To save up to 22% on this flight, we recommend booking at least 36 days prior to travel. The price may fluctuate and will likely increase closer to your departure date. Users on Cheapflights have found tickets from Chicago Midway Airport to Hawaii from $698 1-2 weeks out and tickets from $708 for flights departing within the next 72 hours.
Due to multiple factors, expect to potentially pay more when booking in June. For low rates, September can be a great choice for travel to Hawaii. Flights to Hawaii from Chicago Midway Airport in September are about $762 on average during September, but can be found for as low as $437.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago Midway Airport to Hawaii as you normally would.
Fly from
Fly to
Budget
$496 - $560
Route
Depart
Return
Price
Chicago MidwayKahului
MDW - OGG
MDWOGG
Chicago Midway
Mon 8/26
2 stops15h 35m
Kahului
Wed 9/4
2 stops15h 28m
Chicago MidwayKona Intl
MDW - KOA
MDWKOA
Chicago Midway
Wed 9/4
2 stops13h 50m
Kona Intl
Fri 9/13
2 stops16h 20m
Chicago MidwayHonolulu
MDW - HNL
MDWHNL
Chicago Midway
Mon 8/26
1 stop11h 18m
Honolulu
Thu 9/5
1 stop12h 24m
Chicago MidwayHonolulu
MDW - HNL
MDWHNL
Chicago Midway
Mon 8/26
2 stops14h 26m
Honolulu
Thu 9/5
1 stop12h 24m
Chicago MidwayKahului
MDW - OGG
MDWOGG
Chicago Midway
Sat 8/24
2 stops23h 07m
Kahului
Wed 9/4
2 stops15h 28m
Chicago MidwayLihue
MDW - LIH
MDWLIH
Chicago Midway
Tue 8/20
2 stops27h 37m
Lihue
Mon 8/26
2 stops16h 13m
Chicago MidwayHonolulu
MDW - HNL
MDWHNL
Chicago Midway
Sun 9/1
1 stop11h 18m
Honolulu
Wed 9/11
1 stop12h 25m
Chicago MidwayKona Intl
MDW - KOA
MDWKOA
Chicago Midway
Fri 9/6
2 stops13h 50m
Kona Intl
Fri 9/13
2 stops16h 20m
Chicago MidwayHonolulu
MDW - HNL
MDWHNL
Chicago Midway
Sun 9/1
1 stop11h 18m
Honolulu
Wed 9/11
2 stops14h 33m
No data available for this route at this time. Please check back soon.
Boarding
Overall
Entertainment
Food
Comfort
Crew
Reviews
Terrible flight crew that skipped our row for service multiple times.
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