Cheap flights from Hawaii to Chicago from $209
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Hawaii to Chicago departing on 10/28. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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How to get the cheapest flight ticket from Hawaii to Chicago
Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip
What is the cheapest month to fly to Chicago?
The month of November is, on average, the cheapest month to fly to Chicago from Hawaii, with most prices found around $569. If you’re not able to fly to Chicago in November, then October is your next best option. Flight prices from Hawaii to Chicago during October average around $573.
What is the cheapest day to depart on your flight to Chicago?
The cheapest day to depart on your flight to Chicago is on a Wednesday when prices can be found for as low as $871. 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 $1,136.
What is the cheapest time of day to depart on your flight to Chicago?
Our most recent data shows that the best time of day to fly to Chicago is at noon. Flights from Hawaii to Chicago during this time can be as low as $618. In contrast, the most expensive time of day to depart to Chicago is in the evening when prices are around $938.
What is the cheapest Hawaii to Chicago flight route?
Fly from Honolulu to Chicago O'Hare Intl for the best Hawaii - Chicago flight prices
How far in advance should I book a flight to Chicago?
You are more likely to see cheaper flights to Chicago from Hawaii when booking 5 weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $803 when searching 5 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 $698 on momondo.
What cabin class options are available on Hawaii to Chicago flights?
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.
What is the cheapest airline that flies from Hawaii to Chicago?
American Airlines, Delta, and Hawaiian Airlines are the most popular carriers operating from Hawaii to Chicago
What airlines fly to Chicago?
United Airlines, American Airlines and Alaska Airlines 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 38% 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.
How many flights depart from Hawaii to Chicago on average per day?
The number of flights available between Hawaii and Chicago is 3 per day as of June 2025. The most frequent departure time is 5:00PM, with 100% of daily flights leaving in the afternoon.
How many flights depart from Hawaii to Chicago on average per week?
The number of flights available between Hawaii and Chicago is 21 per week as of June 2025. The most frequent departure day is Mon, with 14% of weekly flights leaving on this day.
Cheap Hawaii to Chicago flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Hawaii to Chicago
When did momondo last update prices for flights from Hawaii to Chicago?
Prices for flights from Hawaii to Chicago are updated daily.
How many operators does momondo search for flights from Hawaii to Chicago?
The number of operators available for flights from Hawaii to Chicago is 6 as of June 2025.
How old do you have to be to fly from Hawaii to Chicago?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Hawaii to Chicago.
What documentation or ID do you need to fly to Chicago?
The travel and health documents required for your trip to Chicago can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular plane model from Hawaii to Chicago?
Based on momondo bookings for flights between Hawaii and Chicago, the leading plane model is Boeing 787-10 Dreamliner, making up 46.82% of the total bookings. Other popular models include Boeing 787-8 Dreamliner with 9.83%, Boeing 767-300 (winglets) with 9.25%, and Airbus A330-200 with 9.25%.
Best airlines flying from Hawaii to Chicago
Compare and see reviews for airlines that fly from Hawaii to Chicago with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $223 | Free Cancellation | Rating 8.0 7,946 reviews | |||
| PriceFrom $280 | Free Cancellation | Rating 7.8 2,494 reviews | |||
| PriceFrom $349 | Free Cancellation | Rating 7.2 10,000 reviews | |||
| PriceFrom $418 | Free Cancellation | Rating 8.0 10,000 reviews | |||
| PriceFrom $429 | Free Cancellation | Rating 7.4 8,790 reviews | |||
| PriceFrom $606 | Free Cancellation | Rating 8.0 4,287 reviews |
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsWhy use momondo?
Why should I use momondo to find a flight deal from Hawaii to Chicago?
We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Hawaii to Chicago for you.
Can I find flights from Hawaii to Chicago with flexible booking policies on momondo?
Yes. momondo enables you to select and highlight flights to Chicago from Hawaii with this policy.
How can momondo help me find flights from Hawaii to Chicago?
Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Hawaii.
I’m not ready to book a flight from Hawaii to Chicago right now. Can momondo alert me if prices change?
Yes momondo offers price alerts on flights to Chicago from Hawaii. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.