Events in Chicago in May

100 confirmed events are on sale in Chicago for May, with dates running from Sat, May 1 through Sun, May 16 — headliners include Chicago White Sox vs. Los Angeles Angels, Reunion in Bartersville and Hadestown.

Tickets currently start from $21, with live pricing for every date on the secure checkout.

Chicago Symphony Orchestra: Einstein's Imagination on Sat, May 15 currently has the lowest starting price at $21.

May's lineup in Chicago is mostly concerts (82), plus 15 sports events and 3 theatre events.

If an event is cancelled, refunds are handled by the verified seller per its policy — usually returned to the original payment method automatically. Rescheduled events are typically honoured on the new date.

The headline events in Chicago for May are listed at the top of the schedule above, sorted by date. Filter by category to surface the most-anticipated concerts, sports and shows.

Live sports in Chicago for May cover league fixtures and one-off events across the major sports. The Sports category filter surfaces every fixture with on-sale tickets.

Chicago typically programmes a mix of touring concerts, league sports fixtures and stage productions in May. The listings on this page are pulled live, so the schedule reflects what is actually on sale.

Yes — every May listing for Chicago on TheTicketers comes from a verified resale seller, backed by our 100% Buyer Guarantee and delivered instantly.

Arrive 45 to 60 minutes before showtime for a Chicago event in May to clear security and find your seat. Larger arenas typically take longer to fill at door-open.