Chicago, IL

After my first visit to Chicago Memorial Day weekend of 2023, I was eager to return. I discovered Chicago is a gastronomical scene, beyond the deep dish pizzas I had associated with the Windy City. When I heard they had a food festival in September, I planned my return visit. I attended the Taste of Chicago, which ran from September 5–7 in 2025.

Admission & Location

Taste of Chicago is free to attend, no tickets required. Entrants pass through metal detectors and all bags are checked. I saw plastic bottle drinks like Gatorade and water confiscated. Only service dogs are allowed.

The food festival spanned three days from 11 am–9 pm Friday–Sunday.

The Taste of Chicago took place at Grant Park. Buckingham Fountain (first photo below) is the landmark for the festival (you may recognize it from the opening in the ’90s sitcom Married with Children). A map (second photo below) shows that Columbus Drive was closed to traffic. Booths for food, wine and beer (third photo below), and even lotto lined up both sides of Columbus. Surrounding Buckingham Fountain were food trucks (fourth photo below). CTA buses and the “L” train are accessible to the park.

Prices & Payment

Taste of Chicago highlighted smaller bites in the booths along Columbus Drive, which enabled me to try a variety. Vendors offered “tastes” for $5, 6, 7 each (photos below). There were larger portions as well, if desired.

No cash was accepted; booth menus stated a debit/credit card surcharge of 1.5% to be assessed. That came out to: $5.08, 6.09, 7.10 respectively.

Food trucks offered their standard menu items, which tended to be bigger portions at a higher cost. I opted to bypass the food trucks so I could eat more food.

Entertainment & Activities

Several stages dotted the Taste of Chicago. Music from the Goose Island Stage welcomed visitors at the entrance. Music wasn’t too loud and it added to the vibe, which was more street festival than fair. Besides food vendors, the festival featured a Rivian electric vehicle booth, a Disney Resorts Family Village for families with children, a karaoke contest (this was entertaining to watch as I savored my bites), and a ferris wheel (photos below).

My favorite tastes

Photos from left to right:

• Crunchy chocolate banana dipper by Eli’s Cheesecake. Original plain cheesecake with banana puree and dipped into chocolate and nuts. The chocolate coating and cheesecake were both firm enough that I could it eat it on the stick while standing.
• Yucca stuffed with shredded beef or cheese by ArePa’ George. Accompanied by a ketchup-based sauce and a chimichurri (green sauce). I love yucca, usually fried like french fries. I came back the next day and ordered two more of the cheese-stuffed yucca (the cheese was mild and stretchy like mozzarella).
• Chocolate-filled churro by Churro Factory (xurro). This was a sweet finish to my Taste of Chicago experience. I alternated between salty savory and sweet dessert bites. For $5, this is cheaper than I would get at a state fair and felt like an upgrade (they gave me options on the filling).

Taste of Chicago delivers

My first trip to the Taste of Chicago was satisfying and enjoyable, perfect for solo travel. The crowd was smaller on Friday than Saturday. Even with more people on Saturday afternoon, the lines weren’t bad (by NYC standards). Saturday ended with fireworks. Limited seating, but people also sat on the grass and sidewalks, which were clean. I saw rows of porta-potties. You can stay at the festival all day since there’s live entertainment, but two hours is enough to peruse the options and take your time eating. That allows time for other Chicago sites.

From my hotel off the Magnificent Mile (a stretch of N. Michigan Avenue with high-end shops, restaurants, and famous sites like the Wrigley Building), I walked or took the bus to Grant Park (about a 30-minute walk). I sampled assorted foods on a budget (quite a value). I spent the money saved for a meal at Pequod’s Pizza (Chicago has many noteworthy places to visit).

Although Chicago earned PETA’s top spot as most vegan-friendly city, vegan options didn’t stand out to me at the Taste of Chicago.

The weather was pleasant, reminiscent of fall: bouts of sun with a breeze (there was a gale warning Friday morning). Most people wore pants and brought light jackets. The Taste of Chicago is an ideal way to experience Chicago on a weekend getaway and to get a flavor of the Windy City.