- The original poster pointed out there’s no Chicago date on the residency graphic and asked if that means Harry can’t be Lolla’s #1.
- Several commenters flagged hard conflicts: Mexico City dates (reported July 31 + August 1) could overlap with the festival weekend.
- Others referenced an MSG email claiming the NYC shows are his only U.S. dates in 2026, which would make a Chicago appearance unlikely.
- Some tried to find loopholes — e.g., could he do a late-night festival set or fit Lolla on a different day of the weekend? The consensus: logistics make it unlikely, but not strictly impossible.
Festival headline slots require precise timing and routing. Multi-night residencies and arena runs (especially long NYC residencies) often mean an artist won’t be doing one-off festival gigs in the same window. If Harry’s U.S. commitments are limited to a long NYC residency and the Mexico City dates are locked in around the festival weekend, those are big scheduling hurdles for a Chicago headliner slot.
- Official announcements from Lollapalooza and Harry’s team — those settle it.
- Tour date confirmations and venue emails (MSG statements in the thread were cited by fans).
- Any surprise add-ons or one-off festival announcements — artists sometimes add isolated festival dates around residencies, though it’s rare.
Source: https://www.reddit.com/r/Lollapalooza/comments/1qk035n/harry_styles_residencies_no_chicago/