Cheap flights from Hawaii to Chicago from $212

The month of January is, on average, the cheapest month to fly to Chicago from Hawaii, with most prices found around $527. If you’re not able to fly to Chicago in January, then February is your next best option. Flight prices from Hawaii to Chicago during February average around $578.

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 Saturday, the most expensive travel day of the week, you can expect to see flight prices from Hawaii to Chicago for around $992.

Our most recent data shows that the best time of day to fly to Chicago is in the afternoon. Flights from Hawaii to Chicago during this time can be as low as $814. In contrast, the most expensive time of day to depart to Chicago is in the evening when prices are around $821.

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

You are more likely to see cheaper flights to Chicago from Hawaii when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $797 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Hawaii for as low as $590 on momondo.

There are 4 cabin classes available to choose from on Hawaii to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Delta, American Airlines, and United Airlines are the most popular carriers operating from Hawaii to Chicago

United Airlines, American Airlines and Delta are the top three most popular airlines that fly to Chicago from Hawaii according to our data. United Airlines is the first choice among our users, with 45% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 5 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

The number of flights available between Hawaii and Chicago is 3 per day as of September 2026. The most frequent departure time is 4:00PM, with 100% of daily flights leaving in the afternoon.

The number of flights available between Hawaii and Chicago is 22 per week as of September 2026. The most frequent departure day is Sat, with 23% of weekly flights leaving on this day.