Cheap flights from Kailua-Kona to Chicago

Flights overview

Useful information for finding cheap flights from Kailua-Kona to Chicago and booking your next trip
Cheapest round-trip flights $508
United 1 stop 18 hr Thu, May 28 — Wed, Jun 3
The cheapest round-trip flight from Kailua-Kona to Chicago is currently $508
Cheapest one-way flight $222
United 1 stop 21 hr Mon, Jun 1
The cheapest one-way flight from Kailua-Kona to Chicago is currently $222
Last-minute weekend getaway $640
United 2 stops 19 hr Fri, May 8 — Sun, May 10
The cheapest last-minute weekend getaway from Kailua-Kona to Chicago is currently $640
Cheapest business class flights $1,793
United 1 stop 14 hr Sun, May 24 — Tue, Jun 2
The cheapest business class round-trip flight from Kailua-Kona to Chicago is currently $1,793
Fastest flight 9 hr 31 min The fastest flight with stops from Kailua-Kona to Chicago takes 9 hr 31 min
Nonstop flights None There are no direct flights on this route.

When is the cheapest time to fly?

The cheapest month to fly from Kailua-Kona to Chicago is typically January. The most expensive month to fly is typically June.
January
Cheapest
Typical prices: $405–830
June
Most expensive
Typical prices: $620–760

Popular airlines from Kailua-Kona to Chicago

  • Southwest
    from $715
    Typical price: $630–990
    1794 weekly connecting flights
    KOA - MDW, ORD Every day
  • United
    from $508
    Typical price: $500–850
    320 weekly connecting flights
    KOA - ORD Every day
  • American
    from $713
    Typical price: $520–900
    142 weekly connecting flights
    KOA - ORD Every day
  • Delta
    from $637
    Typical price: $540–1,150
    103 weekly connecting flights
    KOA - MDW, ORD Every day
  • Alaska
    from $640
    Typical price: $520–980
    47 weekly connecting flights
    KOA - ORD Every day

Popular airports near Kailua-Kona

  • Ellison Onizuka Kona International Airport (KOA)
    Kailua-Kona United States 17 min 7 mi
  • Hilo International Airport (ITO)
    Hilo United States 1 hr 37 min 62 mi
  • Waimea-Kohala Airport (MUE) (MUE)
    Waimea United States 50 min 32 mi

Popular airports near Chicago

  • Chicago O'Hare International Airport (ORD)
    Chicago United States 26 min 16 mi
  • Chicago Midway International Airport (MDW)
    Chicago United States 25 min 9 mi
  • Milwaukee Mitchell International Airport (MKE)
    Milwaukee United States 1 hr 23 min 75 mi
  • Indianapolis International Airport (IND)
    Indianapolis United States 2 hr 58 min 165 mi

Frequently asked questions about flying from Kailua-Kona to Chicago

The cheapest flights from Kailua-Kona to Chicago are usually in January. Typical ticket prices in January range from $405 to $830.
The cheapest round-trip flight from Kailua-Kona to Chicago recently found on Google Flights was with United from $508. The cheapest one-way flight was with United from $222.

Some of the cheapest round-trip deals we found with different airlines:
  • The cheapest Southwest flight from Kailua-Kona to Chicago is $715, flying from May 28 to Jun 3.
  • The cheapest United flight from Kailua-Kona to Chicago is $508, flying from May 28 to Jun 3.
  • The cheapest American flight from Kailua-Kona to Chicago is $713, flying from May 21 to May 28.
  • The cheapest Delta flight from Kailua-Kona to Chicago is $637, flying from May 21 to May 27.
  • The cheapest Alaska flight from Kailua-Kona to Chicago is $640, flying from May 28 to Jun 3.
The cheapest round-trip flight from Kailua-Kona to Chicago starts at $508 from Thu, May 28 to Wed, Jun 3. The cheapest one-way flight starts at $222 and departs on Mon, Jun 1.
9 hr 31 min is the shortest flight time from Kailua-Kona to Chicago.
Chicago's peak season is Jun–Aug. Popular events throughout year include St. Patrick's Day, when the river is tinted green (Mar 17); the Pride Parade (Jun); the Taste of Chicago culinary festival (Jul) and the Jazz Festival (Sep). During the holiday season (Nov–Dec), the Magnificent Mile Lights Festival and Christkindlmarket, a German Christmas market in Daley Plaza, draw crowds to the city.
It's easy to use Google Flights to find the cheapest days to fly from Kailua-Kona to Chicago.
Just click the Departure label near the top of the page to open the calendar. Choose a start date and a return date to see how the round-trip fare changes on those specific days.
Adjust the trip type to see one-way fares. The cheapest available flights are highlighted and easy to spot. Once you settle on dates, click the Search button to see flight options and book the deal.

You can also turn on price tracking to get alerts if the price changes for a route or flight.
What counts as the best airline for your flights from Kailua-Kona to Chicago really depends on your individual needs. You may have a favorite carrier or a loyalty program you like, but price, convenience, and airports served also come into play. Flexibility and booking terms – Can you change flights if you want to stay longer or get a refund if you have to postpone your trip? – are also factors that help determine which airline is best to fly from Kailua-Kona to Chicago.

In terms of flights, Southwest is the most popular. Southwest offers 1,794 connecting flights per week. Southwest flies from Ellison Onizuka Kona International Airport (KOA) to Chicago Midway International Airport (MDW) , Chicago O'Hare International Airport (ORD) .

Other popular airlines flying from Kailua-Kona to Chicago are:
  • United offers 320 connecting flights per week. United flies from Ellison Onizuka Kona International Airport (KOA) to Chicago O'Hare International Airport (ORD) .
  • American offers 142 connecting flights per week. American flies from Ellison Onizuka Kona International Airport (KOA) to Chicago O'Hare International Airport (ORD) .
  • Delta offers 103 connecting flights per week. Delta flies from Ellison Onizuka Kona International Airport (KOA) to Chicago Midway International Airport (MDW) , Chicago O'Hare International Airport (ORD) .
  • Alaska offers 47 connecting flights per week. Alaska flies from Ellison Onizuka Kona International Airport (KOA) to Chicago O'Hare International Airport (ORD) .
The number of connecting flights refers to distinct flights with at least one stop between Kailua-Kona and Chicago.
The cheapest round-trip flight from Kailua-Kona to Chicago recently found on Google Flights was with United from $508. The cheapest one-way flight was with United from $222.

Some of the cheapest round-trip deals we found with different airlines:
  • The cheapest Southwest flight from Kailua-Kona to Chicago is $715, flying from May 28 to Jun 3.
  • The cheapest United flight from Kailua-Kona to Chicago is $508, flying from May 28 to Jun 3.
  • The cheapest American flight from Kailua-Kona to Chicago is $713, flying from May 21 to May 28.
  • The cheapest Delta flight from Kailua-Kona to Chicago is $637, flying from May 21 to May 27.
  • The cheapest Alaska flight from Kailua-Kona to Chicago is $640, flying from May 28 to Jun 3.
No airline flies direct from Kailua-Kona to Chicago.
  • There are 1794 Southwest connecting flights from Kailua-Kona to Chicago per week. Flights are available every day.
  • There are 320 United connecting flights from Kailua-Kona to Chicago per week. Flights are available every day.
  • There are 142 American connecting flights from Kailua-Kona to Chicago per week. Flights are available every day.
  • There are 103 Delta connecting flights from Kailua-Kona to Chicago per week. Flights are available every day.
  • There are 47 Alaska connecting flights from Kailua-Kona to Chicago per week. Flights are available every day.
Use the Stops filter while searching for flights, to see only nonstop options in your results.
The cheapest last-minute deal between Kailua-Kona and Chicago at price $640 is offered by United from Fri, May 8 to Sun, May 10.
No airline flies direct from Kailua-Kona to Chicago.
  • There are 1794 Southwest connecting flights from Kailua-Kona to Chicago per week. Flights are available every day.
  • There are 320 United connecting flights from Kailua-Kona to Chicago per week. Flights are available every day.
  • There are 142 American connecting flights from Kailua-Kona to Chicago per week. Flights are available every day.
  • There are 103 Delta connecting flights from Kailua-Kona to Chicago per week. Flights are available every day.
  • There are 47 Alaska connecting flights from Kailua-Kona to Chicago per week. Flights are available every day.
Use the Stops filter while searching for flights, to see only nonstop options in your results.
There are no direct flights from Kailua-Kona to Chicago.
It's easy to find nonstop flights with Google Flights! Once you've searched for flights from Kailua-Kona to Chicago, just select the nonstop flights only option in the 'Stops’ filter in the search form and view all available direct flights and their prices.
The cheapest business class round-trip flights between Kailua-Kona and Chicago start at $1,793 from Sun, May 24 to Tue, Jun 2 with United.
The cheapest economy class round-trip flights between Kailua-Kona and Chicago start at $508 from Thu, May 28 to Wed, Jun 3.
To book business class trips from Kailua-Kona to Chicago, look for the default Economy selection at the top, and change it to your desired cabin class such as Premium Economy, Business Class, or First Class. You can then select your departure and arrival dates, consider available options, and book your business travel.

You can also adjust the trip type to view one-way fares.
The best last-minute getaway deal for the next weekend between Kailua-Kona and Chicago starts at $640 from Fri, May 8 to Sun, May 10 with United.
The cheapest last-minute deal between Kailua-Kona and Chicago at price $640 is offered by United from Fri, May 8 to Sun, May 10.
To find last-minute flight deals from Kailua-Kona to Chicago, start by entering the city names, select the desired departure and return dates, and hit the Search button to view flight options.

You can check for last-minute flights for the same day or adjust the trip type to see one-way fares.

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