12 days in Kauai & Honolulu Itinerary
Created using Klarna Trips Hawaii travel route builder
Start: Chicago
Fly
1
Koloa
— 8 nights
Fly
2
Honolulu
— 2 nights
Fly
End: Chicago
Tue, Dec 27 - Sat, Jan 7
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Koloa — 8 nights

Kōloa is an unincorporated census-designated place (CDP) in Kauai County, Hawaii, United States. Venture out of the city with trips to Kayak Hanalei (in Hanalei), Pihea Trail (in Kekaha) and Waimea (Canyon Trail, Waipo’o Falls, &more). And it doesn't end there: kick back and relax at Poipu Beach Park, appreciate the extensive heritage of Kalalau Lookout, browse the different shops at Poipu Shopping Village, and see the world from above with a helicopter tour.
For where to stay, reviews, ratings, and tourist information, refer to the Koloa planner.
Chicago to Koloa is an approximately 13-hour flight. The time zone difference moving from Central Standard Time to Hawaii-Aleutian Standard Time is minus 4 hours. Plan for warmer temperatures traveling from Chicago in December, with highs in Koloa at 79°F and lows at 67°F. You will have some time to spend on the 4th (Wed) before leaving for Honolulu.
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For where to stay, reviews, ratings, and tourist information, refer to the Koloa planner.
Chicago to Koloa is an approximately 13-hour flight. The time zone difference moving from Central Standard Time to Hawaii-Aleutian Standard Time is minus 4 hours. Plan for warmer temperatures traveling from Chicago in December, with highs in Koloa at 79°F and lows at 67°F. You will have some time to spend on the 4th (Wed) before leaving for Honolulu.
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Find places to stay Dec 27 — Jan 4:
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Honolulu — 2 nights

Big Pineapple
In many ways much more Asian than American, Honolulu is Hawaii's largest city and its center of government, transportation, commerce, and tourism.Change things up with a short trip to Kailua Beach Park in Kailua (about 32 minutes away). There's lots more to do: contemplate the long history of USS Arizona Memorial, kick back and relax at Kapiolani Regional Park, test your problem-solving skills at popular escape rooms, and tour the pleasant surroundings at Waikiki Beach.
To find traveler tips, reviews, maps, and more tourist information, refer to the Honolulu vacation tool.
Getting from Koloa to Honolulu by flight takes about 2.5 hours. Expect a daytime high around 81°F in January, and nighttime lows around 67°F. Wrap up your sightseeing on the 6th (Fri) early enough to fly back home.
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Find places to stay Jan 4 — 6:
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Kauai travel guide
The Garden Isle
The northernmost of Hawaii's major islands, Kauai earned the nickname "Garden Island" because of its abundance of lush greenery and tropical plants, watered frequently with plentiful rainfall. Kauai's landscape continues to suffer from powerful erosion, resulting in natural attractions that include plunging canyons, tall mountain peaks, and the longest sandy coastline of all the Hawaiian islands. Offering a mild tropical climate and pristine wilderness areas largely unspoiled by mass tourism, Kauai is a great vacation destination for visitors eager to escape Hawaii's more crowded tourist resorts. For a genuine Kauai experience, join the locals for one of their famous traditional meat and vegetable feasts, prepared in underground pits lined with hot rocks.