Discover Chicago’s Top Festivals in May: Your Ultimate Guide for Music, Food, and Fun

2023 Chicago Festivals Happening in May You Won’t Want to Miss

April showers bring Chicago’s May tulips. Along with the tulips, it is almost festival season in Chicago. May brings an exciting lineup of festivals celebrating the city’s culture, music, food, and art. One thing I love about Chicago is the city’s vibrant energy. If you are visiting from out of town or a Chicago resident, these May festivals are a fun way to kick off the summer season and celebrate with the city community. Here are the Chicago festivals in May that you will want to attend.

Green City Market – Saturdays April-November

Nothing screams summer like ice cream and farmer’s markets. It’s not quite summer yet, but a few markets are opening in May- Green City Market is one of them. Green City Market opens starting May 11th. The market has dozens of vendors who sell local produce. You can purchase blueberries, bread, and of course, ice cream. There are locations in Lincoln Park, West Loop, and Avondale.

Manifest Arts Festival – May 12th

Chicago’s Columbia students host the Manifest Urban Art Festival again this year to display hundreds of readings, showings, and exhibitions of the artist’s work for the year. See the latest pieces of the bright graduates of the Manifest Arts Festival.

Chicago Mayfest- May 12-14th

Chicago Mayfest is one of the first festivals of the summer hosted by
the city. Sip on a cold cocktail and indulge in festival foods while
listening to the talented musical lineup. Don’t just go to this festival
for the festivities. Chicago Mayfest is a benefit festival located in
Lincoln Park. The proceeds go towards the Ranch Community Conservation Association.

Mole de Mayo- May 26-28

Do you love Mole? The Mole de Mayo Festival offers a variety of
vendors, all serving delicious Mole dishes. Beyond the food, you can shop for art and jewelry by local artisans at the market, live music, and cultural performances such as the Aztec-Mexica dance rituals and Chinelo costumed dancers. But what I am most excited about is the live music. A talented lineup starts Friday-Sunday with Latin, Soul, reggae, and salsa.

Live on the Lake May 27th

Nothing says summer like live music, cold coffee, and dancing on Navy Pier starting May 27th-September 4th. Live on the Lake is a popular summer concert series in Chicago at Navy Pier. The series features a variety of musical artists ranging from jazz and blues to rock and pop. The event is free, but VIP tickets, including exclusive seating and amenities, are also available for purchase. If you enjoy live music as much as I do or are looking for a fun night out in the city, Live on the Lake is a must-visit event for the perfect Chicago summer.

Suenos Music Festival- May 27th

The Latinx community is vibrant and diverse in Chicago; the Suenos Music Festival is a testament to that. The Suenos Music Festival is a memorable weekend in May. With artists like Archangel and Becky G., This festival has a full lineup of musical artisans. From salsa and cumbia to reggaeton and hip hop, the Suenos Music Festival gets the whole crowd dancing. Aside from the live music, a wide variety of food and drink vendors and artisan booths and vendors showcase the rich cultural heritage of the Latinx community in Chicago.

Belmont-Sheffield Music Fest May 27th-28th

If you love a block party, the Belmont-Sheffield Music Fest will be the event to attend. The Music Fest is in the Lakeview neighborhood with beer, wine, street, food, and live music. The festival takes place over two days and features live performances from various local and national musicians, spanning genres from rock and pop to blues and jazz. Although the music is the fest’s highlight, the food and art vendors make this one I am eager to attend.

Randolph Street Market May 27th-28th

Randolph Street Market is for all the Chicago thrifter and vintage lovers. It’s one giant treasure hunt. You are bound to find unique clothing, decor, and art pieces. Dance to the live music and enjoy the vendor food at this European-style flea market. If you get thirsty, there will be a market bar and cabana for a tipsy thrifting experience.

Maxwell Street Market May 28th

The treasure hunt doesn’t have to end at Randolph Street Market, Maxwell Street Market sells crafts and art from local artisans, resellers, and farmers. It’s a great place to find eclectic artwork, fresh produce, and some of Chicago’s tastiest street food. The market offers a diverse array of goods and foods worldwide. The Maxwell Street Market’s history is a cultural exchange and entrepreneurship hub. Once the market opens on May 28th, it is open from 9-3 pm every Sunday until October.

Jazz’n on the Steps May 28th

Jazz has a personality of its own, with an improvisational and lively feel. I went on a school trip to New Orleans in college and have been interested in live jazz ever since. We found the best jazz cafes to drink strawberry margaritas and enjoy the music. I could sit for hours and listen to the sophisticated swing and complex harmonies for hours. Luckily, I can on May 28th.Jazz’n on the Steps starts May 28th and continues each Sunday at St. Moses The Black Parish throughout the summer. It costs nothing to listen to but bring a lawn chair and some snacks to enjoy the music.

Summer Night Markets at Navy Pier

Summer nights in Chicago are fun and exciting. The lights glow when the sun goes down, and the city comes alive. A great way to spend them is at Summer Night Markets at Navy Pier. Every last Wednesday from 6-9 pm, Navy Pier is lively with musical performances and local shops.

As the spring comes to a close and the temperatures start to rise, I feel a special kind of excitement. From concerts, days laying out on North Avenue Beach, Aperol Spritz on rooftops, and festivals, I am excited about what this Chicago summer brings. I am eager to soak up the sun and enjoy all the city has to offer- it’s sure to be an unforgettable summer. Stay tuned as I keep you up to date on all the fun and exciting things happening in Chicago this summer.

Less or Morgan