Should I use a soft-sided cooler with big wheels instead of a hard cooler for airports?

Yes, soft-sided coolers with oversized wheels beat hard coolers for airports. Hard coolers like the Pelican or Yeti Tundra are heavy, awkward in narrow aisles, and can’t fit in overhead bins. A soft-sided cooler with big wheels rolls smoothly over carpet and curbs, is light to lift, and flexible enough to stow overhead. Ice retention is fine for a travel day.