Honolulu to Chicago

HNLMDW

Fly from Honolulu to Chicago starting at USD 321 with Southwest Airlines.Best fare available on Sep 1, 2026.Limited seats. Better plans. Book before it's gone.

Honolulu to Chicago cheapest flights this week

6 Aug
United Airlines
21:40HNL
04:51MDW
2 StopUSD 342VIEW DEAL
7 Aug
Southwest Airlines
11:55HNL
00:45MDW
1 StopUSD 417VIEW DEAL
8 Aug
Southwest Airlines
20:55HNL
06:55MDW
1 StopUSD 509VIEW DEAL
10 Aug
Southwest Airlines
11:55HNL
00:45MDW
1 StopUSD 417VIEW DEAL
11 Aug
Southwest Airlines
20:55HNL
12:40MDW
1 StopUSD 475VIEW DEAL
12 Aug
Southwest Airlines
08:15HNL
00:00MDW
1 StopUSD 374VIEW DEAL
13 Aug
Southwest Airlines
20:55HNL
10:15MDW
1 StopUSD 393VIEW DEAL
15 Aug
Southwest Airlines
11:55HNL
00:45MDW
1 StopUSD 485VIEW DEAL
16 Aug
Southwest Airlines
21:00HNL
12:00MDW
1 StopUSD 461VIEW DEAL
1 Sept
Southwest Airlines
21:55HNL
12:05MDW
1 StopUSD 321VIEW DEAL

Honolulu to Chicago monthly flight fare trend

Aug
from USD 342
Sep
from USD 301
Oct
from USD 285
Nov
No flights
Dec
from USD 333
Jan
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