13 Airlines & Hotels to Watch for Cyber Monday Deals — Your Cheat Sheet

Cyber Monday and the surrounding holiday sales are prime chances to shave hundreds off travel costs if you know where to look. Major hotel chains tend to run the deepest room discounts during the Cyber Monday window, often pairing percentage savings with resort credits or bundled perks. Airlines usually emphasize Travel Tuesday — the Tuesday after Cyber Monday — with targeted fare sales on select routes. This cheat sheet highlights 13 hotels, chains, and carriers to watch for Cyber Monday and Travel Tuesday deals, plus practical tips for turning a listed sale into a booked trip. The list is based on recent deal patterns and expert coverage by travel outlets; where exact 2025 terms vary by brand, I note typical deal formats and what to watch for. Use the list in two ways: quickly scan brand names to prioritize alerts, then read the short strategy for each entry before you click through. For flights, set flexible-date searches and fare alerts; Google Flights data suggests weekday travel and well-timed advance booking matter more than the precise booking day. For hotels, compare prepaid discounts with flexible rates and factor in resort credits or free breakfast offers. Below are the 13 brands and topics that tend to deliver the best Cyber Monday value.

1. Hilton Hotels

Hilton is consistently one of the headline names during Cyber Monday travel sales. Reporting has shown Hilton offers among the deepest room discounts in some years, and the brand often supports percentage discounts with member-only extras through Hilton Honors. In past holiday windows, offers have included straight rate reductions and promotional package options that add resort credits or waived resort fees for select properties. When a large chain like Hilton runs a sale, the real value often depends on which properties are included and whether the rate requires full prepayment. Read cancellation rules closely. If you’re flexible on destination, watch upscale Hilton-branded resorts where resort credits can make a small percentage discount feel like a much bigger saving. For city stays, compare the advertised Cyber Monday rate to member or AAA pricing to confirm the best net cost. Sign up for Hilton Honors emails and set a hotel-specific alert; large chains sometimes release targeted promo codes that stack with published sale rates.