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 $371. 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
$418 - $531
Route
Depart
Return
Price
Chicago MidwayKahului
MDW - OGG
MDWOGG
Chicago Midway
Fri 8/23
2 stops15h 35m
Kahului
Sun 9/1
2 stops15h 28m
Chicago O'Hare IntlKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Thu 8/8
1 stop13h 36m
Kahului
Wed 8/14
1 stop13h 08m
Chicago O'Hare IntlKona Intl
ORD - KOA
ORDKOA
Chicago O'Hare Intl
Fri 5/31
1 stop28h 39m
Kona Intl
Mon 6/3
1 stop22h 18m
Chicago O'Hare IntlKona Intl
ORD - KOA
ORDKOA
Chicago O'Hare Intl
Fri 5/31
1 stop10h 38m
Kona Intl
Mon 6/3
1 stop11h 00m
Chicago O'Hare IntlHonolulu
ORD - HNL
ORDHNL
Chicago O'Hare Intl
Tue 8/20
1 stop11h 58m
Honolulu
Tue 8/27
1 stop12h 30m
Chicago O'Hare IntlLihue
ORD - LIH
ORDLIH
Chicago O'Hare Intl
Tue 9/24
1 stop16h 54m
Lihue
Tue 10/1
1 stop11h 25m
Chicago O'Hare IntlHonolulu
ORD - HNL
ORDHNL
Chicago O'Hare Intl
Tue 11/5
1 stop34h 05m
Honolulu
Tue 11/12
1 stop19h 58m
Chicago O'Hare IntlKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Tue 7/23
1 stop14h 03m
Kahului
Tue 7/30
1 stop10h 05m
Chicago O'Hare IntlHonolulu
ORD - HNL
ORDHNL
Chicago O'Hare Intl
Fri 8/16
2 stops31h 15m
Honolulu
Thu 8/22
2 stops20h 13m
No data available for this route at this time. Please check back soon.
Crew
Overall
Comfort
Entertainment
Boarding
Food
Reviews
Paid a lot for our exit row seats and they weren’t that roomy.
Crew
Overall
Comfort
Entertainment
Boarding
Food
Reviews
Paid a lot for our exit row seats and they weren’t that roomy.
Crew
Overall
Comfort
Entertainment
Boarding
Food
Reviews
Paid a lot for our exit row seats and they weren’t that roomy.
Crew
Overall
Comfort
Entertainment
Boarding
Food
Reviews
Paid a lot for our exit row seats and they weren’t that roomy.
Crew
Overall
Comfort
Entertainment
Boarding
Food
Reviews
Paid a lot for our exit row seats and they weren’t that roomy.
Crew
Overall
Comfort
Entertainment
Boarding
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.
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 |