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 January 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.

$218 Cheap Flights from Chicago Midway Airport to Honolulu in 2026

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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.

5:00 am - 1:15 pm

MDW

HNL

12h 15m

1 stop

2:50 pm - 5:55 am

HNL

MDW

11h 05m

1 stop

$393Southwest

Thu, Feb 26 - Thu, Mar 5

10:15 pm - 11:15 am

MDW

HNL

17h 00m

1 stop

9:55 pm - 6:00 pm

HNL

MDW

16h 05m

2 stops

$399Southwest

Thu, Feb 26 - Wed, Mar 4

10:15 pm - 11:15 am

MDW

HNL

17h 00m

1 stop

2:50 pm - 11:05 am

HNL

MDW

16h 15m

1 stop

$403Southwest

Thu, Feb 26 - Thu, Mar 5

10:05 am - 9:00 pm

MDW

HNL

15h 55m

1 stop

1:00 pm - 5:50 am

HNL

MDW

11h 50m

1 stop

$413Southwest

Tue, Apr 14 - Tue, Apr 21

8:05 am - 9:00 pm

MDW

HNL

16h 55m

2 stops

8:10 am - 4:35 am

HNL

MDW

15h 25m

1 stop

$419Southwest

Mon, Feb 23 - Tue, Mar 10

8:00 am - 9:00 pm

MDW

HNL

17h 00m

1 stop

9:55 pm - 6:20 pm

HNL

MDW

16h 25m

1 stop

$421Southwest

Thu, Feb 19 - Thu, Feb 26

7:55 am - 4:30 pm

MDW

HNL

12h 35m

1 stop

11:25 am - 5:45 am

HNL

MDW

13h 20m

1 stop

$422Southwest

Mon, Mar 2 - Mon, Mar 9

6:00 am - 1:45 pm

MDW

HNL

12h 45m

1 stop

3:15 pm - 8:42 am

HNL

MDW

12h 27m

1 stop

$424Delta

Sun, May 3 - Wed, May 6

8:00 am - 9:00 pm

MDW

HNL

17h 00m

1 stop

9:55 pm - 1:40 pm

HNL

MDW

11h 45m

2 stops

$427Southwest

Thu, Feb 19 - Thu, Feb 26

8:05 am - 9:00 pm

MDW

HNL

16h 55m

2 stops

12:25 pm - 5:45 am

HNL

MDW

13h 20m

1 stop

$428Southwest

Mon, Mar 2 - Thu, Mar 5

Delta flights from Chicago Midway Airport to Honolulu

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

Delta

Apr 13

MDW6:00 amChicago Midway

12h 45m

1 stop

HNL1:45 pmHonolulu

Apr 20

HNL3:15 pmHonolulu

12h 32m

1 stop

MDW8:47 amChicago Midway

$424

Delta

Apr 29

MDW9:31 amChicago Midway

17h 14m

2 stops

HNL9:45 pmHonolulu

May 6

HNL3:15 pmHonolulu

12h 27m

1 stop

MDW8:42 amChicago Midway

$430

Delta

Feb 25

MDW9:34 amChicago Midway

16h 20m

2 stops

HNL9:54 pmHonolulu

Mar 3

HNL1:55 pmHonolulu

14h 59m

2 stops

MDW8:54 amChicago Midway

$435

Southwest flights from Chicago Midway Airport to Honolulu

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

Southwest

Feb 26

MDW5:00 amChicago Midway

12h 15m

1 stop

HNL1:15 pmHonolulu

Mar 5

HNL2:50 pmHonolulu

11h 05m

1 stop

MDW5:55 amChicago Midway

$393

Southwest

Feb 26

MDW10:15 pmChicago Midway

17h 00m

1 stop

HNL11:15 amHonolulu

Mar 4

HNL9:55 pmHonolulu

16h 05m

2 stops

MDW6:00 pmChicago Midway

$399

Southwest

Feb 26

MDW10:15 pmChicago Midway

17h 00m

1 stop

HNL11:15 amHonolulu

Mar 5

HNL2:50 pmHonolulu

16h 15m

1 stop

MDW11:05 amChicago Midway

$403

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

Thu 2/26

5:00 am-1:15 pm

1 stop12h 15m

Honolulu

Thu 3/5

2:50 pm-5:55 am

1 stop11h 05m

$393

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Thu 2/26

10:15 pm-11:15 am

1 stop17h 00m

Honolulu

Wed 3/4

9:55 pm-6:00 pm

2 stops16h 05m

$399

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Thu 2/26

10:15 pm-11:15 am

1 stop17h 00m

Honolulu

Thu 3/5

2:50 pm-11:05 am

1 stop16h 15m

$403

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Tue 4/14

10:05 am-9:00 pm

1 stop15h 55m

Honolulu

Tue 4/21

1:00 pm-5:50 am

1 stop11h 50m

$413

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Mon 2/23

8:05 am-9:00 pm

2 stops16h 55m

Honolulu

Tue 3/10

8:10 am-4:35 am

1 stop15h 25m

$419

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Thu 2/19

8:00 am-9:00 pm

1 stop17h 00m

Honolulu

Thu 2/26

9:55 pm-6:20 pm

1 stop16h 25m

$421

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Mon 3/2

7:55 am-4:30 pm

1 stop12h 35m

Honolulu

Mon 3/9

11:25 am-5:45 am

1 stop13h 20m

$422

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Sun 5/3

6:00 am-1:45 pm

1 stop12h 45m

Honolulu

Wed 5/6

3:15 pm-8:42 am

1 stop12h 27m

$424

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Thu 2/19

8:00 am-9:00 pm

1 stop17h 00m

Honolulu

Thu 2/26

9:55 pm-1:40 pm

2 stops11h 45m

$427

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Mon 3/2

8:05 am-9:00 pm

2 stops16h 55m

Honolulu

Thu 3/5

12:25 pm-5:45 am

1 stop13h 20m

$428

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 $429. If you’re not able to fly to Honolulu in January, then April is your next best option. Flight prices from Chicago Midway Airport to Honolulu during April average around $613.

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

Our data shows that Monday is the least expensive day to fly to Honolulu. Tickets to fly out on this day can be as low as $910. 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 $1,109.

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 morning. momondo users have found flights departing from Chicago Midway Airport to Honolulu in the morning for as low as $991. 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 45% 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	12h 15m
Direct flights	None

The fastest flight from Chicago Midway Airport to Honolulu takes 12h 15m

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. 12h 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 January 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 80% of all bookings. The subsequent popular airline is Delta at 20%.

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 8,127 reviews		Search Delta flights
Southwest	PriceFrom $553	Free Cancellation	Rating 8.0 4,267 reviews		Search Southwest flights

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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.