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

Alaska Airlines, Hawaiian Airlines, and American Airlines are the most popular carriers operating from Chicago to Maui

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.

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 September 2025.

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.

$196 Cheap Flights from Chicago to Maui in 2025/26

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Find the cheapest flights from Chicago to Maui

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

9:20 am - 11:09 pmORD-OGG

17h 49m2 stops

11:50 pm - 7:53 pmOGG-ORD

16h 03m1 stop

$438Alaska Airlines

Find Deal

อ., พ.ย. 18 - อา., พ.ย. 23

3:05 pm - 11:40 pmORD-OGG

12h 35m1 stop

6:00 am - 11:50 pmOGG-ORD

13h 50m2 stops

$439Alaska Airlines

Find Deal

อ., ธ.ค. 2 - พ., ธ.ค. 10

2:59 pm - 10:30 amORD-OGG

23h 31m2 stops

11:20 pm - 11:10 pmOGG-ORD

19h 50m1 stop

$440Alaska Airlines

Find Deal

พ., ม.ค. 21 - ศ., ม.ค. 30

2:59 pm - 10:48 pmORD-OGG

11h 49m1 stop

11:20 pm - 1:59 pmOGG-ORD

10h 39m1 stop

$441Alaska Airlines

Find Deal

อา., ก.พ. 1 - อ., ก.พ. 10

5:18 am - 1:17 pmORD-OGG

11h 59m1 stop

7:00 pm - 11:47 amOGG-ORD

12h 47m1 stop

$479American Airlines

Find Deal

อ., ธ.ค. 2 - อ., ธ.ค. 9

5:25 am - 1:05 pmMDW-OGG

11h 40m1 stop

9:25 pm - 3:00 pmOGG-MDW

13h 35m1 stop

$479Southwest

Find Deal

อ., ธ.ค. 9 - อ., ธ.ค. 16

3:05 pm - 11:40 pmORD-OGG

12h 35m1 stop

11:18 pm - 2:39 pmOGG-ORD

11h 21m1 stop

$480Hawaiian Airlines

Find Deal

พฤ., ธ.ค. 4 - จ., ธ.ค. 8

6:10 am - 4:25 pmMDW-OGG

14h 15m2 stops

9:25 pm - 11:10 amOGG-MDW

9h 45m1 stop

$484Southwest

Find Deal

พ., ก.พ. 18 - พ., มี.ค. 4

10:35 am - 12:20 pmMDW-OGG

29h 45m2 stops

1:45 pm - 8:54 amOGG-MDW

15h 09m2 stops

$500Delta

Find Deal

พ., ม.ค. 21 - พ., ม.ค. 28

9:32 am - 7:21 pmMDW-OGG

13h 49m2 stops

1:45 pm - 9:01 amOGG-MDW

15h 16m2 stops

$522Delta

Find Deal

อ., พ.ย. 11 - อ., พ.ย. 18

Alaska Airlines flights from Chicago to Maui

Our best Alaska Airlines deals on Chicago to Maui flight tickets

Alaska Airlines

Nov 18

ORD9:20 amChicago O'Hare Intl

17h 49m

2 stops

OGG11:09 pmKahului

Nov 23

OGG11:50 pmKahului

16h 03m

1 stop

ORD7:53 pmChicago O'Hare Intl

$438

Find similar

Alaska Airlines

Dec 2

ORD3:05 pmChicago O'Hare Intl

12h 35m

1 stop

OGG11:40 pmKahului

Dec 10

OGG6:00 amKahului

13h 50m

2 stops

ORD11:50 pmChicago O'Hare Intl

$439

Find similar

Alaska Airlines

Jan 21

ORD2:59 pmChicago O'Hare Intl

23h 31m

2 stops

OGG10:30 amKahului

Jan 30

OGG11:20 pmKahului

19h 50m

1 stop

ORD11:10 pmChicago O'Hare Intl

$440

Find similar

Southwest flights from Chicago to Maui

Our best Southwest deals on Chicago to Maui flight tickets

Southwest

Dec 9

MDW5:25 amChicago Midway

11h 40m

1 stop

OGG1:05 pmKahului

Dec 16

OGG9:25 pmKahului

13h 35m

1 stop

MDW3:00 pmChicago Midway

$479

Find similar

Southwest

Feb 18

MDW6:10 amChicago Midway

14h 15m

2 stops

OGG4:25 pmKahului

Mar 4

OGG9:25 pmKahului

9h 45m

1 stop

MDW11:10 amChicago Midway

$484

Find similar

Southwest

Nov 10

MDW5:30 amChicago Midway

11h 35m

1 stop

OGG1:05 pmKahului

Nov 18

OGG9:35 pmKahului

12h 05m

1 stop

MDW1:40 pmChicago Midway

$511

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

อ. 11/18

9:20 am-11:09 pm

2 stops17h 49m

Kahului

อา. 11/23

11:50 pm-7:53 pm

1 stop16h 03m

$438

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

อ. 12/2

3:05 pm-11:40 pm

1 stop12h 35m

Kahului

พ. 12/10

6:00 am-11:50 pm

2 stops13h 50m

$439

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

พ. 1/21

2:59 pm-10:30 am

2 stops23h 31m

Kahului

ศ. 1/30

11:20 pm-11:10 pm

1 stop19h 50m

$440

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

อา. 2/1

2:59 pm-10:48 pm

1 stop11h 49m

Kahului

อ. 2/10

11:20 pm-1:59 pm

1 stop10h 39m

$441

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

อ. 12/2

5:18 am-1:17 pm

1 stop11h 59m

Kahului

อ. 12/9

7:00 pm-11:47 am

1 stop12h 47m

$479

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

อ. 12/9

5:25 am-1:05 pm

1 stop11h 40m

Kahului

อ. 12/16

9:25 pm-3:00 pm

1 stop13h 35m

$479

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

พฤ. 12/4

3:05 pm-11:40 pm

1 stop12h 35m

Kahului

จ. 12/8

11:18 pm-2:39 pm

1 stop11h 21m

$480

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

พ. 2/18

6:10 am-4:25 pm

2 stops14h 15m

Kahului

พ. 3/4

9:25 pm-11:10 am

1 stop9h 45m

$484

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

พ. 1/21

10:35 am-12:20 pm

2 stops29h 45m

Kahului

พ. 1/28

1:45 pm-8:54 am

2 stops15h 09m

$500

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

อ. 11/11

9:32 am-7:21 pm

2 stops13h 49m

Kahului

อ. 11/18

1:45 pm-9:01 am

2 stops15h 16m

$522

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

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 November is, on average, the cheapest month to fly to Maui from Chicago, with most prices found around $561. If you are unable to visit Maui during the month of November, then departing from Chicago during the month October is also very affordable. Most momondo users find prices during this month for around $581.

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 Tuesday, with ticket prices averaging around $1,198.

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

Flying to Maui from Chicago in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $531 when looking at flights departing in the afternoon. Flights to Maui are more costly in the morning, with an average ticket price of $1,103. Departure times in the morning fall within the peak daily travel times, which is why tickets can be more expensive.

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 $795 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 $661 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	$467
Fastest flight time	8h 48m
Direct flights	Every day
Airports in Maui	1 airport

The best one-way flight to Maui from Chicago in the past 72 hours is $467. The best round-trip flight deal from Chicago to Maui found on momondo in the last 72 hours is $882.

The fastest flight from Chicago to Maui takes 8h 48m

Direct flights go from Chicago to Maui every day.

There is 1 airport near Maui: 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 September 2025.
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 Boeing 737-800 (19.33% of total bookings). The next most popular plane models are Airbus A321neo (8.81%), Boeing 737-900 (8.69%), and Airbus A321-100/200 (7.67%).

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 $341	Free Cancellation	Rating 7.9 7,957 reviews	Search Delta flights
Hawaiian Airlines	PriceFrom $357	Free Cancellation	Rating 7.8 2,724 reviews	Search Hawaiian Airlines flights
American Airlines	PriceFrom $398	Free Cancellation	Rating 7.2 10,000 reviews	Search American Airlines flights
Alaska Airlines	PriceFrom $425	Free Cancellation	Rating 8.0 10,000 reviews	Search Alaska Airlines flights
Southwest	PriceFrom $543	Free Cancellation	Rating 8.0 4,242 reviews	Search Southwest flights
United Airlines	PriceFrom $546	Free Cancellation	Rating 7.4 8,924 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.