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Cheap flights from Chicago to Maui from $181

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 1/18. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Cheap round-trip flights

Enter your travel dates to find the best prices.
Alaska Airlines Logo
9:00 am - 10:59 pm
ORD
-
OGG
17h 59m1 stop
Alaska Airlines Logo
11:59 pm - 2:29 pm
OGG
-
ORD
10h 30m1 stop
$403Alaska Airlines
Wed, Jan 21 - Fri, Jan 30
Alaska Airlines Logo
9:00 am - 10:59 pm
ORD
-
OGG
17h 59m1 stop
Alaska Airlines Logo
11:59 pm - 2:29 pm
OGG
-
ORD
10h 30m1 stop
$404Alaska Airlines
Thu, Jan 22 - Wed, Jan 28
Multiple Airlines Logo
8:20 am - 10:21 pm
ORD
-
OGG
18h 01m2 stops
Multiple Airlines Logo
10:08 pm - 4:33 pm
OGG
-
ORD
13h 25m1 stop
$405Multiple Airlines
Wed, Mar 4 - Wed, Mar 11
Alaska Airlines Logo
9:00 am - 10:59 pm
ORD
-
OGG
17h 59m1 stop
Alaska Airlines Logo
11:59 pm - 2:29 pm
OGG
-
ORD
10h 30m1 stop
$406Alaska Airlines
Mon, Jan 19 - Sun, Jan 25
Delta Logo
7:30 am - 6:04 pm
ORD
-
OGG
14h 34m1 stop
Delta Logo
10:00 pm - 9:43 pm
OGG
-
ORD
19h 43m2 stops
$407Delta
Mon, Jan 19 - Tue, Jan 27
Multiple Airlines Logo
9:00 am - 10:21 pm
ORD
-
OGG
17h 21m2 stops
Multiple Airlines Logo
11:59 pm - 11:37 pm
OGG
-
ORD
19h 38m1 stop
$408Multiple Airlines
Sun, Jan 18 - Mon, Jan 26
Multiple Airlines Logo
3:44 pm - 5:04 pm
ORD
-
OGG
29h 20m2 stops
Multiple Airlines Logo
11:59 pm - 11:37 pm
OGG
-
ORD
19h 38m1 stop
$409Multiple Airlines
Mon, Jan 12 - Wed, Jan 21
Multiple Airlines Logo
9:00 am - 8:30 pm
ORD
-
OGG
15h 30m2 stops
Multiple Airlines Logo
11:59 pm - 2:29 pm
OGG
-
ORD
10h 30m1 stop
$411Multiple Airlines
Sun, Jan 18 - Thu, Jan 29
Delta Logo
7:20 am - 7:15 pm
ORD
-
OGG
15h 55m1 stop
Delta Logo
10:00 pm - 1:22 pm
OGG
-
ORD
11h 22m1 stop
$412Delta
Sun, Jan 18 - Thu, Jan 29
Delta Logo
6:00 am - 3:37 pm
MDW
-
OGG
13h 37m1 stop
Delta Logo
10:00 pm - 6:36 pm
OGG
-
MDW
16h 36m2 stops
$417Delta
Sun, Jan 25 - Tue, Feb 3

Delta flights from Chicago to Maui

Our best Delta deals on Chicago to Maui flight tickets
Delta
Jan 19
ORD7:30 amChicago O'Hare Intl
14h 34m
1 stop
OGG6:04 pmKahului
Jan 27
OGG10:00 pmKahului
19h 43m
2 stops
ORD9:43 pmChicago O'Hare Intl
$407
Find similar
Delta
Jan 18
ORD5:30 amChicago O'Hare Intl
14h 07m
1 stop
OGG3:37 pmKahului
Jan 28
OGG10:00 pmKahului
21h 53m
1 stop
ORD11:53 pmChicago O'Hare Intl
$412
Find similar
Delta
Jan 25
MDW6:00 amChicago Midway
13h 37m
1 stop
OGG3:37 pmKahului
Feb 3
OGG10:00 pmKahului
16h 36m
2 stops
MDW6:36 pmChicago Midway
$417
Find similar

Southwest flights from Chicago to Maui

Our best Southwest deals on Chicago to Maui flight tickets
Southwest
Jan 5
MDW7:45 amChicago Midway
12h 25m
1 stop
OGG4:10 pmKahului
Jan 8
OGG9:25 pmKahului
13h 20m
1 stop
MDW2:45 pmChicago Midway
$713
Find similar
Southwest
Jan 5
MDW9:45 pmChicago Midway
19h 25m
2 stops
OGG1:10 pmKahului
Jan 8
OGG9:35 pmKahului
11h 00m
1 stop
MDW12:35 pmChicago Midway
$718
Find similar
Southwest
Jan 5
MDW9:45 pmChicago Midway
19h 25m
2 stops
OGG1:10 pmKahului
Jan 8
OGG9:35 pmKahului
13h 10m
2 stops
MDW2:45 pmChicago Midway
$724
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago to Maui that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated December 23, 2025.
Use the filters below to find and compare flights from Chicago to Maui that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Wed 1/21

9:00 am-10:59 pm

1 stop17h 59m

Kahului

Fri 1/30

11:59 pm-2:29 pm

1 stop10h 30m

$403

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Thu 1/22

9:00 am-10:59 pm

1 stop17h 59m

Kahului

Wed 1/28

11:59 pm-2:29 pm

1 stop10h 30m

$404

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Wed 3/4

8:20 am-10:21 pm

2 stops18h 01m

Kahului

Wed 3/11

10:08 pm-4:33 pm

1 stop13h 25m

$405

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Mon 1/19

9:00 am-10:59 pm

1 stop17h 59m

Kahului

Sun 1/25

11:59 pm-2:29 pm

1 stop10h 30m

$406

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Mon 1/19

7:30 am-6:04 pm

1 stop14h 34m

Kahului

Tue 1/27

10:00 pm-9:43 pm

2 stops19h 43m

$407

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Sun 1/18

9:00 am-10:21 pm

2 stops17h 21m

Kahului

Mon 1/26

11:59 pm-11:37 pm

1 stop19h 38m

$408

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Mon 1/12

3:44 pm-5:04 pm

2 stops29h 20m

Kahului

Wed 1/21

11:59 pm-11:37 pm

1 stop19h 38m

$409

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Sun 1/18

9:00 am-8:30 pm

2 stops15h 30m

Kahului

Thu 1/29

11:59 pm-2:29 pm

1 stop10h 30m

$411

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Sun 1/18

7:20 am-7:15 pm

1 stop15h 55m

Kahului

Thu 1/29

10:00 pm-1:22 pm

1 stop11h 22m

$412

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Sun 1/25

6:00 am-3:37 pm

1 stop13h 37m

Kahului

Tue 2/3

10:00 pm-6:36 pm

2 stops16h 36m

$417

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Maui from

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

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 $591. 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 $1,219.

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 $1,100. 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 $825 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 $704 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

9h 08m

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 $928.
The fastest flight from Chicago to Maui takes 9h 08m
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?

  • 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?

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
DeltaPriceFrom $355Free CancellationRating
7.9
8,015 reviews
Search Delta flights
Hawaiian AirlinesPriceFrom $357Free CancellationRating
7.8
2,820 reviews
Search Hawaiian Airlines flights
Alaska AirlinesPriceFrom $383Free CancellationRating
8.0
11,514 reviews
Search Alaska Airlines flights
American AirlinesPriceFrom $447Free CancellationRating
7.2
11,051 reviews
Search American Airlines flights
SouthwestPriceFrom $568Free CancellationRating
8.0
4,255 reviews
Search Southwest flights
United AirlinesPriceFrom $742Free CancellationRating
7.4
9,106 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.

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