Cheap flights from Hawaii to Chicago from $209

The month of August is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Hawaii averaging around $554.

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Wednesday when prices can be found for as low as $759. This is often the case because there is less demand to fly during this day of the week. On the other hand, Saturday is the most expensive day to depart from Hawaii because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $998.

Flying to Chicago O'Hare Intl Airport from Hawaii in the evening is the least expensive time of day to depart. momondo users have found prices as low as $808 when looking at flights departing in the evening. Try not to purchase tickets in the afternoon because they tend to be around $826. Of course, these prices can vary depending on the time of year and what airport you fly to.

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

You are more likely to see cheaper flights to Chicago O'Hare Intl Airport from Hawaii when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago O'Hare Intl Airport for around $784 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago O'Hare Intl Airport from Hawaii for as low as $590 on momondo.

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

Alaska Airlines, United Airlines, and Delta are the most popular carriers operating from Hawaii to Chicago O'Hare Intl

United Airlines, American Airlines and Delta are the top three most popular airlines that fly to Chicago O'Hare Intl Airport from Hawaii according to our data. United Airlines is the first choice among our users, with 46% of people opting to fly with this airline when traveling to Chicago O'Hare Intl Airport. Keep in mind that there are 4 different airlines that fly to Chicago O'Hare Intl Airport on a routine basis, so you have a few additional options to choose from.

As of October 2026, 1 flights take off from Hawaii and land in Chicago O'Hare Intl Airport each day. The most common flight departure time for this route is 4:00PM, with 71% of daily flights taking off in the afternoon.

As of October 2026, 13 flights take off from Hawaii and land in Chicago O'Hare Intl Airport each week. The most common flight departure day for this route is Thu, with 38% of weekly flights taking off on this day.