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

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

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

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

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

As of May 2026, there are 2 operators available to choose from for flights from Chicago Midway Airport to Hawaii.

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

The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago Midway Airport to Hawaii.

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

The travel and health documents required for your trip to Hawaii can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Hawaii. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

$277 Cheap Flights from Chicago Midway Airport to Hawaii in 2026

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Find the cheapest flights from Chicago Midway Airport to Hawaii

Round-trip

One-way

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

6:50 am - 12:40 pm

MDW

KOA

10h 50m

1 stop

10:00 am - 5:45 am

KOA

MDW

14h 45m

1 stop

$544Southwest

Tue, Aug 18 - Tue, Aug 25

6:50 am - 12:40 pm

MDW

KOA

10h 50m

1 stop

10:00 am - 5:40 am

KOA

MDW

14h 40m

2 stops

$550Southwest

Tue, Aug 18 - Tue, Aug 25

8:50 pm - 12:40 pm

MDW

KOA

20h 50m

2 stops

10:00 am - 5:45 am

KOA

MDW

14h 45m

2 stops

$560Southwest

Tue, Aug 18 - Tue, Aug 25

9:20 am - 6:34 pm

MDW

KOA

14h 14m

2 stops

8:40 pm - 6:05 pm

KOA

MDW

16h 25m

2 stops

$565Delta

Tue, Sep 29 - Fri, Oct 2

10:05 am - 4:05 pm

MDW

OGG

11h 00m

1 stop

8:55 pm - 12:35 pm

OGG

MDW

10h 40m

1 stop

$577Southwest

Thu, May 28 - Thu, Jun 4

10:05 am - 7:45 pm

MDW

HNL

13h 40m

1 stop

10:05 pm - 5:10 pm

HNL

MDW

15h 05m

1 stop

$584Southwest

Mon, Nov 2 - Tue, Nov 10

9:22 am - 7:35 pm

MDW

OGG

15h 13m

2 stops

12:55 pm - 8:42 am

OGG

MDW

14h 47m

2 stops

$588Delta

Thu, May 28 - Tue, Jun 2

7:30 am - 9:10 pm

MDW

HNL

17h 40m

2 stops

10:05 pm - 5:10 pm

HNL

MDW

15h 05m

1 stop

$590Southwest

Mon, Nov 2 - Tue, Nov 10

6:15 am - 12:35 pm

MDW

HNL

11h 20m

1 stop

8:10 am - 4:30 am

HNL

MDW

15h 20m

1 stop

$592Southwest

Thu, Sep 10 - Thu, Sep 17

11:10 am - 9:20 pm

MDW

HNL

15h 10m

2 stops

8:15 am - 5:55 am

HNL

MDW

16h 40m

2 stops

$595Southwest

Tue, Sep 15 - Tue, Sep 22

Delta flights from Chicago Midway Airport to Hawaii

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

Delta

Sep 14

MDW9:20 amChicago Midway

14h 14m

2 stops

KOA6:34 pmKona Intl

Sep 28

KOA8:40 pmKona Intl

16h 25m

2 stops

MDW6:05 pmChicago Midway

$561

Delta

Sep 29

MDW9:20 amChicago Midway

14h 14m

2 stops

KOA6:34 pmKona Intl

Oct 2

KOA8:40 pmKona Intl

16h 25m

2 stops

MDW6:05 pmChicago Midway

$565

Delta

May 28

MDW9:22 amChicago Midway

15h 13m

2 stops

OGG7:35 pmKahului

Jun 2

OGG12:55 pmKahului

14h 47m

2 stops

MDW8:42 amChicago Midway

$588

Southwest flights from Chicago Midway Airport to Hawaii

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

Southwest

Aug 18

MDW6:50 amChicago Midway

10h 50m

1 stop

KOA12:40 pmKona Intl

Aug 25

KOA10:00 amKona Intl

14h 45m

1 stop

MDW5:45 amChicago Midway

$544

Southwest

Aug 18

MDW6:50 amChicago Midway

10h 50m

1 stop

KOA12:40 pmKona Intl

Aug 25

KOA10:00 amKona Intl

14h 40m

2 stops

MDW5:40 amChicago Midway

$550

Southwest

Sep 16

MDW6:50 amChicago Midway

14h 20m

2 stops

OGG4:10 pmKahului

Sep 30

OGG8:35 pmKahului

11h 40m

1 stop

MDW1:15 pmChicago Midway

$560

momondo Fare Finder

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

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Tue 8/18

6:50 am-12:40 pm

1 stop10h 50m

Kona Intl

Tue 8/25

10:00 am-5:45 am

1 stop14h 45m

$544

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Tue 8/18

6:50 am-12:40 pm

1 stop10h 50m

Kona Intl

Tue 8/25

10:00 am-5:40 am

2 stops14h 40m

$550

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Tue 8/18

8:50 pm-12:40 pm

2 stops20h 50m

Kona Intl

Tue 8/25

10:00 am-5:45 am

2 stops14h 45m

$560

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Tue 9/29

9:20 am-6:34 pm

2 stops14h 14m

Kona Intl

Fri 10/2

8:40 pm-6:05 pm

2 stops16h 25m

$565

Quickest round-trip

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Thu 5/28

10:05 am-4:05 pm

1 stop11h 00m

Kahului

Thu 6/4

8:55 pm-12:35 pm

1 stop10h 40m

$577

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Mon 11/2

10:05 am-7:45 pm

1 stop13h 40m

Honolulu

Tue 11/10

10:05 pm-5:10 pm

1 stop15h 05m

$584

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Thu 5/28

9:22 am-7:35 pm

2 stops15h 13m

Kahului

Tue 6/2

12:55 pm-8:42 am

2 stops14h 47m

$588

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Mon 11/2

7:30 am-9:10 pm

2 stops17h 40m

Honolulu

Tue 11/10

10:05 pm-5:10 pm

1 stop15h 05m

$590

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Thu 9/10

6:15 am-12:35 pm

1 stop11h 20m

Honolulu

Thu 9/17

8:10 am-4:30 am

1 stop15h 20m

$592

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Tue 9/15

11:10 am-9:20 pm

2 stops15h 10m

Honolulu

Tue 9/22

8:15 am-5:55 am

2 stops16h 40m

$595

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 Hawaii

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

What is the cheapest month to fly to Hawaii?

If you don’t want to visit Hawaii in January, then you should wait until April to fly from Chicago Midway Airport, when ticket prices are also cheap, with an average price of $502.

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

You could potentially save up to 5% on your flight if you consider stops on a Chicago Midway Airport to Hawaii flight.

Cheap Chicago Midway Airport to Hawaii flight deals and tips

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

Fastest flight time	10h 45m
Direct flights	None

The fastest flight from Chicago Midway Airport to Hawaii takes 10h 45m

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

Search flight deals

Frequently asked questions about flying from Chicago Midway Airport to Hawaii

When did momondo last update prices for flights from Chicago Midway Airport to Hawaii?
Prices for flights from Chicago Midway Airport to Hawaii refresh daily.
How many operators does momondo search for flights from Chicago Midway Airport to Hawaii?
As of May 2026, there are 2 operators available to choose from for flights from Chicago Midway Airport to Hawaii.
How old do you have to be to fly from Chicago Midway Airport to Hawaii?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago Midway Airport to Hawaii.
What documentation or ID do you need to fly to Hawaii?
The travel and health documents required for your trip to Hawaii can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Hawaii. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

Best airlines flying from Chicago Midway Airport to Hawaii

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

Airline	Rating	Free Cancellation	Price
Delta	PriceFrom $429	Free Cancellation	Rating 7.9 8,453 reviews		Search Delta flights
Southwest	PriceFrom $553	Free Cancellation	Rating 8.0 4,299 reviews		Search Southwest flights

Why use momondo?

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

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Chicago to Hawaii for you.

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

Yes. momondo allows you to filter the results for Chicago to Hawaii flights to just show those with flexible booking policies.

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

momondo provides multiple filters to help you find the best flight to Hawaii from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

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

Yes. momondo can track prices for Chicago to Hawaii flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.