
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $424 (Delta) |
One-way from | $212 (American Airlines) |
Popular in | June |
Cheapest in | January |
Average price | $767 |
Good round-trip deal | $652 or less |
Good one-way deal | $386 or less |
Fly from
Fly to
Route
Depart
Return
ChicagoLihue
ORD - LIH
ORDLIH
Chicago O'Hare Intl
Mon 9/21
7:30 am-7:20 pm
2 stops16h 50m
Lihue
Tue 9/29
9:45 pm-5:22 pm
1 stop14h 37m
ChicagoLihue
ORD - LIH
ORDLIH
Chicago O'Hare Intl
Mon 4/20
7:15 am-5:40 pm
1 stop15h 25m
Lihue
Mon 4/27
9:25 pm-6:04 pm
2 stops15h 39m
ChicagoLihue
ORD - LIH
ORDLIH
Chicago O'Hare Intl
Tue 4/28
7:15 am-5:40 pm
1 stop15h 25m
Lihue
Tue 5/5
8:20 pm-6:52 pm
2 stops17h 32m
ChicagoLihue
ORD - LIH
ORDLIH
Chicago O'Hare Intl
Mon 8/24
7:30 am-7:20 pm
2 stops16h 50m
Lihue
Mon 8/31
9:26 pm-2:00 pm
1 stop11h 34m
ChicagoLihue
ORD - LIH
ORDLIH
Chicago O'Hare Intl
Mon 5/11
6:24 am-5:40 pm
2 stops16h 16m
Lihue
Mon 5/18
9:55 pm-1:45 pm
1 stop10h 50m
ChicagoLihue
ORD - LIH
ORDLIH
Chicago O'Hare Intl
Sat 5/9
12:47 pm-7:06 pm
1 stop11h 19m
Lihue
Sat 5/23
9:55 pm-5:13 pm
1 stop14h 18m
ChicagoLihue
ORD - LIH
ORDLIH
Chicago O'Hare Intl
Wed 4/22
7:35 am-5:40 pm
2 stops15h 05m
Lihue
Tue 4/28
8:20 pm-4:39 pm
1 stop15h 19m
ChicagoLihue
ORD - LIH
ORDLIH
Chicago O'Hare Intl
Mon 4/20
6:15 am-4:10 pm
2 stops14h 55m
Lihue
Mon 4/27
8:10 pm-1:55 pm
1 stop12h 45m
ChicagoLihue
MDW - LIH
MDWLIH
Chicago Midway
Tue 8/18
6:50 am-4:10 pm
2 stops14h 20m
Lihue
Mon 8/24
8:25 pm-2:45 pm
2 stops13h 20m
ChicagoLihue
ORD - LIH
ORDLIH
Chicago O'Hare Intl
Fri 5/1
7:15 am-5:40 pm
1 stop15h 25m
Lihue
Sun 5/10
9:55 pm-6:50 pm
2 stops15h 55m
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 $557). 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.
Entertainment
Food
Comfort
Crew
Boarding
Overall
Reviews
Dominic,Mar 2026
MCO - SMF
Entertainment
Food
Comfort
Crew
Boarding
Overall
Reviews
Dominic,Mar 2026
MCO - SMF
Entertainment
Food
Comfort
Crew
Boarding
Overall
Reviews
Dominic,Mar 2026
MCO - SMF
Entertainment
Food
Comfort
Crew
Boarding
Overall
Reviews
Dominic,Mar 2026
MCO - SMF
Entertainment
Food
Comfort
Crew
Boarding
Overall
Reviews
Dominic,Mar 2026
MCO - SMF
Entertainment
Food
Comfort
Crew
Boarding
Overall
Reviews
Dominic,Mar 2026
MCO - SMF
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$610 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$316 | Average$649 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$363 | Average$700 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$401 | Average$882 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$423 | Average$706 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$442 | Average$806 | FlexibilityNo cancel fee | On-time63% |