Whether you can take two carry-on bags depends entirely on the airline's "Personal Item" vs. "Carry-on Bag" definitions. Standard legacy carriers (like Delta, United, or American) typically allow one carry-on bag (to be stored in the overhead bin) and one personal item (like a purse, laptop bag, or small backpack to be stored under the seat in front of you). This effectively gives you "two bags," but the second must be small. However, "Ultra-Low-Cost Carriers" (ULCCs) like Spirit, Frontier, or Ryanair have much stricter rules. Their basic fares often only include a single "personal item." If you bring a standard-sized carry-on bag (the "second bag"), you must pay a significant fee, often $50 or more. Furthermore, if you are traveling on a "Basic Economy" ticket with a major airline, you may be restricted to only a personal item, with no overhead bin access permitted. Always check the specific "dimensions" listed on your airline's website; in 2026, many airlines use "sizing boxes" at the gate to ensure that your "personal item" isn't actually a disguised second carry-on, which could lead to an expensive gate-check fee.