Start: Chicago
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Wailea
— 5 nights
Fly
End: Chicago
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See full calendar
Wailea
— 5 nights
Wailea is a census-designated place (CDP) in Maui County, Hawaii, United States. Escape the urban bustle at Honolua Bay and Kamaole Beach Park III. Explore Wailea's surroundings by going to Lahaina (Kayaking & Canoeing & River Rafting & Tubing), Zipline (in Haiku) and Ho'okipa Beach Park (in Paia). The adventure continues: kick back and relax at Kapalua Beach, stroll through Ulua Beach, and work some fitness into your day at Wailea Beach Path.
To find maps, photos, traveler tips, and more tourist information, read Wailea online trip planner.
Chicago to Wailea is an approximately 14-hour flight. You'll gain 4 hours traveling from Chicago to Wailea due to the time zone difference. Traveling from Chicago in May, expect Wailea to be somewhat warmer, temps between 86°F and 68°F. Wrap up your sightseeing on the 21st (Mon) to allow time to travel back home.
To find maps, photos, traveler tips, and more tourist information, read Wailea online trip planner.
Chicago to Wailea is an approximately 14-hour flight. You'll gain 4 hours traveling from Chicago to Wailea due to the time zone difference. Traveling from Chicago in May, expect Wailea to be somewhat warmer, temps between 86°F and 68°F. Wrap up your sightseeing on the 21st (Mon) to allow time to travel 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.
