Some of the best Milwaukee concerts and comedy shows this winter
Here are some top shows to check out in Milwaukee from December 2025 through February 2026.
Pitbull is celebrating his 45th birthday Jan. 15 by announcing a North American tour – including the first 2026 show announcement for Alpine Valley Music Theatre.
The historic amphitheater in East Troy will host Pitbull and special guest Lil Jon as part of the “I’m Back” tour on Sept. 12, officials with tour promoter and venue operator Live Nation announced Jan. 15.
Pitbull last played the Milwaukee area in 2024 at a packed American Family Insurance Amphitheater.
Tickets for Pitbull’s Alpine Valley concert go on sale at 10 a.m. Jan. 30 at livenation.com. Presale registration is available online now at livemu.sc/pitbull, with the presale starting at 10 a.m. Jan. 28. Prices have yet to be announced.
