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Chicago to Kapalua Flights

Flight only Hotel only Flight + Hotel

Flight type

Round-trip One-way
Age of children at time of trip

We will search for applicable airfare discounts. Must have 1 adult for each infant in lap

Chicago and Kapalua airports and terminals

Airports in Chicago IL, US
map of airports in Chicago
  • 1

    Midway Airport (MDW)

    Distance from City Center: 9.5 miles

  • 2

    O'Hare Airport (ORD)

    Distance from City Center: 15.1 miles

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Airports in Kapalua HI, US
map of airports in Kapalua
  • 1

    Kahului Airport (OGG)

    Distance from City Center: 16.9 miles

  • 2

    Kapalua Airport (JHM)

    Distance from City Center: 3 miles

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Cheap flights from Chicago to Kapalua

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Highlighted price = Cheapest round-trip flights

Prices are round trip per person (conditions apply)

Featured Kapalua Airport Hotels

Hotel only $169

Aston Kaanapali Shores

4 stars
4.0 / 5 455 reviews

3445 Honoapiilani Road Map

Save With Already Reduced Non-Refundable Rates

You will be welcomed, Polynesian-style, in the open-air lobby of the Aston Kaanapali Shore Resort, situated on the tropical Kaanapali Beach. Suites are beautifully furnished in relaxing neutral... More

Hotel only $169

Kahana Beach

3 stars
3.7 / 5 22 reviews

4221 Lower Honoapiilani Hwy Map

The Kahana Beach Resort blends tradition with excitement to reflect the beauty of Hawaii as it was. Discover the golden sand beach and pristine waters that invite you to sail, swim, or snorkel.... More

Hotel only $275

Sands of Kahana

3 stars
3.5 / 5 4 reviews

4299 Lower Honoapiilani Hwy Map

Accommodations at this Kahana area resort feature 1, 2, and 3 bedrooms with full kitchens, dining areas, living rooms, and lanais. Sands of Kahana offers an onsite restaurant, poolside bar, outdoor... More

Hotel only $135

Outrigger Royal Kahana

3 stars
3.9 / 5 192 reviews

4365 Lower Honapilani Road Map

No Resort Fees

Outrigger Royal Kahana in Lahaina is a collection of studio and condo-style suites in Maui, Hawaii. Molokai and Lanai islands, as well as a seasonal glimpse of native whales, provide the views, and... More

Kahana Reef - Maui Condo & Home

2 stars
4.3 / 5 23 reviews

4471 Lower Honoapiilani Rd Map

No Resort or Cleaning Fees

...Kapalua West Maui Airport (1.2 mi/2 km).... Kahului Airport (29.9 mi/48.1 km) Attractions.... More

Hotel only $131

Aston Paki Maui

3 stars
3.3 / 5 103 reviews

3615 Lower Honoapiilani Road Map

Save With Already Reduced Non-Refundable Rates

...Golf (nearby) Transportation Kapalua West Maui Airport (1.2 mi/2 km).... Kahului Airport (28.2 mi/45.4 km) Attractions Whalers Village (2.4 mi/3.9 km).... More

Chicago to Kapalua Intro 13

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