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

Delta and Southwest are the most popular carriers 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 October 2025.

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.

$251 Cheap Flights from Chicago Midway Airport to Honolulu in 2025/26

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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.

9:34 am - 9:28 pmMDW-HNL

15h 54m2 stops

1:55 pm - 8:54 amHNL-MDW

14h 59m2 stops

$502Delta

Find Deal

Fri, Jan 9 - Tue, Jan 13

7:55 am - 4:30 pmMDW-HNL

12h 35m1 stop

9:55 pm - 12:35 pmHNL-MDW

10h 40m1 stop

$511Southwest

Find Deal

Fri, Jan 16 - Mon, Jan 26

9:34 am - 9:28 pmMDW-HNL

15h 54m2 stops

4:50 pm - 10:34 amHNL-MDW

13h 44m1 stop

$522Delta

Find Deal

Thu, Jan 8 - Mon, Jan 12

9:34 am - 9:28 pmMDW-HNL

15h 54m2 stops

1:55 pm - 9:08 amHNL-MDW

15h 13m2 stops

$525Delta

Find Deal

Tue, Jan 27 - Tue, Feb 3

9:34 am - 9:28 pmMDW-HNL

15h 54m2 stops

10:55 pm - 5:34 pmHNL-MDW

14h 39m2 stops

$528Delta

Find Deal

Thu, Jan 8 - Mon, Jan 12

6:00 am - 5:00 pmMDW-HNL

15h 00m1 stop

4:44 pm - 8:54 amHNL-MDW

12h 10m1 stop

$546Delta

Find Deal

Thu, Jan 1 - Mon, Jan 19

6:12 am - 12:48 amMDW-HNL

22h 36m2 stops

10:23 am - 10:13 amHNL-MDW

19h 50m1 stop

$547Multiple Airlines

Find Deal

Wed, Dec 31 - Sat, Jan 17

9:59 am - 9:48 pmMDW-HNL

15h 49m2 stops

5:37 pm - 12:34 pmHNL-MDW

14h 57m2 stops

$548Delta

Find Deal

Wed, Dec 10 - Tue, Dec 16

7:55 am - 4:30 pmMDW-HNL

12h 35m1 stop

9:55 pm - 12:30 pmHNL-MDW

10h 35m1 stop

$567Southwest

Find Deal

Fri, Jan 16 - Sat, Jan 24

5:15 am - 1:20 pmMDW-HNL

12h 05m1 stop

8:00 am - 10:55 pmHNL-MDW

10h 55m1 stop

$569Southwest

Find Deal

Tue, Dec 2 - Wed, Dec 10

Delta flights from Chicago Midway Airport to Honolulu

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

Delta

Jan 9

MDW9:34 amChicago Midway

15h 54m

2 stops

HNL9:28 pmHonolulu

Jan 13

HNL1:55 pmHonolulu

14h 59m

2 stops

MDW8:54 amChicago Midway

$502

Find similar

Delta

Jan 8

MDW9:34 amChicago Midway

15h 54m

2 stops

HNL9:28 pmHonolulu

Jan 12

HNL4:50 pmHonolulu

13h 44m

1 stop

MDW10:34 amChicago Midway

$522

Find similar

Delta

Jan 27

MDW9:34 amChicago Midway

15h 54m

2 stops

HNL9:28 pmHonolulu

Feb 3

HNL1:55 pmHonolulu

15h 13m

2 stops

MDW9:08 amChicago Midway

$525

Find similar

Southwest flights from Chicago Midway Airport to Honolulu

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

Southwest

Jan 16

MDW7:55 amChicago Midway

12h 35m

1 stop

HNL4:30 pmHonolulu

Jan 26

HNL9:55 pmHonolulu

10h 40m

1 stop

MDW12:35 pmChicago Midway

$511

Find similar

Southwest

Jan 16

MDW7:55 amChicago Midway

12h 35m

1 stop

HNL4:30 pmHonolulu

Jan 24

HNL9:55 pmHonolulu

10h 35m

1 stop

MDW12:30 pmChicago Midway

$567

Find similar

Southwest

Dec 2

MDW5:15 amChicago Midway

12h 05m

1 stop

HNL1:20 pmHonolulu

Dec 10

HNL8:00 amHonolulu

10h 55m

1 stop

MDW10:55 pmChicago Midway

$569

Find similar

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

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Fri 1/9

9:34 am-9:28 pm

2 stops15h 54m

Honolulu

Tue 1/13

1:55 pm-8:54 am

2 stops14h 59m

$502

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Fri 1/16

7:55 am-4:30 pm

1 stop12h 35m

Honolulu

Mon 1/26

9:55 pm-12:35 pm

1 stop10h 40m

$511

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Thu 1/8

9:34 am-9:28 pm

2 stops15h 54m

Honolulu

Mon 1/12

4:50 pm-10:34 am

1 stop13h 44m

$522

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Tue 1/27

9:34 am-9:28 pm

2 stops15h 54m

Honolulu

Tue 2/3

1:55 pm-9:08 am

2 stops15h 13m

$525

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Thu 1/8

9:34 am-9:28 pm

2 stops15h 54m

Honolulu

Mon 1/12

10:55 pm-5:34 pm

2 stops14h 39m

$528

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Thu 1/1

6:00 am-5:00 pm

1 stop15h 00m

Honolulu

Mon 1/19

4:44 pm-8:54 am

1 stop12h 10m

$546

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Wed 12/31

6:12 am-12:48 am

2 stops22h 36m

Honolulu

Sat 1/17

10:23 am-10:13 am

1 stop19h 50m

$547

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Wed 12/10

9:59 am-9:48 pm

2 stops15h 49m

Honolulu

Tue 12/16

5:37 pm-12:34 pm

2 stops14h 57m

$548

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Fri 1/16

7:55 am-4:30 pm

1 stop12h 35m

Honolulu

Sat 1/24

9:55 pm-12:30 pm

1 stop10h 35m

$567

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Tue 12/2

5:15 am-1:20 pm

1 stop12h 05m

Honolulu

Wed 12/10

8:00 am-10:55 pm

1 stop10h 55m

$569

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 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 $465. 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 $617.

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 $1,037. 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 $1,121.

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

According to our data, the cheapest time of day to fly to Honolulu is in the afternoon. momondo users have found flights departing from Chicago Midway Airport to Honolulu in the afternoon for as low as $664. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. At noon is when there is more demand to fly to Honolulu, so prices are often more expensive at around $1,268 per ticket.

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

You could potentially save up to 32% 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

Direct flights	None

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

Search flight deals

How far is Chicago Midway to Honolulu by plane?
A flight from Chicago Midway to Honolulu will travel around 4240.6 mi. 11h 35m 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 October 2025.
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 82% of all bookings. The subsequent popular airline is Delta at 18%.

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 $442	Free Cancellation	Rating 7.9 7,998 reviews		Search Delta flights
Southwest	PriceFrom $553	Free Cancellation	Rating 8.0 4,243 reviews		Search Southwest flights

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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.