Our data shows that March tends to be the cheapest month to fly to Chicago from Maui. Users have commonly found prices around $666 for the month, but tickets can be as low as $445. Due to multiple factors, prepare for potentially higher prices in June.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Maui to Chicago as you normally would.
Fly from
Fly to
Budget
$515 - $657
Route
Depart
Return
Price
KahuluiChicago O'Hare Intl
OGG - ORD
OGGORD
Kahului
Fri 5/24
1 stop32h 44m
Chicago O'Hare Intl
Thu 5/30
1 stop28h 22m
KahuluiChicago O'Hare Intl
OGG - ORD
OGGORD
Kahului
Tue 7/23
1 stop10h 58m
Chicago O'Hare Intl
Tue 7/30
1 stop20h 07m
KahuluiChicago O'Hare Intl
OGG - ORD
OGGORD
Kahului
Wed 6/5
1 stop26h 58m
Chicago O'Hare Intl
Wed 6/12
1 stop28h 19m
KahuluiChicago O'Hare Intl
OGG - ORD
OGGORD
Kahului
Wed 6/5
1 stop11h 41m
Chicago O'Hare Intl
Wed 6/12
2 stops17h 42m
KahuluiChicago O'Hare Intl
OGG - ORD
OGGORD
Kahului
Tue 7/23
1 stop10h 50m
Chicago O'Hare Intl
Tue 7/30
2 stops18h 34m
KahuluiChicago O'Hare Intl
OGG - ORD
OGGORD
Kahului
Fri 5/24
2 stops12h 05m
Chicago O'Hare Intl
Thu 5/30
1 stop10h 46m
KahuluiChicago O'Hare Intl
OGG - ORD
OGGORD
Kahului
Thu 7/4
1 stop10h 45m
Chicago O'Hare Intl
Tue 7/9
1 stop10h 49m
KahuluiChicago Midway
OGG - MDW
OGGMDW
Kahului
Mon 8/12
2 stops15h 28m
Chicago Midway
Sat 8/31
2 stops15h 36m
KahuluiChicago O'Hare Intl
OGG - ORD
OGGORD
Kahului
Fri 5/24
2 stops15h 54m
Chicago O'Hare Intl
Thu 5/30
2 stops18h 41m
No data available for this route at this time. Please check back soon.
Crew
Entertainment
Boarding
Food
Comfort
Overall
Reviews
Paid a lot for our exit row seats and they weren’t that roomy.
Crew
Entertainment
Boarding
Food
Comfort
Overall
Reviews
Paid a lot for our exit row seats and they weren’t that roomy.
Crew
Entertainment
Boarding
Food
Comfort
Overall
Reviews
Paid a lot for our exit row seats and they weren’t that roomy.
Crew
Entertainment
Boarding
Food
Comfort
Overall
Reviews
Paid a lot for our exit row seats and they weren’t that roomy.
Crew
Entertainment
Boarding
Food
Comfort
Overall
Reviews
Paid a lot for our exit row seats and they weren’t that roomy.
Cheapflights helps you search for flights from Maui to Chicago via 900+ travel sites so you don’t have to. After performing a flight search, users can also filter their flight selection by filtering for price, number of stops, airlines, and so on.
Cheapflights simply makes it quick and affordable to book flights from Maui to Chicago by bringing together all flight options from hundreds of airlines and agencies online — and put it in one place for you to choose from. Plus, Cheapflights is 100% free to use for all.
Cheapflights does show flights with no change fees to all users. To see these options for flights from Maui to Chicago, users can toggle the no change fees filter when performing a flight search.
Not ready to book yet? You can track prices for flights from Maui to Chicago on Cheapflights with our Price Alert feature and get notified when better prices are available.