I've found that October is a great time for travel deals since it's generally off-peak for many destinations. For discounted flights, I like using Google Flights to track prices, and Skyscanner can also unearth some good deals if you're flexible with your dates. As for destinations, Eastern Europe or Southeast Asia can be quite affordable during this time, plus they offer a unique experience away from the usual tourist crowds. Consider places like Budapest or Chiang Mai for great value. Backpacker hostels often have discounts in the shoulder season too—worth checking out!