Hey Chicago!
Summer is finally just around the corner, and you know what that means – we’re about to enter full-on festival season! There’s a lot going on in Chicago this summer, so we’re going to be breaking down our event articles monthly to make sure all the best and most interesting events are covered.
This week’s article is about what’s happening in June. There are free concerts in Millennium Park, neighborhood street fests, Pride celebrations, art fairs, and food crawls.
Before we get started: if you’re new here, welcome!
We’re the Ben Lalez Team, an award‑winning real estate team serving buyers and sellers all over Chicago and the suburbs. For more than a decade, we’ve been helping people find the right home in the right neighborhood. Every week, we publish a new article about something interesting, useful, or fun going on around the city. If you’d like these guides sent straight to your inbox every week, make sure you’re subscribed to our newsletter.
With that, let’s take a look at what June is bringing to Chicago.
| Date | Event | Location |
| June 4 – 7 | Chicago Blues Festival | Millennium Park & Ramova Theatre |
| June 6 – 7 | 57th Street Art Fair | Hyde Park |
| June 12 – 14 | Andersonville Midsommarfest | Andersonville, Clark St. |
| June 11 – 14 | Puerto Rican Festival Chicago | Humboldt Park |
| June 19 – 21 | Taste of Randolph | West Loop, Randolph St. |
| June 20 – 21 | Gold Coast Art Fair | Grant Park |
| June 20 – 21 | Chicago Pride Fest | Northalsted (Boystown) |
| June 24 | Flavors of Albany Park | Albany Park |
| June 26 – 28 | Logan Square Arts Fest | Logan Square |
| June 26 – 27 | Chicago Taco & Tequila Fest | Wrightwood Park, Lincoln Park |
| June 28 | Roscoe Village PorchFest | Roscoe Village |
| June 28 | North Center Garden Walk | North Center |
| June 28 | Chicago Pride Parade | Northhalsted (click to see route) |
Chicago Blues Festival
June 4 -7
The city’s signature Chicago Blues Festival returns with four days of free performances, opening with a kickoff night at the newly restored Ramova Theatre and then spreading across multiple stages in Millennium Park. Expect tributes to Chicago blues legends, afternoon sets on the lawn, and evening headliners that draw big crowds.
The festival is produced by the City of Chicago’s Department of Cultural Affairs and Special Events, and as always, admission is free. Make sure to plan ahead for crowds, transit, and where you want to sit or stand.
57th Street Art Fair
June 6 – 7
Held every year on the first full weekend in June, the 57th Street Art Fair brings nearly 200 artists to the streets around the University of Chicago campus for what’s billed as the Midwest’s oldest juried outdoor art fair. You’ll find everything from paintings and photography to ceramics, jewelry, and sculpture, with artists on-site to talk about their work.
It’s a great opportunity to spend several hours browsing, talking with artists, and grabbing snacks from pop‑ups and nearby coffee shops, especially if you pair it with a visit to the Museum of Science and Industry or the lakefront.
Andersonville Midsommarfest
June 12 – 14
Andersonville Midsommarfest turns Clark Street into a 3-day celebration of Swedish summer traditions. There’ll be multiple stages of live music, Swedish and global food, kids activities, and local vendors.
The suggested donation of $10 at the gate, along with beverage sales, goes back into neighborhood events and community programs. This is their 60th year, so if you haven’t checked it out in a while, make sure to stop by this year to enjoy the festivities.
Puerto Rican Festival Chicago (Fiestas Puertorriqueñas)
June 11 – 14
Humboldt Park hosts the multi‑day Puerto Rican Festival, a major cultural celebration that features carnival rides and vendors with live music, performances, and of course, tons of good eats. Weekend tickets get you into the fenced festival area where you’ll find stages, rides, and a big selection of Puerto Rican and Latin American food.
And if you’re into running, on June 21st, the annual San Juan 5k Run is taking place at 7:30am.
Taste of Randolph
June 19 – 21
Taste of Randolph turns Restaurant Row into one long block party, with the West Loop Community Organization closing Randolph between Peoria and Racine for a weekend of live music and food from some of the neighborhood’s best-known restaurants. Multiple stages feature national and local acts, while pop‑up booths and beer tents line the street.
There’s a suggested donation at the gate that helps pay for the festival and supports community programming, but once you’re in, you can wander your way down one of Chicago’s most talked‑about dining corridors.
Gold Coast Art Fair
June 20 – 21
The Gold Coast Art Fair features a variety of artists across different media. You can browse paintings, prints, jewelry, ceramics, and more over the course of the weekend.
If you’re thinking about how to decorate a new place, or you’re just looking for something unique to hang on the wall, this is a good event to check out.
Chicago Pride Fest
June 20 – 21
Chicago Pride Fest is a 2‑day street festival in Boystown, held the weekend before the city’s main Pride Parade. Stages along Halsted will feature pop acts, DJs, and drag shows all day, while vendors line the street with food, drinks, and Pride merch.
It’s one of the biggest neighborhood festivals of the month, and you’ll get an up‑close look at the energy along Halsted.
Chicago Pride Parade
June 28
On the last Sunday in June, the Chicago Pride Parade kicks off in Northalsted, drawing hundreds of thousands of spectators to celebrate LGBTQ+ life and community. Floats, marching contingents, and neighborhood groups will wind through Lakeview and surrounding areas over the course of the afternoon.
If you’ve never experienced the parade, it’s worth experiencing at least once. If you’re planning on attending, note that there is a long list of prohibited items:
- Alcohol
- Bicycles, scooters
- Coolers
- Drones
- Fireworks
- Folding chairs
- Propane, propane Tanks
- Tents, canopies, or structures
- Tripods, monopods, selfie Sticks
- Vending
- Weapons
Make sure to check the event website to find everything you need to know.
Flavors Of Albany Park
June 24
Flavors of Albany Park is a one-night restaurant crawl that turns one of Chicago’s most diverse neighborhoods into a global tasting route. Your ticket gets you access to a curated path across 60‑plus participating restaurants, with small bites at each stop along Lawrence, Montrose, and Kedzie.
Albany Park is one of Chicago’s most diverse zip codes, and the event reflects this through food from the Middle East, Mexico, the Philippines, Korea, Eastern Europe, and many other cuisines.
Logan Square Arts Fest
June 26 – 28
Logan Square Arts Fest returns this year after a construction‑related pause in 2025, and organizers are calling it “back and bigger than ever.”
Since its launch in 2009, the festival has attracted hundreds of thousands of visitors and raised tens of thousands of dollars for local nonprofits, with proceeds supporting neighborhood arts and preservation groups. Expect a mix of local bands, indie touring acts, pop‑up galleries, interactive art pieces, family‑friendly daytime activities, and a beer and cocktail presence from local bars and breweries.
Chicago Taco & Tequila Fest
June 26 – 27
Chicago Taco & Tequila Fest is a ticketed tasting event held in Wrightwood Park that brings together taco vendors, tequila brands, and live entertainment over two days. Tickets are typically sold in tasting sessions, with each admission including a set number of taco samples and the option to add tequila tastings or cocktail samples, depending on the ticket tier.
Roscoe Village PorchFest
June 28
Roscoe Village PorchFest is one of a series of porch‑based music festivals organized by the Lakeview Roscoe Village Chamber of Commerce. Homeowners volunteer their porches as mini‑stages, and local musicians are assigned time slots, with a printed or digital map guiding visitors from set to set through the afternoon.
Genres range widely, and the scale is intentionally small, more like a neighborhood block party than a full‑blown street closure. We highly recommend you check it out.
North Center Garden Walk
June 28
The North Center Garden Walk is a self‑guided tour of residential gardens, organized by the North Center Neighbors Association. Participants receive a map and program listing all featured gardens, along with notes on which locations have extras like live acoustic music, refreshments, or plant swaps.
Gardens range from small parkways with carefully planned perennials to full backyards with vegetable beds, water features, or pollinator‑friendly plantings. If you like seeing how people actually use their outdoor space for container gardens on decks, creative shade solutions, or front‑yard landscaping ideas, this is a good place to get inspiration.
A Few Other Things Worth Keeping on Your Radar
Beyond the big marquee events, June also brings:
- Free Grant Park Music Festival concerts at the Jay Pritzker Pavilion, with the Grant Park Orchestra and Chorus performing classical and contemporary works on many Wednesdays, Fridays, and Saturdays.
- City and neighborhood farmers markets that get busier in June, including long‑running markets like Division Street and Daley Plaza, plus dozens of smaller neighborhood markets.
Final Thoughts
This is it, the few months in Chicago where we can enjoy the summer weather and everything that’s awesome about spending time outdoors in the city. Next month, we’ll cover the events happening in July, so stay tuned.
In the meantime, if you’re checking out an event and find a neighborhood that feels like home and you want to talk next steps (buying, selling, or just getting a sense of what’s possible), reach out to us at the Ben Lalez Team. We’d be happy to help you figure out the right move for you and your family!
Until next week, break out the sunscreen and enjoy the rest of May!
