S$342 Cheap Flights from Chicago to Honolulu

View S$342 flight on Tue, 26 Aug, 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$342 for one-way flights and S$1,351 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Tue, 26 Aug - Sat, 30 Aug
MDW
Chicago
HNL
Oahu
S$1,351 Return, found 16 hours ago
S$1,351
Return
found 16 hours ago
Select Delta flight, departing Tue, 26 Aug from Chicago to Oahu, returning Sat, 30 Aug, priced at S$1,351 found 16 hours ago
Delta
Tue, 26 Aug - Sat, 30 Aug
MDW
Chicago
HNL
Oahu
S$1,387 Return, found 6 days ago
S$1,387
Return
found 6 days ago
Select Delta flight, departing Tue, 26 Aug from Chicago to Oahu, returning Sat, 30 Aug, priced at S$1,387 found 6 days ago
Delta
Wed, 16 Jul - Mon, 28 Jul
MDW
Chicago
HNL
Oahu
S$1,535 Return, found 2 days ago
S$1,535
Return
found 2 days ago
Select Delta flight, departing Wed, 16 Jul from Chicago to Oahu, returning Mon, 28 Jul, priced at S$1,535 found 2 days ago
Delta
Tue, 26 Aug - Sat, 30 Aug
MDW
Chicago
HNL
Oahu
S$1,707 Return, found 16 hours ago
S$1,707
Return
found 16 hours ago
Select Delta flight, departing Tue, 26 Aug from Chicago to Oahu, returning Sat, 30 Aug, priced at S$1,707 found 16 hours ago
Delta
Tue, 26 Aug - Sat, 30 Aug
MDW
Chicago
HNL
Oahu
S$1,743 Return, found 6 days ago
S$1,743
Return
found 6 days ago
Select Delta flight, departing Tue, 26 Aug from Chicago to Oahu, returning Sat, 30 Aug, priced at S$1,743 found 6 days ago
Delta
Mon, 14 Jul - Mon, 21 Jul
MDW
Chicago
HNL
Oahu
S$1,990 Return, found 4 days ago
S$1,990
Return
found 4 days ago
Select Delta flight, departing Mon, 14 Jul from Chicago to Oahu, returning Mon, 21 Jul, priced at S$1,990 found 4 days ago
Delta
Mon, 14 Jul - Mon, 28 Jul
MDW
Chicago
HNL
Oahu
S$1,998 Return, found 1 day ago
S$1,998
Return
found 1 day ago
Select Delta flight, departing Mon, 14 Jul from Chicago to Oahu, returning Mon, 28 Jul, priced at S$1,998 found 1 day ago
Delta
Mon, 14 Jul - Mon, 21 Jul
MDW
Chicago
HNL
Oahu
S$2,001 Return, found 4 days ago
S$2,001
Return
found 4 days ago
Select Delta flight, departing Mon, 14 Jul from Chicago to Oahu, returning Mon, 21 Jul, priced at S$2,001 found 4 days ago
Delta
Sun, 20 Jul - Sun, 27 Jul
MDW
Chicago
HNL
Oahu
S$2,015 Return, found 5 days ago
S$2,015
Return
found 5 days ago
Select Delta flight, departing Sun, 20 Jul from Chicago to Oahu, returning Sun, 27 Jul, priced at S$2,015 found 5 days ago
Delta
Fri, 25 Jul - Fri, 1 Aug
MDW
Chicago
HNL
Oahu
S$2,030 Return, found 9 hours ago
S$2,030
Return
found 9 hours ago
Select Delta flight, departing Fri, 25 Jul from Chicago to Oahu, returning Fri, 1 Aug, priced at S$2,030 found 9 hours ago
Delta
Sun, 20 Jul - Sun, 27 Jul
MDW
Chicago
HNL
Oahu
S$2,194 Return, found 5 days ago
S$2,194
Return
found 5 days ago
Select Delta flight, departing Sun, 20 Jul from Chicago to Oahu, returning Sun, 27 Jul, priced at S$2,194 found 5 days ago
Delta
Fri, 25 Jul - Fri, 1 Aug
MDW
Chicago
HNL
Oahu
S$2,199 Return, found 9 hours ago
S$2,199
Return
found 9 hours ago
Select Delta flight, departing Fri, 25 Jul from Chicago to Oahu, returning Fri, 1 Aug, priced at S$2,199 found 9 hours ago
Delta
Fri, 25 Jul - Fri, 1 Aug
MDW
Chicago
HNL
Oahu
S$2,559 Return, found 9 hours ago
S$2,559
Return
found 9 hours ago
Select Delta flight, departing Fri, 25 Jul from Chicago to Oahu, returning Fri, 1 Aug, priced at S$2,559 found 9 hours ago
Chicago to Honolulu route information
Origin airport
Midway Intl.
Destination airport
Daniel K. Inouye Intl.
Airlines serving
Delta
Return price
S$1,350
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 20 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$342 and roundtrip prices from S$1,351*.
 

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$1,351. 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$759.20
*Available to Expedia members.