To save on the cost of your flight from Hawaii to Chicago Midway Airport, book at least 44 days before your planned departure. Booking around this time can save you about 46% on the cost of this flight compared to booking a flight leaving this week. We have found prices from $715 if you need a flight within two weeks. For flights within the next 72 hours, you can find tickets from as low as $715.
Flights from Hawaii to Chicago Midway Airport lean towards being more expensive in July. Prices are generally better when you fly from Hawaii to Chicago Midway Airport in November, with the cheapest ticket starting at $426.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Hawaii to Chicago Midway Airport as you normally would.
Fly from
Fly to
Budget
$509 - $652
Route
Depart
Return
Price
HonoluluChicago Midway
HNL - MDW
HNLMDW
Honolulu
Wed 10/30
1 stop12h 05m
Chicago Midway
Wed 11/6
2 stops14h 42m
HonoluluChicago Midway
HNL - MDW
HNLMDW
Honolulu
Tue 9/24
2 stops15h 25m
Chicago Midway
Mon 9/30
2 stops16h 04m
Kona IntlChicago Midway
KOA - MDW
KOAMDW
Kona Intl
Mon 8/26
2 stops15h 18m
Chicago Midway
Tue 9/24
2 stops13h 59m
Kona IntlChicago Midway
KOA - MDW
KOAMDW
Kona Intl
Mon 8/26
2 stops15h 18m
Chicago Midway
Tue 9/24
2 stops13h 59m
HonoluluChicago Midway
HNL - MDW
HNLMDW
Honolulu
Tue 9/24
1 stop12h 25m
Chicago Midway
Mon 9/30
2 stops14h 42m
HonoluluChicago Midway
HNL - MDW
HNLMDW
Honolulu
Tue 9/24
2 stops15h 25m
Chicago Midway
Sun 9/29
1 stop12h 55m
HonoluluChicago Midway
HNL - MDW
HNLMDW
Honolulu
Tue 9/24
1 stop12h 25m
Chicago Midway
Mon 9/30
1 stop12h 55m
HonoluluChicago Midway
HNL - MDW
HNLMDW
Honolulu
Tue 9/24
1 stop12h 25m
Chicago Midway
Sun 9/29
1 stop12h 55m
HonoluluChicago Midway
HNL - MDW
HNLMDW
Honolulu
Sun 10/6
2 stops14h 33m
Chicago Midway
Sat 10/19
2 stops15h 49m
No data available for this route at this time. Please check back soon.
Crew
Entertainment
Overall
Comfort
Boarding
Food
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Crew
Entertainment
Overall
Comfort
Boarding
Food
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
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