Cheap flights from Chicago to Honolulu from $209

The month of February is, on average, the cheapest month to fly to Honolulu from Chicago, with most prices found around $629. If you’re not able to fly to Honolulu in February, then April is your next best option. Flight prices from Chicago to Honolulu during April average around $665.

Our data shows that Tuesday is the least expensive day to fly to Honolulu. Tickets to fly out on this day can be as low as $731. Be sure to avoid booking your departure on a Saturday as prices are generally higher than usual. According to our data, the average ticket price to Honolulu on Saturday is $1,075.

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

You are more likely to see cheaper flights to Honolulu from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Honolulu for around $840 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Honolulu from Chicago for as low as $670 on momondo.

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

You could potentially save up to 20% on your flight if you consider stops on a Chicago to Honolulu flight.

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

United Airlines, American Airlines and Delta are the top three most popular airlines that fly to Honolulu from Chicago according to our data. United Airlines is the first choice among our users, with 54% of people opting to fly with this airline when traveling to Honolulu. Keep in mind that there are 5 different airlines that fly to Honolulu on a routine basis, so you have a few additional options to choose from.

Historically, on average around 19% of flights between Chicago and Honolulu have experienced a delay on any given week. The average delay length over the past 12 months has been 203 minutes.

Generally, flights departing in the morning tend to experience fewer delays. Flights in the evening have, in the past, seen delays more frequently in comparison.

Wednesday is statistically the day of the week which experiences the fewest number of delays on this flight route. Friday has historically seen more delays on average compared to the rest of the week.

According to our data, United Airlines have had the least number of delays on this route over the last 12 months; with about 15% of their flights experiencing any sort of delay.

Los Angeles (LAX) was the most common stop: 44% of momondo users choosing 1-stop flights on this route connected there.

Flights via Detroit (DTW) offer the lowest average round-trip price of $424.

Flights connecting via Los Angeles (LAX) have the shortest average one-way travel time: 11h 10m.

Dallas (DFW) has the shortest average layover time for this route: 0h 53m.

2 flights are operational daily from Chicago to Honolulu as of October 2026. The most popular departure time for this route is 9:00AM, with 100% of flights per day taking off at noon.

As of October 2026, 19 flights take off from Chicago and land in Honolulu each week. The most common flight departure day for this route is Thu, with 26% of weekly flights taking off on this day.