
CHIHNL· United States
Chicago
Round trip from
$271
98/100
Deal score · stronger than 98%
At or below this price in 1 of 8 observed months.
- Travel dates
- Feb 15 '27 – Feb 18 '27 · 3 nights
- Airline
Southwest- Flight
- 11.5h · 2 stops
Display prices in
Destination market · HNL
Waikīkī sunsets and volcanic ridgelines — mainland fare wars put Hawai‘i under $300 more often than you’d think.

9 featured deals, followed by the complete origin-by-origin comparison. Best months to be there: Apr–Jun · Sep–Nov.

CHIHNL· United States
Round trip from
$271
98/100
Deal score · stronger than 98%
At or below this price in 1 of 8 observed months.

LAXHNL· United States
Round trip from
$168
95/100
Deal score · stronger than 95%
At or below this price in 1 of 9 observed months.

SFOHNL· United States
Round trip from
$177
92/100
Deal score · stronger than 92%
At or below this price in 1 of 6 observed months.

TYOHNL· Japan
Round trip from
$600
83/100
Deal score · stronger than 83%
At or below this price in 1 of 8 observed months.

SHAHNL· China
Round trip from
$773
61/100
Deal score · stronger than 61%
At or below this price in 1 of 4 observed months.

SELHNL· South Korea
Round trip from
$469
49/100
Deal score · stronger than 49%
At or below this price in 1 of 7 observed months.

ISTHNL· Türkiye
Round trip from
$1,099
49/100
Deal score · stronger than 49%
At or below this price in 1 of 4 observed months.

NYCHNL· United States
Round trip from
$629
38/100
Deal score · stronger than 38%
At or below this price in 1 of 8 observed months.
Showing 9 of 40 live fares · compare every departure city ↓
The best live fare on our board is $168 round-trip from Los Angeles (48% below that route's typical price), found on a real search within the last two days. Fares are cached and re-priced when you click through.
Across the routes we have enough cached history for, Feb comes out cheapest on average. The sweet spot for being there is Apr–Jun · Sep–Nov — when the two overlap, book without hesitating.
Honolulu is served by Daniel K. Inouye (HNL). All fares on this page are round-trip to those airports unless marked otherwise.
Apr–Jun · Sep–Nov offers the best balance of weather and prices. Waikīkī sunsets and volcanic ridgelines — mainland fare wars put Hawai‘i under $300 more often than you’d think.
Hotels / after the flight
AffiliateFare first.
Bed second.
Once the flight dates make sense, compare stays in Honolulu without losing the flight context.