Cheap flights from Chicago (CHI) to Maui

CHI — OGG
Dec 4 — Dec 111

How far in advance should I book a flight from Chicago to Maui?

To save on the cost of your flight from Chicago to Maui, book at least 31 days before your planned departure. Booking around this time can save you about 18% on the cost of this flight compared to booking a flight leaving this week. We have found prices from $837 if you need a flight within two weeks. For flights within the next 72 hours, you can find tickets from as low as $913.

What is the cheapest month to fly from Chicago to Maui?

January is one of the best times of the year to fly to Maui from Chicago. Prices for January average $794 per person but you can even find prices for as low as $366. The most expensive prices can be found in the month of June. Opting for a January flight can save you 20% on your journey compared to booking in June

When is the cheapest time to fly from Chicago to Maui (CHI - FUK)?

When flying from Chicago to Maui, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Cheap flights from Chicago to Maui in November, December 2022

The best prices found for CHI to Maui flights for November, December
Dec 6 - Dec 13
ORD

Chicago O'Hare Intl

OGG

Kahului

1 stop

22h 51m
OGG

Kahului

ORD

Chicago O'Hare Intl

1 stop

26h 40m
$483

United Airlines

Pick Dates

Deal found 11/26

Dec 7 - Dec 14
ORD

Chicago O'Hare Intl

OGG

Kahului

1 stop

22h 51m
OGG

Kahului

ORD

Chicago O'Hare Intl

1 stop

16h 56m
$485

United Airlines

Pick Dates

Deal found 11/27

Dec 7 - Dec 14
ORD

Chicago O'Hare Intl

OGG

Kahului

1 stop

25h 14m
OGG

Kahului

ORD

Chicago O'Hare Intl

2 stops

17h 16m
$489

United Airlines

Pick Dates

Deal found 11/26

Chicago to Maui 2022 flight deals

Cheap flights to Maui from Chicago found for this year
Dec 31 - Jan 19
ORD

Chicago O'Hare Intl

OGG

Kahului

1 stop

22h 06m
OGG

Kahului

ORD

Chicago O'Hare Intl

1 stop

10h 37m
$461

Multiple Airlines

Pick Dates

Deal found 11/29

Dec 6 - Dec 13
ORD

Chicago O'Hare Intl

OGG

Kahului

1 stop

22h 51m
OGG

Kahului

ORD

Chicago O'Hare Intl

1 stop

26h 40m
$483

United Airlines

Pick Dates

Deal found 11/26

Dec 7 - Dec 14
ORD

Chicago O'Hare Intl

OGG

Kahului

1 stop

22h 51m
OGG

Kahului

ORD

Chicago O'Hare Intl

1 stop

16h 56m
$485

United Airlines

Pick Dates

Deal found 11/27

Cheap Delta flights from Chicago to Maui

Feb 21 - Mar 1
MDW

Chicago Midway

OGG

Kahului

1 stop

13h 55m
OGG

Kahului

MDW

Chicago Midway

1 stop

12h 28m
$417

Delta

Pick Dates

Deal found 11/28

Mar 2 - Mar 7
MDW

Chicago Midway

OGG

Kahului

1 stop

13h 55m
OGG

Kahului

MDW

Chicago Midway

1 stop

12h 28m
$418

Delta

Pick Dates

Deal found 11/28

Jan 18 - Jan 24
MDW

Chicago Midway

OGG

Kahului

1 stop

14h 05m
OGG

Kahului

MDW

Chicago Midway

2 stops

15h 40m
$422

Delta

Pick Dates

Deal found 11/28

Cheap Alaska Airlines flights from Chicago to Maui

Feb 7 - Feb 14
ORD

Chicago O'Hare Intl

OGG

Kahului

1 stop

23h 30m
OGG

Kahului

ORD

Chicago O'Hare Intl

1 stop

20h 00m
$363

Alaska Airlines

Pick Dates

Deal found 11/28

Jan 18 - Jan 24
ORD

Chicago O'Hare Intl

OGG

Kahului

1 stop

23h 30m
OGG

Kahului

ORD

Chicago O'Hare Intl

1 stop

20h 00m
$369

Alaska Airlines

Pick Dates

Deal found 11/29

Jan 17 - Jan 24
ORD

Chicago O'Hare Intl

OGG

Kahului

1 stop

23h 30m
OGG

Kahului

ORD

Chicago O'Hare Intl

1 stop

20h 00m
$373

Alaska Airlines

Pick Dates

Deal found 11/29

Last minute flights from Chicago to Maui

Late deals on return flights to Maui from Chicago, departing today and this week
Dec 6 - Dec 13
ORD

Chicago O'Hare Intl

OGG

Kahului

1 stop

22h 51m
OGG

Kahului

ORD

Chicago O'Hare Intl

1 stop

26h 40m
$483

United Airlines

Pick Dates

Deal found 11/26

Dec 7 - Dec 14
ORD

Chicago O'Hare Intl

OGG

Kahului

1 stop

22h 51m
OGG

Kahului

ORD

Chicago O'Hare Intl

1 stop

16h 56m
$485

United Airlines

Pick Dates

Deal found 11/27

Dec 7 - Dec 14
ORD

Chicago O'Hare Intl

OGG

Kahului

1 stop

25h 14m
OGG

Kahului

ORD

Chicago O'Hare Intl

2 stops

17h 16m
$489

United Airlines

Pick Dates

Deal found 11/26

One-way flights to Maui from Chicago

The cheapest one-way flights from Chicago to Maui
Feb 11
ORD

Chicago O'Hare Intl

OGG

Kahului

2 stops

41h 00m
$173

Multiple Airlines

Pick Dates

Deal found 11/28

Jan 7
ORD

Chicago O'Hare Intl

OGG

Kahului

2 stops

41h 55m
$175

Multiple Airlines

Pick Dates

Deal found 11/28

Jan 7
ORD

Chicago O'Hare Intl

OGG

Kahului

2 stops

41h 55m
$178

Multiple Airlines

Pick Dates

Deal found 11/27

Related info for your journey

Useful info, stats and facts about Chicago to Maui flights.

Which airlines flying from Chicago to Maui have flexible cancellations due to COVID-19?

United Airlines, American Airlines, and Alaska Airlines are some of the carriers that may have flexible cancellation policies. You can use our site to filter for other airlines that may also have this kind of flexibility.

Can I find flights from Chicago to Maui for under $400 on Cheapflights?

Yes, there are multiple flights from Chicago to Maui for under $400. The cheapest flight booked recently is on Multiple Airlines for just $360, but on average you can expect to pay $385.

Are there last-minute flights available from Chicago to Maui for under $500?

There are currently 20+ open flights from Chicago to Maui within the next 7 days for less than $500.

What are the cheapest airlines to fly from Chicago to Maui one-way?

For one-way options, check prices for Alaska Airlines. According to our data, you can fly for as low as $181. Users have also found prices from $195 and $209 on American Airlines and Delta, respectively.

What are the most popular routes from Chicago to Maui?

Most travelers choose Chicago O'Hare Intl - Kahului, Chicago Midway - Kahului or Chicago O'Hare Intl - Kapalua West Maui when deciding on the best route from Chicago to Maui.

What are the most popular airlines that fly from Chicago to Maui?

Before booking your flight from Chicago to Maui check out the most popular airlines for this route: American Airlines, Alaska Airlines or Delta.

What are the cheapest flights from Chicago to Maui?

Looking at all options, your cheapest flight can be booked for $298. While the most popular route (Chicago O'Hare Intl - Kahului) can be booked for $360 on average our data indicates $1,749 when flying from Chicago to Maui.

Alternative routes for Chicago to Maui

See prices for flight routes from nearby airports that may be better suited for you.
Moline to Honolulufrom $583 pp
Moline to Kahuluifrom $800 pp
Peoria to Honolulufrom $1,067 pp
Peoria to Kahuluifrom $1,473 pp

Destination points for flights from Chicago to Maui

Select to see more specific information for flights from Chicago to all places in Maui

Top 6 airlines flying from Chicago to Maui

The chart below displays the airlines Cheapflights users traveling from Chicago to Maui choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
AirlineCheapestAverageFlexibilityOn-timeCOVID-19 safety
Juneyao AirlinesCheapest$14Average$18FlexibilityNo cancel feeOn-time66%COVID-19 safety
Search Juneyao Airlines flights
Alaska AirlinesCheapest$313Average$693FlexibilityNo cancel feeOn-time75%COVID-19 safety
Search Alaska Airlines flights
DeltaCheapest$352Average$704FlexibilityNo cancel feeOn-timeN/ACOVID-19 safety
Search Delta flights
American AirlinesCheapest$415Average$652FlexibilityNo cancel feeOn-time71%COVID-19 safety
Search American Airlines flights
United AirlinesCheapest$521Average$909FlexibilityNo cancel feeOn-time69%COVID-19 safety
Search United Airlines flights
Linear Air TaxiCheapest$123,902Average$247,796FlexibilityNo cancel feeOn-timeN/ACOVID-19 safety
Search Linear Air Taxi flights

Hourly flight availability from Chicago to Maui

See what time of day planes typically take off from Chicago to Maui
0%of flight departuresEarly morningMidnight to 6 am
100%of flight departuresMorning6 am to noon
0%of flight departuresAfternoonNoon to 6 pm
0%of flight departuresEvening6 pm to midnight
Midnight
6 AM
Noon
6 PM