
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $424 (American Airlines) |
One-way from | $253 (Alaska Airlines) |
Popular in | June |
Cheapest in | January |
Average price | $801 |
Good round-trip deal | $954 or less |
Good one-way deal | $312 or less |
Fly from
Fly to
Route
Depart
Return
ChicagoLihue
ORD - LIH
ORDLIH
Chicago O'Hare Intl
Sun 9/13
7:35 am-5:12 pm
1 stop14h 37m
Lihue
Sun 9/20
9:26 pm-2:00 pm
1 stop11h 34m
ChicagoLihue
ORD - LIH
ORDLIH
Chicago O'Hare Intl
Mon 10/19
12:40 pm-7:22 pm
1 stop11h 42m
Lihue
Sun 10/25
9:26 pm-1:47 pm
1 stop11h 21m
ChicagoLihue
ORD - LIH
ORDLIH
Chicago O'Hare Intl
Wed 5/27
12:47 pm-7:06 pm
1 stop11h 19m
Lihue
Tue 6/2
9:55 pm-1:45 pm
1 stop10h 50m
ChicagoLihue
ORD - LIH
ORDLIH
Chicago O'Hare Intl
Mon 10/19
12:40 pm-7:22 pm
1 stop11h 42m
Lihue
Thu 10/29
9:45 pm-7:34 pm
2 stops16h 49m
ChicagoLihue
ORD - LIH
ORDLIH
Chicago O'Hare Intl
Tue 8/18
6:25 am-5:41 pm
2 stops16h 16m
Lihue
Thu 8/27
9:55 pm-1:23 pm
1 stop10h 28m
ChicagoLihue
ORD - LIH
ORDLIH
Chicago O'Hare Intl
Sun 10/18
7:35 am-5:20 pm
1 stop14h 45m
Lihue
Sat 10/31
9:26 pm-1:47 pm
1 stop12h 21m
ChicagoLihue
ORD - LIH
ORDLIH
Chicago O'Hare Intl
Fri 8/28
6:25 am-5:41 pm
2 stops16h 16m
Lihue
Fri 9/4
9:26 pm-4:48 pm
2 stops14h 22m
ChicagoKahului
ORD - OGG
ORDOGG
Chicago O'Hare Intl
Fri 5/29
7:12 am-5:48 pm
1 stop15h 36m
Kahului
Mon 6/8
8:05 pm-12:00 pm
1 stop10h 55m
ChicagoLihue
ORD - LIH
ORDLIH
Chicago O'Hare Intl
Thu 7/2
6:30 am-7:02 pm
2 stops17h 32m
Lihue
Mon 7/13
9:55 pm-1:28 pm
1 stop10h 33m
ChicagoKailua-Kona
ORD - KOA
ORDKOA
Chicago O'Hare Intl
Tue 6/2
9:25 am-7:20 pm
2 stops14h 55m
Kona Intl
Tue 6/9
8:50 pm-4:45 pm
1 stop14h 55m
To ensure you get the cheapest price possible for a flight from Chicago to Hawaii, you should look to book at least 50 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
Currently, February is the cheapest month in which you can book a flight from Chicago to Hawaii (average of $537). Flying from Chicago to Hawaii in July is currently the most expensive (average of $1,021). 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 Thursday (3 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (2 on average).
Comfort
Overall
Food
Entertainment
Boarding
Crew
Reviews
Dominic,Mar 2026
MCO - SMF
Comfort
Overall
Food
Entertainment
Boarding
Crew
Reviews
Dominic,Mar 2026
MCO - SMF
Comfort
Overall
Food
Entertainment
Boarding
Crew
Reviews
Dominic,Mar 2026
MCO - SMF
Comfort
Overall
Food
Entertainment
Boarding
Crew
Reviews
Dominic,Mar 2026
MCO - SMF
Comfort
Overall
Food
Entertainment
Boarding
Crew
Reviews
Dominic,Mar 2026
MCO - SMF
Comfort
Overall
Food
Entertainment
Boarding
Crew
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$241 | Average$602 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$295 | Average$612 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$363 | Average$700 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$394 | Average$880 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$422 | Average$701 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$442 | Average$797 | FlexibilityNo cancel fee | On-time63% |