How long is the flight from Chicago to Hawaii ? The flight from Chicago to Hawaii is a captivating journey spanning thousands of miles across the United States to the tropical paradise of the Pacific. This transcontinental voyage typically takes around 9 to 11 hours, depending on factors like specific departure and arrival airports, layovers, and prevailing weather conditions. As you soar over the vast expanse of the Pacific Ocean, you'll be on your way to experiencing the enchanting landscapes and rich culture that await you in Hawaii.