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

Delta and Southwest 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 April 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.

$238 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.

10:20 am - 5:40 pm

MDW

HNL

12h 20m

1 stop

9:25 pm - 4:35 pm

HNL

MDW

14h 10m

1 stop

$454Southwest

Tue, Apr 28 - Tue, May 5

9:22 am - 7:06 pm

MDW

LIH

14h 44m

2 stops

9:55 pm - 5:56 pm

LIH

MDW

15h 01m

2 stops

$459Delta

Fri, May 15 - Fri, May 22

11:45 am - 9:05 pm

MDW

HNL

14h 20m

2 stops

1:00 pm - 5:50 am

HNL

MDW

11h 50m

1 stop

$460Southwest

Wed, Apr 22 - Tue, Apr 28

12:10 pm - 9:05 pm

MDW

HNL

13h 55m

2 stops

8:50 pm - 2:20 pm

HNL

MDW

12h 30m

2 stops

$465Southwest

Mon, May 4 - Thu, May 7

6:10 am - 1:05 pm

MDW

HNL

11h 55m

1 stop

9:05 pm - 5:50 pm

HNL

MDW

15h 45m

1 stop

$475Southwest

Wed, Apr 22 - Wed, Apr 22

9:45 pm - 9:50 am

MDW

HNL

17h 05m

1 stop

1:00 pm - 11:05 am

HNL

MDW

17h 05m

1 stop

$477Southwest

Thu, Apr 23 - Thu, May 7

10:20 am - 5:40 pm

MDW

HNL

12h 20m

1 stop

9:05 pm - 5:55 pm

HNL

MDW

15h 50m

2 stops

$481Southwest

Wed, Apr 22 - Wed, Apr 22

10:05 am - 5:40 pm

MDW

HNL

12h 35m

2 stops

8:10 am - 4:35 am

HNL

MDW

15h 25m

1 stop

$483Southwest

Thu, Apr 23 - Thu, May 7

7:30 am - 9:00 pm

MDW

HNL

18h 30m

2 stops

9:05 pm - 2:10 pm

HNL

MDW

12h 05m

2 stops

$486Southwest

Tue, Apr 28 - Tue, May 5

6:00 am - 1:15 pm

MDW

HNL

12h 15m

1 stop

2:55 pm - 8:42 am

HNL

MDW

12h 47m

1 stop

$489Delta

Tue, Sep 1 - Wed, Sep 9

Delta flights from Chicago Midway Airport to Hawaii

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

Delta

May 15

MDW9:22 amChicago Midway

14h 44m

2 stops

LIH7:06 pmLihue

May 22

LIH9:55 pmLihue

15h 01m

2 stops

MDW5:56 pmChicago Midway

$459

Delta

Apr 22

MDW6:00 amChicago Midway

12h 45m

1 stop

HNL1:45 pmHonolulu

Apr 24

HNL3:15 pmHonolulu

12h 32m

1 stop

MDW8:47 amChicago Midway

$494

Delta

May 6

MDW6:00 amChicago Midway

20h 45m

2 stops

HNL9:45 pmHonolulu

May 11

HNL2:45 pmHonolulu

12h 58m

1 stop

MDW8:43 amChicago Midway

$497

Southwest flights from Chicago Midway Airport to Hawaii

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

Southwest

Apr 28

MDW10:20 amChicago Midway

12h 20m

1 stop

HNL5:40 pmHonolulu

May 5

HNL9:25 pmHonolulu

14h 10m

1 stop

MDW4:35 pmChicago Midway

$454

Southwest

Apr 22

MDW11:45 amChicago Midway

14h 20m

2 stops

HNL9:05 pmHonolulu

Apr 28

HNL1:00 pmHonolulu

11h 50m

1 stop

MDW5:50 amChicago Midway

$460

Southwest

May 4

MDW12:10 pmChicago Midway

13h 55m

2 stops

HNL9:05 pmHonolulu

May 7

HNL8:50 pmHonolulu

12h 30m

2 stops

MDW2:20 pmChicago Midway

$465

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

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Tue 4/28

10:20 am-5:40 pm

1 stop12h 20m

Honolulu

Tue 5/5

9:25 pm-4:35 pm

1 stop14h 10m

$454

ChicagoLihue

MDW - LIH

MDWLIH

Chicago Midway

Fri 5/15

9:22 am-7:06 pm

2 stops14h 44m

Lihue

Fri 5/22

9:55 pm-5:56 pm

2 stops15h 01m

$459

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Wed 4/22

11:45 am-9:05 pm

2 stops14h 20m

Honolulu

Tue 4/28

1:00 pm-5:50 am

1 stop11h 50m

$460

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Mon 5/4

12:10 pm-9:05 pm

2 stops13h 55m

Honolulu

Thu 5/7

8:50 pm-2:20 pm

2 stops12h 30m

$465

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Wed 4/22

6:10 am-1:05 pm

1 stop11h 55m

Honolulu

Wed 4/22

9:05 pm-5:50 pm

1 stop15h 45m

$475

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Thu 4/23

9:45 pm-9:50 am

1 stop17h 05m

Honolulu

Thu 5/7

1:00 pm-11:05 am

1 stop17h 05m

$477

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Wed 4/22

10:20 am-5:40 pm

1 stop12h 20m

Honolulu

Wed 4/22

9:05 pm-5:55 pm

2 stops15h 50m

$481

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Thu 4/23

10:05 am-5:40 pm

2 stops12h 35m

Honolulu

Thu 5/7

8:10 am-4:35 am

1 stop15h 25m

$483

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Tue 4/28

7:30 am-9:00 pm

2 stops18h 30m

Honolulu

Tue 5/5

9:05 pm-2:10 pm

2 stops12h 05m

$486

Quickest round-trip

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Tue 9/1

6:00 am-1:15 pm

1 stop12h 15m

Honolulu

Wed 9/9

2:55 pm-8:42 am

1 stop12h 47m

$489

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 $582.

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

You could potentially save up to 8% 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 April 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 8,370 reviews		Search Delta flights
Southwest	PriceFrom $553	Free Cancellation	Rating 8.0 4,337 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.