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Cheap flights from Kahului to Chicago from $337

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 8/27. 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 Kahului to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
8:00 pm - 6:33 pm
OGG
-
MDW
17h 33m
2 stops
Delta Logo
9:23 am - 7:35 pm
MDW
-
OGG
15h 12m
2 stops
$700Delta
Thu, May 21 - Sun, May 24
Delta Logo
1:19 pm - 8:37 am
OGG
-
MDW
14h 18m
2 stops
Delta Logo
9:49 am - 7:34 pm
MDW
-
OGG
14h 45m
2 stops
$715Delta
Tue, Jul 7 - Mon, Jul 13
Southwest Logo
8:35 pm - 2:10 pm
OGG
-
MDW
12h 35m
1 stop
Southwest Logo
6:15 am - 12:35 pm
MDW
-
OGG
11h 20m
1 stop
$765Southwest
Tue, May 19 - Sat, May 23
Southwest Logo
8:35 pm - 2:15 pm
OGG
-
MDW
12h 40m
2 stops
Southwest Logo
6:15 am - 12:35 pm
MDW
-
OGG
11h 20m
1 stop
$771Southwest
Tue, May 19 - Sat, May 23
Southwest Logo
10:00 am - 6:00 am
OGG
-
MDW
15h 00m
1 stop
Southwest Logo
5:20 am - 12:40 pm
MDW
-
OGG
12h 20m
1 stop
$798Southwest
Tue, Jun 2 - Mon, Jun 8
Southwest Logo
11:50 am - 5:25 am
OGG
-
MDW
12h 35m
2 stops
Southwest Logo
5:25 am - 12:40 pm
MDW
-
OGG
12h 15m
1 stop
$806Southwest
Tue, Jun 16 - Tue, Jun 23
Southwest Logo
8:35 pm - 4:15 pm
OGG
-
MDW
14h 40m
1 stop
Southwest Logo
7:15 am - 2:05 pm
MDW
-
OGG
11h 50m
1 stop
$810Southwest
Thu, May 21 - Sun, May 24
Southwest Logo
8:35 pm - 4:15 pm
OGG
-
MDW
14h 40m
1 stop
Southwest Logo
7:10 am - 2:50 pm
MDW
-
OGG
12h 40m
2 stops
$816Southwest
Thu, May 21 - Sun, May 24
Southwest Logo
10:00 am - 6:00 am
OGG
-
MDW
15h 00m
1 stop
Southwest Logo
7:30 am - 4:10 pm
MDW
-
OGG
13h 40m
2 stops
$824Southwest
Tue, Jun 2 - Mon, Jun 8
Southwest Logo
11:50 am - 5:45 am
OGG
-
MDW
12h 55m
1 stop
Southwest Logo
5:25 am - 12:40 pm
MDW
-
OGG
12h 15m
1 stop
$845Southwest
Tue, Jun 16 - Tue, Jun 23

Delta flights from Kahului to Chicago Midway Airport

Our best Delta deals on Kahului to Chicago Midway Airport flight tickets
Delta
May 21
OGG8:00 pmKahului
17h 33m
2 stops
MDW6:33 pmChicago Midway
May 24
MDW9:23 amChicago Midway
15h 12m
2 stops
OGG7:35 pmKahului
$700
Delta
Jul 7
OGG1:19 pmKahului
14h 18m
2 stops
MDW8:37 amChicago Midway
Jul 13
MDW9:49 amChicago Midway
14h 45m
2 stops
OGG7:34 pmKahului
$715
Delta
May 19
OGG8:00 pmKahului
15h 12m
2 stops
MDW4:12 pmChicago Midway
May 23
MDW9:22 amChicago Midway
15h 13m
2 stops
OGG7:35 pmKahului
$980

Southwest flights from Kahului to Chicago Midway Airport

Our best Southwest deals on Kahului to Chicago Midway Airport flight tickets
Southwest
May 19
OGG8:35 pmKahului
12h 35m
1 stop
MDW2:10 pmChicago Midway
May 23
MDW6:15 amChicago Midway
11h 20m
1 stop
OGG12:35 pmKahului
$765
Southwest
May 19
OGG8:35 pmKahului
12h 40m
2 stops
MDW2:15 pmChicago Midway
May 23
MDW6:15 amChicago Midway
11h 20m
1 stop
OGG12:35 pmKahului
$771
Southwest
Jun 2
OGG10:00 amKahului
15h 00m
1 stop
MDW6:00 amChicago Midway
Jun 8
MDW5:20 amChicago Midway
12h 20m
1 stop
OGG12:40 pmKahului
$798

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 May 6, 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

Thu 5/21

8:00 pm-6:33 pm

2 stops17h 33m

Chicago Midway

Sun 5/24

9:23 am-7:35 pm

2 stops15h 12m

$700

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Tue 7/7

1:19 pm-8:37 am

2 stops14h 18m

Chicago Midway

Mon 7/13

9:49 am-7:34 pm

2 stops14h 45m

$715
Quickest round-trip

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Tue 5/19

8:35 pm-2:10 pm

1 stop12h 35m

Chicago Midway

Sat 5/23

6:15 am-12:35 pm

1 stop11h 20m

$765

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Tue 5/19

8:35 pm-2:15 pm

2 stops12h 40m

Chicago Midway

Sat 5/23

6:15 am-12:35 pm

1 stop11h 20m

$771

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Tue 6/2

10:00 am-6:00 am

1 stop15h 00m

Chicago Midway

Mon 6/8

5:20 am-12:40 pm

1 stop12h 20m

$798

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Tue 6/16

11:50 am-5:25 am

2 stops12h 35m

Chicago Midway

Tue 6/23

5:25 am-12:40 pm

1 stop12h 15m

$806

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Thu 5/21

8:35 pm-4:15 pm

1 stop14h 40m

Chicago Midway

Sun 5/24

7:15 am-2:05 pm

1 stop11h 50m

$810

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Thu 5/21

8:35 pm-4:15 pm

1 stop14h 40m

Chicago Midway

Sun 5/24

7:10 am-2:50 pm

2 stops12h 40m

$816

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Tue 6/2

10:00 am-6:00 am

1 stop15h 00m

Chicago Midway

Mon 6/8

7:30 am-4:10 pm

2 stops13h 40m

$824

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Tue 6/16

11:50 am-5:45 am

1 stop12h 55m

Chicago Midway

Tue 6/23

5:25 am-12:40 pm

1 stop12h 15m

$845

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 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 10% 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

12h 35m

Direct flights

None
The fastest flight from Kahului to Chicago Midway Airport takes 12h 35m
There are no direct flights from Kahului to Chicago Midway Airport. There are no popular flight routes from Kahului to Chicago Midway Airport.
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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. 12h 35m 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
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Munster
Schererville
Crown Point
Monticello
Chesterton
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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