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Cheap flights from Kahului to Chicago from $236

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 12/15. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Kahului to Chicago (OGG-MDW)

Cheap round-trip flights

Southwest Logo
8:25 pm - 2:30 pmOGG-MDW
13h 05m1 stop
Southwest Logo
6:10 am - 4:30 pmMDW-OGG
15h 20m2 stops
$506Southwest
Find Deal
Thu, Aug 28 - Tue, Sep 2
Southwest Logo
8:25 pm - 2:30 pmOGG-MDW
13h 05m1 stop
Southwest Logo
6:10 am - 12:25 pmMDW-OGG
11h 15m1 stop
$526Southwest
Find Deal
Thu, Aug 28 - Tue, Sep 2
Southwest Logo
8:30 pm - 2:40 pmOGG-MDW
13h 10m2 stops
Southwest Logo
6:10 am - 4:30 pmMDW-OGG
15h 20m2 stops
$566Southwest
Find Deal
Thu, Aug 28 - Tue, Sep 2
Delta Logo
9:10 pm - 5:37 pmOGG-MDW
15h 27m2 stops
Delta Logo
6:00 am - 5:08 pmMDW-OGG
16h 08m2 stops
$633Delta
Find Deal
Wed, Sep 3 - Wed, Sep 10
Southwest Logo
6:00 am - 11:25 pmOGG-MDW
12h 25m2 stops
Southwest Logo
6:10 am - 12:25 pmMDW-OGG
11h 15m1 stop
$698Southwest
Find Deal
Fri, Sep 5 - Tue, Sep 9
Southwest Logo
6:00 am - 11:25 pmOGG-MDW
12h 25m2 stops
Southwest Logo
7:50 am - 4:35 pmMDW-OGG
13h 45m2 stops
$704Southwest
Find Deal
Fri, Sep 5 - Tue, Sep 9
Southwest Logo
8:25 pm - 11:55 amOGG-MDW
10h 30m1 stop
Southwest Logo
6:40 am - 1:00 pmMDW-OGG
11h 20m1 stop
$728Southwest
Find Deal
Fri, Sep 5 - Tue, Sep 9
Southwest Logo
6:00 am - 11:05 pmOGG-MDW
12h 05m2 stops
Southwest Logo
8:20 am - 4:30 pmMDW-OGG
13h 10m1 stop
$833Southwest
Find Deal
Sat, Sep 27 - Sun, Sep 28
Southwest Logo
6:00 am - 11:05 pmOGG-MDW
12h 05m2 stops
Southwest Logo
8:20 am - 6:15 pmMDW-OGG
14h 55m2 stops
$839Southwest
Find Deal
Sat, Sep 27 - Sun, Sep 28
Delta Logo
11:40 am - 8:35 amOGG-MDW
15h 55m2 stops
Delta Logo
6:04 am - 5:21 pmMDW-OGG
16h 17m2 stops
$1,184Delta
Find Deal
Mon, Aug 18 - Fri, Aug 22

Delta flights from Kahului to Chicago Midway Airport

Our best Delta deals on Kahului to Chicago Midway Airport flight tickets
Delta
Sep 3
OGG9:10 pmKahului
15h 27m
2 stops
MDW5:37 pmChicago Midway
Sep 10
MDW6:00 amChicago Midway
16h 08m
2 stops
OGG5:08 pmKahului
$633
Find similar
Delta
Aug 18
OGG11:40 amKahului
15h 55m
2 stops
MDW8:35 amChicago Midway
Aug 22
MDW6:04 amChicago Midway
16h 17m
2 stops
OGG5:21 pmKahului
$1,184
Find similar
Delta
Sep 11
OGG9:07 pmKahului
15h 28m
2 stops
MDW5:35 pmChicago Midway
Sep 18
MDW6:00 amChicago Midway
16h 06m
2 stops
OGG5:06 pmKahului
$4,280
Find similar

Southwest flights from Kahului to Chicago Midway Airport

Our best Southwest deals on Kahului to Chicago Midway Airport flight tickets
Southwest
Aug 28
OGG8:25 pmKahului
13h 05m
1 stop
MDW2:30 pmChicago Midway
Sep 2
MDW6:10 amChicago Midway
15h 20m
2 stops
OGG4:30 pmKahului
$506
Find similar
Southwest
Aug 28
OGG8:25 pmKahului
13h 05m
1 stop
MDW2:30 pmChicago Midway
Sep 2
MDW6:10 amChicago Midway
11h 15m
1 stop
OGG12:25 pmKahului
$526
Find similar
Southwest
Aug 28
OGG8:30 pmKahului
13h 10m
2 stops
MDW2:40 pmChicago Midway
Sep 2
MDW6:10 amChicago Midway
15h 20m
2 stops
OGG4:30 pmKahului
$566
Find similar

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 August 4, 2025.
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

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Thu 8/28

8:25 pm-2:30 pm

1 stop13h 05m

Chicago Midway

Tue 9/2

6:10 am-4:30 pm

2 stops15h 20m

$506

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Thu 8/28

8:25 pm-2:30 pm

1 stop13h 05m

Chicago Midway

Tue 9/2

6:10 am-12:25 pm

1 stop11h 15m

$526

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Thu 8/28

8:30 pm-2:40 pm

2 stops13h 10m

Chicago Midway

Tue 9/2

6:10 am-4:30 pm

2 stops15h 20m

$566

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Wed 9/3

9:10 pm-5:37 pm

2 stops15h 27m

Chicago Midway

Wed 9/10

6:00 am-5:08 pm

2 stops16h 08m

$633

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Fri 9/5

6:00 am-11:25 pm

2 stops12h 25m

Chicago Midway

Tue 9/9

6:10 am-12:25 pm

1 stop11h 15m

$698

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Fri 9/5

6:00 am-11:25 pm

2 stops12h 25m

Chicago Midway

Tue 9/9

7:50 am-4:35 pm

2 stops13h 45m

$704

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Fri 9/5

8:25 pm-11:55 am

1 stop10h 30m

Chicago Midway

Tue 9/9

6:40 am-1:00 pm

1 stop11h 20m

$728

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Sat 9/27

6:00 am-11:05 pm

2 stops12h 05m

Chicago Midway

Sun 9/28

8:20 am-4:30 pm

1 stop13h 10m

$833

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Sat 9/27

6:00 am-11:05 pm

2 stops12h 05m

Chicago Midway

Sun 9/28

8:20 am-6:15 pm

2 stops14h 55m

$839

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Mon 8/18

11:40 am-8:35 am

2 stops15h 55m

Chicago Midway

Fri 8/22

6:04 am-5:21 pm

2 stops16h 17m

$1,184

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 9% 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

Best Price Found

$236

Fastest flight time

10h 20m

Direct flights

None
The best one-way flight to Chicago Midway Airport from Kahului in the past 72 hours is $236. The best round-trip flight deal from Kahului to Chicago Midway Airport found on momondo in the last 72 hours is $506.
The fastest flight from Kahului to Chicago Midway Airport takes 10h 20m
There are no direct flights from Kahului to Chicago Midway Airport. Popular non-direct route for this connection is Kahului Airport - Chicago Midway Airport.
Search flight deals

  • How far is Kahului to Chicago Midway by plane?

    The straight-line distance from Kahului to Chicago Midway is 4186.6 mi. 10h 30m 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
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Crown Point
Munster
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.

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