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Cheap flights from Kahului to Chicago from $247

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Kahului to Chicago departing on 9/15. 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
1 adult, Economy, 0 bags

Find the cheapest flights from Kahului to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
8:55 pm - 12:55 pm
OGG
-
MDW
11h 00m
1 stop
Southwest Logo
6:50 am - 4:10 pm
MDW
-
OGG
14h 20m
2 stops
$590Southwest
Mon, Aug 17 - Wed, Aug 19
Southwest Logo
8:55 pm - 12:55 pm
OGG
-
MDW
11h 00m
1 stop
Southwest Logo
10:15 am - 4:10 pm
MDW
-
OGG
10h 55m
1 stop
$614Southwest
Mon, Aug 17 - Wed, Aug 19
Southwest Logo
8:55 pm - 2:45 pm
OGG
-
MDW
12h 50m
2 stops
Southwest Logo
6:50 am - 4:10 pm
MDW
-
OGG
14h 20m
2 stops
$625Southwest
Mon, Aug 17 - Wed, Aug 19
Southwest Logo
8:35 pm - 12:05 pm
OGG
-
MDW
10h 30m
1 stop
Southwest Logo
5:25 am - 12:35 pm
MDW
-
OGG
12h 10m
1 stop
$660Southwest
Thu, Aug 6 - Sun, Aug 16
Southwest Logo
8:35 pm - 12:05 pm
OGG
-
MDW
10h 30m
1 stop
Southwest Logo
5:25 am - 1:45 pm
MDW
-
OGG
13h 20m
2 stops
$676Southwest
Thu, Aug 6 - Sun, Aug 16
Southwest Logo
8:35 pm - 11:45 am
OGG
-
MDW
10h 10m
1 stop
Southwest Logo
5:30 am - 4:10 pm
MDW
-
OGG
15h 40m
2 stops
$725Southwest
Wed, Jul 22 - Tue, Jul 28
Southwest Logo
8:35 pm - 11:45 am
OGG
-
MDW
10h 10m
1 stop
Southwest Logo
10:00 am - 4:10 pm
MDW
-
OGG
11h 10m
1 stop
$760Southwest
Wed, Jul 22 - Tue, Jul 28
Southwest Logo
6:00 am - 12:25 am
OGG
-
MDW
13h 25m
2 stops
Southwest Logo
5:25 am - 1:45 pm
MDW
-
OGG
13h 20m
2 stops
$791Southwest
Thu, Aug 6 - Sun, Aug 16
Southwest Logo
8:25 pm - 11:20 am
OGG
-
MDW
9h 55m
1 stop
Southwest Logo
8:00 am - 4:10 pm
MDW
-
OGG
13h 10m
2 stops
$806Southwest
Tue, Jul 7 - Sat, Jul 11
Southwest Logo
8:35 pm - 1:25 pm
OGG
-
MDW
11h 50m
1 stop
Southwest Logo
5:10 am - 12:40 pm
MDW
-
OGG
12h 30m
1 stop
$810Southwest
Tue, Jul 7 - Sat, Jul 11

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Delta flights from Kahului to Chicago Midway Airport

Our best Delta deals on Kahului to Chicago Midway Airport flight tickets
Delta
Oct 18
OGG12:45 pmKahului
15h 00m
2 stops
MDW8:45 amChicago Midway
Oct 24
MDW6:00 amChicago Midway
16h 46m
2 stops
OGG5:46 pmKahului
$1,018
Delta
Jul 5
OGG9:50 pmKahului
15h 41m
2 stops
MDW6:31 pmChicago Midway
Jul 11
MDW9:19 amChicago Midway
15h 15m
2 stops
OGG7:34 pmKahului
$4,200

Southwest flights from Kahului to Chicago Midway Airport

Our best Southwest deals on Kahului to Chicago Midway Airport flight tickets
Southwest
Aug 17
OGG8:55 pmKahului
11h 00m
1 stop
MDW12:55 pmChicago Midway
Aug 19
MDW6:50 amChicago Midway
14h 20m
2 stops
OGG4:10 pmKahului
$590
Southwest
Aug 17
OGG8:55 pmKahului
11h 00m
1 stop
MDW12:55 pmChicago Midway
Aug 19
MDW10:15 amChicago Midway
10h 55m
1 stop
OGG4:10 pmKahului
$614
Southwest
Aug 17
OGG8:55 pmKahului
12h 50m
2 stops
MDW2:45 pmChicago Midway
Aug 19
MDW6:50 amChicago Midway
14h 20m
2 stops
OGG4:10 pmKahului
$625

momondo Fare Finder

 
Customize your flight search to find flights from Kahului to Chicago Midway Airport 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 June 23, 2026.
Use the filters below to find and compare flights from Kahului to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Mon 8/17

8:55 pm-12:55 pm

1 stop11h 00m

Chicago Midway

Wed 8/19

6:50 am-4:10 pm

2 stops14h 20m

$590

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Mon 8/17

8:55 pm-12:55 pm

1 stop11h 00m

Chicago Midway

Wed 8/19

10:15 am-4:10 pm

1 stop10h 55m

$614

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Mon 8/17

8:55 pm-2:45 pm

2 stops12h 50m

Chicago Midway

Wed 8/19

6:50 am-4:10 pm

2 stops14h 20m

$625

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Thu 8/6

8:35 pm-12:05 pm

1 stop10h 30m

Chicago Midway

Sun 8/16

5:25 am-12:35 pm

1 stop12h 10m

$660

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Thu 8/6

8:35 pm-12:05 pm

1 stop10h 30m

Chicago Midway

Sun 8/16

5:25 am-1:45 pm

2 stops13h 20m

$676

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Wed 7/22

8:35 pm-11:45 am

1 stop10h 10m

Chicago Midway

Tue 7/28

5:30 am-4:10 pm

2 stops15h 40m

$725
Quickest round-trip

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Wed 7/22

8:35 pm-11:45 am

1 stop10h 10m

Chicago Midway

Tue 7/28

10:00 am-4:10 pm

1 stop11h 10m

$760

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Thu 8/6

6:00 am-12:25 am

2 stops13h 25m

Chicago Midway

Sun 8/16

5:25 am-1:45 pm

2 stops13h 20m

$791

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Tue 7/7

8:25 pm-11:20 am

1 stop9h 55m

Chicago Midway

Sat 7/11

8:00 am-4:10 pm

2 stops13h 10m

$806

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Tue 7/7

8:35 pm-1:25 pm

1 stop11h 50m

Chicago Midway

Sat 7/11

5:10 am-12:40 pm

1 stop12h 30m

$810

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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2

See travel insights to Chicago from

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

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

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

You could potentially save up to 4% on your flight if you consider stops on a Kahului to Chicago Midway Airport flight.

When to book flights from Kahului to Chicago Midway Airport

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

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

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

Fastest flight time

9h 55m

Direct flights

None
The fastest flight from Kahului to Chicago Midway Airport takes 9h 55m
There are no direct flights from Kahului to Chicago Midway Airport. There are no popular flight routes from Kahului to Chicago Midway Airport.
Search flight deals

Frequently asked questions about flying from Kahului to Chicago Midway Airport

  • How far is Kahului to Chicago Midway by plane?

    The straight-line distance from Kahului to Chicago Midway is 4186.6 mi. 9h 55m is a normal flight duration for this route.

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

    Prices for flights from Kahului Airport to Chicago Midway Airport are refreshed on a daily basis.

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

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Kahului Airport to Chicago Midway Airport.

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

    The required travel and health documents for your Chicago Midway Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago Midway Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Portage
Benton Harbor
Saint Joseph
Lansing
Valparaiso
Schererville
Munster
Crown Point
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

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

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Kahului.

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

Flights from Kahului to Chicago 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 Kahului to Chicago?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Kahului.

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

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Kahului and alert you when they change.

An easier way to manage your Chicago Midway Airport trip

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