Honolulu to Chicago

HNLMDW

Fly from Honolulu to Chicago starting at USD 266 with Southwest Airlines.Best fare available on Sep 24, 2026.Limited seats. Better plans. Book before it's gone.

Honolulu to Chicago cheapest flights this week

4 Sept
Southwest Airlines
21:55HNL
11:05MDW
1 StopUSD 474VIEW DEAL
7 Sept
Alaska Airlines
23:59HNL
15:00MDW
1 StopUSD 338VIEW DEAL
8 Sept
Alaska Airlines
23:30HNL
16:05MDW
2 StopUSD 349VIEW DEAL
12 Sept
Alaska Airlines
08:00HNL
00:55MDW
1 StopUSD 333VIEW DEAL
13 Sept
Southwest Airlines
08:00HNL
20:00MDW
1 StopUSD 371VIEW DEAL
16 Sept
Southwest Airlines
08:10HNL
23:30MDW
1 StopUSD 315VIEW DEAL
18 Sept
Southwest Airlines
21:55HNL
23:30MDW
1 StopUSD 307VIEW DEAL
19 Sept
Southwest Airlines
06:10HNL
00:45MDW
2 StopUSD 285VIEW DEAL
23 Sept
Southwest Airlines
08:10HNL
23:30MDW
1 StopUSD 301VIEW DEAL
24 Sept
Southwest Airlines
08:10HNL
18:50MDW
1 StopUSD 266VIEW DEAL

Honolulu to Chicago monthly flight fare trend

Sep
from USD 266
Oct
from USD 285
Nov
from USD 235
Dec
from USD 333
Jan
from USD 268
Feb
No flights

Airport Details

Origin

Honolulu

Daniel K Inouye International Airport (HNL)

Honolulu, Oahu, HNL
Zone

Honolulu

Elev

13 ft

Destination

Chicago

Chicago Midway International Airport (MDW)

Chicago, MDW
Zone

Chicago

Elev

620 ft

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