Skip to main content
Beginning of main content

Cheap Flights from Chicago to Honolulu $730.73

Search over 321,000 hotels worldwide and 400 airlines worldwide.
Secure incredible value with Expedia’s Price Guarantee
No Expedia cancellation fee to change or cancel almost any hotel reservation.

Cheapest Flights from Chicago to Honolulu (MDW to HNL)

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Interesting Facts About Flights from Chicago to Honolulu (MDW to HNL)

Question : Is there an alternative to Chicago Midway International Airport (MDW) for getting you to Honolulu?
Answer : Chicago Midway International Airport is a superb airport, but there is a cheaper option - O'Hare International Airport. It's just 16 miles away, and flights are 14% cheaper over the next two months.

Question : Do travelers from Chicago typically stay in Honolulu for very long?
Answer : The average time spent in Honolulu by travelers flying from MDW is eight days.

Question : If your plans are flexible, have you considered changing your departure day?
Answer : For the month of February, the cheapest day to fly is Friday. Having flexibility in your travel plans means you can save, so be sure to plan ahead when possible.

Question : How often are prices changing for this route?
Answer : Prices for this trip tend to change a lot more than others. The further out you book a route, the more likely you are to save.