Chicago to Honolulu

MDWHNL

Fly from Chicago to Honolulu starting at USD 286 with Southwest Airlines.Best fare available on Sep 30, 2026.Limited seats. Better plans. Book before it's gone.

Chicago to Honolulu cheapest flights this week

30 Sept
Southwest Airlines
17:15MDW
03:56HNL
1 StopUSD 440VIEW DEAL
30 Sept
Southwest Airlines
15:05MDW
02:25HNL
1 StopUSD 286VIEW DEAL
1 Oct
Southwest Airlines
14:35MDW
02:25HNL
1 StopUSD 341VIEW DEAL
1 Oct
Southwest Airlines
15:55MDW
03:56HNL
1 StopUSD 446VIEW DEAL
2 Oct
Southwest Airlines
05:10MDW
18:20HNL
1 StopUSD 304VIEW DEAL
3 Oct
Southwest Airlines
19:05MDW
16:54HNL
1 StopUSD 389VIEW DEAL
3 Oct
Southwest Airlines
11:00MDW
02:20HNL
1 StopUSD 379VIEW DEAL
4 Oct
Southwest Airlines
05:10MDW
21:25HNL
1 StopUSD 379VIEW DEAL
4 Oct
Southwest Airlines
05:20MDW
18:25HNL
1 StopUSD 354VIEW DEAL
5 Oct
Southwest Airlines
05:25MDW
17:40HNL
1 StopUSD 349VIEW DEAL

Chicago to Honolulu monthly flight fare trend

Sep
from USD 286
Oct
from USD 267
Nov
from USD 240
Dec
from USD 300
Jan
from USD 360
Feb
from USD 268

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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