Cheap flights from Honolulu to Chicago from $246

The month of August is, on average, the cheapest month to fly to Chicago from Honolulu, with most prices found around $215. If you’re not able to fly to Chicago in August, then May is your next best option. Flight prices from Honolulu to Chicago during May average around $230.

The cheapest day to depart on your flight to Chicago is on a Wednesday when prices can be found for as low as $762. This is often the case because there is less demand to fly during this day of the week. When flying out on a Friday, the most expensive travel day of the week, you can expect to see flight prices from Honolulu to Chicago for around $1,015.

Our most recent data shows that the best time of day to fly to Chicago is in the afternoon. Flights from Honolulu to Chicago during this time can be as low as $836. In contrast, the most expensive time of day to depart to Chicago is in the evening when prices are around $838.

Fly from Honolulu to Chicago O'Hare Intl for the best Honolulu - Chicago flight prices

You are more likely to see cheaper flights to Chicago from Honolulu when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $774 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Honolulu for as low as $548 on momondo.

You could potentially save up to 10% on your flight if you consider stops on a Honolulu to Chicago flight.

As of May 2026, prices for Honolulu to Chicago flights are approximately 0% more expensive when compared to flights at the same time last year.

Delta, Southwest, and Alaska Airlines are the most popular carriers operating from Honolulu to Chicago

United Airlines, American Airlines and Alaska Airlines are the top three most popular airlines that fly to Chicago from Honolulu according to our data. United Airlines is the first choice among our users, with 44% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 6 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

As of May 2026, there are 2 flights per day flying from Honolulu to Chicago. The most common time of day flights depart is 4:00PM, with 100% of flights taking off in the afternoon.

The number of flights available between Honolulu and Chicago is 14 per week as of May 2026. The most frequent departure day is Mon, with 14% of weekly flights leaving on this day.