Round-trip from | $405 (Alaska Airlines) |
---|---|
One-way from | $194 (Alaska Airlines) |
Popular in | December |
Cheapest in | February |
Average price | $866 |
Good round-trip deal | $938 or less |
Good one-way deal | $502 or less |
Fly from
Fly to
Route
Depart
Return
Price
ChicagoKailua-Kona
ORD - KOA
ORDKOA
Chicago O'Hare Intl
Wed 10/8
6:03 am-1:58 pm
1 stop12h 55m
Kona Intl
Wed 10/22
9:45 pm-2:15 pm
1 stop11h 30m
ChicagoLihue
ORD - LIH
ORDLIH
Chicago O'Hare Intl
Wed 9/3
7:15 am-3:36 pm
1 stop13h 21m
Lihue
Tue 9/30
7:40 pm-11:28 am
1 stop10h 48m
ChicagoKailua-Kona
ORD - KOA
ORDKOA
Chicago O'Hare Intl
Sun 8/24
6:20 am-3:51 pm
2 stops14h 31m
Kona Intl
Thu 9/4
12:16 pm-5:00 am
1 stop11h 44m
ChicagoLihue
ORD - LIH
ORDLIH
Chicago O'Hare Intl
Wed 9/3
6:00 am-12:14 pm
1 stop11h 14m
Lihue
Tue 9/30
9:40 pm-3:10 pm
2 stops12h 30m
ChicagoKailua-Kona
ORD - KOA
ORDKOA
Chicago O'Hare Intl
Mon 9/8
3:20 pm-10:09 pm
1 stop11h 49m
Kona Intl
Fri 9/12
12:16 pm-5:00 am
1 stop11h 44m
ChicagoLihue
ORD - LIH
ORDLIH
Chicago O'Hare Intl
Sun 10/26
2:54 pm-11:41 am
2 stops25h 47m
Lihue
Sun 11/2
5:49 am-10:59 pm
2 stops13h 10m
ChicagoKailua-Kona
ORD - KOA
ORDKOA
Chicago O'Hare Intl
Tue 9/9
7:15 am-5:34 pm
1 stop15h 19m
Kona Intl
Thu 9/18
9:30 pm-5:15 pm
1 stop14h 45m
ChicagoLihue
ORD - LIH
ORDLIH
Chicago O'Hare Intl
Thu 10/23
7:37 am-7:03 pm
1 stop16h 26m
Lihue
Tue 10/28
9:40 pm-5:49 pm
1 stop15h 09m
ChicagoHilo
ORD - ITO
ORDITO
Chicago O'Hare Intl
Wed 10/15
7:59 pm-7:20 pm
2 stops28h 21m
Hilo Intl
Tue 10/28
7:25 pm-1:09 pm
2 stops12h 44m
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Thu 8/21
7:15 am-5:08 pm
1 stop14h 53m
Kahului
Thu 9/4
9:10 pm-1:17 pm
1 stop11h 07m
Currently, November is the cheapest month in which you can book a flight from Chicago to Hawaii (average of $469). Flying from Chicago to Hawaii in June is currently the most expensive (average of $687). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
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.
The most flights from CHI to USHI are scheduled on a Monday (3 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (2 on average).
Food
Entertainment
Boarding
Overall
Crew
Comfort
Reviews
Jonathan,Jul 2025
SEA - BOS
Food
Entertainment
Boarding
Overall
Crew
Comfort
Reviews
Jonathan,Jul 2025
SEA - BOS
Food
Entertainment
Boarding
Overall
Crew
Comfort
Reviews
Jonathan,Jul 2025
SEA - BOS
Food
Entertainment
Boarding
Overall
Crew
Comfort
Reviews
Jonathan,Jul 2025
SEA - BOS
Food
Entertainment
Boarding
Overall
Crew
Comfort
Reviews
Jonathan,Jul 2025
SEA - BOS
Food
Entertainment
Boarding
Overall
Crew
Comfort
Reviews
Jonathan,Jul 2025
SEA - BOS
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 |
---|---|---|---|---|
Cheapest$316 | Average$566 | FlexibilityNo cancel fee | On-timeN/A | |
Cheapest$346 | Average$739 | FlexibilityNo cancel fee | On-time85% | |
Cheapest$349 | Average$663 | FlexibilityNo cancel fee | On-time71% | |
Cheapest$420 | Average$714 | FlexibilityNo cancel fee | On-time75% | |
Cheapest$424 | Average$771 | FlexibilityNo cancel fee | On-time63% | |
Cheapest$425 | Average$937 | FlexibilityNo cancel fee | On-time69% |