Explore flight options from Kailua to Chicago with competitive pricing starting from $585.
Kailua
HNL
→
Chicago
ORD
11/04/2025 – 11/11/2025
Cheap flight deals from Kailua to Chicago
Average price start from:
i
$454
Round-trip flights from Kailua to Chicago starting at $454. Book now for the best deals!
One-way from:
i
$228
One-way flights from Kailua to Chicago starting at $228. Great for flexible travel!
Cheapest day:
i
Wednesday
Wednesday is the cheapest day to fly from Kailua to Chicago. Save more by booking on this day!
Cheapest In:
i
$415
Jan 2025
Jan 2025 is the cheapest month to fly from Kailua to Chicago with prices starting at $415.
Find flight deals from Kailua to Chicago
Cheapest flights from Kailua to Chicago
ONEWAY FLIGHTS
LAST MINUTE
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Explore the cheapest oneway flights from Kailua to Chicago spotted daily.
HNL
Kailua
HNL - Kailua • 2025-11-04 • 09:00
Unknown
60 min
ORD
Unknown City
$228
Non-stop • 60 min
HNL
Kailua
HNL - Kailua • 2025-11-04 • 09:00
Unknown
60 min
ORD
Unknown City
$262
Non-stop • 60 min
HNL
Kailua
HNL - Kailua • 2025-11-04 • 09:00
Unknown
60 min
MDW
Unknown City
$268
Non-stop • 60 min
HNL
Kailua
HNL - Kailua • 2025-11-04 • 09:00
Unknown
60 min
ORD
Unknown City
$274
Non-stop • 60 min
HNL
Kailua
HNL - Kailua • 2025-11-04 • 09:00
Unknown
60 min
MDW
Unknown City
$297
Non-stop • 60 min
HNL
Kailua
HNL - Kailua • 2025-11-04 • 09:00
Unknown
60 min
ORD
Unknown City
$302
Non-stop • 60 min
HNL
Kailua
HNL - Kailua • 2025-11-04 • 09:00
Unknown
60 min
ORD
Unknown City
$329
Non-stop • 60 min
HNL
Kailua
HNL - Kailua • 2025-11-04 • 09:00
Unknown
60 min
ORD
Unknown City
$346
Non-stop • 60 min
HNL
Kailua
HNL - Kailua • 2025-11-04 • 09:00
Unknown
60 min
ORD
Unknown City
$889
Non-stop • 60 min
Price Trends & Analysis
Weekly Price Trends
Save money by choosing Wednesday flights to Chicago.
Monthly Price Trends
Lowest fares from Kailua to Chicago typically available in February.
Weather & Climate Information
Temperature
Chicago experiences a humid continental climate, with winter temperatures often ranging from 20°F to 30°F and summer temperatures from 70°F to 85°F. The best times for comfortable travel are late spring (May) and early fall (September to October), when temperatures are mild and precipitation is lower.
Rainfall
The best time to visit Chicago is during late spring (May to early June) or early fall (September to October) when temperatures are mild and the city is vibrant with events like the Chicago Blues Festival and the Chicago Gourmet. These seasons also offer fewer crowds compared to peak summer tourism, allowing for a more enjoyable experience.
Airlines at Chicago
Traveling from Kailua to Chicago has never been more convenient, thanks to several reputable airlines offering seamless connectivity between these vibrant cities. Airlines such as Delta Air Lines, Alaska Airlines, American Airlines, Hawaiian Airlines provide regular flights, ensuring travelers have flexible options to suit their schedules.
Typically, the flight duration is around 10-15 hours, depending on layovers and the chosen route. Most flights from Kailua to Chicago include one stopover, often in major hubs, allowing for a comfortable transition. For those seeking to explore Chicago, booking with these airlines ensures a smooth travel experience, complete with modern amenities and excellent service.
Places to Visit in Chicago
Nestled by the shimmering shores of Lake Michigan, Chicago pulsates with a vibrant blend of architectural marvels and rich cultural heritage. Visitors can explore the iconic Art Institute, home to masterpieces that tell stories of creativity, while the historic streets of the Loop invite strolls past stunning skyscrapers and the famed Chicago Riverwalk. From savoring deep-dish pizza to catching a live jazz performance, the Windy City promises an unforgettable tapestry of experiences that celebrate its dynamic spirit and welcoming heart.
About Chicago
Explore the wonders of Chicago on your journey from Kailua. This remarkable destination blends cultural treasures with modern amenities, creating an enriching travel experience. Consider visiting during off-peak seasons for better value and fewer crowds.
Airlines Flying from Kailua to Chicago
Traveling from Kailua to Chicago has never been more convenient, thanks to several reputable airlines offering seamless connectivity between these vibrant cities. Airlines such as Delta Air Lines, Alaska Airlines, American Airlines, Hawaiian Airlines provide regular flights, ensuring travelers have flexible options to suit their schedules.
Typically, the flight duration is around 10-15 hours, depending on layovers and the chosen route. Most flights from Kailua to Chicago include one stopover, often in major hubs, allowing for a comfortable transition. For those seeking to explore Chicago, booking with these airlines ensures a smooth travel experience, complete with modern amenities and excellent service.
Hotels in Chicago
When staying in Chicago, look for hotels with easy access to ORD Airport. Most properties provide shuttle services for seamless airport transfers.
About Chicago
Explore the wonders of Chicago on your journey from Kailua. This remarkable destination blends cultural treasures with modern amenities, creating an enriching travel experience. Consider visiting during off-peak seasons for better value and fewer crowds.
Places to Visit in Chicago
Nestled by the shimmering shores of Lake Michigan, Chicago pulsates with a vibrant blend of architectural marvels and rich cultural heritage. Visitors can explore the iconic Art Institute, home to masterpieces that tell stories of creativity, while the historic streets of the Loop invite strolls past stunning skyscrapers and the famed Chicago Riverwalk. From savoring deep-dish pizza to catching a live jazz performance, the Windy City promises an unforgettable tapestry of experiences that celebrate its dynamic spirit and welcoming heart.
Hotels in Chicago
When staying in Chicago, look for hotels with easy access to ORD Airport. Most properties provide shuttle services for seamless airport transfers.
Airlines Flying from Kailua to Chicago
Traveling from Kailua to Chicago has never been more convenient, thanks to several reputable airlines offering seamless connectivity between these vibrant cities. Airlines such as Delta Air Lines, Alaska Airlines, American Airlines, Hawaiian Airlines provide regular flights, ensuring travelers have flexible options to suit their schedules.
Typically, the flight duration is around 10-15 hours, depending on layovers and the chosen route. Most flights from Kailua to Chicago include one stopover, often in major hubs, allowing for a comfortable transition. For those seeking to explore Chicago, booking with these airlines ensures a smooth travel experience, complete with modern amenities and excellent service.
Frequently Asked Questions
What's the lowest price for flights from Kailua to Chicago?
You can find flights starting from $228. For better deals, book during February and choose Wednesday departures.
How long is the journey from Kailua to Chicago?
The average flight time is about 10-15 hours, with most routes including one stopover for better pricing and comfort.
What airlines operate flights on this route?
Several airlines serve this route including Delta Air Lines, Alaska Airlines, American Airlines. Research current schedules and compare prices for the best deal.
How far in advance should I book?
For the best prices, book 2-3 months ahead and consider traveling during February when prices are typically lower.
What accommodation options are near ORD Airport?
ORD Airport has several nearby hotels with shuttle services, making it convenient for travelers with early or late flights.
What attractions can I visit in Chicago?
Chicago features a wonderful combination of historical sites and modern attractions. The best time to visit is during pleasant weather months for optimal sightseeing.
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