$269 Find Cheap Flights from Kailua-Kona to Chicago - Compare and Save

These are the earliest and latest flight times available from Kailua-Kona to Chicago:

• Earliest: departs at 5:50 pm and lands at 1:52 am
• Latest: departs at 6:05 pm and lands at 2:07 am.

The flight takes about 8h 02m.

Three cabin classes are available on flights from Kailua-Kona to Chicago:

• Economy Class
• Business Class
• First Class

A nonstop flight from Kailua-Kona to Chicago takes 8h 02m, covering 4,219 miles.

No, a passport is not required for this domestic route, but you will need a real ID-compliant driver's license, a state ID or another TSA-accepted form of identification.

Round-trip flights from Kailua-Kona to Chicago range from $468 to $853, with an average of $653 over the past 12 months. Anything below $468 counts as a good deal.

On this route, layover flights are cheaper than nonstop options on average. Layover fares average $486 round-trip via Denver Intl (DEN), compared to $3,352 for nonstop.

Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $470 to $1,370. That means the highest observed fare was about 3x higher than the lowest one.

One-way fares from Kailua-Kona to Chicago are currently lower than usual. Average one-way flight prices are about $298, which is 20% below the typical average for this route.

Since Chicago is served by multiple airports, car rental options and rates can vary depending on which one you fly into.
Near Chicago O'Hare Intl Airport (ORD) — daily rates from around $17:

• Routes Car & Truck Rentals
• Europcar
• Hertz
• Dollar
• Ace

Near Chicago Midway Airport (MDW) — daily rates from around $32:

• Hertz
• Dollar
• Budget
• Alamo
• Rent-A-Wreck

Near Chicago Greater Rockford Airport (RFD) — daily rates from around $30:

• Alamo
• Enterprise Rent-A-Car
• Budget
• Avis
• National

Flights from Kailua-Kona to Chicago usually depart from Kona Intl (KOA) and may arrive at several airports in Chicago area, including Chicago Midway (MDW), Chicago O'Hare Intl (ORD) and Chicago Greater Rockford (RFD).

One-stop flights from Kailua-Kona to Chicago most commonly connect through:

• Los Angeles (LAX) - 28% of one-stop connections
• Seattle/Tacoma Intl (SEA) - 28% of one-stop connections
• Denver Intl (DEN) - 20% of one-stop connections
• Phoenix Sky Harbor Intl (PHX) - 12% of one-stop connections

Yes. Flexible dates can save you up to 84% on flights from Kailua-Kona to Chicago. Wednesday is the cheapest departure day at $550 round-trip on average, while Saturday is the most expensive at $3,352, a difference of $2,802.

KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

Only United Airlines operates flights between Kailua-Kona and Chicago.

Flying via San Francisco (SFO) gives the shortest average 1-stop total travel time at 10h 37m, compared with 10h 58m via Denver Intl (DEN) and 11h 58m via Los Angeles (LAX).

Chicago is 5 hours ahead of Kailua-Kona (Central Time vs Hawaii-Aleutian Time). Plan for the time shift when scheduling connections or first-day activities.

Some of the most popular sights in Chicago are Magnificent Mile, Grant Park and River North. These are among the most viewed places in Chicago on KAYAK.