
Most accurate provider | eDreams 3 stars |
|---|---|
Most trusted provider | eDreams 3 stars |
Round-trip from | $363 (Alaska Airlines) |
One-way from | $183 (Kiwi.com) |
Popular in | December |
Cheapest in | February |
Average price | $794 |
Good round-trip deal | $699 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 1/27
9:00 am-8:30 pm
2 stops15h 30m
Lihue
Mon 2/2
7:49 pm-2:29 pm
2 stops14h 40m
ChicagoLihue
ORD - LIH
ORDLIH
Chicago O'Hare Intl
Mon 1/26
3:49 pm-1:03 pm
1 stop25h 14m
Lihue
Mon 2/2
7:49 pm-11:37 pm
2 stops23h 48m
ChicagoLihue
ORD - LIH
ORDLIH
Chicago O'Hare Intl
Sun 1/25
9:00 am-1:45 pm
1 stop32h 45m
Lihue
Mon 2/2
7:49 pm-2:29 pm
2 stops14h 40m
ChicagoLihue
ORD - LIH
ORDLIH
Chicago O'Hare Intl
Sun 2/1
9:00 am-1:45 pm
1 stop32h 45m
Lihue
Tue 2/3
6:00 am-11:37 pm
2 stops13h 37m
ChicagoLihue
ORD - LIH
ORDLIH
Chicago O'Hare Intl
Sun 2/1
9:00 am-1:45 pm
1 stop32h 45m
Lihue
Mon 2/2
7:49 pm-11:37 pm
2 stops23h 48m
ChicagoLihue
ORD - LIH
ORDLIH
Chicago O'Hare Intl
Mon 2/2
3:49 pm-1:03 pm
1 stop25h 14m
Lihue
Wed 2/4
10:25 am-2:29 pm
1 stop24h 04m
ChicagoLihue
ORD - LIH
ORDLIH
Chicago O'Hare Intl
Mon 1/26
3:49 pm-1:03 pm
1 stop25h 14m
Lihue
Thu 2/5
10:25 am-2:29 pm
1 stop24h 04m
ChicagoLihue
ORD - LIH
ORDLIH
Chicago O'Hare Intl
Mon 2/2
3:49 pm-1:03 pm
1 stop25h 14m
Lihue
Thu 2/5
6:47 am-11:37 pm
2 stops12h 50m
ChicagoKailua-Kona
ORD - KOA
ORDKOA
Chicago O'Hare Intl
Sun 1/25
3:49 pm-10:44 am
2 stops22h 55m
Kona Intl
Thu 1/29
2:51 pm-2:29 pm
1 stop19h 38m
ChicagoLihue
ORD - LIH
ORDLIH
Chicago O'Hare Intl
Wed 1/21
9:00 am-1:03 pm
1 stop32h 03m
Lihue
Wed 4/15
6:15 pm-1:59 pm
2 stops14h 44m
Currently, September is the cheapest month in which you can book a flight from Chicago to Hawaii (average of $231). 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).
Comfort
Boarding
Food
Entertainment
Crew
Overall
Reviews
Anonymous,Sep 2025
BOS - HNL
Comfort
Boarding
Food
Entertainment
Crew
Overall
Reviews
Anonymous,Sep 2025
BOS - HNL
Comfort
Boarding
Food
Entertainment
Crew
Overall
Reviews
Anonymous,Sep 2025
BOS - HNL
Comfort
Boarding
Food
Entertainment
Crew
Overall
Reviews
Anonymous,Sep 2025
BOS - HNL
Comfort
Boarding
Food
Entertainment
Crew
Overall
Reviews
Anonymous,Sep 2025
BOS - HNL
Comfort
Boarding
Food
Entertainment
Crew
Overall
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$636 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$334 | Average$591 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$380 | Average$724 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$394 | Average$679 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$424 | Average$771 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$443 | Average$984 | FlexibilityNo cancel fee | On-time69% |