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Plan your trip to this cozy city in late summer for the best deals on airfare. According to Travel Agent Central, Portland is the destination with the cheapest flights in August 2019. The temperature during the summer months ranges from low to high 70s, making it prime weather for outdoor activities. Listen to music at free outdoor concerts; have some fun in the sun at Edward Payson Park; take a tour of the Spring Point Ledge Lighthouse; and walk the trails at Kennebunk Bridle Path.