Round-trip from | $382 (Delta) |
---|---|
One-way from | $181 (Alaska Airlines) |
Popular in | December |
Cheapest in | October |
Average price | $670 |
Good round-trip deal | $754 or less |
Good one-way deal | $386 or less |
Fly from
Fly to
Route
Depart
Return
Price
ChicagoKailua-Kona
ORD - KOA
ORDKOA
Chicago O'Hare Intl
Wed 10/8
7:37 am-7:23 pm
2 stops16h 46m
Kona Intl
Wed 10/22
9:30 pm-1:30 pm
1 stop11h 00m
ChicagoKailua-Kona
ORD - KOA
ORDKOA
Chicago O'Hare Intl
Wed 10/22
7:37 am-7:23 pm
2 stops16h 46m
Kona Intl
Mon 10/27
9:30 pm-4:50 pm
2 stops14h 20m
ChicagoKailua-Kona
ORD - KOA
ORDKOA
Chicago O'Hare Intl
Wed 10/29
6:08 am-5:30 pm
2 stops16h 22m
Kona Intl
Tue 11/4
9:30 pm-6:49 pm
2 stops17h 19m
ChicagoLihue
ORD - LIH
ORDLIH
Chicago O'Hare Intl
Thu 12/4
3:05 pm-1:53 pm
1 stop26h 48m
Lihue
Thu 12/11
2:53 pm-6:54 pm
1 stop24h 01m
ChicagoLihue
ORD - LIH
ORDLIH
Chicago O'Hare Intl
Mon 11/3
7:37 am-8:05 pm
1 stop16h 28m
Lihue
Mon 11/10
9:29 pm-5:18 pm
1 stop15h 49m
ChicagoKailua-Kona
ORD - KOA
ORDKOA
Chicago O'Hare Intl
Mon 10/27
6:08 am-5:30 pm
2 stops16h 22m
Kona Intl
Fri 10/31
9:30 pm-4:50 pm
2 stops14h 20m
ChicagoLihue
ORD - LIH
ORDLIH
Chicago O'Hare Intl
Thu 12/4
7:59 pm-1:53 pm
1 stop21h 54m
Lihue
Tue 12/9
2:53 pm-6:54 pm
1 stop24h 01m
ChicagoLihue
ORD - LIH
ORDLIH
Chicago O'Hare Intl
Mon 11/17
7:10 am-4:58 pm
1 stop13h 48m
Lihue
Mon 11/24
2:31 pm-5:00 am
1 stop10h 29m
ChicagoLihue
ORD - LIH
ORDLIH
Chicago O'Hare Intl
Tue 10/21
7:37 am-7:05 pm
1 stop16h 28m
Lihue
Fri 10/31
9:40 pm-5:18 pm
1 stop14h 38m
ChicagoLihue
ORD - LIH
ORDLIH
Chicago O'Hare Intl
Wed 10/22
7:37 am-7:05 pm
1 stop16h 28m
Lihue
Fri 10/31
9:40 pm-5:18 pm
1 stop14h 38m
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 (2 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (2 on average).
Food
Boarding
Overall
Entertainment
Crew
Comfort
Reviews
Anonymous,Sep 2025
BOS - HNL
Food
Boarding
Overall
Entertainment
Crew
Comfort
Reviews
Anonymous,Sep 2025
BOS - HNL
Food
Boarding
Overall
Entertainment
Crew
Comfort
Reviews
Anonymous,Sep 2025
BOS - HNL
Food
Boarding
Overall
Entertainment
Crew
Comfort
Reviews
Anonymous,Sep 2025
BOS - HNL
Food
Boarding
Overall
Entertainment
Crew
Comfort
Reviews
Anonymous,Sep 2025
BOS - HNL
Food
Boarding
Overall
Entertainment
Crew
Comfort
Reviews
Anonymous,Sep 2025
BOS - HNL
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$231 | Average$638 | FlexibilityNo cancel fee | On-time85% | |
Cheapest$330 | Average$588 | FlexibilityNo cancel fee | On-timeN/A | |
Cheapest$379 | Average$707 | FlexibilityNo cancel fee | On-time71% | |
Cheapest$420 | Average$707 | FlexibilityNo cancel fee | On-time75% | |
Cheapest$424 | Average$779 | FlexibilityNo cancel fee | On-time63% | |
Cheapest$441 | Average$937 | FlexibilityNo cancel fee | On-time69% |