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 1 as of September 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.

$245 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.

10:00 am - 9:20 pmMDW Chicago Midway-HNL Honolulu

15h 20m2 stops Phoenix Sky Harbor Intl San Diego

10:00 pm - 12:35 pmHNL Honolulu-MDW Chicago Midway

10h 35m1 stop Los Angeles

$560Southwest

Tue, Feb 23 - Tue, Mar 2

10:00 am - 9:20 pmMDW Chicago Midway-HNL Honolulu

15h 20m2 stops Denver Intl San Diego

10:00 pm - 4:15 pmHNL Honolulu-MDW Chicago Midway

14h 15m1 stop Los Angeles

$560Southwest

Tue, Jan 12 - Tue, Feb 2

10:00 am - 9:20 pmMDW Chicago Midway-HNL Honolulu

15h 20m2 stops Denver Intl San Diego

3:15 pm - 5:50 amHNL Honolulu-MDW Chicago Midway

10h 35m1 stop Oakland

$560Southwest

Wed, Feb 3 - Wed, Feb 10

6:55 am - 9:25 pmMDW Chicago Midway-HNL Honolulu

19h 30m2 stops Phoenix Sky Harbor Intl San Diego

1:10 pm - 5:55 amHNL Honolulu-MDW Chicago Midway

11h 45m1 stop Oakland

$560Southwest

Wed, Oct 21 - Wed, Oct 28

8:50 am - 7:45 pmMDW Chicago Midway-HNL Honolulu

14h 55m2 stops Las Vegas Harry Reid Intl Oakland

3:15 pm - 5:55 amHNL Honolulu-MDW Chicago Midway

10h 40m1 stop Oakland

$560Southwest

Wed, Nov 4 - Wed, Nov 11

5:10 am - 11:50 amMDW Chicago Midway-HNL Honolulu

11h 40m1 stop Las Vegas Harry Reid Intl

8:55 pm - 2:05 pmHNL Honolulu-MDW Chicago Midway

12h 10m2 stops Phoenix Sky Harbor Intl Denver Intl

$560Southwest

Mon, Oct 19 - Tue, Oct 27

11:50 am - 9:30 pmMDW Chicago Midway-HNL Honolulu

14h 40m2 stops Las Vegas Harry Reid Intl San Diego

1:30 pm - 11:50 amHNL Honolulu-MDW Chicago Midway

17h 20m1 stop Oakland

$560Southwest

Mon, Oct 26 - Thu, Oct 29

8:50 am - 7:45 pmMDW Chicago Midway-HNL Honolulu

14h 55m2 stops Las Vegas Harry Reid Intl Oakland

3:15 pm - 5:55 amHNL Honolulu-MDW Chicago Midway

10h 40m1 stop Oakland

$560Southwest

Wed, Nov 4 - Thu, Nov 12

4:19 pm - 12:04 pmMDW Chicago Midway-HNL Honolulu

23h 45m2 stops Atlanta Hartsfield-Jackson Los Angeles

4:45 pm - 9:37 amHNL Honolulu-MDW Chicago Midway

12h 52m1 stop Detroit Metropolitan Wayne County

$561Delta

Fri, Nov 6 - Thu, Dec 3

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

12h 55m1 stop Atlanta Hartsfield-Jackson

4:30 pm - 8:45 amHNL Honolulu-MDW Chicago Midway

12h 15m1 stop Detroit Metropolitan Wayne County

$562Delta

Mon, Feb 22 - Thu, Mar 4

Cheap last minute flights

Enter your travel dates to find the best prices.

2:50 pm - 9:25 pmMDW Chicago Midway-HNL Honolulu

11h 35m1 stop San Diego

2:25 pm - 5:45 amHNL Honolulu-MDW Chicago Midway

10h 20m1 stop Sacramento Intl

$657Southwest

Thu, Sep 24 - Thu, Apr 8

6:15 am - 12:35 pmMDW Chicago Midway-HNL Honolulu

11h 20m1 stop San Diego

8:55 pm - 3:55 pmHNL Honolulu-MDW Chicago Midway

14h 00m2 stops Los Angeles Denver Intl

$663Southwest

Thu, Sep 24 - Thu, Apr 8

12:15 pm - 9:25 pmMDW Chicago Midway-HNL Honolulu

14h 10m2 stops Denver Intl San Diego

8:55 pm - 3:55 pmHNL Honolulu-MDW Chicago Midway

14h 00m2 stops Los Angeles Denver Intl

$668Southwest

Thu, Sep 24 - Thu, Apr 8

6:05 am - 1:18 pmMDW Chicago Midway-HNL Honolulu

12h 13m1 stop Atlanta Hartsfield-Jackson

3:10 pm - 9:49 amHNL Honolulu-MDW Chicago Midway

13h 39m1 stop Atlanta Hartsfield-Jackson

$670Delta

Thu, Sep 24 - Mon, Sep 28

10:15 am - 9:20 pmMDW Chicago Midway-HNL Honolulu

16h 05m1 stop Los Angeles

8:10 am - 11:50 pmHNL Honolulu-MDW Chicago Midway

10h 40m1 stop San Diego

$670Southwest

Wed, Sep 23 - Fri, Sep 25

2:05 pm - 9:25 pmMDW Chicago Midway-HNL Honolulu

12h 20m1 stop San Diego

8:55 pm - 11:55 amHNL Honolulu-MDW Chicago Midway

10h 00m1 stop Phoenix Sky Harbor Intl

$670Southwest

Sat, Sep 26 - Mon, Sep 28

10:15 am - 9:15 pmMDW Chicago Midway-HNL Honolulu

16h 00m1 stop San Jose

11:55 am - 5:45 amHNL Honolulu-MDW Chicago Midway

12h 50m1 stop Ontario

$670Southwest

Fri, Sep 25 - Sun, Sep 27

2:50 pm - 9:25 pmMDW Chicago Midway-HNL Honolulu

11h 35m1 stop San Diego

9:00 pm - 12:05 pmHNL Honolulu-MDW Chicago Midway

10h 05m1 stop Las Vegas Harry Reid Intl

$670Southwest

Fri, Sep 25 - Sun, Sep 27

7:10 am - 1:05 pmMDW Chicago Midway-HNL Honolulu

10h 55m1 stop Phoenix Sky Harbor Intl

11:00 am - 5:45 amHNL Honolulu-MDW Chicago Midway

13h 45m1 stop Sacramento Intl

$670Southwest

Fri, Sep 25 - Sun, Sep 27

9:29 am - 7:28 pmMDW Chicago Midway-HNL Honolulu

14h 59m2 stops Detroit Metropolitan Wayne County Seattle/Tacoma Intl

3:10 pm - 9:49 amHNL Honolulu-MDW Chicago Midway

13h 39m1 stop Atlanta Hartsfield-Jackson

$676Delta

Thu, Sep 24 - Mon, Sep 28

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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

Oct 19

MDW5:10 amChicago Midway

11h 40m

1 stop

HNL11:50 amHonolulu

Oct 27

HNL8:55 pmHonolulu

12h 10m

2 stops

MDW2:05 pmChicago Midway

$560

Southwest

Oct 19

MDW5:10 amChicago Midway

11h 40m

1 stop

HNL11:50 amHonolulu

Oct 26

HNL8:55 pmHonolulu

13h 50m

1 stop

MDW3:45 pmChicago Midway

$562

Southwest

Nov 9

MDW7:30 amChicago Midway

17h 40m

2 stops

HNL9:10 pmHonolulu

Nov 13

HNL10:50 pmHonolulu

15h 05m

2 stops

MDW5:55 pmChicago Midway

$565

Delta flights from Chicago Midway Airport to Honolulu

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

Delta

Nov 6

MDW4:19 pmChicago Midway

23h 45m

2 stops

HNL12:04 pmHonolulu

Dec 3

HNL4:45 pmHonolulu

12h 52m

1 stop

MDW9:37 amChicago Midway

$561

Delta

Oct 28

MDW6:04 amChicago Midway

18h 55m

2 stops

HNL7:59 pmHonolulu

Nov 2

HNL4:15 pmHonolulu

13h 17m

1 stop

MDW9:32 amChicago Midway

$564

Delta

Oct 28

MDW6:04 amChicago Midway

18h 55m

2 stops

HNL7:59 pmHonolulu

Nov 2

HNL4:15 pmHonolulu

15h 32m

2 stops

MDW11:47 amChicago Midway

$569

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

Tue 2/23

10:00 am-9:20 pm

2 stops15h 20m

Honolulu

Tue 3/2

10:00 pm-12:35 pm

1 stop10h 35m

$560

ChicagoHonolulu

MDW Chicago Midway - HNL Honolulu

MDWHNL

Chicago Midway

Tue 1/12

10:00 am-9:20 pm

2 stops15h 20m

Honolulu

Tue 2/2

10:00 pm-4:15 pm

1 stop14h 15m

$560

ChicagoHonolulu

MDW Chicago Midway - HNL Honolulu

MDWHNL

Chicago Midway

Wed 2/3

10:00 am-9:20 pm

2 stops15h 20m

Honolulu

Wed 2/10

3:15 pm-5:50 am

1 stop10h 35m

$560

ChicagoHonolulu

MDW Chicago Midway - HNL Honolulu

MDWHNL

Chicago Midway

Wed 10/21

6:55 am-9:25 pm

2 stops19h 30m

Honolulu

Wed 10/28

1:10 pm-5:55 am

1 stop11h 45m

$560

ChicagoHonolulu

MDW Chicago Midway - HNL Honolulu

MDWHNL

Chicago Midway

Wed 11/4

8:50 am-7:45 pm

2 stops14h 55m

Honolulu

Wed 11/11

3:15 pm-5:55 am

1 stop10h 40m

$560

Quickest round-trip

ChicagoHonolulu

MDW Chicago Midway - HNL Honolulu

MDWHNL

Chicago Midway

Mon 10/19

5:10 am-11:50 am

1 stop11h 40m

Honolulu

Tue 10/27

8:55 pm-2:05 pm

2 stops12h 10m

$560

ChicagoHonolulu

MDW Chicago Midway - HNL Honolulu

MDWHNL

Chicago Midway

Mon 10/26

11:50 am-9:30 pm

2 stops14h 40m

Honolulu

Thu 10/29

1:30 pm-11:50 am

1 stop17h 20m

$560

ChicagoHonolulu

MDW Chicago Midway - HNL Honolulu

MDWHNL

Chicago Midway

Wed 11/4

8:50 am-7:45 pm

2 stops14h 55m

Honolulu

Thu 11/12

3:15 pm-5:55 am

1 stop10h 40m

$560

ChicagoHonolulu

MDW Chicago Midway - HNL Honolulu

MDWHNL

Chicago Midway

Fri 11/6

4:19 pm-12:04 pm

2 stops23h 45m

Honolulu

Thu 12/3

4:45 pm-9:37 am

1 stop12h 52m

$561

ChicagoHonolulu

MDW Chicago Midway - HNL Honolulu

MDWHNL

Chicago Midway

Mon 2/22

6:00 am-2:55 pm

1 stop12h 55m

Honolulu

Thu 3/4

4:30 pm-8:45 am

1 stop12h 15m

$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 $676 to $907.
The lowest price recently found on this route was $560.

What is the cheapest month to fly to Honolulu?

The month of February is, on average, the cheapest month to fly to Honolulu from Chicago Midway Airport, with most prices found around $637. If you’re not able to fly to Honolulu in February, then January is your next best option. Flight prices from Chicago Midway Airport to Honolulu during January average around $654.

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 $743. 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 $1,088.

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

You could potentially save up to 12% 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	$245
Fastest flight time	10h 55m
Direct flights	None

The best one-way flight to Honolulu from Chicago Midway Airport in the past 72 hours is $245. The best round-trip flight deal from Chicago Midway Airport to Honolulu found on momondo in the last 72 hours is $560.

The fastest flight from Chicago Midway Airport to Honolulu takes 10h 55m

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. 10h 55m 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 September 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 $556	Free Cancellation	Rating 8.0 4,196 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.