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

Southwest is the most popular carrier operating from Maui to Chicago Midway

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

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

How old do you have to be to fly from Maui 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 Maui to Chicago Midway Airport.

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

The travel and health documents you'll need for your trip to Chicago Midway Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago Midway Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

$235 Cheap Flights from Maui to Chicago Midway Airport in 2026

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Find the cheapest flights from Maui to Chicago

Round-trip

One-way

Cheap round-trip flights

Enter your travel dates to find the best prices.

8:55 pm - 2:30 pm

OGG

MDW

12h 35m

1 stop

5:25 am - 2:10 pm

MDW

OGG

13h 45m

1 stop

$503Southwest

lun., abr. 27 - lun., may. 4

8:55 pm - 2:30 pm

OGG

MDW

12h 35m

1 stop

6:00 am - 2:10 pm

MDW

OGG

13h 10m

2 stops

$509Southwest

lun., abr. 27 - lun., may. 4

8:35 pm - 2:15 pm

OGG

MDW

12h 40m

2 stops

6:00 am - 2:10 pm

MDW

OGG

13h 10m

2 stops

$541Southwest

lun., abr. 27 - lun., may. 4

8:55 pm - 1:05 pm

OGG

MDW

11h 10m

1 stop

10:00 am - 4:05 pm

MDW

OGG

11h 05m

1 stop

$635Southwest

mié., abr. 15 - mié., abr. 22

8:25 pm - 12:45 pm

OGG

MDW

11h 20m

1 stop

7:55 am - 4:05 pm

MDW

OGG

13h 10m

2 stops

$641Southwest

mié., abr. 15 - mié., abr. 22

8:25 pm - 2:20 pm

OGG

MDW

12h 55m

2 stops

6:10 am - 2:50 pm

MDW

OGG

13h 40m

2 stops

$646Southwest

mié., abr. 15 - mié., abr. 22

10:30 pm - 5:58 pm

OGG

MDW

14h 28m

2 stops

6:00 am - 7:32 pm

MDW

OGG

18h 32m

2 stops

$677Delta

lun., abr. 27 - lun., may. 4

9:55 pm - 5:40 pm

OGG

MDW

14h 45m

1 stop

6:55 am - 4:35 pm

MDW

OGG

14h 40m

2 stops

$688Southwest

sáb., may. 9 - sáb., may. 16

8:35 pm - 4:15 pm

OGG

MDW

14h 40m

1 stop

9:55 am - 4:05 pm

MDW

OGG

11h 10m

1 stop

$734Southwest

mié., abr. 15 - dom., abr. 19

12:40 pm - 5:00 am

OGG

MDW

11h 20m

1 stop

6:55 am - 1:40 pm

MDW

OGG

11h 45m

1 stop

$737Southwest

sáb., may. 9 - sáb., may. 16

Southwest flights from Maui to Chicago Midway Airport

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

Southwest

Apr 27

OGG8:55 pmKahului

12h 35m

1 stop

MDW2:30 pmChicago Midway

May 4

MDW5:25 amChicago Midway

13h 45m

1 stop

OGG2:10 pmKahului

$503

Southwest

Apr 27

OGG8:55 pmKahului

12h 35m

1 stop

MDW2:30 pmChicago Midway

May 4

MDW6:00 amChicago Midway

13h 10m

2 stops

OGG2:10 pmKahului

$509

Southwest

Apr 27

OGG8:35 pmKahului

12h 40m

2 stops

MDW2:15 pmChicago Midway

May 4

MDW6:00 amChicago Midway

13h 10m

2 stops

OGG2:10 pmKahului

$541

Delta flights from Maui to Chicago Midway Airport

Our best Delta deals on Maui to Chicago Midway Airport flight tickets

Delta

May 11

OGG8:00 pmKahului

15h 12m

2 stops

MDW4:12 pmChicago Midway

May 14

MDW6:23 amChicago Midway

18h 12m

2 stops

OGG7:35 pmKahului

$607

Delta

Apr 27

OGG10:30 pmKahului

14h 28m

2 stops

MDW5:58 pmChicago Midway

May 4

MDW6:00 amChicago Midway

18h 32m

2 stops

OGG7:32 pmKahului

$677

Delta

Apr 27

OGG10:30 pmKahului

15h 06m

2 stops

MDW6:36 pmChicago Midway

May 4

MDW9:27 amChicago Midway

15h 05m

2 stops

OGG7:32 pmKahului

$1,686

momondo Fare Finder

Use the filters below to find and compare flights from Maui 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

lun. 4/27

8:55 pm-2:30 pm

1 stop12h 35m

Chicago Midway

lun. 5/4

5:25 am-2:10 pm

1 stop13h 45m

$503

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

lun. 4/27

8:55 pm-2:30 pm

1 stop12h 35m

Chicago Midway

lun. 5/4

6:00 am-2:10 pm

2 stops13h 10m

$509

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

lun. 4/27

8:35 pm-2:15 pm

2 stops12h 40m

Chicago Midway

lun. 5/4

6:00 am-2:10 pm

2 stops13h 10m

$541

Quickest round-trip

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

mié. 4/15

8:55 pm-1:05 pm

1 stop11h 10m

Chicago Midway

mié. 4/22

10:00 am-4:05 pm

1 stop11h 05m

$635

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

mié. 4/15

8:25 pm-12:45 pm

1 stop11h 20m

Chicago Midway

mié. 4/22

7:55 am-4:05 pm

2 stops13h 10m

$641

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

mié. 4/15

8:25 pm-2:20 pm

2 stops12h 55m

Chicago Midway

mié. 4/22

6:10 am-2:50 pm

2 stops13h 40m

$646

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

lun. 4/27

10:30 pm-5:58 pm

2 stops14h 28m

Chicago Midway

lun. 5/4

6:00 am-7:32 pm

2 stops18h 32m

$677

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

sáb. 5/9

9:55 pm-5:40 pm

1 stop14h 45m

Chicago Midway

sáb. 5/16

6:55 am-4:35 pm

2 stops14h 40m

$688

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

mié. 4/15

8:35 pm-4:15 pm

1 stop14h 40m

Chicago Midway

dom. 4/19

9:55 am-4:05 pm

1 stop11h 10m

$734

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

sáb. 5/9

12:40 pm-5:00 am

1 stop11h 20m

Chicago Midway

sáb. 5/16

6:55 am-1:40 pm

1 stop11h 45m

$737

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 Maui 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 Maui to Chicago Midway Airport flights?

No. A direct flight is the cheapest option for a flight between Maui to Chicago Midway Airport.

Cheap Maui to Chicago Midway Airport flight deals and tips

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

Fastest flight time	14h 28m
Direct flights	None

The fastest flight from Maui to Chicago Midway Airport takes 14h 28m

There are no direct flights from Maui to Chicago Midway Airport. There are no popular flight routes from Maui to Chicago Midway Airport.

Search flight deals

Frequently asked questions about flying from Maui to Chicago Midway Airport

When did momondo last update prices for flights from Maui to Chicago Midway Airport?
Prices for flights from Maui to Chicago Midway Airport refresh daily.
How old do you have to be to fly from Maui 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 Maui to Chicago Midway Airport.
What documentation or ID do you need to fly to Chicago Midway Airport?
The travel and health documents you'll need for your trip to Chicago Midway Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago Midway Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Maui to Chicago Midway Airport?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Maui to Chicago Midway Airport is Boeing 737 MAX 8 (18.82% of total bookings). The next most popular plane models are Boeing 737-800 (12.25%), Boeing 737-800 Passenger/BBJ2 (winglets) (11.52%), and Airbus A321neo (8.40%).

Merrillville

New Buffalo

Hammond

Saint Joseph

Benton Harbor

Portage

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 Maui 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 Maui.

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

Yes. All flights to Chicago from Maui on momondo can be compared and filtered by various policies on offer, including flexible booking.

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

Once all potential Maui to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

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

Of course. momondo tracks the price of Maui to Chicago flights. All you need is a valid email address and we will do the rest; it is that quick and easy.