
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $381 (Kiwi.com) |
One-way from | $173 (Kiwi.com) |
Popular in | June |
Cheapest in | February |
Average price | $640 |
Good round-trip deal | $547 or less |
Good one-way deal | $326 or less |
Fly from
Fly to
Route
Depart
Return
Price
ChicagoLihue
ORD - LIH
ORDLIH
Chicago O'Hare Intl
Mon 3/2
8:20 am-6:57 am
2 stops26h 37m
Lihue
Wed 3/4
4:50 pm-11:59 pm
1 stop27h 09m
ChicagoKailua-Kona
ORD - KOA
ORDKOA
Chicago O'Hare Intl
Mon 3/2
8:20 am-8:13 am
2 stops27h 53m
Kona Intl
Wed 3/4
7:50 pm-2:11 pm
2 stops14h 21m
ChicagoLihue
ORD - LIH
ORDLIH
Chicago O'Hare Intl
Tue 2/24
3:07 pm-12:47 pm
1 stop25h 40m
Lihue
Tue 3/3
4:50 pm-11:59 pm
1 stop27h 09m
ChicagoKailua-Kona
ORD - KOA
ORDKOA
Chicago O'Hare Intl
Mon 3/2
7:00 am-5:13 pm
1 stop14h 13m
Kona Intl
Wed 3/4
10:17 pm-2:11 pm
1 stop11h 54m
ChicagoLihue
ORD - LIH
ORDLIH
Chicago O'Hare Intl
Fri 2/27
2:35 pm-10:44 pm
1 stop12h 09m
Lihue
Fri 3/6
2:15 pm-6:20 am
1 stop12h 05m
ChicagoHonolulu
ORD - HNL
ORDHNL
Chicago O'Hare Intl
Mon 4/20
12:46 pm-9:20 pm
1 stop13h 34m
Honolulu
Tue 4/28
7:45 pm-11:51 am
1 stop11h 06m
ChicagoKailua-Kona
ORD - KOA
ORDKOA
Chicago O'Hare Intl
Sun 4/19
7:15 am-7:03 pm
1 stop16h 48m
Kona Intl
Fri 4/24
8:50 pm-1:23 pm
1 stop11h 33m
ChicagoLihue
ORD - LIH
ORDLIH
Chicago O'Hare Intl
Mon 5/11
12:47 pm-7:06 pm
1 stop11h 19m
Lihue
Mon 5/18
9:40 pm-5:04 pm
1 stop14h 24m
ChicagoLihue
ORD - LIH
ORDLIH
Chicago O'Hare Intl
Tue 2/24
3:07 pm-1:49 pm
2 stops26h 42m
Lihue
Tue 3/3
4:50 pm-11:59 pm
1 stop27h 09m
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Tue 4/7
5:30 am-3:13 pm
1 stop14h 43m
Kahului
Wed 4/15
10:30 pm-6:07 pm
2 stops14h 37m
Currently, September is the cheapest month in which you can book a flight from Chicago to Hawaii (average of $237). Flying from Chicago to Hawaii in July is currently the most expensive (average of $545). 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.
Boarding
Comfort
Entertainment
Overall
Crew
Food
Reviews
Anonymous,Jan 2026
STS - LAX
Boarding
Comfort
Entertainment
Overall
Crew
Food
Reviews
Anonymous,Jan 2026
STS - LAX
Boarding
Comfort
Entertainment
Overall
Crew
Food
Reviews
Anonymous,Jan 2026
STS - LAX
Boarding
Comfort
Entertainment
Overall
Crew
Food
Reviews
Anonymous,Jan 2026
STS - LAX
Boarding
Comfort
Entertainment
Overall
Crew
Food
Reviews
Anonymous,Jan 2026
STS - LAX
Boarding
Comfort
Entertainment
Overall
Crew
Food
Reviews
Anonymous,Jan 2026
STS - LAX
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$242 | Average$567 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$307 | Average$667 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$367 | Average$713 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$422 | Average$720 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$443 | Average$999 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$468 | Average$791 | FlexibilityNo cancel fee | On-time63% |