The Best (and Cheapest) Places to Travel This Fall


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We all know that traveling during the “off season” is typically cheaper than traveling in the height of summer. “Shoulder season” the travel period between the peak and off-peak season can offer the best of both worlds. You get the decent weather of the summer (or autumn now, as the case may be), coupled with declining hotel and flight costs.

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As someone who pretty consistently decides to vacation during this time: it’s worth it. I absolutely hate being stuck in lines or trying to get into crowded attractions. When you travel during the off-season (or right before) you don’t have to deal with as much of that, which makes visiting hot spots exceptionally more pleasant.

So, where should you go? The Points Guy just did its own research into where you might get the best deal during shoulder season based on flight data from Skyscanner, Booking.com’s hotel rate data, and a handful of other factors and picked six spots that are worth making a trip to this fall:

Chicago: November is the cheapest time to visit the Windy City, with hotel prices 30% lower than normal during October and November. Flights are also an average of $20.95 cheaper between September 22 and December 21.

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San José del Cabo: Flights to San José del Cabo between September 22 and December 21 are on average $20 cheaper than they are other times of the year.

Copenhagen: I visited Copenhagen last year in December and had an amazing time. If you want to be like me, you can save an average of $189.78 on airfare of you travel between September 22 and December 21. You can get even more savings by taking an airline like WOW Air, which offers one-way tickets for less than $180 to the city during September and October.

Barcelona: Flights to Barcelona are an average of $144.06 cheaper in October and November.

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San Diego: Visit the west coast in October and November and save on average 32% on your hotel stay. You can also save a tiny bit of cash on the flight. San Diego flights between September 22 and December 21 are on average $15.58 cheaper than other times of the year.

Boston: Flights to Boston are on average $34.58 cheaper between September 22 and December 21. You’ll also score an average 31% savings on a hotel during the same time period.

And if you’re thinking of making some of those bookings using all the airline miles and hotel points you’ve accumulated over the past year, be sure to check out The Points Guy for some tips on the best places to go for those as well.

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