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 37% 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.

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

Delta, 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 May 2026, there are 1 flights per week flying from Chicago to Maui. The most common day of the week flights depart is Sat, with 100% of flights taking off on this day.

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 May 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.

$253 Cheap Flights from Chicago to Maui in 2026

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Find the cheapest flights from Chicago to Maui

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

6:29 pm - 11:15 am

ORD

OGG

21h 46m

2 stops

12:55 pm - 5:40 pm

OGG

ORD

23h 45m

1 stop

$525Delta

Tue, Aug 18 - Tue, Aug 25

7:44 pm - 11:15 am

ORD

OGG

20h 31m

2 stops

9:21 pm - 1:23 pm

OGG

ORD

11h 02m

1 stop

$526Delta

Tue, Aug 18 - Wed, Aug 26

6:50 am - 12:35 pm

MDW

OGG

10h 45m

1 stop

8:25 pm - 11:20 am

OGG

MDW

9h 55m

1 stop

$532Southwest

Tue, Sep 15 - Wed, Sep 23

6:29 pm - 11:15 am

ORD

OGG

21h 46m

2 stops

9:21 pm - 11:48 pm

OGG

ORD

21h 27m

2 stops

$532Delta

Tue, Aug 18 - Tue, Aug 25

7:25 pm - 11:15 am

MDW

OGG

20h 50m

2 stops

12:55 pm - 6:01 pm

OGG

MDW

24h 06m

2 stops

$537Delta

Tue, Aug 18 - Tue, Aug 25

6:50 am - 4:10 pm

MDW

OGG

14h 20m

2 stops

8:25 pm - 11:20 am

OGG

MDW

9h 55m

1 stop

$538Southwest

Tue, Sep 15 - Wed, Sep 23

2:36 pm - 11:15 am

ORD

OGG

25h 39m

1 stop

9:21 pm - 11:48 pm

OGG

ORD

21h 27m

2 stops

$547Delta

Tue, Aug 18 - Sun, Aug 23

2:18 pm - 9:37 pm

ORD

OGG

12h 19m

1 stop

7:00 am - 11:59 pm

OGG

ORD

11h 59m

1 stop

$549Alaska Airlines

Tue, Sep 1 - Wed, Sep 2

6:01 am - 8:11 pm

ORD

OGG

19h 10m

2 stops

7:00 am - 11:59 pm

OGG

ORD

11h 59m

1 stop

$554Multiple Airlines

Tue, Sep 1 - Wed, Sep 2

7:25 am - 3:12 pm

ORD

OGG

11h 47m

1 stop

3:49 pm - 5:37 pm

OGG

ORD

21h 48m

2 stops

$555Multiple Airlines

Tue, Nov 3 - Tue, Nov 10

Delta flights from Chicago to Maui

Our best Delta deals on Chicago to Maui flight tickets

Delta

Aug 18

ORD6:29 pmChicago O'Hare Intl

21h 46m

2 stops

OGG11:15 amKahului

Aug 25

OGG12:55 pmKahului

23h 45m

1 stop

ORD5:40 pmChicago O'Hare Intl

$525

Delta

Aug 18

ORD7:44 pmChicago O'Hare Intl

20h 31m

2 stops

OGG11:15 amKahului

Aug 26

OGG9:21 pmKahului

11h 02m

1 stop

ORD1:23 pmChicago O'Hare Intl

$526

Delta

Aug 18

ORD6:29 pmChicago O'Hare Intl

21h 46m

2 stops

OGG11:15 amKahului

Aug 25

OGG9:21 pmKahului

21h 27m

2 stops

ORD11:48 pmChicago O'Hare Intl

$532

Southwest flights from Chicago to Maui

Our best Southwest deals on Chicago to Maui flight tickets

Southwest

Sep 15

MDW6:50 amChicago Midway

10h 45m

1 stop

OGG12:35 pmKahului

Sep 23

OGG8:25 pmKahului

9h 55m

1 stop

MDW11:20 amChicago Midway

$532

Southwest

Sep 15

MDW6:50 amChicago Midway

14h 20m

2 stops

OGG4:10 pmKahului

Sep 23

OGG8:25 pmKahului

9h 55m

1 stop

MDW11:20 amChicago Midway

$538

Southwest

Aug 25

MDW6:50 amChicago Midway

10h 45m

1 stop

OGG12:35 pmKahului

Sep 29

OGG8:55 pmKahului

11h 00m

1 stop

MDW12:55 pmChicago Midway

$554

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Tue 8/18

6:29 pm-11:15 am

2 stops21h 46m

Kahului

Tue 8/25

12:55 pm-5:40 pm

1 stop23h 45m

$525

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Tue 8/18

7:44 pm-11:15 am

2 stops20h 31m

Kahului

Wed 8/26

9:21 pm-1:23 pm

1 stop11h 02m

$526

Quickest round-trip

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Tue 9/15

6:50 am-12:35 pm

1 stop10h 45m

Kahului

Wed 9/23

8:25 pm-11:20 am

1 stop9h 55m

$532

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Tue 8/18

6:29 pm-11:15 am

2 stops21h 46m

Kahului

Tue 8/25

9:21 pm-11:48 pm

2 stops21h 27m

$532

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Tue 8/18

7:25 pm-11:15 am

2 stops20h 50m

Kahului

Tue 8/25

12:55 pm-6:01 pm

2 stops24h 06m

$537

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Tue 9/15

6:50 am-4:10 pm

2 stops14h 20m

Kahului

Wed 9/23

8:25 pm-11:20 am

1 stop9h 55m

$538

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Tue 8/18

2:36 pm-11:15 am

1 stop25h 39m

Kahului

Sun 8/23

9:21 pm-11:48 pm

2 stops21h 27m

$547

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Tue 9/1

2:18 pm-9:37 pm

1 stop12h 19m

Kahului

Wed 9/2

7:00 am-11:59 pm

1 stop11h 59m

$549

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Tue 9/1

6:01 am-8:11 pm

2 stops19h 10m

Kahului

Wed 9/2

7:00 am-11:59 pm

1 stop11h 59m

$554

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Tue 11/3

7:25 am-3:12 pm

1 stop11h 47m

Kahului

Tue 11/10

3:49 pm-5:37 pm

2 stops21h 48m

$555

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 September is, on average, the cheapest month to fly to Maui from Chicago, with most prices found around $232. If you are unable to visit Maui during the month of September, then departing from Chicago during the month October is also very affordable. Most momondo users find prices during this month for around $281.

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 Tuesday. momondo users have found tickets for Tuesday departures for as low as $960. 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 $1,269.

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 from Chicago 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 $807 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 $655 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	$557
Fastest flight time	8h 56m
Direct flights	Sun
Airports in Maui	3 airports

The best one-way flight to Maui from Chicago in the past 72 hours is $557. The best round-trip flight deal from Chicago to Maui found on momondo in the last 72 hours is $944.

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

Direct flights go from Chicago to Maui on Sunday. There are no airlines offering direct flights.

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

Search flight deals

Frequently asked questions about flying from Chicago to Maui

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 May 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 Boeing 737-800 (17.85% of total bookings). The next most popular plane models are Airbus A321neo (15.56%), Boeing 737-900 (8.93%), and Airbus A321-100/200 (7.91%).

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
Hawaiian Airlines	PriceFrom $316	Free Cancellation	Rating 7.8 2,835 reviews	Search Hawaiian Airlines flights
Delta	PriceFrom $355	Free Cancellation	Rating 7.9 8,439 reviews	Search Delta flights
Alaska Airlines	PriceFrom $361	Free Cancellation	Rating 7.9 12,407 reviews	Search Alaska Airlines flights
American Airlines	PriceFrom $422	Free Cancellation	Rating 7.1 11,632 reviews	Search American Airlines flights
Southwest	PriceFrom $568	Free Cancellation	Rating 7.9 4,274 reviews	Search Southwest flights
United Airlines	PriceFrom $741	Free Cancellation	Rating 7.4 9,748 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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Popular cities in Maui

Flights to New Yorkfrom $77

Flights to Los Angelesfrom $49

Flights to Orlandofrom $68

Flights to Miamifrom $60

Flights to Chicagofrom $61

Flights to San Franciscofrom $92

Flights to Las Vegasfrom $56

Flights to Washington, D.C.from $56

Flights to Bostonfrom $70

Flights to Atlantafrom $51

Flights to Fort Lauderdalefrom $57

Flights to Dallasfrom $104

Cheap flights from Chicago to Maui from $253

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 8/18. 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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Our best Delta deals on Chicago to Maui flight tickets

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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 from Chicago 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 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

Frequently asked questions about flying from Chicago to 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?

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

Popular flights according to clicks in the last 7 days on momondo

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