Honolulu to Chicago

HNLMDW

Fly from Honolulu to Chicago starting at USD 285 with Alaska Airlines.Best fare available on Oct 12, 2026.Limited seats. Better plans. Book before it's gone.

Honolulu to Chicago cheapest flights this week

30 Sept
Southwest Airlines
08:10HNL
23:30MDW
1 StopUSD 358VIEW DEAL
4 Oct
Southwest Airlines
09:40HNL
00:55MDW
2 StopUSD 369VIEW DEAL
5 Oct
Southwest Airlines
13:30HNL
00:55MDW
1 StopUSD 357VIEW DEAL
10 Oct
Alaska Airlines
20:35HNL
00:50MDW
1 StopUSD 378VIEW DEAL
12 Oct
Alaska Airlines
20:35HNL
00:50MDW
1 StopUSD 285VIEW DEAL
13 Oct
Southwest Airlines
08:15HNL
00:00MDW
1 StopUSD 330VIEW DEAL
17 Oct
Southwest Airlines
12:05HNL
00:55MDW
1 StopUSD 392VIEW DEAL
18 Oct
Alaska Airlines
20:35HNL
04:30MDW
2 StopUSD 344VIEW DEAL
25 Oct
Southwest Airlines
11:55HNL
00:40MDW
1 StopUSD 323VIEW DEAL
25 Oct
Southwest Airlines
08:10HNL
23:30MDW
1 StopUSD 443VIEW DEAL

Honolulu to Chicago monthly flight fare trend

Sep
from USD 358
Oct
from USD 281
Nov
from USD 255
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

Flights from Honolulu

Flights from Honolulu to AtlantaFlights from Honolulu to AustinFlights from Honolulu to BostonFlights from Honolulu to CharlotteFlights from Honolulu to DenverFlights from Honolulu to DallasFlights from Honolulu to DetroitFlights from Honolulu to NewarkFlights from Honolulu to Fort LauderdaleFlights from Honolulu to Washington