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Traveling in the morning is considered to be cheaper than in the evening. You can get up to 5% of fare drop-in morning flights as compared to the evening flights. Search for roundtrip flights instead of one way if your traveling plans are confirmed. As popular airlines like Southwest, Delta and JetBlue offer the best airfares for roundtrips. Booking flights in offseason does not cost much. Mid of January to March is the best time to book the cheapest flights to Boston from NYC.