Chicago to Honolulu

MDWHNL

Fly from Chicago to Honolulu starting at USD 355 with Southwest Airlines.Best fare available on Aug 9, 2026.Limited seats. Better plans. Book before it's gone.

Chicago to Honolulu cheapest flights this week

28 Jul
Southwest Airlines
06:10MDW
03:11HNL
2 StopUSD 410VIEW DEAL
28 Jul
Southwest Airlines
06:20MDW
17:40HNL
1 StopUSD 405VIEW DEAL
28 Jul
Southwest Airlines
20:55MDW
14:40HNL
1 StopUSD 407VIEW DEAL
1 Aug
Southwest Airlines
10:20MDW
02:05HNL
1 StopUSD 414VIEW DEAL
5 Aug
Frontier Airlines
06:05MDW
02:39HNL
2 StopUSD 390VIEW DEAL
5 Aug
Southwest Airlines
12:00MDW
02:43HNL
2 StopUSD 364VIEW DEAL
6 Aug
Southwest Airlines
07:10MDW
18:05HNL
1 StopUSD 366VIEW DEAL
6 Aug
Southwest Airlines
13:50MDW
02:15HNL
1 StopUSD 401VIEW DEAL
7 Aug
Southwest Airlines
05:40MDW
18:05HNL
1 StopUSD 467VIEW DEAL
9 Aug
Southwest Airlines
05:25MDW
16:45HNL
1 StopUSD 355VIEW DEAL

Chicago to Honolulu monthly flight fare trend

Jul
from USD 405
Aug
from USD 233
Sep
from USD 283
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

Flights from Chicago

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