$181 Cheap Flights from Kahului (OGG) to Chicago (MDW)

View $181 flight on Tue, Nov 4, 2025Opens in a new window

Popular airlines from Kahului Airport (OGG) to Chicago Midway Airport (MDW)

Cheap Flights from Kahului to Chicago (OGG-MDW)

Prices were available within the past 7 days and start at $181 for one-way flights and $421 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Wed, Oct 22 - Wed, Oct 29
OGG
Maui
MDW
Chicago
$421 Roundtrip, found 6 days ago
$421
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Wed, Oct 22 from Maui to Chicago, returning Wed, Oct 29, priced at $421 found 6 days ago
Delta
Thu, Nov 6 - Mon, Nov 10
OGG
Maui
MDW
Chicago
$428 Roundtrip, found 5 days ago
$428
Roundtrip
found 5 days ago
Select Delta flight, departing Thu, Nov 6 from Maui to Chicago, returning Mon, Nov 10, priced at $428 found 5 days ago
Delta
Thu, Nov 6 - Mon, Nov 10
OGG
Maui
MDW
Chicago
$453 Roundtrip, found 5 days ago
$453
Roundtrip
found 5 days ago
Select Delta flight, departing Thu, Nov 6 from Maui to Chicago, returning Mon, Nov 10, priced at $453 found 5 days ago
Southwest Airlines
Wed, Oct 22 - Wed, Oct 29
OGG
Maui
MDW
Chicago
$454 Roundtrip, found 6 days ago
$454
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Wed, Oct 22 from Maui to Chicago, returning Wed, Oct 29, priced at $454 found 6 days ago
Southwest Airlines
Wed, Jan 28 - Tue, Feb 3
OGG
Maui
MDW
Chicago
$457 Roundtrip, found 4 days ago
$457
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Wed, Jan 28 from Maui to Chicago, returning Tue, Feb 3, priced at $457 found 4 days ago
Southwest Airlines
Wed, Oct 22 - Wed, Oct 29
OGG
Maui
MDW
Chicago
$459 Roundtrip, found 6 days ago
$459
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Wed, Oct 22 from Maui to Chicago, returning Wed, Oct 29, priced at $459 found 6 days ago
Southwest Airlines
Wed, Jan 28 - Tue, Feb 3
OGG
Maui
MDW
Chicago
$463 Roundtrip, found 4 days ago
$463
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Wed, Jan 28 from Maui to Chicago, returning Tue, Feb 3, priced at $463 found 4 days ago
Delta
Fri, Dec 5 - Wed, Dec 10
OGG
Maui
MDW
Chicago
$467 Roundtrip, found 21 hours ago
$467
Roundtrip
found 21 hours ago
Select Delta flight, departing Fri, Dec 5 from Maui to Chicago, returning Wed, Dec 10, priced at $467 found 21 hours ago
Southwest Airlines
Tue, Oct 21 - Wed, Oct 29
OGG
Maui
MDW
Chicago
$472 Roundtrip, found 6 days ago
$472
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Tue, Oct 21 from Maui to Chicago, returning Wed, Oct 29, priced at $472 found 6 days ago
Southwest Airlines
Tue, Oct 21 - Wed, Oct 29
OGG
Maui
MDW
Chicago
$478 Roundtrip, found 6 days ago
$478
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Tue, Oct 21 from Maui to Chicago, returning Wed, Oct 29, priced at $478 found 6 days ago

Frequently asked questions

How much does a flight from Kahului Airport (OGG) to Midway Intl. Airport (MDW) cost?
Grab a cheap one-way flight from $181 or cheap return flight from $421 from Kahului Airport (OGG) to Midway Intl. Airport (MDW) 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 Midway Intl. Airport (MDW)?
The cheapest month to fly from OGG to MDW is October, when demand is low. Off-peak months are generally when better flight deals are available between these airports.
What is the cheapest airline that flies from Kahului Airport (OGG) to Midway Intl. Airport (MDW)?
Use the filter tool on Expedia to compare different airlines and find the cheapest carrier that'll fly you from OGG to MDW. Then, sort your results by "Price (lowest to highest)" to snap up a good deal.
How many flights per day from Kahului Airport (OGG) to Midway Intl. Airport (MDW)?
There are no daily nonstop flights available from Kahului Airport (OGG) to Midway Intl. Airport (MDW). But you can choose flights with layovers. Filter your search results on Expedia to include one or more stops, and you'll be on your way in no time.
What day of the week has the most flights from OGG to MDW?
Friday is usually the busiest day for flights, while Tuesday tends to be the quietest.* Keep in mind that flight schedules can change depending on various factors, such as the time of year and airline.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Kahului Airport (OGG) to Midway Intl. Airport (MDW)?
Book a flight from Kahului Airport (OGG) to Midway Intl. Airport (MDW) that leaves before 3 PM to reduce the likelihood of delays. Departures later than this are on average 22% more likely to be 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)?
If you're boarding a direct flight from Kahului Airport (OGG) to Chicago, O'Hare Intl. Airport (ORD) is the only airport you can land at.
Is it cheaper to buy a plane ticket from Kahului Airport (OGG) to Midway Intl. Airport (MDW) last-minute?
Holding off until just before your departure to book your flight from OGG to MDW generally means paying more. Although you may find some last-minute discounts, there's no guarantee. Be flexible with your itinerary to boost your chances of getting a bargain.
Is it cheaper to book an OGG to MDW flight and hotel package?
Compared with arranging hotels and flights separately, booking an OGG to MDW flight and hotel package with Expedia could lead to significant savings. Better still, having everything in one place will take the stress out of planning your trip. Simply secure your flights and select from our wide range of stays, then customize your trip with extras like tours and car rentals.
Can I cancel or change the date of my flight from Kahului Airport (OGG) to Midway Intl. Airport (MDW)?
Generally, it's possible to cancel or reschedule your OGG to MDW flight. However, if the booking was 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 more details on our Customer Service portal.

Travel information

Travel information

Origin airport
Kahului
Destination airport
Midway Intl.
Airlines serving
Delta, Southwest Airlines
Roundtrip price
$421
Distance
4187 mi

Book with confidence

Book with confidence

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 $181 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.

 

Kahului to Chicago Flights

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*Available to One Key members.