Flights on American Airlines from Chicago to Kauai are showing up around $336 roundtrip for travel in January and February — a significant drop from the typical $450+ price point on this route. For Hawaii travel during peak winter months, that’s an exceptional fare.
January and February are especially appealing for Midwest travelers: fewer crowds than the holidays, excellent weather, and the perfect antidote to winter back home.
Why Kauai Is a Favorite for So Many Travelers
Kauai is often called the Garden Isle — and for good reason. It’s less built-up than some of the other Hawaiian islands and leans heavily into natural beauty.
Unmatched scenery
Think dramatic cliffs along the Nā Pali Coast, lush rainforests, waterfalls, and emerald-green valleys. Whether you’re hiking, driving, or just sitting on a beach, Kauai feels cinematic.
Relaxed, low-key island vibe
Kauai is ideal for travelers who want to slow down. Fewer high-rises, quieter beaches, and a more laid-back pace make it perfect for couples, families, and anyone looking to unplug.
Great mix of adventure and downtime
You can hike Waimea Canyon in the morning, snorkel or beach-hop in the afternoon, and still be back in time for sunset. It’s an island that rewards both exploring and doing absolutely nothing.
The takeaway
Winter flights to Hawaii under $350 from Chicago don’t come around often — especially to Kauai. If you’ve been waiting for the right price to make a winter escape happen, this is one of the better Kauai deals we’ve seen.
The Flights
