What is the cheapest airline that flies from Kahului to Chicago Midway?

Southwest and Delta are the most popular carriers operating from Kahului to Chicago Midway

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.

$269 Cheap Flights from Kahului to Chicago Midway Airport in 2026/27

Find the cheapest flights from Kahului to Chicago

Round-trip

One-way

Cheap round-trip flights

Enter your travel dates to find the best prices.

8:45 pm - 1:25 pmOGG Kahului-MDW Chicago Midway

11h 40m1 stop Las Vegas Harry Reid Intl

5:10 am - 12:40 pmMDW Chicago Midway-OGG Kahului

12h 30m1 stop Las Vegas Harry Reid Intl

$538Southwest

Tue, Oct 13 - Mon, Oct 19

8:45 pm - 3:45 pmOGG Kahului-MDW Chicago Midway

14h 00m1 stop Las Vegas Harry Reid Intl

5:40 am - 2:50 pmMDW Chicago Midway-OGG Kahului

14h 10m2 stops Phoenix Sky Harbor Intl Honolulu

$610Southwest

Tue, Oct 13 - Mon, Oct 19

9:55 pm - 3:45 pmOGG Kahului-MDW Chicago Midway

12h 50m2 stops San Diego Phoenix Sky Harbor Intl

5:40 am - 2:50 pmMDW Chicago Midway-OGG Kahului

14h 10m2 stops Phoenix Sky Harbor Intl Honolulu

$703Southwest

Tue, Oct 13 - Mon, Oct 19

8:45 pm - 1:25 pmOGG Kahului-MDW Chicago Midway

11h 40m1 stop Las Vegas Harry Reid Intl

5:25 am - 2:00 pmMDW Chicago Midway-OGG Kahului

13h 35m1 stop San Diego

$833Southwest

Mon, Oct 5 - Fri, Oct 9

8:45 pm - 1:25 pmOGG Kahului-MDW Chicago Midway

11h 40m1 stop Las Vegas Harry Reid Intl

5:15 am - 2:00 pmMDW Chicago Midway-OGG Kahului

13h 45m2 stops Dallas Love Field San Diego

$839Southwest

Mon, Oct 5 - Fri, Oct 9

8:45 pm - 2:05 pmOGG Kahului-MDW Chicago Midway

12h 20m2 stops Las Vegas Harry Reid Intl Denver Intl

5:15 am - 2:00 pmMDW Chicago Midway-OGG Kahului

13h 45m2 stops Dallas Love Field San Diego

$844Southwest

Mon, Oct 5 - Fri, Oct 9

8:45 pm - 2:05 pmOGG Kahului-MDW Chicago Midway

12h 20m2 stops Las Vegas Harry Reid Intl Denver Intl

5:25 am - 2:00 pmMDW Chicago Midway-OGG Kahului

13h 35m1 stop San Diego

$871Southwest

Mon, Oct 5 - Fri, Oct 9

8:15 pm - 2:30 pmOGG Kahului-MDW Chicago Midway

14h 15m1 stop Phoenix Sky Harbor Intl

10:55 pm - 12:55 pmMDW Chicago Midway-OGG Kahului

18h 00m1 stop Phoenix Sky Harbor Intl

$976Southwest

Thu, Dec 17 - Mon, Dec 28

9:25 pm - 1:10 pmOGG Kahului-MDW Chicago Midway

11h 45m1 stop Las Vegas Harry Reid Intl

5:50 am - 4:10 pmMDW Chicago Midway-OGG Kahului

14h 20m2 stops Las Vegas Harry Reid Intl Oakland

$982Southwest

Thu, Dec 17 - Mon, Dec 28

9:25 pm - 2:30 pmOGG Kahului-MDW Chicago Midway

13h 05m2 stops Las Vegas Harry Reid Intl Phoenix Sky Harbor Intl

5:50 am - 4:10 pmMDW Chicago Midway-OGG Kahului

14h 20m2 stops Las Vegas Harry Reid Intl Oakland

$1,016Southwest

Thu, Dec 17 - Mon, Dec 28

Save money when you book flights with momondo

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Not ready to book? to track prices.

Search flight deals

Southwest flights from Kahului to Chicago Midway Airport

Our best Southwest deals on Kahului to Chicago Midway Airport flight tickets

Southwest

Oct 13

OGG8:45 pmKahului

11h 40m

1 stop

MDW1:25 pmChicago Midway

Oct 19

MDW5:10 amChicago Midway

12h 30m

1 stop

OGG12:40 pmKahului

$538

Southwest

Oct 13

OGG8:45 pmKahului

14h 00m

1 stop

MDW3:45 pmChicago Midway

Oct 19

MDW5:40 amChicago Midway

14h 10m

2 stops

OGG2:50 pmKahului

$610

Southwest

Oct 13

OGG9:55 pmKahului

12h 50m

2 stops

MDW3:45 pmChicago Midway

Oct 19

MDW5:40 amChicago Midway

14h 10m

2 stops

OGG2:50 pmKahului

$703

momondo Fare Finder

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

Quickest round-trip

KahuluiChicago

OGG Kahului - MDW Chicago Midway

OGGMDW

Kahului

Tue 10/13

8:45 pm-1:25 pm

1 stop11h 40m

Chicago Midway

Mon 10/19

5:10 am-12:40 pm

1 stop12h 30m

$538

KahuluiChicago

OGG Kahului - MDW Chicago Midway

OGGMDW

Kahului

Tue 10/13

8:45 pm-3:45 pm

1 stop14h 00m

Chicago Midway

Mon 10/19

5:40 am-2:50 pm

2 stops14h 10m

$610

KahuluiChicago

OGG Kahului - MDW Chicago Midway

OGGMDW

Kahului

Tue 10/13

9:55 pm-3:45 pm

2 stops12h 50m

Chicago Midway

Mon 10/19

5:40 am-2:50 pm

2 stops14h 10m

$703

KahuluiChicago

OGG Kahului - MDW Chicago Midway

OGGMDW

Kahului

Mon 10/5

8:45 pm-1:25 pm

1 stop11h 40m

Chicago Midway

Fri 10/9

5:25 am-2:00 pm

1 stop13h 35m

$833

KahuluiChicago

OGG Kahului - MDW Chicago Midway

OGGMDW

Kahului

Mon 10/5

8:45 pm-1:25 pm

1 stop11h 40m

Chicago Midway

Fri 10/9

5:15 am-2:00 pm

2 stops13h 45m

$839

KahuluiChicago

OGG Kahului - MDW Chicago Midway

OGGMDW

Kahului

Mon 10/5

8:45 pm-2:05 pm

2 stops12h 20m

Chicago Midway

Fri 10/9

5:15 am-2:00 pm

2 stops13h 45m

$844

KahuluiChicago

OGG Kahului - MDW Chicago Midway

OGGMDW

Kahului

Mon 10/5

8:45 pm-2:05 pm

2 stops12h 20m

Chicago Midway

Fri 10/9

5:25 am-2:00 pm

1 stop13h 35m

$871

KahuluiChicago

OGG Kahului - MDW Chicago Midway

OGGMDW

Kahului

Thu 12/17

8:15 pm-2:30 pm

1 stop14h 15m

Chicago Midway

Mon 12/28

10:55 pm-12:55 pm

1 stop18h 00m

$976

KahuluiChicago

OGG Kahului - MDW Chicago Midway

OGGMDW

Kahului

Thu 12/17

9:25 pm-1:10 pm

1 stop11h 45m

Chicago Midway

Mon 12/28

5:50 am-4:10 pm

2 stops14h 20m

$982

KahuluiChicago

OGG Kahului - MDW Chicago Midway

OGGMDW

Kahului

Thu 12/17

9:25 pm-2:30 pm

2 stops13h 05m

Chicago Midway

Mon 12/28

5:50 am-4:10 pm

2 stops14h 20m

$1,016

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

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

Prices

Airlines

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

You could potentially save up to 7% 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	$269
Fastest flight time	11h 40m
Direct flights	None

The best one-way flight to Chicago Midway Airport from Kahului in the past 72 hours is $269. The best round-trip flight deal from Kahului to Chicago Midway Airport found on momondo in the last 72 hours is $538.

The fastest flight from Kahului to Chicago Midway Airport takes 11h 40m

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. 11h 40m 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.

Merrillville

New Buffalo

Hammond

Portage

Benton Harbor

Lansing

Saint Joseph

Valparaiso

Schererville

Munster

Chesterton

Monticello

Crown Point

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.