Start: Chicago
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Wailea
— 5 nights
Fly
End: Chicago
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Wailea
— 5 nights
©
Wailea is a census-designated place (CDP) in Maui County, Hawaii, United States. Escape the urban bustle at Kapalua Beach and Kamaole Beach Park II. Step off the beaten path and head to Keawakapu Beach and Wailea Beach Path. Venture out of the city with trips to Lahaina (Kayaking & Canoeing & River Rafting & Tubing), Zipline (in Haiku) and Ho'okipa Beach Park (in Paia). There's still lots to do: kick back and relax at Kamaole Beach Park III and stroll through Honolua Bay.
To find traveler tips, ratings, where to stay, and other tourist information, you can read our Wailea online road trip planner.
Chicago to Wailea is an approximately 11-hour flight. You'll gain 4 hours traveling from Chicago to Wailea due to the time zone difference. Prepare for somewhat warmer weather when traveling from Chicago in May: high temperatures in Wailea hover around 86°F and lows are around 68°F. Finish your sightseeing early on the 21st (Mon) to allow enough time to fly back home.
To find traveler tips, ratings, where to stay, and other tourist information, you can read our Wailea online road trip planner.
Chicago to Wailea is an approximately 11-hour flight. You'll gain 4 hours traveling from Chicago to Wailea due to the time zone difference. Prepare for somewhat warmer weather when traveling from Chicago in May: high temperatures in Wailea hover around 86°F and lows are around 68°F. Finish your sightseeing early on the 21st (Mon) to allow enough time to fly back home.
Things to do in Wailea
Side Trips
Find places to stay May 16 — 21:
Highlights from your trip
Maui travel guide
The Valley Isle
The second largest of the eight major Hawaiian Islands, Maui features a rugged landscape ranging from high mountain peaks to deep valleys. Half of Maui lies within 8 km (5 mi) of the coastline, and most tourists come for the sandy beaches, many of them backed by fashionable resorts offering every modern convenience. Diversity of tourist attractions is Maui's major allure, with each of the island's shores offering a different set of vacation ideas. You can swim with dolphins, snorkel with sea turtles, or hike over the otherworldly landscapes of the world's biggest dormant volcano. A foodie paradise, the island also features dozens of small farms and gourmet restaurants.
