Chicago Events May 2026 – Concerts, Sports & Live Shows

May 2026 in Chicago is packed with live entertainment, sports, and concerts across the city. Fans of pop, hip-hop, rock, country, and professional sports have an exciting schedule at iconic venues including United Center, Wrigley Field, and Allstate Arena.

Whether you’re attending Demi Lovato, Peso Pluma, or A$AP Rocky, or catching Chicago Cubs home games against top MLB rivals, this guide provides all the information you need: dates, venues, ticket tips, and insider guidance.

United Center is Chicago’s premier indoor arena, home to the NBA’s Chicago Bulls and NHL’s Chicago Blackhawks, and a top venue for concerts. With a capacity of ~23,500 for concerts, it hosts the biggest touring artists in the world.

Wrigley Field, home of the Chicago Cubs, is one of the most historic MLB stadiums in the United States. With a capacity of ~41,000, it hosts some of the most memorable baseball experiences, including day games, rivalry matchups, and weekend series.

Allstate Arena in Rosemont, IL is a top venue for concerts, ice shows, and live entertainment. With a capacity of ~18,500, it hosts diverse events from pop, rock, country, and cultural tours.

Top high-demand May events in Chicago include:

• Demi Lovato at United Center
• Peso Pluma (2 nights)
• A$AP Rocky at United Center
• MLB Memorial Day weekend games (Houston Astros series)
• Romeo Santos and Cody Johnson at Allstate Arena

Ticket Tips:

• Buy tickets early for concerts and weekend MLB games.
• Midweek games and shows may have more availability.
• VIP, floor, and lower-level seats sell out fast — early purchase is recommended.

❓ What are the biggest Chicago concerts in May 2026?
May 2026 features some of the most in-demand concerts in Chicago. Top headliners include Demi Lovato at United Center, Peso Pluma performing two nights, A$AP Rocky, Cody Johnson, and Romeo Santos. These events are highly popular, often selling out quickly, and attract fans from across Illinois and neighboring states.

❓ How many Chicago Cubs home games are in May 2026?
The Chicago Cubs host multiple home games at Wrigley Field in May 2026. Series include matchups against the Arizona Diamondbacks, Cincinnati Reds, Milwaukee Brewers, and Houston Astros. Weekend games and Memorial Day matchups are especially popular, with high ticket demand.

❓ Which venues host the most May events in Chicago?
The majority of indoor concerts and shows take place at United Center and Allstate Arena in Rosemont. Wrigley Field hosts MLB games and occasional special events. Each venue offers a unique experience: United Center for major pop, rock, and hip-hop concerts, Allstate Arena for arena shows and cultural events, and Wrigley Field for historic baseball games.

❓ When should I buy tickets for Chicago May 2026 events?
For high-demand concerts and weekend MLB games, it is recommended to purchase tickets as early as possible. Events like Demi Lovato, Peso Pluma, A$AP Rocky, and Memorial Day weekend Cubs games often see price increases and limited availability closer to the date. Early booking also ensures the best seat selection at United Center, Wrigley Field, and Allstate Arena.

❓ Is May a busy tourism month in Chicago?
Yes, May is a peak month for tourism in Chicago. Spring weather, live concerts, MLB games, and Memorial Day weekend attract visitors from across the country. Hotels, parking, and transportation near major venues are in high demand, so planning ahead is strongly advised.

❓ What types of events can I attend in Chicago in May 2026?
Chicago in May 2026 offers a wide variety of events including concerts across genres (pop, hip-hop, country, rock), professional sports (Chicago Cubs MLB games), comedy shows (Katt Williams), and cultural events like Stars on Ice. There’s something for every type of fan throughout the month.

❓ Are there any multi-day events or series in May 2026?
Yes. Peso Pluma performs two consecutive nights at United Center, and the Chicago Cubs host multiple series throughout May, including Memorial Day weekend against the Houston Astros. These multi-day events are especially popular and often sell out quickly.

❓ Which Chicago events are best for families?
Family-friendly events in May 2026 include afternoon Cubs games at Wrigley Field, Stars on Ice at Allstate Arena, and some weekend concerts with age-appropriate content. Early planning is recommended for seating and parking convenience.