Chicago May 2026

Chicago May 2026 Events

Chicago May 2026 Events

Chicago Welcomes May's Warm Weather

Average temperature low and high: 53°-66°
Chicago's warm (but comfortable) May temperatures are perfect for kicking off summer with one of the city's many outdoor events. Annual favorites like Chicago Mayfest and the Sheffield-Belmont Music Festival are perfect for partygoers looking for live music, great food, and even better vibes; while events like the city's Memorial Day Wreath Laying Ceremony & Parade honor the holiday with city traditions dating back over 150 years. From balmy spring weather to fun festivals and Memorial Day events, Chicago in May has something for every visitor.

May Event Calendar

Titanic - The Musical

The biggest Broadway musical about the largest disaster in oceanic history sails into the Marriot Theatre for an unsinkable two-month voyage. Steer clear of icebergs, but don't miss the one-and-only Titanic - The Musical. Book your passage with tickets starting at 

Legions Of Metal Festival

Legions Of Metal Festival

The Legions of Metal Festival features explosive performances by classic metal bands from the 1980s and newer talents. This year's lineup will feature Heathen, Crimson Glory, Seven Spires, and many more. 

Art in Wilder Park

Art in Wilder Park

If you're an art lover, be sure to visit Art in Wilder Park. This 2-day arts and crafts celebration attracts over 10,000 attendees and over 100 artists selling their pieces. Rain or shine, the massive art show will also feature live music entertainment, and admission is free for all ages.

Chicago Pickle Fest

Chicago Pickle Fest

Pickles, pickles, and even more pickles. Not to worry, pickle lovers, the Chicago Pickle Fest has heard your cries for pickles and is here to save the day. Delight in pickle beer, pickle cocktails, and special pickle-picked treats. Sorry, no kiddos or pets, Pickle Fest is 21 and over. Tickets for Pickle Fest start at $10 and cover multiple venues, all within walking distance. 

Chicago Mayfest

Chicago Mayfest

Get ready to rock for 3 days straight at Chicago Mayfest. Now in its 28th year, the music fest serves as the kick-off for the city's lively summer festival season. Held in the heart of Lincoln Park at Armitage & Sheffield, Mayfest features live music, an art show, a family carnival area, food, beer, and more. 

Chicago Horror Film Festival

Chicago Horror Film Festival

Thrills, spills, and chills come to haunt The Logan Theater with the 26th Annual Chicago Horror Film Festival. Catch the scariest features, shorts, documentaries,  and the latest splatterfests from the world's leading indie masters of horror. 

Belmont-Sheffield Music Festival

Belmont-Sheffield Music Festival

Celebrate Memorial Day Weekend with the 40th annual Belmont-Sheffield Music Festival in the heart of Chicago's hip Lakeview neighborhood. This unique outdoor festival starts Friday at 5 pm, showcasing a wide range of music from talented community performers and will feature plenty of food and drinks, arts and crafts, local vendors, and more. 

Belmont Sheffield Music Festival

Belmont Sheffield Music Festival

Start the summer with a 40-Year Chicago Tradition, the Belmont Sheffield Music Festival. Catch your favorite local Chicago bands, mouthwatering food and drinks, local artists and vendors, and community talent. It's the ultimate Chicago block party. The neighborhood fun kicks off Friday evening. 

Sueños Music Festival

The Sueños Music Festival is a two-day event celebrating the Latino culture with Latin and Reggaeton music, experiences, activities, and more. The fest features live performances from world-renowned artists such as the one and only Shakira, Don Omar, Peso Pluma, and more, plus a variety of mouth-watering food and drinks, art installations, and workshops. 

AC/DC & The Pretty Reckless

Australian rock gods AC/DC are Back in Black to do their Dirty Deeds with their friends, heavy rockers The Pretty Reckless, featuring Taylor Momsen. The Thunder from Down Under storms Soldier Field at 8 pm. Tickets for AC/DC & The Pretty Reckless start at $129. 

Chicago Memorial Day Wreath Laying Ceremony & Parade

Chicago Memorial Day Wreath Laying Ceremony & Parade

Honor America's fallen Heroes through the Chicago Memorial Day Wreath Laying Ceremony & Parade. The wreath-laying ceremony begins at 11 am in Daley Plaza, followed by the Memorial Day Parade taking route along State Street.​

Navy Pier Fireworks

Navy Pier Fireworks

The Chicago Summer starts with a bang on May 24 with the launch of the Navy Pier Fireworks season. Don't miss Chicagoland's Summertime iconic weekly riverfront fireworks extravaganza lighting up the night sky every Saturday at 9 pm.

Chicago Events in May

Concerts

Theater & Headliners

Sports

Nightclubs

Things to do in Chicago

Things to Do in Chicago in May

Explore Chicago on a Night Tour

Explore Chicago on a Night Tour
Chicago doesn't stop buzzing at night, so why should you stop exploring? Switch things up and venture into the Windy City on a night tour. From ghosts and riverwalk walking tours to architectural boat tours, Chicago has lots to see. Book with a tour guide, or go the independent route with self-guided and audio tours. You won't regret exploring Chicago.

Spend a Day at Millennium Park

Spend a Day at Millennium Park
Millennium Park was converted from an industrial wasteland into a 25-acre park. Thoughtfully filled with beautiful landscaping, architecture, and art, the park is known to host events free and open to the public like concerts, performances, and movie screenings. Whether you want to stroll and explore or just bring a picnic blanket to relax, this is a must when visiting Chicago.