What is the cheapest airline that flies from Chicago to Maui?

Alaska Airlines and Southwest are the most popular carriers operating from Chicago to Maui

How many flights depart from Chicago to Maui on average per week?

As of February 2026, there are 7 flights per week flying from Chicago to Maui. The most common day of the week flights depart is Mon, with 14% of flights taking off on this day.

What airlines fly to Maui?

United Airlines, American Airlines and Alaska Airlines are the top three most popular airlines that fly to Maui from Chicago according to our data. United Airlines is the first choice among our users, with 39% of people opting to fly with this airline when traveling to Maui. Keep in mind that there are 6 different airlines that fly to Maui on a routine basis, so you have a few additional options to choose from.

How many flights depart from Chicago to Maui on average per day?

1 flights are operational daily from Chicago to Maui as of February 2026. The most popular departure time for this route is 9:00AM, with 100% of flights per day taking off at noon.

When did momondo last update prices for flights from Chicago to Maui?

Prices for flights from Chicago to Maui were last updated today.

How many operators does momondo search for flights from Chicago to Maui?

There are 6 operators available for flights from Chicago to Maui as of February 2026.

How old do you have to be to fly from Chicago to Maui?

The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago to Maui.

What documentation or ID do you need to fly to Maui?

The travel and health documents you'll need for your trip to Maui may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Maui. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

$146 Cheap Flights from Chicago to Maui in 2026

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Find the cheapest flights from Chicago to Maui

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One-way

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Cheap round-trip flights

Enter your travel dates to find the best prices.

7:35 am - 7:32 pm

ORD

OGG

16h 57m

2 stops

10:30 pm - 9:18 pm

OGG

ORD

17h 48m

2 stops

$466Delta

pt., kwi 17 - pt., kwi 24

7:10 am - 6:25 pm

ORD

OGG

16h 15m

2 stops

9:09 pm - 7:49 pm

OGG

ORD

17h 40m

2 stops

$467Delta

wt., mar 17 - wt., mar 24

4:10 pm - 10:02 pm

ORD

OGG

34h 52m

1 stop

11:02 pm - 2:21 pm

OGG

ORD

10h 19m

1 stop

$468Alaska Airlines

pon., kwi 6 - wt., kwi 14

7:35 am - 7:32 pm

ORD

OGG

16h 57m

2 stops

10:30 pm - 9:18 pm

OGG

ORD

17h 48m

2 stops

$469Delta

pt., kwi 17 - pon., kwi 20

6:45 am - 12:35 pm

MDW

OGG

10h 50m

1 stop

8:55 pm - 4:35 pm

OGG

MDW

14h 40m

1 stop

$470Southwest

śr., kwi 29 - pon., maj 4

7:39 pm - 11:24 am

ORD

OGG

20h 45m

1 stop

3:45 pm - 4:49 am

OGG

ORD

32h 04m

2 stops

$470Multiple Airlines

pon., mar 23 - pon., mar 30

6:00 am - 7:39 pm

ORD

OGG

18h 39m

2 stops

11:02 pm - 7:03 pm

OGG

ORD

15h 01m

1 stop

$471Alaska Airlines

wt., kwi 14 - wt., kwi 21

8:20 am - 10:02 pm

ORD

OGG

18h 42m

1 stop

11:02 pm - 11:59 pm

OGG

ORD

19h 57m

1 stop

$472Alaska Airlines

pon., kwi 13 - ndz., kwi 19

10:05 am - 4:05 pm

MDW

OGG

11h 00m

1 stop

8:55 pm - 4:35 pm

OGG

MDW

14h 40m

1 stop

$473Southwest

czw., maj 7 - pon., maj 11

8:50 am - 10:10 pm

ORD

OGG

18h 20m

2 stops

10:51 pm - 11:43 pm

OGG

ORD

19h 52m

1 stop

$475Multiple Airlines

pt., maj 1 - śr., maj 6

Delta flights from Chicago to Maui

Our best Delta deals on Chicago to Maui flight tickets

Delta

Apr 17

ORD7:35 amChicago O'Hare Intl

16h 57m

2 stops

OGG7:32 pmKahului

Apr 22

OGG10:30 pmKahului

14h 34m

2 stops

ORD6:04 pmChicago O'Hare Intl

$466

Delta

Mar 17

ORD7:10 amChicago O'Hare Intl

16h 15m

2 stops

OGG6:25 pmKahului

Mar 24

OGG9:09 pmKahului

17h 40m

2 stops

ORD7:49 pmChicago O'Hare Intl

$467

Delta

Apr 17

ORD7:35 amChicago O'Hare Intl

16h 57m

2 stops

OGG7:32 pmKahului

Apr 20

OGG10:30 pmKahului

17h 48m

2 stops

ORD9:18 pmChicago O'Hare Intl

$469

Alaska Airlines flights from Chicago to Maui

Our best Alaska Airlines deals on Chicago to Maui flight tickets

Alaska Airlines

Apr 6

ORD4:10 pmChicago O'Hare Intl

34h 52m

1 stop

OGG10:02 pmKahului

Apr 14

OGG11:02 pmKahului

10h 19m

1 stop

ORD2:21 pmChicago O'Hare Intl

$468

Alaska Airlines

Apr 14

ORD6:00 amChicago O'Hare Intl

18h 39m

2 stops

OGG7:39 pmKahului

Apr 21

OGG11:02 pmKahului

15h 01m

1 stop

ORD7:03 pmChicago O'Hare Intl

$471

Alaska Airlines

Apr 13

ORD8:20 amChicago O'Hare Intl

18h 42m

1 stop

OGG10:02 pmKahului

Apr 19

OGG11:02 pmKahului

19h 57m

1 stop

ORD11:59 pmChicago O'Hare Intl

$472

Fly from

Fly to

Route

Depart

Return

Price

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

pt. 4/17

7:35 am-7:32 pm

2 stops16h 57m

Kahului

pt. 4/24

10:30 pm-9:18 pm

2 stops17h 48m

$466

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

wt. 3/17

7:10 am-6:25 pm

2 stops16h 15m

Kahului

wt. 3/24

9:09 pm-7:49 pm

2 stops17h 40m

$467

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

pon. 4/6

4:10 pm-10:02 pm

1 stop34h 52m

Kahului

wt. 4/14

11:02 pm-2:21 pm

1 stop10h 19m

$468

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

pt. 4/17

7:35 am-7:32 pm

2 stops16h 57m

Kahului

pon. 4/20

10:30 pm-9:18 pm

2 stops17h 48m

$469

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

śr. 4/29

6:45 am-12:35 pm

1 stop10h 50m

Kahului

pon. 5/4

8:55 pm-4:35 pm

1 stop14h 40m

$470

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

pon. 3/23

7:39 pm-11:24 am

1 stop20h 45m

Kahului

pon. 3/30

3:45 pm-4:49 am

2 stops32h 04m

$470

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

wt. 4/14

6:00 am-7:39 pm

2 stops18h 39m

Kahului

wt. 4/21

11:02 pm-7:03 pm

1 stop15h 01m

$471

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

pon. 4/13

8:20 am-10:02 pm

1 stop18h 42m

Kahului

ndz. 4/19

11:02 pm-11:59 pm

1 stop19h 57m

$472

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

czw. 5/7

10:05 am-4:05 pm

1 stop11h 00m

Kahului

pon. 5/11

8:55 pm-4:35 pm

1 stop14h 40m

$473

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

pt. 5/1

8:50 am-10:10 pm

2 stops18h 20m

Kahului

śr. 5/6

10:51 pm-11:43 pm

1 stop19h 52m

$475

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How to get the cheapest flight ticket from Chicago to Maui

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

Other information

What is the cheapest month to fly to Maui?

The month of October is, on average, the cheapest month to fly to Maui from Chicago, with most prices found around $581. If you are unable to visit Maui during the month of October, then departing from Chicago during the month January is also very affordable. Most momondo users find prices during this month for around $608.

What is the cheapest day to depart on your flight to Maui?

On average, the least expensive day to fly to Maui from Chicago is on a Monday. momondo users have found tickets for Monday departures for as low as $1,033. However, this price may fluctuate depending on the airline, the season, and holidays. The most expensive day to fly to Maui is Friday, with ticket prices averaging around $1,264.

What is the cheapest Chicago to Maui flight route?

Fly from Chicago O'Hare Intl to Kahului for the best Chicago - Maui flight prices

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

You are more likely to see cheaper flights to Maui from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Maui for around $823 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Maui from Chicago for as low as $673 on momondo.

What cabin class options are available on Chicago to Maui flights?

There are 4 cabin classes available to choose from on Chicago to Maui flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Chicago to Maui flights?

No. A direct flight is the cheapest option for a flight between Chicago to Maui.

Cheap Chicago to Maui flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Maui

Best Price Found	$497
Fastest flight time	8h 56m
Direct flights	Every day
Airports in Maui	3 airports

The best one-way flight to Maui from Chicago in the past 72 hours is $497. The best round-trip flight deal from Chicago to Maui found on momondo in the last 72 hours is $954.

The fastest flight from Chicago to Maui takes 8h 56m

Direct flights go from Chicago to Maui every day.

There are 3 airports in Maui. From Chicago there are direct flights to Kahului (OGG).

Search flight deals

When did momondo last update prices for flights from Chicago to Maui?
Prices for flights from Chicago to Maui were last updated today.
How many operators does momondo search for flights from Chicago to Maui?
There are 6 operators available for flights from Chicago to Maui as of February 2026.
How old do you have to be to fly from Chicago to Maui?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago to Maui.
What documentation or ID do you need to fly to Maui?
The travel and health documents you'll need for your trip to Maui may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Maui. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Chicago to Maui?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Chicago to Maui is Airbus A321neo (16.64% of total bookings). The next most popular plane models are Boeing 737-800 (15.87%), Boeing 737-900 (7.54%), and Boeing 737 MAX 8 (7.49%).

Best airlines flying from Chicago to Maui

Compare and see reviews for airlines that fly from Chicago to Maui with momondo

Airline	Rating	Free Cancellation	Price
Delta	PriceFrom $311	Free Cancellation	Rating 7.9 8,240 reviews	Search Delta flights
Hawaiian Airlines	PriceFrom $316	Free Cancellation	Rating 7.8 2,835 reviews	Search Hawaiian Airlines flights
Alaska Airlines	PriceFrom $363	Free Cancellation	Rating 8.0 11,928 reviews	Search Alaska Airlines flights
American Airlines	PriceFrom $426	Free Cancellation	Rating 7.2 11,338 reviews	Search American Airlines flights
Southwest	PriceFrom $568	Free Cancellation	Rating 8.0 4,299 reviews	Search Southwest flights
United Airlines	PriceFrom $753	Free Cancellation	Rating 7.4 9,341 reviews	Search United Airlines flights

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Maui?

It is quick and easy to find Chicago to Maui flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Maui that suits you.

Can I find flights from Chicago to Maui with flexible booking policies on momondo?

Flights from Chicago to Maui with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Chicago to Maui?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Chicago to Maui.

I’m not ready to book a flight from Chicago to Maui right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Maui from Chicago. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

An easier way to manage your Maui trip

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Flights to New Yorkfrom $54

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Flights to Chicagofrom $53

Flights to San Franciscofrom $70

Flights to Las Vegasfrom $30

Flights to Washington, D.C.from $56

Flights to Bostonfrom $72

Flights to Atlantafrom $49

Flights to Dallasfrom $53

Flights to Seattlefrom $55

Cheap flights from Chicago to Maui from $146

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Maui departing on 4/20. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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How to get the cheapest flight ticket from Chicago to Maui

What is the cheapest month to fly to Maui?

What is the cheapest day to depart on your flight to Maui?

What is the cheapest Chicago to Maui flight route?

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

What cabin class options are available on Chicago to Maui flights?

Can stopping save me money on Chicago to Maui flights?

What is the cheapest airline that flies from Chicago to Maui?

What airlines fly to Maui?

How many flights depart from Chicago to Maui on average per day?

How many flights depart from Chicago to Maui on average per week?

Cheap Chicago to Maui flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Maui

Best Price Found

Fastest flight time

Direct flights

Airports in Maui

Best airlines flying from Chicago to Maui

Compare and see reviews for airlines that fly from Chicago to Maui with momondo

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Maui?

Can I find flights from Chicago to Maui with flexible booking policies on momondo?

How can momondo help me find flights from Chicago to Maui?

I’m not ready to book a flight from Chicago to Maui right now. Can momondo alert me if prices change?

An easier way to manage your Maui trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to Maui

Popular cities in Maui

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