$284 Find Cheap Flights from The Big Island to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Chicago departing on 5/12. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Flight Deals

Cheap Flights from The Big Island to Chicago

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from The Big Island to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from The Big Island to Chicago

Thu, Sep 10 - Sat, Sep 26
Alaska Airlines Logo
10:35 am - 1:22 pm
KOA
-
ORD
21h 47m
1 stop
Alaska Airlines Logo
7:59 pm - 2:51 pm
ORD
-
KOA
23h 52m
1 stop
$494Alaska Airlines
Thu, Sep 10 - Sat, Sep 26
Multiple Airlines Logo
6:00 am - 11:57 pm
KOA
-
ORD
12h 57m
2 stops
Multiple Airlines Logo
7:59 pm - 2:51 pm
ORD
-
KOA
23h 52m
1 stop
$499Multiple Airlines
Thu, Sep 24 - Mon, Sep 28
Multiple Airlines Logo
6:00 am - 11:57 pm
KOA
-
ORD
12h 57m
2 stops
Multiple Airlines Logo
6:01 am - 2:51 pm
ORD
-
KOA
13h 50m
1 stop
$500Multiple Airlines
Thu, Sep 24 - Mon, Sep 28
Alaska Airlines Logo
10:25 pm - 2:54 pm
KOA
-
ORD
11h 29m
1 stop
Alaska Airlines Logo
6:01 am - 2:51 pm
ORD
-
KOA
13h 50m
1 stop
$509Alaska Airlines
Thu, Sep 24 - Mon, Sep 28
Alaska Airlines Logo
12:35 pm - 6:22 am
KOA
-
ORD
12h 47m
1 stop
Alaska Airlines Logo
6:01 am - 2:51 pm
ORD
-
KOA
13h 50m
1 stop
$515Alaska Airlines
Thu, May 28 - Thu, Jun 4
Delta Logo
8:50 pm - 1:45 pm
KOA
-
ORD
11h 55m
1 stop
Delta Logo
7:12 am - 5:35 pm
ORD
-
KOA
15h 23m
1 stop
$531Delta
Wed, May 27 - Wed, Jun 3
United Airlines Logo
10:15 pm - 2:35 pm
KOA
-
ORD
11h 20m
1 stop
United Airlines Logo
6:00 am - 11:42 am
ORD
-
KOA
10h 42m
1 stop
$534United Airlines
Wed, May 27 - Wed, Jun 3
Delta Logo
8:50 pm - 4:51 pm
KOA
-
ORD
15h 01m
2 stops
Delta Logo
7:12 am - 5:35 pm
ORD
-
KOA
15h 23m
1 stop
$544Delta
Tue, Jun 2 - Thu, Jul 30
Southwest Logo
10:00 am - 5:45 am
KOA
-
MDW
14h 45m
1 stop
Southwest Logo
5:45 am - 2:10 pm
MDW
-
KOA
13h 25m
2 stops
$722Southwest
Tue, May 12 - Sat, May 16
Southwest Logo
8:25 pm - 2:10 pm
KOA
-
MDW
12h 45m
1 stop
Southwest Logo
6:55 am - 1:15 pm
MDW
-
KOA
11h 20m
1 stop
$734Southwest
Useful Info

Good to know

Low seasonFebruary
Cheapest flight$284
Best time to beat the crowds with an average 5% drop in price.
Most popular time to fly with an average 7% increase in price.
Flight from Kailua-Kona to Chicago O'Hare Airport

FAQs for booking flights from The Big Island to Chicago

  • How does KAYAK find such low prices on flights from The Big Island to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from The Big Island to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from The Big Island to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from The Big Island is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from The Big Island to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to The Big Island with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from The Big Island to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from The Big Island up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Saint Joseph
Hammond
Portage
Lansing
Valparaiso
Chesterton
Schererville
Munster
Porter
Monticello
Saint John
Griffith

Everything you need to know for your flight to Chicago

Cabin class types available on flights to The Big Island

Cabin classes available on flights to Chicago. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.
First Class flights to Chicagofrom $386
Business Class flights to Chicagofrom $315
Premium Economy Class flights to Chicagofrom $133
Economy Class flights to Chicagofrom $41