Southwest just dropped an unbelievable deal from Chicago Midway (MDW) to Kahului, Maui (OGG) — $282 roundtrip for travel in April and May. This route normally runs $600+, so finding a fare this low is a true outlier and one of the best Hawaii deals of the year. Spring is also one of the most comfortable times to visit Maui, with warm temperatures in the low 80s, lighter crowds, and perfect conditions for beaches, hiking, and sightseeing.