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 festivals that I plan on attending this year) that give you a true taste of Chicago. Many of these festivals were the first to host some of the food trucks and eateries that showcase at the Taste of Chicago year after year. They have built a reputation within many of Chicago’s communities have the opportunity to feature their items to a broader audience (an estimated 1.4 million people).

This list is no shade to the OG of food festivals, 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 out of their comfort zones and attend festivals that are a good value and inspire great vibes.



Little Italy Festa- Taylor St.

Thursday – Sunday | August 16th – 19th | Time Varies

Ashland and Taylor St. | Free

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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.

Budweiser’s Taste America Food Truck Festival powered by Chicago Food Truck Festival

Saturday | July 28th | 5:00 p.m. – 10:00 p.m.

Gallagher Way (Wrigley Field) | 3637 N Clark St.| Free

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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

Tacos Y Tamale

Friday – Sunday | July 20th – 22nd | Time Varies

837 W 16th St. | Free

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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 off a traditional market known as Tianguis; where authenticity is at the forefront for our 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.

 

Fiesta Del Sol

Thursday – Sunday| July 27th – 30th | Time Varies

1400 W Cermak Rd.| Free

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Get a Taste of everything, from cheap and savory churros to full fledge meal featuring some of the city’s best South and West Side taquerias, restaurants, and local eateries. Fiesta del Sol is an annual fundraising event organized by Pilsen Neighbors Community Council, a non-profit organization located in the heart of Pilsen in Chicago, IL. One of my favorite food and cultural festivals of in Chicago, the family-friendly festival draws over 1 million visitors during the four-day event, every year bringing 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 Sol.org.

Chicago Japanese Matsuri

Saturday – Sunday | September 29th – 30th  | 11:00 a.m. – 6:00 p.m.

NewCity plaza |1457 N Halsted St. | Free

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Get a Taste of Authentic Japanse cuisine from one of city’s most well-known Ramen spot. Join 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.

Sangria Festival

Saturday & Sunday | August 18th & 19th | 12:00 p.m. – 10:00 p.m.

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

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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 recieve drink tickets included with the purchase of event entry ticket, plus a commemorative glass that will have your reminiscing on the location long after it is over. For more information and to purchase your tickets, visit the Sangria Festival Chicago website. 

Taste of Greektown

Friday – Sunday | August 24th – 26th | Time Varies

Halsted and Van Buren | Free

Get a Taste of melt in your mouth rotisserie skewed beef/lamb better known as a “gyro” 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.

Square Roots Festival

Friday – Sunday | July 13th – 15th | Time Varies

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 experience 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 Festival.org.

 

Taste of Black Chicago

Saturday | August 18th | 1:00 p.m. – 8:00 p.m.

7351 S. Stony Island Ave | Free

Get a Taste of Black-owned and operated restaurants and caterers at a historic venue on South Side of Chicago. Taste of Black Chicago created to celebrate Black people’s contributions to Chicago’s world-class culinary arts scene is back after its first successful year. 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.

Chicago Hot Dog Fest

Saturday | August 18th | 1:00 p.m. – 8:00 p.m.

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

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Get a Taste of Chicago’s most celebrated food. The Hot Dog. Make your way to the Chicago History Museum for a celebration of Chicago’s most loved food. Now in its sixth year, this outdoor festival features live music, games, and hotdogs prepared in various regional and ethnic styles. Each vendor will have their 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.

 



What are your favorite food festivals when you are in the mood for a true Taste of Chicago? Share your thoughts below!

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Taylor J

The Haute Seeker is a digital platform created through the curious lenses of Taylor Justin, whose mission is to actively seek and share the cultural diversity found in the city of Chicago. Taylor is an Ohio-born, Southern-raised transplant who loves to vintage shop, museum hop, and live "like a local" in every city she visits. She is Jill of all trades and has an extensive background in fashion, marketing, sales, event planning, and community engagement.

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