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Chicago, IL, USA to Kailua-Kona, HI, USA from $280: 2 ways by bus, train, flight or car

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from
Chicago, United States of America
to
Kailua-Kona, United States of America

How to Get from Chicago to Kailua-Kona: Cheapest, Fastest and Best Way

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$280 - PlaneBest price
6836 kmDistance
11h 41m Fastest

Compare Train, Bus, Flight, and Driving Options

Get detailed, step-by-step directions below for your trip from Chicago to Kailua-Kona with 1Map travel planner. Easily compare ticket prices, explore various transport options, and find the best routes for a seamless and cost-effective travel experience.

Company
various
Plane
Average Duration
11h  41m
Estimated price
$282-2105
Recommended
route map
Distance: 6836 km
Duration: 11h 41m

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Company
various
Plane
Average Duration
13h  39m
Estimated price
$2122-2125
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Traveling From Chicago to Kailua-Kona

Your journey from Chicago, with its vibrant cityscape and rich history, to Kailua-Kona, where sun-kissed beaches and lush landscapes await, offers a striking contrast in experiences that invites relaxation and adventure.

Best Neighbourhoods in Kailua-Kona

Kailua-Kona boasts diverse neighborhoods, each offering distinct charms for visitors.

Kailua Bay
• Stunning ocean views and access to water sports.
• Vibrant dining and shopping options along the waterfront.
Ali'i Drive
• Scenic coastal road with breathtaking sunsets.
• Home to local markets and cultural events.
Keauhou
• Abundant resorts and luxurious amenities.
• Close proximity to historic sites and parks.

Best Times To Visit Kailua-Kona's Attractions

Discover the ideal times to explore Kailua-Kona's popular attractions for a memorable experience.

Hulihee Palace
Visit mid-week for fewer crowds and a more intimate tour of this historic site.
Kona Coffee Farms
Early mornings are best to enjoy fresh brews and avoid afternoon heat.
Punalu'u Black Sand Beach
Late afternoon offers stunning sunset views and a more peaceful atmosphere.

Kailua-Kona Weather: What to Expect Year-Round

Kailua-Kona boasts a warm, tropical climate with mild temperatures year-round, perfect for beach outings and outdoor adventures. Visiting during the dry season from May to October enhances your experience, allowing you to fully enjoy the stunning landscapes and ocean activities.

Dining Recommendation in Kailua-Kona

Try the fresh poke at Da Poke Shack, a casual spot where the vibrant flavors of the Pacific Ocean come alive in every bite, contrasting sharply with Chicago's hearty deep-dish pizza. The laid-back atmosphere and use of locally sourced fish create a dining experience that celebrates the island’s bounty, making it a refreshing departure from the urban culinary scene.

Chicago - Kailua-Kona operators

Explore transport companies operating between Chicago and Kailua-Kona, with prices starting at . These companies offer competitive pricing, flexible schedules, and comfortable travel experiences.

Plane
Website
united.com

Plane from Chicago O'Hare to Kona

Average Duration
9h 6m
Estimated price
$282050-2900

Plane from Chicago O'Hare to Kona via San Francisco

Average Duration
12h
Estimated price
$282050-2900

Plane from Chicago O'Hare to Kona via Honolulu

Average Duration
11h 48m
Estimated price
$282050-2900
Website
aa.com

Plane from Chicago O'Hare to Kona via Los Angeles

Average Duration
12h 57m
Estimated price
$2825-2600
Website
southwest.com

Plane from Chicago Midway to Kona via Oakland

Average Duration
11h 50m
Estimated price
$2823-2824

Plane from Chicago Midway to Kona via Las Vegas

Average Duration
12h 25m
Estimated price
$2823-2824

Plane from Chicago Midway to Kona via Los Angeles

Average Duration
13h 25m
Estimated price
$2823-2824
Website
kaiserair.com

Plane from Chicago Midway to Kona via Oakland

Average Duration
11h 20m
Estimated price
$2826-2824
Website
alaskaair.com

Plane from Chicago Midway to Kona via San Diego

Average Duration
11h 40m
Estimated price
$2821-2824
Website
delta.com

Plane from Chicago Midway to Kona via Los Angeles

Average Duration
13h 1m
Estimated price
$2827-282050

Frequently asked questions

Find out more about the route from Chicago to Kailua-Kona.

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The distance between Chicago and Kailua-Kona is approximately 4248 miles. The typical travel time from Chicago to Kailua-Kona varies depending on the mode of transportation. If you take a train from Chicago to Milwaukee and then fly from Milwaukee to Kailua-Kona, it would take around 15 hours and 28 minutes. However, if you opt for a direct flight from Chicago to Kailua-Kona, the travel time would be shorter, around 11 hours and 54 minutes.
The most cost-effective and time-efficient transportation option for traveling from Chicago to Kailua-Kona is by taking a train to Milwaukee and then flying. This option typically costs between $390 and $650 and takes about 15 hours and 28 minutes. Alternatively, the quickest way to get to Kailua-Kona from Chicago is to take a direct flight, which typically costs between $360 and $2,200 and takes about 11 hours and 54 minutes.
The flight from Chicago to Kailua-Kona typically takes around 9 hours and 23 minutes on a direct flight. However, it is important to note that flight times can vary depending on factors such as weather conditions and air traffic. In terms of cost, prices for a flight between Kailua-Kona and Chicago can range from $364 to $2107, depending on factors such as the airline, time of booking, and any additional services or amenities chosen.
There are many options for accommodation near Kailua-Kona. With over 645 hotels to choose from, there is something to suit every traveler's needs and budget. Prices for hotels in the area start at $100 per night. Whether you are looking for a luxury resort, a budget-friendly motel, or anything in between, you are sure to find a suitable place to stay near Kailua-Kona.

Trips from Chicago