S$1,208 Cheap Flights from Chicago to Honolulu

View S$1,208 flight on Mon, 15 Dec, 2025Opens in a new window

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

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Cheap Flights from Chicago to Honolulu (MDW-HNL)

Prices were available within the past 7 days and start at S$1,208 for one-way flights and S$1,822 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Mon, 15 Dec - Sun, 21 Dec
MDW
Chicago
HNL
Oahu
S$1,822 Return, found 3 days ago
S$1,822
Return
found 3 days ago
Select Delta flight, departing Mon, 15 Dec from Chicago to Oahu, returning Sun, 21 Dec, priced at S$1,822 found 3 days ago
Delta
Mon, 15 Dec - Sun, 21 Dec
MDW
Chicago
HNL
Oahu
S$1,982 Return, found 3 days ago
S$1,982
Return
found 3 days ago
Select Delta flight, departing Mon, 15 Dec from Chicago to Oahu, returning Sun, 21 Dec, priced at S$1,982 found 3 days ago
Delta
Mon, 15 Dec - Sun, 21 Dec
MDW
Chicago
HNL
Oahu
S$2,406 Return, found 3 days ago
S$2,406
Return
found 3 days ago
Select Delta flight, departing Mon, 15 Dec from Chicago to Oahu, returning Sun, 21 Dec, priced at S$2,406 found 3 days ago

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

January is typically the cheapest month to fly

From S$548 - S$1,378 per traveller.

Graph displaying average flight prices per month

Chicago to Honolulu route information
Origin airport
Midway Intl.
Destination airport
Daniel K. Inouye Intl.
Return price
S$1,822
Distance
6792 km

Perfect flights from Chicago to Honolulu

Your Journey from Chicago to Honolulu

Start your unforgettable journey with Expedia. Our broad selection of flights from Chicago to Honolulu caters to every travel need. Whether you're yearning for a romantic escape, a solo adventure, or a cultural immersion, we've got you covered.
 

Choosing Your Ideal Flight

With Expedia, you have access to a wide range of airlines, including Delta. Our selection of flights from Midway Intl. to Daniel K. Inouye Intl. caters to every traveler's requirements, ensuring your journey aligns with your schedule. With options from 4 airlines, you're bound to find the perfect flight.
 

Maximizing Value with Chicago to Honolulu Flights

Experience the joy of finding cheap flights from Midway Intl. to Daniel K. Inouye Intl. that fit your budget. Keep an eye out for our special deals and discounts, and check our flexible one-way fares from S$1,208 and roundtrip prices from S$1,822*.
 

Pre-Flight Essentials

Ensure a smooth journey from Chicago to Honolulu with Expedia. From information about check-in times and in-flight amenities to guidance on baggage policies, we provide all the essentials to prepare you for your flight.
 

Experience the Vibrant Honolulu

Picture yourself stepping off the plane in Honolulu and immersing yourself in the unique atmosphere of . From local markets to cultural festivals, each city offers its distinct charm. Make the most of your trip by exploring local attractions and indulging in the local cuisine. With Expedia, explore all this and more, tailored to your budget.
 

Added Convenience on Your Chicago to Honolulu Flight

Traveling with Expedia is more than just a flight. We offer details about in-flight amenities, baggage policies, and more to ensure a smooth and hassle-free journey. Choose from our variety of airlines and embark on a memorable journey from Chicago to Honolulu.
 

Beyond the Flight – Exploring Honolulu

With Expedia, your adventure extends beyond the flight. Explore Honolulu at your own pace by renting a car or booking a hotel. Discover hidden gems off the beaten path and create unforgettable memories.
 

Book Your Flight from Chicago to Honolulu with Confidence

Planning your next great adventure is a breeze with Expedia. Our user-friendly platform, unbeatable prices, and round-the-clock customer support make your travel experience seamless and stress-free. Embark on your journey from Chicago to Honolulu with confidence. Book your travel arrangements with Expedia today.
 
*Note: Prices may vary based on availability and are subject to change.

Frequently asked questions

How much is a flight from Chicago Airport to HNL?
Round-trip tickets from Midway Airport to HNL start from S$1,822. This figure is based on fares listed within the last 7 days on Expedia for flights departing within the next year — book now to avoid missing out. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from MDW to Daniel K. Inouye Intl. Airport (HNL)?
The majority of flights can be cancelled online, but every airline has a different set of terms and conditions. If you do decide to cancel your flight, go to our Customer Service Portal and follow the instructions.
How do I find cheap flights from Chicago Airport to Honolulu Intl. Airport that have flexible change policies?
Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you're searching for Midway Intl. Airport (MDW) to Honolulu Intl. Airport flights, you'll see a "no change fees" filter for you to select.
How far is the flight from Midway Airport to Honolulu International Airport?
Chicago to Honolulu is around 6,800 kilometres, so get ready to spend a while in the air. Make sure you pack all the essentials, from your toothbrush to your hairbrush. Throw in some snacks to nibble on throughout your journey too.
Which airlines fly direct from MDW to Honolulu International Airport?
At present, no airlines offer flights directly from Midway Intl. Airport (MDW) to Honolulu Intl. Airport. You'll need to book a flight with one or more stops. To score the best price and connections, lock in your airfare well in advance.
Are MDW to Honolulu Intl. Airport flight tickets cheaper when they're purchased at the last minute?
Fares from Midway Intl. Airport (MDW) to Daniel K. Inouye Intl. Airport (HNL) are available up to 12 months before departure on Expedia. And although you may nab fantastic last-minute deals, it's never a sure thing. Also, booking your flights well in advance means you'll have more options — and you can avoid getting caught in the dreaded middle seat! We regularly update our fares to bring you the best bargains, so keep checking in for all the latest specials.

Explore a world of travel with Expedia

Chicago Airports

Chicago

O'Hare Intl. to Honolulu
S$1,043.10
*Available to Expedia members.