$212 Cheap Flights from Honolulu (HNL) to Chicago (MDW)

View $212 flight on Wed, Jan 28, 2026Opens in a new window

Popular airlines from Daniel K. Inouye Intl. Airport (HNL) to Chicago Midway Airport (MDW)

Cheap Flights from Honolulu to Chicago (HNL-MDW)

Prices were available within the past 7 days and start at $212 for one-way flights and $423 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Fri, Jan 16 - Tue, Jan 20
HNL
Oahu
MDW
Chicago
$423 Roundtrip, found 6 hours ago
$423
Roundtrip
found 6 hours ago
Select Southwest Airlines flight, departing Fri, Jan 16 from Oahu to Chicago, returning Tue, Jan 20, priced at $423 found 6 hours ago
Delta
Fri, Jan 16 - Mon, Jan 19
HNL
Oahu
MDW
Chicago
$425 Roundtrip, found 1 day ago
$425
Roundtrip
found 1 day ago
Select Delta flight, departing Fri, Jan 16 from Oahu to Chicago, returning Mon, Jan 19, priced at $425 found 1 day ago
Southwest Airlines
Wed, Feb 4 - Mon, Feb 9
HNL
Oahu
MDW
Chicago
$428 Roundtrip, found 10 hours ago
$428
Roundtrip
found 10 hours ago
Select Southwest Airlines flight, departing Wed, Feb 4 from Oahu to Chicago, returning Mon, Feb 9, priced at $428 found 10 hours ago
Southwest Airlines
Thu, Jan 15 - Thu, Jan 22
HNL
Oahu
MDW
Chicago
$447 Roundtrip, found 7 hours ago
$447
Roundtrip
found 7 hours ago
Select Southwest Airlines flight, departing Thu, Jan 15 from Oahu to Chicago, returning Thu, Jan 22, priced at $447 found 7 hours ago
Delta
Fri, Jan 16 - Tue, Jan 20
HNL
Oahu
MDW
Chicago
$463 Roundtrip, found 6 hours ago
$463
Roundtrip
found 6 hours ago
Select Delta flight, departing Fri, Jan 16 from Oahu to Chicago, returning Tue, Jan 20, priced at $463 found 6 hours ago
Southwest Airlines
Sat, Jan 17 - Sat, Jan 24
HNL
Oahu
MDW
Chicago
$471 Roundtrip, found 21 hours ago
$471
Roundtrip
found 21 hours ago
Select Southwest Airlines flight, departing Sat, Jan 17 from Oahu to Chicago, returning Sat, Jan 24, priced at $471 found 21 hours ago
Southwest Airlines
Wed, Feb 25 - Sun, Mar 1
HNL
Oahu
MDW
Chicago
$473 Roundtrip, found 5 hours ago
$473
Roundtrip
found 5 hours ago
Select Southwest Airlines flight, departing Wed, Feb 25 from Oahu to Chicago, returning Sun, Mar 1, priced at $473 found 5 hours ago
Southwest Airlines
Wed, Feb 11 - Tue, Feb 17
HNL
Oahu
MDW
Chicago
$478 Roundtrip, found 7 hours ago
$478
Roundtrip
found 7 hours ago
Select Southwest Airlines flight, departing Wed, Feb 11 from Oahu to Chicago, returning Tue, Feb 17, priced at $478 found 7 hours ago
Delta
Thu, Jan 15 - Tue, Jan 20
HNL
Oahu
MDW
Chicago
$493 Roundtrip, found 7 hours ago
$493
Roundtrip
found 7 hours ago
Select Delta flight, departing Thu, Jan 15 from Oahu to Chicago, returning Tue, Jan 20, priced at $493 found 7 hours ago
Delta
Fri, Jan 16 - Mon, Jan 19
HNL
Oahu
MDW
Chicago
$496 Roundtrip, found 1 day ago
$496
Roundtrip
found 1 day ago
Select Delta flight, departing Fri, Jan 16 from Oahu to Chicago, returning Mon, Jan 19, priced at $496 found 1 day ago

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. Average driving time to city center is 23 minutes. Flights from $794
ORD
O'Hare Intl.
Average driving time to city center23 min
Flights from $794

Frequently asked questions

How much does a flight from Daniel K. Inouye Intl. Airport (HNL) to Midway Intl. Airport (MDW) cost?
Grab a cheap one-way flight from $212 or cheap return flight from $423 from Daniel K. Inouye Intl. Airport (HNL) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight offers on this route.
What is the cheapest month to fly from Daniel K. Inouye Intl. Airport (HNL) to Midway Intl. Airport (MDW)?
Planning your trip for January is a great way to save, as it's the cheapest month for flights between HNL and MDW. You'll typically find the lowest prices during off-peak months.
What is the cheapest airline that flies from Daniel K. Inouye Intl. Airport (HNL) to Midway Intl. Airport (MDW)?
To find the cheapest airline flying from HNL to MDW, use Expedia's filter tool. Tailor your search based on your travel style, such as preferred carriers and seat class. You can then sort your results by "Price (lowest to highest)" to discover the cheapest flight right away.
How many flights per day from Daniel K. Inouye Intl. Airport (HNL) to Midway Intl. Airport (MDW)?
You'll have to catch a flight with a layover if you're traveling from Daniel K. Inouye Intl. Airport (HNL) to Midway Intl. Airport (MDW). There are no daily direct flights on this route. However, simply filter your search to include one or two stops to discover an option that works for you.
What day of the week has the most flights from HNL to MDW?
Typically you'll find the widest variety of flight choices on a Friday. Tuesdays tend to be the quietest.* But this can vary depending on the airline, season and other factors.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Daniel K. Inouye Intl. Airport (HNL) to Midway Intl. Airport (MDW)?
To avoid possible delays on the Daniel K. Inouye Intl. Airport (HNL) to Midway Intl. Airport (MDW) route, aim to travel before 3 PM. Later flights have a 22% higher chance of cancellation.**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 Daniel K. Inouye Intl. Airport (HNL)?
If you're on a direct flight from Daniel K. Inouye Intl. Airport (HNL) to Chicago, O'Hare Intl. Airport (ORD) is the only airport you can touch down at.
Is it cheaper to buy a plane ticket from Daniel K. Inouye Intl. Airport (HNL) to Midway Intl. Airport (MDW) last-minute?
Booking your plane ticket from HNL to MDW right before your trip is usually more expensive. However, if there's some wiggle room with your departure times and dates, you could snag a cheap last-minute fare.
Is it cheaper to book a HNL to MDW flight and hotel package?
You'll typically save money by securing a HNL to MDW flight and hotel package compared to booking separately. In fact, travelers could save hundreds of dollars by bundling with Expedia. And it's simple to manage it all in one convenient place. Once you've selected your preferred accommodations and flights, consider other add-ons like tours, activities and car rentals.
Can I cancel or change the date of my flight from Daniel K. Inouye Intl. Airport (HNL) to Midway Intl. Airport (MDW)?
Typically, it's possible to reschedule or cancel your HNL to MDW flight. However, if the booking was made more than 24 hours ago, additional charges 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.

Travel information

Origin airport
Daniel K. Inouye Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, Southwest Airlines
Roundtrip price
$423
Distance
4245 mi

Book with confidence

Honolulu to Chicago Flights

The cheapest times to fly from Honolulu 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 Honolulu to Chicago are during the month of January. You can find some of the cheapest flights from Honolulu to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Honolulu to Chicago

Sunday is one of the best days to book for cheap flights from Honolulu 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 Honolulu 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 Honolulu to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $212 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 Honolulu 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 Honolulu 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.

 

Honolulu to Chicago Flights

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*Available to One Key members.