
Most accurate provider | eDreams 3 stars |
|---|---|
Most trusted provider | eDreams 3 stars |
Round-trip from | $374 (Delta) |
One-way from | $181 (Kiwi.com) |
Popular in | July |
Cheapest in | January |
Average price | $900 |
Good round-trip deal | $590 or less |
Good one-way deal | $386 or less |
Fly from
Fly to
Route
Depart
Return
Price
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
ChicagoLihue
ORD - LIH
ORDLIH
Chicago O'Hare Intl
Wed 3/11
3:07 pm-11:47 am
1 stop25h 40m
Lihue
Tue 3/17
3:50 pm-2:26 pm
1 stop17h 36m
ChicagoLihue
ORD - LIH
ORDLIH
Chicago O'Hare Intl
Wed 2/25
3:07 pm-10:46 am
2 stops23h 39m
Lihue
Tue 3/3
4:50 pm-11:59 pm
1 stop27h 09m
ChicagoLihue
ORD - LIH
ORDLIH
Chicago O'Hare Intl
Wed 3/11
7:40 am-11:47 am
1 stop33h 07m
Lihue
Tue 3/17
6:00 am-11:59 pm
2 stops12h 59m
ChicagoKailua-Kona
ORD - KOA
ORDKOA
Chicago O'Hare Intl
Tue 1/20
9:00 am-3:27 pm
1 stop34h 27m
Kona Intl
Tue 1/27
9:10 pm-5:10 pm
1 stop16h 00m
ChicagoKailua-Kona
ORD - KOA
ORDKOA
Chicago O'Hare Intl
Wed 2/25
3:07 pm-12:53 pm
2 stops25h 46m
Kona Intl
Tue 3/3
6:00 am-11:59 pm
2 stops13h 59m
ChicagoLihue
ORD - LIH
ORDLIH
Chicago O'Hare Intl
Mon 2/2
9:00 am-1:03 pm
1 stop32h 03m
Lihue
Mon 2/9
9:00 pm-2:29 pm
2 stops13h 29m
ChicagoLihue
ORD - LIH
ORDLIH
Chicago O'Hare Intl
Wed 1/21
9:00 am-6:17 am
2 stops25h 17m
Lihue
Mon 1/26
10:20 pm-11:50 pm
1 stop21h 30m
ChicagoKailua-Kona
ORD - KOA
ORDKOA
Chicago O'Hare Intl
Mon 1/26
9:00 am-3:27 pm
1 stop34h 27m
Kona Intl
Wed 1/28
2:51 pm-11:37 pm
1 stop28h 46m
ChicagoLihue
ORD - LIH
ORDLIH
Chicago O'Hare Intl
Wed 2/4
9:00 am-1:03 pm
1 stop32h 03m
Lihue
Wed 4/29
1:36 pm-2:41 pm
1 stop20h 05m
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.
One of the essential ways to save on airfare from Chicago to Hawaii is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight in the afternoon could potentially save you up to 25% on airfare.
Travelers seeking maximum savings on their Chicago to Hawaii flight should consider departing on Friday evenings when fares are most often at their lowest. Saturday mornings flights should be avoided if possible as fares are typically the most expensive at this time.
The most flights from CHI to USHI are scheduled on a Monday (5 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (5 on average).
Boarding
Crew
Comfort
Food
Overall
Entertainment
Reviews
Georgana,Dec 2025
ORD - PDX
Boarding
Crew
Comfort
Food
Overall
Entertainment
Reviews
Georgana,Dec 2025
ORD - PDX
Boarding
Crew
Comfort
Food
Overall
Entertainment
Reviews
Georgana,Dec 2025
ORD - PDX
Boarding
Crew
Comfort
Food
Overall
Entertainment
Reviews
Georgana,Dec 2025
ORD - PDX
Boarding
Crew
Comfort
Food
Overall
Entertainment
Reviews
Georgana,Dec 2025
ORD - PDX
Boarding
Crew
Comfort
Food
Overall
Entertainment
Reviews
Georgana,Dec 2025
ORD - PDX
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$633 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$311 | Average$584 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$383 | Average$702 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$391 | Average$725 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$443 | Average$1,025 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$468 | Average$787 | FlexibilityNo cancel fee | On-time63% |