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 5 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?

Alaska Airlines, Southwest, and Delta are the most popular carriers operating 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 5 operators available for flights from Chicago to Maui as of September 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.

$213 Cheap Flights from Chicago to Maui in 2026/27

Discover deals from 900+ travel sites with momondo.

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.

7:40 am - 6:38 pmORD Chicago O'Hare Intl-OGG Kahului

14h 58m1 stop San Diego

11:55 pm - 10:08 pmOGG Kahului-ORD Chicago O'Hare Intl

18h 13m1 stop San Diego

$420Alaska Airlines

Tue, Jan 19 - Tue, Jan 19

2:54 pm - 11:01 pmORD Chicago O'Hare Intl-OGG Kahului

12h 07m1 stop San Diego

11:59 pm - 6:55 pmOGG Kahului-ORD Chicago O'Hare Intl

14h 56m1 stop San Diego

$425Alaska Airlines

Tue, Feb 16 - Tue, Feb 23

7:40 am - 6:38 pmORD Chicago O'Hare Intl-OGG Kahului

14h 58m1 stop San Diego

1:57 pm - 1:15 pmOGG Kahului-ORD Chicago O'Hare Intl

19h 18m1 stop San Diego

$425Multiple Airlines

Wed, Jan 13 - Tue, Jan 19

7:40 am - 6:38 pmORD Chicago O'Hare Intl-OGG Kahului

14h 58m1 stop San Diego

1:57 pm - 1:15 pmOGG Kahului-ORD Chicago O'Hare Intl

19h 18m1 stop San Diego

$425Multiple Airlines

Wed, Jan 13 - Fri, Jan 22

5:50 am - 1:10 pmMDW Chicago Midway-OGG Kahului

11h 20m1 stop Las Vegas Harry Reid Intl

10:30 pm - 3:05 pmOGG Kahului-MDW Chicago Midway

12h 35m2 stops Oakland Las Vegas Harry Reid Intl

$510Southwest

Tue, Nov 17 - Wed, Nov 25

5:50 am - 2:40 pmMDW Chicago Midway-OGG Kahului

12h 50m2 stops Las Vegas Harry Reid Intl San Diego

10:30 pm - 3:05 pmOGG Kahului-MDW Chicago Midway

12h 35m2 stops Oakland Las Vegas Harry Reid Intl

$515Southwest

Tue, Nov 17 - Wed, Nov 25

11:55 am - 5:40 pmORD Chicago O'Hare Intl-OGG Kahului

9h 45mnonstop

7:30 pm - 7:30 amOGG Kahului-ORD Chicago O'Hare Intl

8h 00mnonstop

$519American Airlines

Tue, Feb 16 - Tue, Feb 23

11:55 am - 5:40 pmORD Chicago O'Hare Intl-OGG Kahului

9h 45mnonstop

7:30 pm - 7:30 amOGG Kahului-ORD Chicago O'Hare Intl

8h 00mnonstop

$519American Airlines

Sun, Feb 14 - Thu, Feb 25

7:30 am - 3:30 pmORD Chicago O'Hare Intl-OGG Kahului

12h 00m1 stop Salt Lake City

9:30 pm - 12:25 pmOGG Kahului-ORD Chicago O'Hare Intl

10h 55m1 stop Salt Lake City

$538Delta

Wed, Jan 6 - Tue, Jan 19

7:30 am - 3:30 pmORD Chicago O'Hare Intl-OGG Kahului

12h 00m1 stop Salt Lake City

12:45 pm - 8:58 amOGG Kahului-ORD Chicago O'Hare Intl

16h 13m2 stops Los Angeles Detroit Metropolitan Wayne County

$544Delta

Wed, Jan 6 - Tue, Jan 19

Cheap last minute flights

Enter your travel dates to find the best prices.

10:15 am - 4:10 pmMDW Chicago Midway-OGG Kahului

10h 55m1 stop Oakland

8:35 pm - 11:55 amOGG Kahului-MDW Chicago Midway

10h 20m1 stop Las Vegas Harry Reid Intl

$670Southwest

Wed, Sep 23 - Tue, Sep 29

7:45 am - 2:01 pmORD Chicago O'Hare Intl-OGG Kahului

11h 16m1 stop Salt Lake City

9:10 pm - 1:29 pmOGG Kahului-ORD Chicago O'Hare Intl

11h 19m1 stop Seattle/Tacoma Intl

$670Delta

Wed, Sep 23 - Wed, Sep 30

7:00 am - 5:53 pmORD Chicago O'Hare Intl-OGG Kahului

15h 53m1 stop Seattle/Tacoma Intl

8:00 pm - 11:55 amOGG Kahului-ORD Chicago O'Hare Intl

10h 55m1 stop Salt Lake City

$670Delta

Wed, Sep 23 - Wed, Sep 30

8:35 am - 4:10 pmMDW Chicago Midway-OGG Kahului

12h 35m2 stops Las Vegas Harry Reid Intl Oakland

10:00 am - 5:55 amOGG Kahului-MDW Chicago Midway

14h 55m1 stop Oakland

$676Southwest

Wed, Sep 23 - Tue, Sep 29

6:50 am - 6:10 pmMDW Chicago Midway-OGG Kahului

16h 20m2 stops Las Vegas Harry Reid Intl Honolulu

8:55 pm - 2:45 pmOGG Kahului-MDW Chicago Midway

12h 50m2 stops San Diego Phoenix Sky Harbor Intl

$731Southwest

Wed, Sep 23 - Tue, Sep 29

2:18 pm - 9:37 pmORD Chicago O'Hare Intl-OGG Kahului

12h 19m1 stop San Diego

7:00 am - 11:59 pmOGG Kahului-ORD Chicago O'Hare Intl

11h 59m1 stop Seattle/Tacoma Intl

$758Alaska Airlines

Wed, Sep 23 - Sun, Sep 27

2:18 pm - 9:37 pmORD Chicago O'Hare Intl-OGG Kahului

12h 19m1 stop San Diego

10:40 pm - 7:21 pmOGG Kahului-ORD Chicago O'Hare Intl

15h 41m1 stop San Diego

$758Alaska Airlines

Sat, Sep 26 - Tue, Sep 29

1:03 pm - 11:56 amORD Chicago O'Hare Intl-OGG Kahului

27h 53m1 stop Seattle/Tacoma Intl

9:15 am - 6:20 amOGG Kahului-ORD Chicago O'Hare Intl

16h 05m2 stops Honolulu Seattle/Tacoma Intl

$763Multiple Airlines

Wed, Sep 23 - Sun, Sep 27

4:08 pm - 7:40 amORD Chicago O'Hare Intl-OGG Kahului

20h 32m2 stops Seattle/Tacoma Intl Honolulu

12:50 pm - 6:20 amOGG Kahului-ORD Chicago O'Hare Intl

12h 30m1 stop Seattle/Tacoma Intl

$764Multiple Airlines

Sat, Sep 26 - Tue, Sep 29

12:40 pm - 7:10 pmORD Chicago O'Hare Intl-OGG Kahului

11h 30m1 stop San Francisco

4:10 pm - 5:00 amOGG Kahului-ORD Chicago O'Hare Intl

7h 50mnonstop

$776United Airlines

Thu, Sep 24 - Sat, Sep 26

Cheap direct flights

Enter your travel dates to find the best prices.

11:55 am - 5:40 pmORD Chicago O'Hare Intl-OGG Kahului

9h 45mnonstop

7:30 pm - 7:30 amOGG Kahului-ORD Chicago O'Hare Intl

8h 00mnonstop

$519American Airlines

Tue, Feb 16 - Tue, Feb 23

11:55 am - 5:40 pmORD Chicago O'Hare Intl-OGG Kahului

9h 45mnonstop

7:30 pm - 7:30 amOGG Kahului-ORD Chicago O'Hare Intl

8h 00mnonstop

$519American Airlines

Sun, Feb 14 - Thu, Feb 25

11:55 am - 5:40 pmORD Chicago O'Hare Intl-OGG Kahului

9h 45mnonstop

7:30 pm - 7:30 amOGG Kahului-ORD Chicago O'Hare Intl

8h 00mnonstop

$519American Airlines

Wed, Jan 6 - Wed, Jan 20

11:55 am - 5:40 pmORD Chicago O'Hare Intl-OGG Kahului

9h 45mnonstop

7:30 pm - 7:30 amOGG Kahului-ORD Chicago O'Hare Intl

8h 00mnonstop

$519American Airlines

Tue, Feb 16 - Tue, Feb 23

11:55 am - 5:40 pmORD Chicago O'Hare Intl-OGG Kahului

9h 45mnonstop

7:30 pm - 7:30 amOGG Kahului-ORD Chicago O'Hare Intl

8h 00mnonstop

$519American Airlines

Tue, Jan 26 - Wed, Feb 3

11:55 am - 5:40 pmORD Chicago O'Hare Intl-OGG Kahului

9h 45mnonstop

7:30 pm - 7:30 amOGG Kahului-ORD Chicago O'Hare Intl

8h 00mnonstop

$543American Airlines

Sun, Feb 21 - Mon, Mar 1

11:55 am - 5:40 pmORD Chicago O'Hare Intl-OGG Kahului

9h 45mnonstop

7:30 pm - 7:30 amOGG Kahului-ORD Chicago O'Hare Intl

8h 00mnonstop

$543American Airlines

Thu, Jan 28 - Thu, Feb 4

11:55 am - 5:40 pmORD Chicago O'Hare Intl-OGG Kahului

9h 45mnonstop

7:30 pm - 7:30 amOGG Kahului-ORD Chicago O'Hare Intl

8h 00mnonstop

$561American Airlines

Wed, Feb 24 - Wed, Feb 24

9:20 am - 2:40 pmORD Chicago O'Hare Intl-OGG Kahului

9h 20mnonstop

5:05 pm - 5:03 amOGG Kahului-ORD Chicago O'Hare Intl

7h 58mnonstop

$567United Airlines

Wed, Jan 6 - Tue, Jan 19

9:20 am - 2:40 pmORD Chicago O'Hare Intl-OGG Kahului

9h 20mnonstop

5:05 pm - 5:03 amOGG Kahului-ORD Chicago O'Hare Intl

7h 58mnonstop

$567United Airlines

Wed, Jan 6 - Wed, Jan 20

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Alaska Airlines flights from Chicago to Maui

Our best Alaska Airlines deals on Chicago to Maui flight tickets

Alaska Airlines

Jan 19

ORD7:40 amChicago O'Hare Intl

14h 58m

1 stop

OGG6:38 pmKahului

Jan 19

OGG11:55 pmKahului

18h 13m

1 stop

ORD10:08 pmChicago O'Hare Intl

$420

Alaska Airlines

Feb 23

ORD2:54 pmChicago O'Hare Intl

12h 07m

1 stop

OGG11:01 pmKahului

Mar 2

OGG11:59 pmKahului

9h 55m

1 stop

ORD1:54 pmChicago O'Hare Intl

$444

Alaska Airlines

Jan 13

ORD7:40 amChicago O'Hare Intl

14h 58m

1 stop

OGG6:38 pmKahului

Jan 21

OGG11:55 pmKahului

18h 13m

1 stop

ORD10:08 pmChicago O'Hare Intl

$456

Southwest flights from Chicago to Maui

Our best Southwest deals on Chicago to Maui flight tickets

Southwest

Nov 17

MDW5:50 amChicago Midway

11h 20m

1 stop

OGG1:10 pmKahului

Nov 25

OGG10:30 pmKahului

12h 35m

2 stops

MDW3:05 pmChicago Midway

$510

Southwest

Nov 17

MDW5:50 amChicago Midway

12h 50m

2 stops

OGG2:40 pmKahului

Nov 25

OGG10:30 pmKahului

12h 35m

2 stops

MDW3:05 pmChicago Midway

$515

Southwest

Nov 16

MDW5:50 amChicago Midway

13h 00m

2 stops

OGG2:50 pmKahului

Nov 23

OGG9:25 pmKahului

11h 45m

1 stop

MDW1:10 pmChicago Midway

$523

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoKahului

ORD Chicago O'Hare Intl - OGG Kahului

ORDOGG

Chicago O'Hare Intl

Tue 1/19

7:40 am-6:38 pm

1 stop14h 58m

Kahului

Tue 1/19

11:55 pm-10:08 pm

1 stop18h 13m

$420

ChicagoKahului

ORD Chicago O'Hare Intl - OGG Kahului

ORDOGG

Chicago O'Hare Intl

Tue 2/16

2:54 pm-11:01 pm

1 stop12h 07m

Kahului

Tue 2/23

11:59 pm-6:55 pm

1 stop14h 56m

$425

ChicagoKahului

ORD Chicago O'Hare Intl - OGG Kahului

ORDOGG

Chicago O'Hare Intl

Wed 1/13

7:40 am-6:38 pm

1 stop14h 58m

Kahului

Tue 1/19

1:57 pm-1:15 pm

1 stop19h 18m

$425

ChicagoKahului

ORD Chicago O'Hare Intl - OGG Kahului

ORDOGG

Chicago O'Hare Intl

Wed 1/13

7:40 am-6:38 pm

1 stop14h 58m

Kahului

Fri 1/22

1:57 pm-1:15 pm

1 stop19h 18m

$425

ChicagoKahului

MDW Chicago Midway - OGG Kahului

MDWOGG

Chicago Midway

Tue 11/17

5:50 am-1:10 pm

1 stop11h 20m

Kahului

Wed 11/25

10:30 pm-3:05 pm

2 stops12h 35m

$510

ChicagoKahului

MDW Chicago Midway - OGG Kahului

MDWOGG

Chicago Midway

Tue 11/17

5:50 am-2:40 pm

2 stops12h 50m

Kahului

Wed 11/25

10:30 pm-3:05 pm

2 stops12h 35m

$515

Quickest round-trip

ChicagoKahului

ORD Chicago O'Hare Intl - OGG Kahului

ORDOGG

Chicago O'Hare Intl

Tue 2/16

11:55 am-5:40 pm

Nonstop9h 45m

Kahului

Tue 2/23

7:30 pm-7:30 am

Nonstop8h 00m

$519

ChicagoKahului

ORD Chicago O'Hare Intl - OGG Kahului

ORDOGG

Chicago O'Hare Intl

Sun 2/14

11:55 am-5:40 pm

Nonstop9h 45m

Kahului

Thu 2/25

7:30 pm-7:30 am

Nonstop8h 00m

$519

ChicagoKahului

ORD Chicago O'Hare Intl - OGG Kahului

ORDOGG

Chicago O'Hare Intl

Wed 1/6

7:30 am-3:30 pm

1 stop12h 00m

Kahului

Tue 1/19

9:30 pm-12:25 pm

1 stop10h 55m

$538

ChicagoKahului

ORD Chicago O'Hare Intl - OGG Kahului

ORDOGG

Chicago O'Hare Intl

Wed 1/6

7:30 am-3:30 pm

1 stop12h 00m

Kahului

Tue 1/19

12:45 pm-8:58 am

2 stops16h 13m

$544

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

What is the cheapest month to fly to Maui?

The month of January is, on average, the cheapest month to fly to Maui from Chicago, with most prices found around $659. If you are unable to visit Maui during the month of January, then departing from Chicago during the month September is also very affordable. Most momondo users find prices during this month for around $686.

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 $884. However, this price may fluctuate depending on the airline, the season, and holidays. The most expensive day to fly to Maui is Saturday, with ticket prices averaging around $1,165.

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 $808 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 $677 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	$213
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 $213. The best round-trip flight deal from Chicago to Maui found on momondo in the last 72 hours is $420.

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

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 5 operators available for flights from Chicago to Maui as of September 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 (17.32% of total bookings). The next most popular plane models are Boeing 737-800 (17.06%), Boeing 737-900 (9.78%), and Airbus A321-100/200 (8.93%).

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
Alaska Airlines	PriceFrom $352	Free Cancellation	Rating 7.9 12,953 reviews	Search Alaska Airlines flights
Delta	PriceFrom $355	Free Cancellation	Rating 7.8 8,597 reviews	Search Delta flights
American Airlines	PriceFrom $431	Free Cancellation	Rating 7.0 12,076 reviews	Search American Airlines flights
Southwest	PriceFrom $626	Free Cancellation	Rating 8.0 4,194 reviews	Search Southwest flights
United Airlines	PriceFrom $706	Free Cancellation	Rating 7.4 10,222 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.