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 July 2026, there is 1 operator 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.

$219 Cheap Flights from Chicago Midway Airport to Hawaii in 2026

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.

10:15 am - 4:10 pm

MDW

LIH

10h 55m

1 stop

8:25 pm - 12:05 pm

LIH

MDW

10h 40m

1 stop

$464Southwest

Mon, Aug 31 - Thu, Sep 10

10:15 am - 4:10 pm

MDW

LIH

10h 55m

1 stop

8:25 pm - 4:15 pm

LIH

MDW

14h 50m

2 stops

$470Southwest

Mon, Aug 31 - Thu, Sep 10

6:40 am - 2:10 pm

MDW

LIH

12h 30m

2 stops

9:25 pm - 4:10 pm

LIH

MDW

13h 45m

2 stops

$476Southwest

Mon, Aug 31 - Thu, Sep 10

6:15 am - 2:15 pm

MDW

LIH

13h 00m

2 stops

8:25 pm - 1:30 pm

LIH

MDW

12h 05m

1 stop

$528Southwest

Mon, Sep 14 - Mon, Sep 21

6:15 am - 2:15 pm

MDW

LIH

13h 00m

2 stops

8:25 pm - 1:30 pm

LIH

MDW

12h 05m

1 stop

$530Southwest

Mon, Sep 14 - Mon, Sep 21

6:40 am - 12:40 pm

MDW

KOA

11h 00m

1 stop

8:35 pm - 12:05 pm

KOA

MDW

10h 30m

1 stop

$534Southwest

Mon, Aug 24 - Fri, Aug 28

8:20 pm - 4:10 pm

MDW

LIH

24h 50m

2 stops

8:25 pm - 2:45 pm

LIH

MDW

13h 20m

2 stops

$535Southwest

Wed, Aug 19 - Tue, Aug 25

7:10 am - 6:05 pm

MDW

KOA

15h 55m

2 stops

10:00 am - 5:45 am

KOA

MDW

14h 45m

1 stop

$540Southwest

Mon, Aug 24 - Fri, Aug 28

9:24 am - 7:17 pm

MDW

KOA

14h 53m

2 stops

8:42 pm - 6:01 pm

KOA

MDW

16h 19m

2 stops

$545Delta

Mon, Aug 24 - Fri, Aug 28

9:24 am - 9:20 pm

MDW

HNL

16h 56m

2 stops

2:50 pm - 9:07 am

HNL

MDW

13h 17m

1 stop

$677Delta

Sat, Sep 5 - Sun, Sep 13

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Delta flights from Chicago Midway Airport to Hawaii

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

Delta

Aug 24

MDW9:24 amChicago Midway

14h 53m

2 stops

KOA7:17 pmKona Intl

Aug 28

KOA8:42 pmKona Intl

16h 19m

2 stops

MDW6:01 pmChicago Midway

$545

Delta

Oct 27

MDW9:29 amChicago Midway

15h 00m

2 stops

KOA7:29 pmKona Intl

Nov 11

KOA9:40 pmKona Intl

15h 10m

2 stops

MDW4:50 pmChicago Midway

$565

Delta

Nov 3

MDW5:21 pmChicago Midway

31h 08m

2 stops

KOA8:29 pmKona Intl

Nov 6

KOA10:05 pmKona Intl

14h 34m

2 stops

MDW4:39 pmChicago Midway

$583

Southwest flights from Chicago Midway Airport to Hawaii

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

Southwest

Aug 31

MDW10:15 amChicago Midway

10h 55m

1 stop

LIH4:10 pmLihue

Sep 10

LIH8:25 pmLihue

10h 40m

1 stop

MDW12:05 pmChicago Midway

$464

Southwest

Aug 31

MDW10:15 amChicago Midway

10h 55m

1 stop

LIH4:10 pmLihue

Sep 10

LIH8:25 pmLihue

14h 50m

2 stops

MDW4:15 pmChicago Midway

$470

Southwest

Aug 31

MDW6:40 amChicago Midway

12h 30m

2 stops

LIH2:10 pmLihue

Sep 10

LIH9:25 pmLihue

13h 45m

2 stops

MDW4:10 pmChicago Midway

$476

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

ChicagoLihue

MDW - LIH

MDWLIH

Chicago Midway

Mon 8/31

10:15 am-4:10 pm

1 stop10h 55m

Lihue

Thu 9/10

8:25 pm-12:05 pm

1 stop10h 40m

$464

ChicagoLihue

MDW - LIH

MDWLIH

Chicago Midway

Mon 8/31

10:15 am-4:10 pm

1 stop10h 55m

Lihue

Thu 9/10

8:25 pm-4:15 pm

2 stops14h 50m

$470

ChicagoLihue

MDW - LIH

MDWLIH

Chicago Midway

Mon 8/31

6:40 am-2:10 pm

2 stops12h 30m

Lihue

Thu 9/10

9:25 pm-4:10 pm

2 stops13h 45m

$476

ChicagoLihue

MDW - LIH

MDWLIH

Chicago Midway

Mon 9/14

6:15 am-2:15 pm

2 stops13h 00m

Lihue

Mon 9/21

8:25 pm-1:30 pm

1 stop12h 05m

$528

ChicagoLihue

MDW - LIH

MDWLIH

Chicago Midway

Mon 9/14

6:15 am-2:15 pm

2 stops13h 00m

Lihue

Mon 9/21

8:25 pm-1:30 pm

1 stop12h 05m

$530

Quickest round-trip

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Mon 8/24

6:40 am-12:40 pm

1 stop11h 00m

Kona Intl

Fri 8/28

8:35 pm-12:05 pm

1 stop10h 30m

$534

ChicagoLihue

MDW - LIH

MDWLIH

Chicago Midway

Wed 8/19

8:20 pm-4:10 pm

2 stops24h 50m

Lihue

Tue 8/25

8:25 pm-2:45 pm

2 stops13h 20m

$535

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Mon 8/24

7:10 am-6:05 pm

2 stops15h 55m

Kona Intl

Fri 8/28

10:00 am-5:45 am

1 stop14h 45m

$540

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Mon 8/24

9:24 am-7:17 pm

2 stops14h 53m

Kona Intl

Fri 8/28

8:42 pm-6:01 pm

2 stops16h 19m

$545

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Sat 9/5

9:24 am-9:20 pm

2 stops16h 56m

Honolulu

Sun 9/13

2:50 pm-9:07 am

1 stop13h 17m

$677

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 21% 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 50m
Direct flights	None

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

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 July 2026, there is 1 operator 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
Southwest	PriceFrom $553	Free Cancellation	Rating 7.9 4,249 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.