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

Southwest and Delta 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 1 as of November 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.

$209 Cheap Flights from Chicago Midway Airport to Honolulu in 2026/27

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.

7:15 am - 6:30 pmMDW Chicago Midway-HNL Honolulu

15h 15m2 stops Phoenix Sky Harbor Intl Los Angeles

11:20 pm - 5:15 pmHNL Honolulu-MDW Chicago Midway

13h 55m2 stops San Diego Portland

$557Southwest

Mon, Mar 8 - Wed, Mar 10

7:15 am - 6:30 pmMDW Chicago Midway-HNL Honolulu

15h 15m2 stops Phoenix Sky Harbor Intl Los Angeles

11:20 pm - 4:35 pmHNL Honolulu-MDW Chicago Midway

13h 15m2 stops San Diego Denver Intl

$557Southwest

Mon, Mar 1 - Mon, Mar 8

7:30 am - 9:10 pmMDW Chicago Midway-HNL Honolulu

17h 40m2 stops Baltimore/Washington San Jose

8:15 am - 1:25 amHNL Honolulu-MDW Chicago Midway

13h 10m2 stops San Jose Las Vegas Harry Reid Intl

$558Southwest

Sun, Dec 6 - Mon, Dec 21

6:00 am - 2:59 pmMDW Chicago Midway-HNL Honolulu

12h 59m1 stop Atlanta Hartsfield-Jackson

4:49 pm - 9:00 amHNL Honolulu-MDW Chicago Midway

12h 11m1 stop Detroit Metropolitan Wayne County

$562Delta

Sun, Feb 14 - Mon, Feb 22

6:00 am - 3:10 pmMDW Chicago Midway-HNL Honolulu

13h 10m1 stop Atlanta Hartsfield-Jackson

9:34 pm - 12:04 pmHNL Honolulu-MDW Chicago Midway

10h 30m1 stop Minneapolis St Paul

$562Delta

Thu, Jan 14 - Thu, Jan 21

10:15 am - 6:30 pmMDW Chicago Midway-HNL Honolulu

12h 15m1 stop Los Angeles

10:05 pm - 12:35 pmHNL Honolulu-MDW Chicago Midway

10h 30m1 stop Los Angeles

$562Southwest

Tue, Jan 19 - Mon, Jan 25

6:00 am - 2:55 pmMDW Chicago Midway-HNL Honolulu

12h 55m1 stop Atlanta Hartsfield-Jackson

4:40 pm - 8:49 amHNL Honolulu-MDW Chicago Midway

12h 09m1 stop Detroit Metropolitan Wayne County

$562Delta

Mon, Dec 7 - Mon, Dec 21

6:00 am - 3:10 pmMDW Chicago Midway-HNL Honolulu

13h 10m1 stop Atlanta Hartsfield-Jackson

9:35 pm - 11:57 amHNL Honolulu-MDW Chicago Midway

10h 22m1 stop Minneapolis St Paul

$562Delta

Sun, Feb 7 - Mon, Feb 15

6:00 am - 2:55 pmMDW Chicago Midway-HNL Honolulu

12h 55m1 stop Atlanta Hartsfield-Jackson

4:59 pm - 9:13 amHNL Honolulu-MDW Chicago Midway

12h 14m1 stop Atlanta Hartsfield-Jackson

$562Delta

Mon, Dec 7 - Mon, Dec 21

6:00 am - 2:59 pmMDW Chicago Midway-HNL Honolulu

12h 59m1 stop Atlanta Hartsfield-Jackson

5:18 pm - 10:05 amHNL Honolulu-MDW Chicago Midway

12h 47m1 stop Atlanta Hartsfield-Jackson

$562Delta

Thu, Feb 11 - Thu, Feb 18

Cheap last minute flights

Enter your travel dates to find the best prices.

10:10 am - 9:10 pmMDW Chicago Midway-HNL Honolulu

15h 00m1 stop San Jose

3:15 pm - 12:30 pmHNL Honolulu-MDW Chicago Midway

17h 15m1 stop Oakland

$578Southwest

Mon, Nov 9 - Mon, Dec 14

10:10 am - 9:10 pmMDW Chicago Midway-HNL Honolulu

15h 00m1 stop San Jose

3:15 pm - 12:30 pmHNL Honolulu-MDW Chicago Midway

17h 15m1 stop Oakland

$590Southwest

Mon, Nov 9 - Mon, Nov 16

10:10 am - 9:10 pmMDW Chicago Midway-HNL Honolulu

15h 00m1 stop San Jose

11:15 pm - 5:25 pmHNL Honolulu-MDW Chicago Midway

14h 10m1 stop San Diego

$590Southwest

Mon, Nov 9 - Tue, Nov 17

7:30 am - 9:10 pmMDW Chicago Midway-HNL Honolulu

17h 40m2 stops Baltimore/Washington San Jose

3:15 pm - 11:35 amHNL Honolulu-MDW Chicago Midway

16h 20m1 stop Oakland

$596Southwest

Thu, Nov 5 - Thu, Nov 12

7:30 am - 9:10 pmMDW Chicago Midway-HNL Honolulu

17h 40m2 stops Baltimore/Washington San Jose

3:15 pm - 11:35 amHNL Honolulu-MDW Chicago Midway

16h 20m1 stop Oakland

$596Southwest

Thu, Nov 5 - Sat, Nov 7

7:25 am - 9:05 pmMDW Chicago Midway-HNL Honolulu

17h 40m2 stops Los Angeles Sacramento Intl

11:15 pm - 5:25 pmHNL Honolulu-MDW Chicago Midway

14h 10m1 stop San Diego

$596Southwest

Mon, Nov 9 - Tue, Nov 17

7:30 am - 9:10 pmMDW Chicago Midway-HNL Honolulu

17h 40m2 stops Baltimore/Washington San Jose

11:15 pm - 5:40 pmHNL Honolulu-MDW Chicago Midway

14h 25m1 stop San Diego

$596Southwest

Thu, Nov 5 - Thu, Nov 12

10:10 am - 9:10 pmMDW Chicago Midway-HNL Honolulu

15h 00m1 stop San Jose

11:15 pm - 5:25 pmHNL Honolulu-MDW Chicago Midway

14h 10m2 stops San Diego Denver Intl

$596Southwest

Mon, Nov 9 - Mon, Nov 16

9:30 am - 8:38 pmMDW Chicago Midway-HNL Honolulu

15h 08m2 stops Detroit Metropolitan Wayne County Seattle/Tacoma Intl

1:59 pm - 9:37 amHNL Honolulu-MDW Chicago Midway

15h 38m2 stops Seattle/Tacoma Intl Detroit Metropolitan Wayne County

$639Delta

Mon, Nov 9 - Mon, Dec 14

6:00 am - 2:40 pmMDW Chicago Midway-HNL Honolulu

12h 40m1 stop Atlanta Hartsfield-Jackson

9:35 pm - 11:50 amHNL Honolulu-MDW Chicago Midway

10h 15m1 stop Minneapolis St Paul

$647Delta

Tue, Nov 10 - Wed, Nov 18

Save money when you book flights with momondo

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Not ready to book? to track prices.

Search flight deals

Delta flights from Chicago Midway Airport to Honolulu

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

Delta

Dec 7

MDW6:00 amChicago Midway

12h 55m

1 stop

HNL2:55 pmHonolulu

Dec 21

HNL4:40 pmHonolulu

12h 09m

1 stop

MDW8:49 amChicago Midway

$562

Delta

Dec 7

MDW6:00 amChicago Midway

12h 55m

1 stop

HNL2:55 pmHonolulu

Dec 21

HNL4:59 pmHonolulu

12h 14m

1 stop

MDW9:13 amChicago Midway

$563

Delta

Dec 7

MDW9:37 amChicago Midway

15h 20m

2 stops

HNL8:57 pmHonolulu

Dec 21

HNL4:59 pmHonolulu

12h 14m

1 stop

MDW9:13 amChicago Midway

$568

Southwest flights from Chicago Midway Airport to Honolulu

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

Southwest

Dec 6

MDW7:30 amChicago Midway

17h 40m

2 stops

HNL9:10 pmHonolulu

Dec 21

HNL8:15 amHonolulu

13h 10m

2 stops

MDW1:25 amChicago Midway

$558

Southwest

Dec 4

MDW10:00 amChicago Midway

13h 45m

1 stop

HNL7:45 pmHonolulu

Dec 11

HNL2:40 pmHonolulu

11h 00m

1 stop

MDW5:40 amChicago Midway

$564

Southwest

Nov 30

MDW5:10 amChicago Midway

18h 20m

1 stop

HNL7:30 pmHonolulu

Dec 7

HNL3:15 pmHonolulu

17h 15m

1 stop

MDW12:30 pmChicago Midway

$565

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 Chicago Midway - HNL Honolulu

MDWHNL

Chicago Midway

Mon 3/8

7:15 am-6:30 pm

2 stops15h 15m

Honolulu

Wed 3/10

11:20 pm-5:15 pm

2 stops13h 55m

$557

ChicagoHonolulu

MDW Chicago Midway - HNL Honolulu

MDWHNL

Chicago Midway

Mon 3/1

7:15 am-6:30 pm

2 stops15h 15m

Honolulu

Mon 3/8

11:20 pm-4:35 pm

2 stops13h 15m

$557

ChicagoHonolulu

MDW Chicago Midway - HNL Honolulu

MDWHNL

Chicago Midway

Sun 12/6

7:30 am-9:10 pm

2 stops17h 40m

Honolulu

Mon 12/21

8:15 am-1:25 am

2 stops13h 10m

$558

ChicagoHonolulu

MDW Chicago Midway - HNL Honolulu

MDWHNL

Chicago Midway

Sun 2/14

6:00 am-2:59 pm

1 stop12h 59m

Honolulu

Mon 2/22

4:49 pm-9:00 am

1 stop12h 11m

$562

ChicagoHonolulu

MDW Chicago Midway - HNL Honolulu

MDWHNL

Chicago Midway

Thu 1/14

6:00 am-3:10 pm

1 stop13h 10m

Honolulu

Thu 1/21

9:34 pm-12:04 pm

1 stop10h 30m

$562

Quickest round-trip

ChicagoHonolulu

MDW Chicago Midway - HNL Honolulu

MDWHNL

Chicago Midway

Tue 1/19

10:15 am-6:30 pm

1 stop12h 15m

Honolulu

Mon 1/25

10:05 pm-12:35 pm

1 stop10h 30m

$562

ChicagoHonolulu

MDW Chicago Midway - HNL Honolulu

MDWHNL

Chicago Midway

Mon 12/7

6:00 am-2:55 pm

1 stop12h 55m

Honolulu

Mon 12/21

4:40 pm-8:49 am

1 stop12h 09m

$562

ChicagoHonolulu

MDW Chicago Midway - HNL Honolulu

MDWHNL

Chicago Midway

Sun 2/7

6:00 am-3:10 pm

1 stop13h 10m

Honolulu

Mon 2/15

9:35 pm-11:57 am

1 stop10h 22m

$562

ChicagoHonolulu

MDW Chicago Midway - HNL Honolulu

MDWHNL

Chicago Midway

Mon 12/7

6:00 am-2:55 pm

1 stop12h 55m

Honolulu

Mon 12/21

4:59 pm-9:13 am

1 stop12h 14m

$562

ChicagoHonolulu

MDW Chicago Midway - HNL Honolulu

MDWHNL

Chicago Midway

Thu 2/11

6:00 am-2:59 pm

1 stop12h 59m

Honolulu

Thu 2/18

5:18 pm-10:05 am

1 stop12h 47m

$562

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?

Prices are currently low for flights on this route.

Typical prices usually range from $590 to $840.
The lowest price recently found on this route was $557.

What is the cheapest month to fly to Honolulu?

The month of September is, on average, the cheapest month to fly to Honolulu from Chicago Midway Airport, with most prices found around $0. If you’re not able to fly to Honolulu in September, then November is your next best option. Flight prices from Chicago Midway Airport to Honolulu during November average around $644.

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 $726. 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 $1,067.

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

You could potentially save up to 23% 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

Best Price Found	$209
Fastest flight time	11h 45m
Direct flights	None

The best one-way flight to Honolulu from Chicago Midway Airport in the past 72 hours is $209. The best round-trip flight deal from Chicago Midway Airport to Honolulu found on momondo in the last 72 hours is $557.

The fastest flight from Chicago Midway Airport to Honolulu takes 11h 45m

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

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 45m 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 1 as of November 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 100% of all bookings.

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
Southwest	PriceFrom $536	Free Cancellation	Rating 8.0 4,214 reviews		Search Southwest flights

Kahuku

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.