Events in Chicago in May 2027
Chicago has 12 sourced events in May 2027. Compare dates, venues, and ticket sources below, then build the rest of your trip around the events you choose.
The Chicago calendar for May 2027 leads with these:
- Reunion in BartersvilleMay 1The Yard at Chicago Shakespeare · Source: SeatGeek
- Hisaishi Conducts HisaishiMay 1 - May 28Symphony Center-IL · Source: Ticketmaster
- HealingMay 2George Van Dusen Theatre at North Shore Center · Source: Ticketmaster
By TripSapien · Updated September 3, 2026
Sourced events
- May 4 - May 5
- May 5 - May 14
Next Page Productions Presents: James and the Giant Peach
North Theatre at North Shore Center for the Performing Arts . Arts & Theatre · Children's Theatre.
Source: Ticketmaster
- May 6
Chicago Symphony Orchestra - Honeck Conducts Mahler & Bruckner 9
Chicago Symphony Center. theater.
Source: SeatGeek
- May 7
Chicago Symphony Orchestra - Honeck Conducts Mahler & Bruckner 9
Chicago Symphony Center. theater.
Source: SeatGeek
- May 8
Chicago Symphony Orchestra - Honeck Conducts Mahler & Bruckner 9
Chicago Symphony Center. theater.
Source: SeatGeek
- May 9
- May 10
- May 13
- May 13
Chicago Symphony Orchestra - Mäkelä, Batiashvili & Sibelius 1
Chicago Symphony Center. theater.
Source: SeatGeek
Going to Chicago in May?
Add your dates and we'll build the rest of your trip around these events — every place checked for closures and booking needs.
Planning leads
Early leads on events still lining up. Exact dates and details firm up closer to your trip.
- May 7 - May 16
Chicago Craft Beer Week
A city-wide celebration of craft beer with tastings, brewery tours, and special events at bars and breweries throughout Chicago.
Planning lead · details firm up closer in · Source: festival research
- May 14 - May 16
Chicago Mayfest
An annual neighborhood festival in the Lincoln Square area featuring live music, food vendors, arts and crafts, and family-friendly activities.
Planning lead · details firm up closer in · Source: festival research
- May 15 - May 16
Chicago Garden Walk
A self-guided tour of private and public gardens in the Chicago area, showcasing local horticulture and garden design.
Planning lead · details firm up closer in · Source: festival research
Holidays, observances & long weekends
Holiday and observance schedules can affect services and venue hours; confirm each place directly.
- Memorial Day · publicMay 31
- Long weekendMay 29–May 31
Holiday data: date-holidays (ISC/CC-BY-3.0).
Ready to plan Chicago?
Turn these May events into a full Chicago plan, every place checked for closures, limited hours, and booking needs on your dates.