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

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

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

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

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

The number of operators available for flights from Chicago Midway Airport to Honolulu Airport is 2 as of May 2026.

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

The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago Midway Airport to Honolulu Airport.

What documentation or ID do you need to fly to Honolulu Airport?

The travel and health documents required for your trip to Honolulu Airport 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 Honolulu Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

$322 Cheap Flights from Chicago Midway Airport to Honolulu in 2026

Q: What is the typical price of a round-trip flight between Chicago Midway Airport and Honolulu?

Prices are currently low for flights on this route. Typical prices usually range from $774 to $674. The lowest price recently found on this route was $565.

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Find the cheapest flights from Chicago Midway Airport to Honolulu

Round-trip

One-way

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

12:00 pm - 9:20 pm

MDW

HNL

14h 20m

2 stops

8:15 am - 5:55 am

HNL

MDW

16h 40m

2 stops

$565Southwest

Tue, Aug 25 - Tue, Sep 1

9:20 am - 8:47 pm

MDW

HNL

16h 27m

2 stops

2:55 pm - 8:42 am

HNL

MDW

12h 47m

1 stop

$568Delta

Tue, Aug 18 - Thu, Sep 3

9:20 am - 8:47 pm

MDW

HNL

16h 27m

2 stops

4:05 pm - 12:30 pm

HNL

MDW

15h 25m

2 stops

$573Delta

Tue, Aug 18 - Thu, Sep 3

6:00 am - 1:15 pm

MDW

HNL

12h 15m

1 stop

4:05 pm - 12:30 pm

HNL

MDW

15h 25m

2 stops

$603Delta

Tue, Sep 1 - Wed, Sep 9

9:20 am - 8:47 pm

MDW

HNL

16h 27m

2 stops

1:30 pm - 8:38 am

HNL

MDW

14h 08m

2 stops

$608Delta

Wed, Sep 2 - Wed, Sep 9

9:20 am - 8:47 pm

MDW

HNL

16h 27m

2 stops

9:59 pm - 8:42 am

HNL

MDW

29h 43m

2 stops

$612Delta

Tue, Aug 18 - Mon, Aug 24

6:40 am - 1:20 pm

MDW

HNL

11h 40m

1 stop

8:15 am - 5:00 am

HNL

MDW

15h 45m

1 stop

$614Southwest

Fri, Aug 21 - Fri, Aug 28

5:25 pm - 4:05 pm

MDW

HNL

27h 40m

2 stops

2:50 pm - 8:42 am

HNL

MDW

12h 52m

1 stop

$615Delta

Tue, Sep 15 - Wed, Sep 23

6:45 pm - 4:05 pm

MDW

HNL

26h 20m

2 stops

1:30 pm - 8:38 am

HNL

MDW

14h 08m

2 stops

$620Delta

Tue, Sep 15 - Wed, Sep 23

11:10 am - 9:20 pm

MDW

HNL

15h 10m

2 stops

10:20 pm - 3:15 pm

HNL

MDW

11h 55m

2 stops

$625Southwest

Tue, Sep 22 - Sun, Sep 27

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Southwest flights from Chicago Midway Airport to Honolulu

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

Southwest

May 12

MDW10:10 amChicago Midway

15h 55m

1 stop

HNL9:05 pmHonolulu

Jun 3

HNL1:00 pmHonolulu

11h 50m

1 stop

MDW5:50 amChicago Midway

$637

Southwest

May 28

MDW9:45 pmChicago Midway

17h 05m

1 stop

HNL9:50 amHonolulu

Jun 4

HNL12:15 pmHonolulu

12h 25m

1 stop

MDW5:40 amChicago Midway

$638

Southwest

May 12

MDW7:30 amChicago Midway

18h 30m

2 stops

HNL9:00 pmHonolulu

Jun 3

HNL1:00 pmHonolulu

11h 50m

1 stop

MDW5:50 amChicago Midway

$643

Delta flights from Chicago Midway Airport to Honolulu

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

Delta

May 26

MDW7:13 pmChicago Midway

21h 27m

2 stops

HNL11:40 amHonolulu

Jun 2

HNL7:00 amHonolulu

20h 42m

2 stops

MDW8:42 amChicago Midway

$661

Delta

May 26

MDW7:13 pmChicago Midway

21h 27m

2 stops

HNL11:40 amHonolulu

Jun 3

HNL1:50 pmHonolulu

13h 52m

2 stops

MDW8:42 amChicago Midway

$681

Delta

May 26

MDW7:13 pmChicago Midway

21h 27m

2 stops

HNL11:40 amHonolulu

Jun 8

HNL7:00 amHonolulu

20h 37m

2 stops

MDW8:37 amChicago Midway

$692

momondo Fare Finder

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

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Tue 8/25

12:00 pm-9:20 pm

2 stops14h 20m

Honolulu

Tue 9/1

8:15 am-5:55 am

2 stops16h 40m

$565

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Tue 8/18

9:20 am-8:47 pm

2 stops16h 27m

Honolulu

Thu 9/3

2:55 pm-8:42 am

1 stop12h 47m

$568

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Tue 8/18

9:20 am-8:47 pm

2 stops16h 27m

Honolulu

Thu 9/3

4:05 pm-12:30 pm

2 stops15h 25m

$573

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Tue 9/1

6:00 am-1:15 pm

1 stop12h 15m

Honolulu

Wed 9/9

4:05 pm-12:30 pm

2 stops15h 25m

$603

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Wed 9/2

9:20 am-8:47 pm

2 stops16h 27m

Honolulu

Wed 9/9

1:30 pm-8:38 am

2 stops14h 08m

$608

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Tue 8/18

9:20 am-8:47 pm

2 stops16h 27m

Honolulu

Mon 8/24

9:59 pm-8:42 am

2 stops29h 43m

$612

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Fri 8/21

6:40 am-1:20 pm

1 stop11h 40m

Honolulu

Fri 8/28

8:15 am-5:00 am

1 stop15h 45m

$614

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Tue 9/15

5:25 pm-4:05 pm

2 stops27h 40m

Honolulu

Wed 9/23

2:50 pm-8:42 am

1 stop12h 52m

$615

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Tue 9/15

6:45 pm-4:05 pm

2 stops26h 20m

Honolulu

Wed 9/23

1:30 pm-8:38 am

2 stops14h 08m

$620

Quickest round-trip

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Tue 9/22

11:10 am-9:20 pm

2 stops15h 10m

Honolulu

Sun 9/27

10:20 pm-3:15 pm

2 stops11h 55m

$625

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 Honolulu

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 typical price of a round-trip flight between Chicago Midway Airport and Honolulu?

What is the cheapest month to fly to Honolulu?

The month of January is, on average, the cheapest month to fly to Honolulu from Chicago Midway Airport, with most prices found around $429. If you’re not able to fly to Honolulu in January, then February is your next best option. Flight prices from Chicago Midway Airport to Honolulu during February average around $640.

What is the cheapest day to depart on your flight to Honolulu?

Our data shows that Tuesday is the least expensive day to fly to Honolulu. Tickets to fly out on this day can be as low as $760. Be sure to avoid booking your departure on a Saturday as prices are generally higher than usual. According to our data, the average ticket price to Honolulu on Saturday is $1,069.

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

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

When to book flights from Chicago Midway Airport to Honolulu

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport to Honolulu according to our flight data. Find out which month and days have the cheapest flights.

Estimated round-trip price

Cheap Chicago Midway Airport to Honolulu (MDW to HNL) flight deals and tips

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

Fastest flight time	11h 15m
Direct flights	None

The fastest flight from Chicago Midway Airport to Honolulu takes 11h 15m

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

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Frequently asked questions about flying from Chicago Midway Airport to Honolulu

How far is Chicago Midway to Honolulu by plane?
A flight from Chicago Midway to Honolulu will travel around 4240.6 mi. 11h 15m is a normal flight duration for this route.
When did momondo last update prices for flights from Chicago Midway Airport to Honolulu Airport?
Prices for flights from Chicago Midway Airport to Honolulu Airport are refreshed on a daily basis.
How many operators does momondo search for flights from Chicago Midway Airport to Honolulu Airport?
The number of operators available for flights from Chicago Midway Airport to Honolulu Airport is 2 as of May 2026.
How old do you have to be to fly from Chicago Midway Airport to Honolulu Airport?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago Midway Airport to Honolulu Airport.
What documentation or ID do you need to fly to Honolulu Airport?
The travel and health documents required for your trip to Honolulu Airport 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 Honolulu Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular airline from Chicago Midway Airport to Honolulu?
momondo data reveals that the most frequently booked airline on the route from Chicago Midway Airport to Honolulu is Southwest, representing 85% of all bookings. The subsequent popular airline is Delta at 15%.

Best airlines flying from Chicago Midway Airport to Honolulu

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

Airline	Rating	Free Cancellation	Price
Delta	PriceFrom $429	Free Cancellation	Rating 7.9 8,459 reviews		Search Delta flights
Southwest	PriceFrom $553	Free Cancellation	Rating 7.9 4,307 reviews		Search Southwest flights

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Kailua

Aiea

Why use momondo?

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

Finding the right flight to Honolulu from Chicago is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Honolulu quick and easy, saving you time and money.

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

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

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

momondo provides multiple filters to help you find the best flight to Honolulu 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 Honolulu right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Honolulu 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.