Chicago May 2025

Chicago May 2025 Events

Chicago May 2025 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

Tim McGraw Standing Room Only Tour '24

Country music superstar Tim McGraw brings his Standing Room Only Tour '24 to Chicago's United Center on May 31 with special guest Carly Pearce. One of the most recognizable artists in country music, McGraw will be sure to dazzle fans with his line-up of iconic songs like "I Like It, I Love It" and "Just to See You Smile" along with hits from his 2023 release Standing Room Only. Get tickets now. 

Augmented Chicago: Inaugural Realities

Augmented Chicago: Inaugural Realities

Augmented Chicago: Inaugural Realities displays the ground-breaking virtual artworks of four celebrated Chicago-based artists, Claire Ashley, Faheem Majeed, Yvette Mayorga, and Carlos Rolón, through the technical wonders of augmented reality. AR combines the existing environment and virtual elements through VR or your phone. Experience the future of art at Millennium Park. Admission is free, and the exhibits run through November 25th. 

Spring Flower Show: Rooted in Mystery

Spring Flower Show: Rooted in Mystery

This year's Spring Flower Show at Garfield Park Conservatory explores the roots, the foundation of plants and flowers. Roots not only deliver water and nutrients to plant life but also "communicate" with other plants via chemical and electrical signals. Discover more at the show, which runs from 10 a.m. to 8 p.m.

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. 

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. 

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.