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Cheap flights from Chicago Midway Airport to Kahului from $250

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 Midway Airport to Kahului departing on 2/7. 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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Find the cheapest flights from Chicago Midway Airport to Kahului

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
6:00 am - 3:24 pmMDW-OGG
13h 24m1 stop
Delta Logo
10:00 pm - 6:18 pmOGG-MDW
16h 18m2 stops
$437Delta
Find Deal
Thu, Dec 4 - Thu, Dec 11
Delta Logo
6:00 am - 8:18 pmMDW-OGG
18h 18m2 stops
Delta Logo
5:10 pm - 9:54 amOGG-MDW
12h 44m1 stop
$438Delta
Find Deal
Wed, Dec 10 - Mon, Dec 15
Delta Logo
6:00 am - 7:26 pmMDW-OGG
17h 26m2 stops
Delta Logo
10:00 pm - 4:31 pmOGG-MDW
14h 31m2 stops
$443Delta
Find Deal
Thu, Jan 1 - Thu, Jan 8
Delta Logo
6:00 am - 3:24 pmMDW-OGG
13h 24m1 stop
Delta Logo
5:10 pm - 9:54 amOGG-MDW
12h 44m1 stop
$461Delta
Find Deal
Thu, Dec 4 - Mon, Dec 15
Delta Logo
6:45 am - 3:37 pmMDW-OGG
12h 52m1 stop
Delta Logo
5:10 pm - 1:09 pmOGG-MDW
15h 59m2 stops
$466Delta
Find Deal
Thu, Jan 8 - Thu, Jan 15
Delta Logo
6:00 am - 3:24 pmMDW-OGG
13h 24m1 stop
Delta Logo
10:00 pm - 6:18 pmOGG-MDW
16h 18m2 stops
$468Delta
Find Deal
Sat, Dec 6 - Thu, Dec 11
Delta Logo
6:00 am - 3:24 pmMDW-OGG
13h 24m1 stop
Delta Logo
10:00 pm - 6:18 pmOGG-MDW
16h 18m2 stops
$469Delta
Find Deal
Fri, Dec 5 - Tue, Dec 9
Delta Logo
6:00 am - 8:18 pmMDW-OGG
18h 18m2 stops
Delta Logo
5:10 pm - 9:54 amOGG-MDW
12h 44m1 stop
$470Delta
Find Deal
Wed, Dec 10 - Sun, Dec 14
Southwest Logo
5:25 am - 1:05 pmMDW-OGG
11h 40m1 stop
Southwest Logo
9:35 pm - 11:35 amOGG-MDW
10h 00m1 stop
$552Southwest
Find Deal
Wed, Dec 10 - Mon, Dec 15
Southwest Logo
5:15 am - 4:35 pmMDW-OGG
15h 20m2 stops
Southwest Logo
10:00 am - 5:05 amOGG-MDW
15h 05m2 stops
$563Southwest
Find Deal
Tue, Dec 16 - Sun, Dec 21

Delta flights from Chicago Midway Airport to Kahului

Our best Delta deals on Chicago Midway Airport to Kahului flight tickets
Delta
Dec 4
MDW6:00 amChicago Midway
13h 24m
1 stop
OGG3:24 pmKahului
Dec 11
OGG10:00 pmKahului
16h 18m
2 stops
MDW6:18 pmChicago Midway
$437
Find similar
Delta
Dec 10
MDW6:00 amChicago Midway
18h 18m
2 stops
OGG8:18 pmKahului
Dec 15
OGG5:10 pmKahului
12h 44m
1 stop
MDW9:54 amChicago Midway
$438
Find similar
Delta
Jan 1
MDW6:00 amChicago Midway
17h 26m
2 stops
OGG7:26 pmKahului
Jan 8
OGG10:00 pmKahului
14h 31m
2 stops
MDW4:31 pmChicago Midway
$443
Find similar

Southwest flights from Chicago Midway Airport to Kahului

Our best Southwest deals on Chicago Midway Airport to Kahului flight tickets
Southwest
Dec 10
MDW5:25 amChicago Midway
11h 40m
1 stop
OGG1:05 pmKahului
Dec 15
OGG9:35 pmKahului
10h 00m
1 stop
MDW11:35 amChicago Midway
$552
Find similar
Southwest
Dec 16
MDW5:15 amChicago Midway
15h 20m
2 stops
OGG4:35 pmKahului
Dec 21
OGG10:00 amKahului
15h 05m
2 stops
MDW5:05 amChicago Midway
$563
Find similar
Southwest
Jan 29
MDW5:05 amChicago Midway
17h 05m
2 stops
OGG6:10 pmKahului
Feb 5
OGG7:00 pmKahului
13h 10m
2 stops
MDW12:10 pmChicago Midway
$609
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to Kahului 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 November 10, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Kahului that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Thu 12/4

6:00 am-3:24 pm

1 stop13h 24m

Kahului

Thu 12/11

10:00 pm-6:18 pm

2 stops16h 18m

$437

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Wed 12/10

6:00 am-8:18 pm

2 stops18h 18m

Kahului

Mon 12/15

5:10 pm-9:54 am

1 stop12h 44m

$438

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Thu 1/1

6:00 am-7:26 pm

2 stops17h 26m

Kahului

Thu 1/8

10:00 pm-4:31 pm

2 stops14h 31m

$443

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Thu 12/4

6:00 am-3:24 pm

1 stop13h 24m

Kahului

Mon 12/15

5:10 pm-9:54 am

1 stop12h 44m

$461

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Thu 1/8

6:45 am-3:37 pm

1 stop12h 52m

Kahului

Thu 1/15

5:10 pm-1:09 pm

2 stops15h 59m

$466

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Sat 12/6

6:00 am-3:24 pm

1 stop13h 24m

Kahului

Thu 12/11

10:00 pm-6:18 pm

2 stops16h 18m

$468

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Fri 12/5

6:00 am-3:24 pm

1 stop13h 24m

Kahului

Tue 12/9

10:00 pm-6:18 pm

2 stops16h 18m

$469

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Wed 12/10

6:00 am-8:18 pm

2 stops18h 18m

Kahului

Sun 12/14

5:10 pm-9:54 am

1 stop12h 44m

$470

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Wed 12/10

5:25 am-1:05 pm

1 stop11h 40m

Kahului

Mon 12/15

9:35 pm-11:35 am

1 stop10h 00m

$552

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Tue 12/16

5:15 am-4:35 pm

2 stops15h 20m

Kahului

Sun 12/21

10:00 am-5:05 am

2 stops15h 05m

$563

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 Kahului from

How to get the cheapest flight ticket from Chicago Midway Airport to Kahului

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 day to depart on your flight to Kahului?

Our data shows that Monday is the least expensive day to fly to Kahului. Tickets to fly out on this day can be as low as $1,033. When flying out on a Friday, the most expensive travel day of the week, you can expect to see flight prices from Chicago Midway Airport to Kahului for around $1,202.

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

Our data shows that the cheapest Chicago Midway Airport to Kahului flights are usually those with departure times in the afternoon. Our users have found flights to Kahului in the afternoon for as low as $543. Flights in the morning are often more expensive with an average ticket price of $1,094.

Can stopping save me money on Chicago Midway Airport to Kahului flights?

You could potentially save up to 7% on your flight if you consider stops on a Chicago Midway Airport to Kahului flight.

When to book flights from Chicago Midway Airport to Kahului

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport to Kahului according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago Midway Airport to Kahului (MDW to OGG) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Kahului

Direct flights

None
There are no direct flights from Chicago Midway Airport to Kahului. There are no popular flight routes from Chicago Midway Airport to Kahului.
Search flight deals

  • How far is Chicago Midway to Kahului by plane?

    Kahului is 4186.6 mi away from Chicago Midway. Flights usually cover this in 11h 20m, depending on flying conditions and air traffic around both airports.

  • When did momondo last update prices for flights from Chicago Midway Airport to Kahului Airport?

    Prices for flights from Chicago Midway Airport to Kahului Airport refresh daily.

  • How many operators does momondo search for flights from Chicago Midway Airport to Kahului Airport?

  • How old do you have to be to fly from Chicago Midway Airport to Kahului Airport?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago Midway Airport to Kahului Airport.

  • What documentation or ID do you need to fly to Kahului Airport?

    The necessary travel and health documents for your Kahului Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular airline from Chicago Midway Airport to Kahului?

Best airlines flying from Chicago Midway Airport to Kahului

Compare and see reviews for airlines that fly from Chicago Midway Airport to Kahului with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $479Free CancellationRating
8.0
4,238 reviews
Search Southwest flights

Traveling to a place near Kahului?

Book flights to Kahului if you plan to visit one of these locations
Wailea
Paia

Why use momondo?

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

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Chicago to Kahului. Millions of users trust and use momondo every year so you are in good hands.

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

Yes. momondo allows you to filter the results for Chicago to Kahului flights to just show those with flexible booking policies.

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

Once you have performed a search for Chicago to Kahului flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

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

Yes. momondo can track prices for Chicago to Kahului flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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