When Is Sweetest Day 2025 Schedule. Love sweetest day comedy jam? Nephew tommy, billy bellamy, luenell & tony roberts live at wintrust arena on october 19,2025, 08:00 pm cdt.
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Sweetest Day Events 2025 Schedule Lila Shelba, @therealtank returns to wintrust arena on friday, december 6, with the r&b.
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