$252 Cheap Delta flights Chicago (MDW) to Honolulu (HNL)

Make use of the “Price (lowest to highest)” filter on Expedia to look for cheap Delta Air Lines round-trip flights from $504 from MDW to HNL. Affordable one-way tickets from $252 are available as well.**These prices were available on Expedia within the past 7 days, for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.

Delta Air Lines flights to Honolulu tend to be more affordable in the quieter months of November and October. Whether you’re in search of a round-trip or one-way ticket, you could land a better deal then.

Search for affordable Delta Air Lines flights from Midway Intl. Airport (MDW) to Daniel K. Inouye Intl. Airport (HNL) one to three months ahead of your day of departure. Travelers who book domestic flights 34 to 86 days in advance can save 25% compared to those who book just 6 to 12 days ahead. Regardless of fare class and itinerary, the best day to book a domestic flight is usually Sunday and the most expensive tends to be Monday. Passengers who book on a Sunday can save 6% on average compared to those who book on a Monday.**Ideal booking window recommendation is based on average round-trip ticket prices for January through November for 2024. Best day of the week to book recommendation is based on average round-trip ticket prices for January through October 2024. All data sourced from ARC’s global airline sales database.

To figure out if there’s a direct journey from MDW to HNL with Delta Air Lines or another airline, use our “Nonstop” filter when searching for flights.

Sort your results by “Early Morning” and “Morning” to find the earliest flights from MDW to HNL. Leaving early means flight cancellations are less likely.**Most reliable time of the day recommendation is based on January through August 2024 flight status data sourced from OAG’s global flight data platform.

Daniel K. Inouye Intl. Airport (HNL) is the main Honolulu hub for Delta Air Lines flights from Midway Intl. Airport (MDW).

Jetting off from MDW to HNL with Delta Air Lines means enjoying a range of perks, including a rewarding loyalty program and an excellent in-flight experience. Plus, when you book through Expedia, One Key™ members can collect OneKeyCash™* to use on select future travel purchases. That’s in addition to the Delta SkyMiles points you can earn with Delta Air Lines.*OneKeyCash™ disclaimer - OneKeyCash™ is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.

It’s usually possible to cancel or modify your flight, although there may be additional charges if you booked over 24 hours ago. Need to keep your options open? Use Expedia’s “Changes included” and “No cancel fee” filters to find flights that won’t charge you extra if you have to revise your plans. To update your itinerary, head to “Trips,” select your flight and click on “Manage Booking” for more details.