Travelers have found it’s best to book a flight 56 days in advance to save up to 21% compared to booking the same week of travel. As your travel date approaches, the cost of this flight route may potentially increase. While opting to book 56 days out may not be an option for all, there are still additional ways to secure a deal in the near future. You might find a flight from Chicago to Hawaii 1-2 weeks in advance for as low as $670, or $705 for flights within the next 24 hours.
January is one of the best times of the year to fly to Hawaii from Chicago. Prices for January average $770 per person but you can even find prices for as low as $370. The most expensive prices can be found in the month of June. Opting for a January flight can save you 29% on your journey compared to booking in June
When flying from Chicago to Hawaii, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
Fly from
Fly to
Budget
$417 - $540
Route
Depart
Return
Price
Chicago O'Hare IntlKona Intl
ORD - KOA
ORDKOA
Chicago O'Hare Intl
Thu 8/15
1 stop20h 00m
Kona Intl
Mon 8/19
1 stop11h 46m
Chicago O'Hare IntlKona Intl
ORD - KOA
ORDKOA
Chicago O'Hare Intl
Thu 8/15
1 stop20h 00m
Kona Intl
Mon 8/19
1 stop11h 46m
Chicago O'Hare IntlLihue
ORD - LIH
ORDLIH
Chicago O'Hare Intl
Wed 8/14
2 stops16h 22m
Lihue
Thu 8/22
1 stop11h 35m
Chicago O'Hare IntlLihue
ORD - LIH
ORDLIH
Chicago O'Hare Intl
Wed 8/14
2 stops16h 22m
Lihue
Thu 8/22
2 stops16h 06m
Chicago O'Hare IntlLihue
ORD - LIH
ORDLIH
Chicago O'Hare Intl
Mon 9/2
1 stop11h 06m
Lihue
Mon 9/9
1 stop12h 43m
Chicago O'Hare IntlLihue
ORD - LIH
ORDLIH
Chicago O'Hare Intl
Thu 8/22
1 stop11h 44m
Lihue
Thu 8/29
1 stop10h 58m
Chicago O'Hare IntlLihue
ORD - LIH
ORDLIH
Chicago O'Hare Intl
Mon 9/2
1 stop11h 06m
Lihue
Mon 9/9
2 stops14h 16m
Chicago O'Hare IntlKona Intl
ORD - KOA
ORDKOA
Chicago O'Hare Intl
Tue 6/4
1 stop28h 39m
Kona Intl
Tue 6/11
2 stops32h 29m
Chicago O'Hare IntlKona Intl
ORD - KOA
ORDKOA
Chicago O'Hare Intl
Sat 5/25
2 stops24h 47m
Kona Intl
Tue 5/28
1 stop15h 42m
No data available for this route at this time. Please check back soon.
Boarding
Overall
Entertainment
Crew
Food
Comfort
Reviews
Paid a lot for our exit row seats and they weren’t that roomy.
Boarding
Overall
Entertainment
Crew
Food
Comfort
Reviews
Paid a lot for our exit row seats and they weren’t that roomy.
Boarding
Overall
Entertainment
Crew
Food
Comfort
Reviews
Paid a lot for our exit row seats and they weren’t that roomy.
Boarding
Overall
Entertainment
Crew
Food
Comfort
Reviews
Paid a lot for our exit row seats and they weren’t that roomy.
Boarding
Overall
Entertainment
Crew
Food
Comfort
Reviews
Paid a lot for our exit row seats and they weren’t that roomy.
When you're looking for a tropical escape from the hustle and bustle of the Windy City, Hawaii makes a great choice. With their perfect weather and laid-back lifestyle, the Hawaiian Islands can help you relax and recharge. Whether you want to kick back with a book on Hulopoe Beach or hike through the jungle on the Manoa Falls Trail, the friendly locals and well-developed infrastructure make your journey a breeze. A direct flight between Chicago and Hawaii reduces travel time, so you can reach the islands quickly.
Hawaii is the perfect island vacation spot for travelers from Chicago: it's accessible by a direct flight, and it requires no passport or customs. Once you arrive on Oahu or Maui, you'll be greeted with balmy breezes and smiling locals. If you're longing for sunshine and sunbathing, head for the islands' many stunning beaches. On Maui, try Kaanapali Beach or Wailea Beach, and on the Big Island, check out the unusual Punaluu Black Sand Beach. If you're visiting Honolulu, the famous Waikiki Beach is a must-see. When you're ready to get out into the wild, check out the lava flows at Hawaii Volcanoes National Park or hike through the otherworldly landscapes of Haleakala National Park. Cool off in Hanakapiai Falls, or marvel at the steep cliffs of the Na Pali Coast.
If you're dreaming of a vacation to sunny Hawaii, start planning today. Use the Cheapflights search engine to browse a wide variety of fares on nonstop flights between Chicago and Honolulu or Kahului.
0%of flight departures | Early morningMidnight to 6 am |
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100%of flight departures | Morning6 am to noon |
0%of flight departures | AfternoonNoon to 6 pm |
0%of flight departures | Evening6 pm to midnight |
900+ travel sites are searched through when a user searches for a flight using Cheapflights. From the search interface, users can use filters to choose airlines, airports, flight times, cabin classes and more to their preference. Book your flight to Hawaii from Chicago today with Cheapflights!
Cheapflights simply makes it quick and affordable to book flights from Chicago to Hawaii by bringing together all flight options from hundreds of airlines and agencies online — and put it in one place for you to choose from. Plus, Cheapflights is 100% free to use for all.
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