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

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

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

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

How many operators does momondo search for flights from Chicago Midway Airport to Maui?

As of April 2026, there is 1 operator available to choose from for flights from Chicago Midway Airport to Maui.

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

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 Chicago Midway Airport to Maui.

What documentation or ID do you need to fly to Maui?

The travel and health documents you'll need for your trip to Maui 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 Maui. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

$241 Cheap Flights from Chicago Midway Airport to Maui in 2026

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Find the cheapest flights from Chicago Midway Airport to Maui

Round-trip

One-way

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

5:25 am - 2:10 pm

MDW

OGG

13h 45m

1 stop

8:35 pm - 1:10 pm

OGG

MDW

11h 35m

1 stop

$497Southwest

Thu, May 7 - Thu, May 14

6:40 am - 12:35 pm

MDW

OGG

10h 55m

1 stop

12:40 pm - 5:00 am

OGG

MDW

11h 20m

1 stop

$500Southwest

Mon, Apr 20 - Sat, Apr 25

6:10 am - 2:10 pm

MDW

OGG

13h 00m

1 stop

8:55 pm - 1:05 pm

OGG

MDW

11h 10m

1 stop

$503Southwest

Wed, Apr 22 - Wed, Apr 29

9:27 am - 7:32 pm

MDW

OGG

15h 05m

2 stops

12:30 pm - 8:46 am

OGG

MDW

15h 16m

2 stops

$505Delta

Wed, Apr 22 - Wed, Apr 29

9:27 am - 7:32 pm

MDW

OGG

15h 05m

2 stops

12:30 pm - 8:46 am

OGG

MDW

15h 16m

2 stops

$508Delta

Wed, Apr 22 - Wed, Apr 29

6:00 am - 7:32 pm

MDW

OGG

18h 32m

2 stops

12:55 pm - 8:42 am

OGG

MDW

14h 47m

2 stops

$509Delta

Thu, Apr 30 - Thu, May 7

6:40 am - 12:35 pm

MDW

OGG

10h 55m

1 stop

8:25 pm - 12:15 pm

OGG

MDW

10h 50m

1 stop

$512Southwest

Fri, Apr 24 - Fri, Apr 24

6:55 am - 4:05 pm

MDW

OGG

14h 10m

2 stops

8:25 pm - 2:20 pm

OGG

MDW

12h 55m

2 stops

$514Southwest

Mon, Apr 27 - Thu, Apr 30

6:40 am - 12:35 pm

MDW

OGG

10h 55m

1 stop

8:25 pm - 2:45 pm

OGG

MDW

13h 20m

2 stops

$518Southwest

Fri, Apr 24 - Fri, Apr 24

5:10 am - 1:10 pm

MDW

OGG

13h 00m

1 stop

8:35 pm - 4:15 pm

OGG

MDW

14h 40m

1 stop

$525Southwest

Thu, Apr 30 - Thu, May 7

Delta flights from Chicago Midway Airport to Maui

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

Delta

Apr 22

MDW9:27 amChicago Midway

15h 05m

2 stops

OGG7:32 pmKahului

Apr 29

OGG12:30 pmKahului

15h 16m

2 stops

MDW8:46 amChicago Midway

$505

Delta

Apr 22

MDW9:27 amChicago Midway

15h 05m

2 stops

OGG7:32 pmKahului

Apr 29

OGG12:30 pmKahului

15h 16m

2 stops

MDW8:46 amChicago Midway

$508

Delta

Apr 30

MDW6:00 amChicago Midway

18h 32m

2 stops

OGG7:32 pmKahului

May 7

OGG12:55 pmKahului

14h 47m

2 stops

MDW8:42 amChicago Midway

$509

Southwest flights from Chicago Midway Airport to Maui

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

Southwest

May 7

MDW5:25 amChicago Midway

13h 45m

1 stop

OGG2:10 pmKahului

May 14

OGG8:35 pmKahului

11h 35m

1 stop

MDW1:10 pmChicago Midway

$497

Southwest

Apr 20

MDW6:40 amChicago Midway

10h 55m

1 stop

OGG12:35 pmKahului

Apr 25

OGG12:40 pmKahului

11h 20m

1 stop

MDW5:00 amChicago Midway

$500

Southwest

Apr 22

MDW6:10 amChicago Midway

13h 00m

1 stop

OGG2:10 pmKahului

Apr 29

OGG8:55 pmKahului

11h 10m

1 stop

MDW1:05 pmChicago Midway

$503

momondo Fare Finder

Use the filters below to find and compare flights from Chicago Midway Airport to Maui that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Thu 5/7

5:25 am-2:10 pm

1 stop13h 45m

Kahului

Thu 5/14

8:35 pm-1:10 pm

1 stop11h 35m

$497

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Mon 4/20

6:40 am-12:35 pm

1 stop10h 55m

Kahului

Sat 4/25

12:40 pm-5:00 am

1 stop11h 20m

$500

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Wed 4/22

6:10 am-2:10 pm

1 stop13h 00m

Kahului

Wed 4/29

8:55 pm-1:05 pm

1 stop11h 10m

$503

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Wed 4/22

9:27 am-7:32 pm

2 stops15h 05m

Kahului

Wed 4/29

12:30 pm-8:46 am

2 stops15h 16m

$505

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Wed 4/22

9:27 am-7:32 pm

2 stops15h 05m

Kahului

Wed 4/29

12:30 pm-8:46 am

2 stops15h 16m

$508

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Thu 4/30

6:00 am-7:32 pm

2 stops18h 32m

Kahului

Thu 5/7

12:55 pm-8:42 am

2 stops14h 47m

$509

Quickest round-trip

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Fri 4/24

6:40 am-12:35 pm

1 stop10h 55m

Kahului

Fri 4/24

8:25 pm-12:15 pm

1 stop10h 50m

$512

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Mon 4/27

6:55 am-4:05 pm

2 stops14h 10m

Kahului

Thu 4/30

8:25 pm-2:20 pm

2 stops12h 55m

$514

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Fri 4/24

6:40 am-12:35 pm

1 stop10h 55m

Kahului

Fri 4/24

8:25 pm-2:45 pm

2 stops13h 20m

$518

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Thu 4/30

5:10 am-1:10 pm

1 stop13h 00m

Kahului

Thu 5/7

8:35 pm-4:15 pm

1 stop14h 40m

$525

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 Chicago Midway Airport to Maui

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 Chicago Midway Airport to Maui flights?

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

Cheap Chicago Midway Airport to Maui flight deals and tips

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

Fastest flight time	10h 50m
Direct flights	None

The fastest flight from Chicago Midway Airport to Maui takes 10h 50m

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

Search flight deals

When did momondo last update prices for flights from Chicago Midway Airport to Maui?
Prices for flights from Chicago Midway Airport to Maui are refreshed on a daily basis.
How many operators does momondo search for flights from Chicago Midway Airport to Maui?
As of April 2026, there is 1 operator available to choose from for flights from Chicago Midway Airport to Maui.
How old do you have to be to fly from Chicago Midway Airport to Maui?
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 Chicago Midway Airport to Maui.
What documentation or ID do you need to fly to Maui?
The travel and health documents you'll need for your trip to Maui 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 Maui. 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 Chicago Midway Airport to Maui?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Chicago Midway Airport to Maui is Boeing 737 MAX 8 (16.06% of total bookings). The next most popular plane models are Boeing 737-800 Passenger/BBJ2 (winglets) (12.42%), Airbus A320neo (11.34%), and Airbus A321neo (11.01%).

Best airlines flying from Chicago Midway Airport to Maui

Compare and see reviews for airlines that fly from Chicago Midway Airport to Maui with momondo

Airline	Rating	Free Cancellation	Price
Southwest	PriceFrom $630	Free Cancellation	Rating 8.0 4,335 reviews		Search Southwest flights

Why use momondo?

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

It is quick and easy to find Chicago to Maui flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Maui that suits you.

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

momondo does allow users to show only those flights to Maui from Chicago which offer a flexible booking policy as well as other useful filters and features.

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

Once you have performed a search for Chicago to Maui flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

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

Yes momondo offers price alerts on flights to Maui from Chicago. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.