$236 Cheap Flights from Chicago (MDW) to Honolulu (HNL)

View $236 flight on Tue, Mar 3, 2026Opens in a new window

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

    notification illustration

    Be in the know

    Get alerts if flight prices drop or rise*
    deals illustration

    Book smarter

    Save up to 30% on select hotels after you book a flight*
    trophy illustration

    Earn twice

    Earn your airline miles on top of our OneKeyCash
    Learn about One Key

Cheap Flights from Chicago to Honolulu (MDW-HNL)

Prices were available within the past 7 days and start at $236 for one-way flights and $424 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Mon, Jan 26 - Fri, Jan 30
MDW
Chicago
HNL
Oahu
$424 Roundtrip, found 4 days ago
$424
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Mon, Jan 26 from Chicago to Oahu, returning Fri, Jan 30, priced at $424 found 4 days ago
Delta
Tue, Feb 3 - Thu, Feb 5
MDW
Chicago
HNL
Oahu
$431 Roundtrip, found 3 days ago
$431
Roundtrip
found 3 days ago
Select Delta flight, departing Tue, Feb 3 from Chicago to Oahu, returning Thu, Feb 5, priced at $431 found 3 days ago
Southwest Airlines
Fri, Jan 16 - Mon, Jan 19
MDW
Chicago
HNL
Oahu
$433 Roundtrip, found 3 days ago
$433
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Fri, Jan 16 from Chicago to Oahu, returning Mon, Jan 19, priced at $433 found 3 days ago
Southwest Airlines
Mon, Jan 26 - Fri, Jan 30
MDW
Chicago
HNL
Oahu
$436 Roundtrip, found 4 days ago
$436
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Mon, Jan 26 from Chicago to Oahu, returning Fri, Jan 30, priced at $436 found 4 days ago
Delta
Fri, Jan 16 - Mon, Jan 19
MDW
Chicago
HNL
Oahu
$442 Roundtrip, found 3 days ago
$442
Roundtrip
found 3 days ago
Select Delta flight, departing Fri, Jan 16 from Chicago to Oahu, returning Mon, Jan 19, priced at $442 found 3 days ago
Southwest Airlines
Mon, Jan 26 - Thu, Feb 5
MDW
Chicago
HNL
Oahu
$449 Roundtrip, found 5 days ago
$449
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Mon, Jan 26 from Chicago to Oahu, returning Thu, Feb 5, priced at $449 found 5 days ago
Delta
Fri, Jan 16 - Mon, Jan 19
MDW
Chicago
HNL
Oahu
$456 Roundtrip, found 3 days ago
$456
Roundtrip
found 3 days ago
Select Delta flight, departing Fri, Jan 16 from Chicago to Oahu, returning Mon, Jan 19, priced at $456 found 3 days ago
Southwest Airlines
Wed, Jan 7 - Mon, Jan 12
MDW
Chicago
HNL
Oahu
$466 Roundtrip, found 3 days ago
$466
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Wed, Jan 7 from Chicago to Oahu, returning Mon, Jan 12, priced at $466 found 3 days ago
Southwest Airlines
Wed, Jan 7 - Thu, Jan 15
MDW
Chicago
HNL
Oahu
$468 Roundtrip, found 5 days ago
$468
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Wed, Jan 7 from Chicago to Oahu, returning Thu, Jan 15, priced at $468 found 5 days ago
Delta
Tue, Mar 3 - Tue, Mar 10
MDW
Chicago
HNL
Oahu
$471 Roundtrip, found 1 hour ago
$471
Roundtrip
found 1 hour ago
Select Delta flight, departing Tue, Mar 3 from Chicago to Oahu, returning Tue, Mar 10, priced at $471 found 1 hour ago

Find the cheapest month to fly from Chicago (MDW) to Honolulu (HNL)

January is typically the cheapest month to fly

From $423 - $1,114 per traveler.

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Daniel K. Inouye Intl. Airport (HNL) cost?
Get a cheap one-way flight from $236 or cheap return flight from $424 from Midway Intl. Airport (MDW) to Daniel K. Inouye Intl. Airport (HNL) 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 Midway Intl. Airport (MDW) to Daniel K. Inouye Intl. Airport (HNL)?
Flying in January may help you find better deals, as it's the cheapest month for flights between MDW and HNL. You'll often find the lowest prices during the off-season.
Which airlines fly direct from Midway Intl. Airport (MDW) to Daniel K. Inouye Intl. Airport (HNL)?
You can't catch a direct flight to Daniel K. Inouye Intl. Airport (HNL) from Chicago, IL (MDW-Midway Intl.). However, you can arrive in Honolulu without any layovers by taking off from O'Hare Intl. Airport (ORD).
What is the cheapest airline that flies from Midway Intl. Airport (MDW) to Daniel K. Inouye Intl. Airport (HNL)?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that'll fly you from MDW to HNL. Then, sort your results by "Price (lowest to highest)" to snag a great deal.
How many flights per day from Midway Intl. Airport (MDW) to Daniel K. Inouye Intl. Airport (HNL)?
There are no daily nonstop flights departing from Midway Intl. Airport (MDW) to Daniel K. Inouye Intl. Airport (HNL). But you can opt for 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 at all.
What day of the week has the most flights from MDW to HNL?
Generally you'll find the widest variety of flight choices on a Friday. Tuesdays tend to be the quietest.* However, this can vary based on the season, carrier 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 Midway Intl. Airport (MDW) to Daniel K. Inouye Intl. Airport (HNL)?
To touch down at Daniel K. Inouye Intl. Airport (HNL) without delays, select a flight that leaves from Midway Intl. Airport (MDW) before 3 PM. The chance of cancellations is 22% higher, on average, for departures after this hour.**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.
Is it cheaper to buy a plane ticket from Midway Intl. Airport (MDW) to Daniel K. Inouye Intl. Airport (HNL) last-minute?
Booking your flight from MDW to HNL shortly before your trip is generally more expensive. But if you're flexible with your departure times and dates, you could land a cheap last-minute fare.
Is it cheaper to book a MDW to HNL flight and hotel package?
Securing a MDW to HNL flight and hotel package is typically cheaper than booking separately. With Expedia, you can enjoy the convenience of organizing your trip all in one place. Select from our extensive range of hotels and then add activities, flights and car rentals to your booking. Bundle it all together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Daniel K. Inouye Intl. Airport (HNL)?
If you booked your MDW to HNL flight within the last 24 hours, you may be able to modify or cancel it at no cost. Depending on the airline and the fare type you purchased, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, visit our Customer Service portal if you want more information.

Travel information

Travel information

Origin airport
Midway Intl.
Destination airport
Daniel K. Inouye Intl.
Airlines serving
Delta, Southwest Airlines
Roundtrip price
$424
Distance
4245 mi

Book with confidence

Book with confidence

Chicago to Honolulu Flights

The cheapest times to fly from Chicago to Honolulu

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

 

The best time to book a flight from Chicago to Honolulu

Sunday is one of the best days to book for cheap flights from Chicago to Honolulu: 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 Chicago to Honolulu

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 Chicago to Honolulu in 2025. You can also book with separate airlines for your outbound and return journeys, from $236 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 Chicago to Honolulu 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 Chicago to Honolulu 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.

 

Chicago to Honolulu Flights

Explore a world of travel with Expedia

Explore a world of travel with Expedia

*Available to One Key members.