Travelers have found it’s best to book a flight 36 days in advance to save up to 22% 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 36 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 $698, or $708 for flights within the next 24 hours.
September is one of the best times of the year to fly to Hawaii from Chicago. Prices for September average $762 per person but you can even find prices for as low as $437. The most expensive prices can be found in the month of June. Opting for a September flight can save you 33% 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
$419 - $503
Route
Depart
Return
Price
Chicago O'Hare IntlKona Intl
ORD - KOA
ORDKOA
Chicago O'Hare Intl
Tue 5/14
1 stop17h 55m
Kona Intl
Mon 5/20
1 stop28h 27m
Chicago O'Hare IntlKona Intl
ORD - KOA
ORDKOA
Chicago O'Hare Intl
Tue 5/14
1 stop17h 55m
Kona Intl
Mon 5/20
1 stop28h 27m
Chicago O'Hare IntlKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Tue 9/24
1 stop14h 53m
Kahului
Tue 10/1
1 stop15h 18m
Chicago O'Hare IntlKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Tue 9/24
1 stop14h 53m
Kahului
Tue 10/1
2 stops16h 08m
Chicago O'Hare IntlKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Wed 5/15
1 stop10h 46m
Kahului
Sun 5/19
1 stop12h 52m
Chicago O'Hare IntlKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Thu 5/16
1 stop14h 01m
Kahului
Tue 5/21
1 stop11h 15m
Chicago O'Hare IntlKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Thu 8/29
1 stop10h 59m
Kahului
Sat 9/7
1 stop10h 53m
Chicago O'Hare IntlKona Intl
ORD - KOA
ORDKOA
Chicago O'Hare Intl
Tue 5/21
1 stop13h 24m
Kona Intl
Mon 5/27
1 stop11h 00m
Chicago O'Hare IntlKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Thu 5/16
1 stop16h 28m
Kahului
Tue 5/21
2 stops14h 45m
No data available for this route at this time. Please check back soon.
Boarding
Overall
Entertainment
Comfort
Crew
Food
Reviews
Paid a lot for our exit row seats and they weren’t that roomy.
Boarding
Overall
Entertainment
Comfort
Crew
Food
Reviews
Paid a lot for our exit row seats and they weren’t that roomy.
Boarding
Overall
Entertainment
Comfort
Crew
Food
Reviews
Paid a lot for our exit row seats and they weren’t that roomy.
Boarding
Overall
Entertainment
Comfort
Crew
Food
Reviews
Paid a lot for our exit row seats and they weren’t that roomy.
Boarding
Overall
Entertainment
Comfort
Crew
Food
Reviews
Paid a lot for our exit row seats and they weren’t that roomy.
Boarding
Overall
Entertainment
Comfort
Crew
Food
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.
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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 |
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