Chicago to Honolulu

MDWHNL

Fly from Chicago to Honolulu starting at USD 341 with Southwest Airlines.Best fare available on Aug 12, 2026.Limited seats. Better plans. Book before it's gone.

Chicago to Honolulu cheapest flights this week

9 Jul
Southwest Airlines
11:00MDW
02:25HNL
1 StopUSD 488VIEW DEAL
10 Jul
Southwest Airlines
14:15MDW
02:30HNL
1 StopUSD 435VIEW DEAL
11 Jul
Southwest Airlines
10:15MDW
02:15HNL
1 StopUSD 441VIEW DEAL
15 Jul
Southwest Airlines
15:05MDW
02:25HNL
1 StopUSD 419VIEW DEAL
16 Jul
Southwest Airlines
20:50MDW
14:40HNL
1 StopUSD 395VIEW DEAL
22 Jul
Southwest Airlines
06:20MDW
17:40HNL
1 StopUSD 454VIEW DEAL
28 Jul
Southwest Airlines
06:10MDW
03:11HNL
2 StopUSD 410VIEW DEAL
5 Aug
Frontier Airlines
06:05MDW
02:39HNL
2 StopUSD 390VIEW DEAL
12 Aug
Southwest Airlines
12:20MDW
01:10HNL
1 StopUSD 341VIEW DEAL
12 Aug
Southwest Airlines
20:45MDW
02:15HNL
1 StopUSD 396VIEW DEAL

Chicago to Honolulu monthly flight fare trend

Jul
from USD 395
Aug
from USD 341
Sep
from USD 459
Oct
from USD 341
Nov
from USD 285
Dec
No flights

Airport Details

Origin

Chicago

Chicago Midway International Airport (MDW)

Chicago, MDW
Zone

Chicago

Elev

620 ft

Destination

Honolulu

Daniel K Inouye International Airport (HNL)

Honolulu, Oahu, HNL
Zone

Honolulu

Elev

13 ft

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