 

7. Taste of Greektown

August |Halsted and Van Buren | Free


Get a Taste of melt-in-your-mouth rotisserie skewed beef/lamb better known as a “gyro, “an iconic Chicago food, plus other Mediterranean dishes and delights. Hellenic pride will take center stage when this acclaimed annual culinary fest on Halsted Street in Chicago’s happening West Loop returns for its 27th year. As most Chicagoans know, this strip of Halsted has been the epicenter of the city’s acclaimed Greek restaurant scene for decades. Quite simply, Taste of Greektown is a romantic weekend celebration for lovers of Mediterranean culture.

8. Square Roots Festival

July | Wilson to Montrose | $10 Donation

Get a Taste of 40 regional craft brews paired with Lincoln Squares’ finest restaurants. The one-of-a-kind craft beer, food, and music festival. The event boasts more than 70 acts on four stages (two indoor, two outdoor) and craft brews paired with local restaurants perfect for the whole family. For more information be sure to check out Square Roots

9. Taste of Black Chicago

August | 7351 S. Stony Island Ave | Free

Get a Taste of Black-owned and operated restaurants and caterers at a historic venue on the South Side of Chicago. Taste of Black Chicago was created to celebrate Black people’s contributions to Chicago’s world-class culinary arts scene. Black chefs, beverage makers, and other food-related vendors come together to celebrate a day of tasting, learning, and experiencing the unique food of black Chicagoans. To learn more about this event be sure to check out the event page.

10. Chicago Hot Dog Fest

August | Chicago History Museum | Stockon and LaSalle Dr. | $25 – $100

Get a Taste of Chicago’s most celebrated Chicago food—The Hot Dog. Make your way to the Chicago History Museum for a celebration of Chicago’s most loved food. Each vendor provides a unique menu and costs with Hot dogs range in price from $4 – $8. Grab your tickets early and save by visiting the event page here.

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