I found flights from Chicago to Kauai on United starting at $360 roundtrip for travel in October and November — a fantastic price for one of Hawaii’s most beautiful islands.
This route typically averages $600+, so this is a strong deal and one of the better Kauai fares I’ve seen from the Midwest.
Why Visit Kauai in October & November?
Fall is one of the best times to go—warm weather, fewer crowds, and often better hotel pricing before the holiday season begins.
You’ll still get beautiful beach days, lush green scenery, and incredible sunsets without peak-season pricing.
A Few Things to Do
🌊 Nā Pali Coast Boat Tour – Kauai’s most iconic experience with cliffs, sea caves, and dolphins
🏞 Waimea Canyon – Known as the “Grand Canyon of the Pacific”
🏖 Poipu Beach – Great for snorkeling, sea turtles, and family beach days
At $360 roundtrip, this is an excellent chance to visit one of Hawaii’s most unforgettable islands.
The Flights
