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 $771 per person but you can even find prices for as low as $374. The most expensive prices can be found in the month of June. Opting for a January flight can save you 28% 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
$348 - $696
Route
Depart
Return
Price
Chicago O'Hare IntlKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Tue 10/29
1 stop20h 38m
Kahului
Tue 11/5
1 stop20h 58m
Chicago O'Hare IntlKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Tue 9/17
1 stop11h 35m
Kahului
Tue 9/24
1 stop12h 52m
Chicago O'Hare IntlKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Tue 9/17
1 stop21h 02m
Kahului
Fri 9/20
1 stop11h 13m
Chicago O'Hare IntlKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Wed 10/30
1 stop14h 53m
Kahului
Wed 11/6
2 stops13h 46m
Chicago O'Hare IntlKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Mon 9/9
1 stop30h 21m
Kahului
Thu 9/19
1 stop19h 08m
Chicago O'Hare IntlKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Wed 10/16
1 stop14h 53m
Kahului
Tue 10/22
1 stop13h 58m
Chicago O'Hare IntlKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Sun 8/25
1 stop12h 52m
Kahului
Sun 9/8
1 stop12h 52m
Chicago O'Hare IntlKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Wed 8/7
1 stop11h 43m
Kahului
Tue 8/13
1 stop12h 03m
Chicago O'Hare IntlHonolulu
ORD - HNL
ORDHNL
Chicago O'Hare Intl
Tue 7/2
2 stops23h 41m
Honolulu
Tue 7/9
2 stops27h 31m
No data available for this route at this time. Please check back soon.
Overall
Food
Comfort
Entertainment
Boarding
Crew
Reviews
Great airline! I would fly with them again. Overall, very positive experience along every step of the way. I was so jazzed they offer direct flights from Denver to Anchorage! Great customer service.
Overall
Food
Comfort
Entertainment
Boarding
Crew
Reviews
Great airline! I would fly with them again. Overall, very positive experience along every step of the way. I was so jazzed they offer direct flights from Denver to Anchorage! Great customer service.
Overall
Food
Comfort
Entertainment
Boarding
Crew
Reviews
Great airline! I would fly with them again. Overall, very positive experience along every step of the way. I was so jazzed they offer direct flights from Denver to Anchorage! Great customer service.
Overall
Food
Comfort
Entertainment
Boarding
Crew
Reviews
Great airline! I would fly with them again. Overall, very positive experience along every step of the way. I was so jazzed they offer direct flights from Denver to Anchorage! Great customer service.
Overall
Food
Comfort
Entertainment
Boarding
Crew
Reviews
Great airline! I would fly with them again. Overall, very positive experience along every step of the way. I was so jazzed they offer direct flights from Denver to Anchorage! Great customer service.
Overall
Food
Comfort
Entertainment
Boarding
Crew
Reviews
Great airline! I would fly with them again. Overall, very positive experience along every step of the way. I was so jazzed they offer direct flights from Denver to Anchorage! Great customer service.
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.
Airline | Cheapest | Average | Flexibility | On-time |
---|---|---|---|---|
Delta | Cheapest$294 | Average$827 | FlexibilityNo cancel fee | On-timeN/A |
Alaska Airlines | Cheapest$331 | Average$659 | FlexibilityNo cancel fee | On-time75% |
American Airlines | Cheapest$421 | Average$693 | FlexibilityNo cancel fee | On-time71% |
United Airlines | Cheapest$454 | Average$886 | FlexibilityNo cancel fee | On-time69% |
Linear Air Taxi | Cheapest$17,578 | Average$250,221 | FlexibilityNo cancel fee | On-timeN/A |
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 |