$204 Cheap Flights from Kahului (OGG) to Chicago (ORD)

View $204 flight on Tue, Nov 4, 2025Opens in a new window

Popular airlines from Kahului Airport (OGG) to Chicago O'Hare Intl. Airport (ORD)

Cheap Flights from Kahului to Chicago (OGG-ORD)

Prices were available within the past 7 days and start at $204 for one-way flights and $367 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Alaska Airlines
Tue, Oct 21 - Tue, Oct 28
OGG
Maui
ORD
Chicago
$367 Roundtrip, found 1 day ago
$367
Roundtrip
found 1 day ago
Select Alaska Airlines flight, departing Tue, Oct 21 from Maui to Chicago, returning Tue, Oct 28, priced at $367 found 1 day ago
Alaska Airlines
Tue, Oct 28 - Tue, Nov 4
OGG
Maui
ORD
Chicago
$372 Roundtrip, found 2 days ago
$372
Roundtrip
found 2 days ago
Select Alaska Airlines flight, departing Tue, Oct 28 from Maui to Chicago, returning Tue, Nov 4, priced at $372 found 2 days ago
Alaska Airlines
Tue, Oct 28 - Tue, Nov 4
OGG
Maui
ORD
Chicago
$377 Roundtrip, found 2 days ago
$377
Roundtrip
found 2 days ago
Select Alaska Airlines flight, departing Tue, Oct 28 from Maui to Chicago, returning Tue, Nov 4, priced at $377 found 2 days ago
Alaska Airlines
Mon, Nov 3 - Tue, Nov 11
OGG
Maui
ORD
Chicago
$392 Roundtrip, found 4 days ago
$392
Roundtrip
found 4 days ago
Select Alaska Airlines flight, departing Mon, Nov 3 from Maui to Chicago, returning Tue, Nov 11, priced at $392 found 4 days ago
Alaska Airlines
Tue, Oct 21 - Mon, Oct 27
OGG
Maui
ORD
Chicago
$395 Roundtrip, found 2 days ago
$395
Roundtrip
found 2 days ago
Select Alaska Airlines flight, departing Tue, Oct 21 from Maui to Chicago, returning Mon, Oct 27, priced at $395 found 2 days ago
Alaska Airlines
Mon, Oct 20 - Mon, Oct 27
OGG
Maui
ORD
Chicago
$405 Roundtrip, found 3 days ago
$405
Roundtrip
found 3 days ago
Select Alaska Airlines flight, departing Mon, Oct 20 from Maui to Chicago, returning Mon, Oct 27, priced at $405 found 3 days ago
Southwest Airlines
Tue, Oct 21 - Tue, Oct 28
OGG
Maui
ORD
Chicago
$429 Roundtrip, found 1 day ago
$429
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Tue, Oct 21 from Maui to Chicago, returning Tue, Oct 28, priced at $429 found 1 day ago
American Airlines
Tue, Oct 21 - Tue, Oct 28
OGG
Maui
ORD
Chicago
$431 Roundtrip, found 1 day ago
$431
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Oct 21 from Maui to Chicago, returning Tue, Oct 28, priced at $431 found 1 day ago
Delta
Wed, Oct 1 - Mon, Oct 6
OGG
Maui
ORD
Chicago
$481 Roundtrip, found 2 hours ago
$481
Roundtrip
found 2 hours ago
Select Delta flight, departing Wed, Oct 1 from Maui to Chicago, returning Mon, Oct 6, priced at $481 found 2 hours ago
United
Mon, Sep 22 - Tue, Sep 23
OGG
Maui
ORD
Chicago
$570 Roundtrip, found 1 day ago
$570
Roundtrip
found 1 day ago
Select United flight, departing Mon, Sep 22 from Maui to Chicago, returning Tue, Sep 23, priced at $570 found 1 day ago

Find the cheapest month to fly from Kahului (OGG) to Chicago (ORD)

February is typically the cheapest month to fly

From $357 - $854 per traveler.

Graph displaying average flight prices per month

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $622
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $622
Flights from Kahului (OGG) to Chicago (ORD)
Origin airport
Kahului
Destination airport
O'Hare Intl.
Airlines serving
Alaska Airlines, American Airlines, Delta, Southwest Airlines, United
Roundtrip price
$363
Distance
4178 mi
Average flight time
15 hours 2 mins

Kahului to Chicago Flights

The cheapest times to fly from Kahului to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Kahului to Chicago are during the month of October. You can find some of the cheapest flights from Kahului to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Kahului to Chicago

Sunday is one of the best days to book for cheap flights from Kahului to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Kahului to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Kahului to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $204 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Kahului to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Kahului to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from Kahului Airport (OGG) to O'Hare Intl. Airport (ORD) cost?
Secure a cheap one-way flight from $204 or cheap return flight from $367 from Kahului Airport (OGG) to O'Hare Intl. Airport (ORD) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight deals on this route.
What is the cheapest month to fly from Kahului Airport (OGG) to O'Hare Intl. Airport (ORD)?
October is the most affordable month to fly from OGG to ORD. Planning your trip for the off-season is often the key to finding better fares.
Which airlines fly direct from Kahului Airport (OGG) to O'Hare Intl. Airport (ORD)?
When flying out of Kahului Airport (OGG), you can jump on a direct flight to O'Hare Intl. Airport (ORD) with United Airlines.
What is the cheapest airline that flies from Kahului Airport (OGG) to O'Hare Intl. Airport (ORD)?
Expedia's filter tool lets you easily compare airlines, flight times and fares all in one place. Choose your preferences, then sort by "Price (lowest to highest)" to find the carrier with the cheapest OGG to ORD flight.
How many flights per day from Kahului Airport (OGG) to O'Hare Intl. Airport (ORD)?
On average, Kahului Airport (OGG) has 5 nonstop flights to O'Hare Intl. Airport (ORD) weekly. If you're looking for more choice, use Expedia's filter tool to find flights with layovers. Fit in a quick visit to another city or simply break up your trip.
What are the most popular departure times for flights from Kahului Airport (OGG) to O'Hare Intl. Airport (ORD)?
The 6 PM departures from OGG to ORD are typically the busiest. These flights can come with a higher price due to their popularity. If you want to save on your trip, choose a less crowded time to fly.
What day of the week has the most flights from OGG to ORD?
Jet off on a Friday if you're looking for the best selection of flights from Kahului Airport (OGG) to O'Hare Intl. Airport (ORD).
What is the earliest flight from Kahului Airport (OGG) to O'Hare Intl. Airport (ORD)?
Hop on the earliest flight at around 5:50PM UTC-10, departing from Kahului Airport (OGG). You'll be in the air for approximately 7h 58m, landing at O'Hare Intl. Airport (ORD) at approximately 5:48AM UTC-6.
How long does it take to fly from Kahului Airport (OGG) to O'Hare Intl. Airport (ORD)?
It usually takes 7 hours and 58 minutes to travel the 4,200 mi from OGG to ORD.
What airline has the least delays from OGG to ORD?
United Airlines has the best track record for on-time direct flights from Kahului Airport (OGG) to O'Hare Intl. Airport (ORD), with an on-time score of 84%. Use the Expedia App to look up your flight status before you leave and get real-time updates about any changes.
What is the best time to fly from Kahului Airport (OGG) to O'Hare Intl. Airport (ORD)?
To avoid potential delays on the Kahului Airport (OGG) to O'Hare Intl. Airport (ORD) route, travel before 3 PM. Later flights have a 22% higher chance of being canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Chicago from Kahului Airport (OGG)?
O'Hare Intl. Airport (ORD) is the only airport in Chicago with direct flights from Kahului Airport (OGG). Browse your options and find affordable fares on Expedia.
Is it cheaper to buy a plane ticket from Kahului Airport (OGG) to O'Hare Intl. Airport (ORD) last-minute?
Last-minute fares from OGG to ORD are typically more expensive. To lock in the cheapest rates, start searching for flights early. That said, if you can play around with your travel dates, it's possible to find a cheap ticket just before your departure.
Is it cheaper to book an OGG to ORD flight and hotel package?
You can save money by booking an OGG to ORD flight and hotel package compared to booking separately. In fact, you could save hundreds of dollars by bundling with Expedia. And it's easy to manage everything in one place. Once you've chosen your ideal flights and accommodations, consider adding extras such as activities, tours and car rentals.
Can I cancel or change the date of my flight from Kahului Airport (OGG) to O'Hare Intl. Airport (ORD)?
Generally, it's possible to reschedule or cancel your OGG to ORD flight. However, for bookings made more than 24 hours ago, additional fees may apply. Refer to your airline's policies in your itinerary to see what changes are allowed and if any costs are involved. You'll also find further details on our Customer Service portal.

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*Available to One Key members.