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 1 as of August 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.

$252 Cheap Flights from Chicago Midway Airport to Honolulu in 2026

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.

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

16h 00m1 stop San Jose

8:55 pm - 3:45 pmHNL Honolulu-MDW Chicago Midway

13h 50m1 stop Phoenix Sky Harbor Intl

$629Southwest

Mon, Sep 21 - Mon, Oct 5

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

16h 00m1 stop San Jose

12:05 pm - 5:40 amHNL Honolulu-MDW Chicago Midway

12h 35m1 stop Ontario

$629Southwest

Mon, Sep 21 - Mon, Oct 5

10:05 am - 7:45 pmMDW Chicago Midway-HNL Honolulu

13h 40m1 stop Oakland

10:15 pm - 2:10 pmHNL Honolulu-MDW Chicago Midway

11h 55m1 stop Las Vegas Harry Reid Intl

$629Southwest

Mon, Nov 9 - Mon, Nov 16

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

16h 00m1 stop San Jose

8:15 am - 5:00 amHNL Honolulu-MDW Chicago Midway

15h 45m1 stop San Jose

$629Southwest

Thu, Sep 17 - Thu, Sep 24

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

16h 00m1 stop San Jose

9:25 pm - 4:35 pmHNL Honolulu-MDW Chicago Midway

14h 10m1 stop Los Angeles

$629Southwest

Thu, Sep 17 - Tue, Sep 22

2:55 pm - 9:25 pmMDW Chicago Midway-HNL Honolulu

11h 30m1 stop San Diego

8:15 am - 5:00 amHNL Honolulu-MDW Chicago Midway

15h 45m1 stop San Jose

$629Southwest

Thu, Oct 22 - Fri, Oct 23

10:20 am - 7:45 pmMDW Chicago Midway-HNL Honolulu

13h 25m1 stop Oakland

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

14h 15m1 stop Los Angeles

$629Southwest

Mon, Jan 18 - Mon, Jan 25

5:50 am - 1:25 pmMDW Chicago Midway-HNL Honolulu

11h 35m1 stop Las Vegas Harry Reid Intl

10:05 pm - 5:15 pmHNL Honolulu-MDW Chicago Midway

15h 10m1 stop Los Angeles

$629Southwest

Wed, Nov 18 - Tue, Dec 1

9:29 am - 9:12 pmMDW Chicago Midway-HNL Honolulu

16h 43m2 stops Detroit Metropolitan Wayne County Los Angeles

12:35 pm - 8:48 amHNL Honolulu-MDW Chicago Midway

15h 13m2 stops Los Angeles Minneapolis St Paul

$636Delta

Tue, Sep 15 - Tue, Sep 22

9:24 am - 9:20 pmMDW Chicago Midway-HNL Honolulu

16h 56m2 stops Detroit Metropolitan Wayne County Los Angeles

2:50 pm - 9:07 amHNL Honolulu-MDW Chicago Midway

13h 17m1 stop Detroit Metropolitan Wayne County

$656Delta

Tue, Sep 1 - Wed, Sep 9

Cheap last minute flights

Enter your travel dates to find the best prices.

2:50 pm - 9:20 pmMDW Chicago Midway-HNL Honolulu

11h 30m1 stop San Diego

8:10 am - 11:45 pmHNL Honolulu-MDW Chicago Midway

10h 35m1 stop San Diego

$742Southwest

Mon, Aug 10 - Fri, Aug 21

1:50 pm - 9:15 pmMDW Chicago Midway-HNL Honolulu

12h 25m2 stops Phoenix Sky Harbor Intl Los Angeles

8:10 am - 11:45 pmHNL Honolulu-MDW Chicago Midway

10h 35m1 stop San Diego

$748Southwest

Mon, Aug 10 - Fri, Aug 21

6:50 am - 1:20 pmMDW Chicago Midway-HNL Honolulu

11h 30m1 stop Las Vegas Harry Reid Intl

8:00 am - 5:40 amHNL Honolulu-MDW Chicago Midway

16h 40m1 stop Las Vegas Harry Reid Intl

$757Southwest

Tue, Aug 11 - Tue, Aug 18

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

15h 50m2 stops Las Vegas Harry Reid Intl San Jose

8:00 am - 5:40 amHNL Honolulu-MDW Chicago Midway

16h 40m1 stop Las Vegas Harry Reid Intl

$763Southwest

Tue, Aug 11 - Tue, Aug 18

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

15h 50m1 stop San Jose

8:10 am - 4:30 amHNL Honolulu-MDW Chicago Midway

15h 20m1 stop San Diego

$780Southwest

Tue, Aug 11 - Tue, Aug 18

10:05 am - 9:20 pmMDW Chicago Midway-HNL Honolulu

16h 15m1 stop San Diego

8:55 pm - 1:20 pmHNL Honolulu-MDW Chicago Midway

11h 25m1 stop Phoenix Sky Harbor Intl

$780Southwest

Tue, Aug 11 - Thu, Aug 13

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

10h 55m1 stop Phoenix Sky Harbor Intl

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

12h 50m1 stop Ontario

$780Southwest

Sun, Aug 9 - Mon, Aug 10

12:20 pm - 9:15 pmMDW Chicago Midway-HNL Honolulu

13h 55m1 stop Los Angeles

8:55 pm - 1:20 pmHNL Honolulu-MDW Chicago Midway

11h 25m1 stop Phoenix Sky Harbor Intl

$780Southwest

Tue, Aug 11 - Thu, Aug 13

6:05 am - 1:20 pmMDW Chicago Midway-HNL Honolulu

12h 15m1 stop Atlanta Hartsfield-Jackson

4:18 pm - 12:39 pmHNL Honolulu-MDW Chicago Midway

15h 21m2 stops Minneapolis St Paul Detroit Metropolitan Wayne County

$949Delta

Thu, Aug 13 - Sat, Aug 22

9:24 am - 7:11 pmMDW Chicago Midway-HNL Honolulu

14h 47m2 stops Detroit Metropolitan Wayne County Seattle/Tacoma Intl

4:18 pm - 12:39 pmHNL Honolulu-MDW Chicago Midway

15h 21m2 stops Minneapolis St Paul Detroit Metropolitan Wayne County

$954Delta

Thu, Aug 13 - Sat, Aug 22

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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

Sep 21

MDW10:15 amChicago Midway

16h 00m

1 stop

HNL9:15 pmHonolulu

Oct 5

HNL8:55 pmHonolulu

13h 50m

1 stop

MDW3:45 pmChicago Midway

$629

Southwest

Sep 21

MDW10:15 amChicago Midway

16h 00m

1 stop

HNL9:15 pmHonolulu

Oct 5

HNL10:25 pmHonolulu

12h 20m

2 stops

MDW3:45 pmChicago Midway

$635

Southwest

Oct 1

MDW2:55 pmChicago Midway

11h 30m

1 stop

HNL9:25 pmHonolulu

Oct 8

HNL12:05 pmHonolulu

12h 35m

1 stop

MDW5:40 amChicago Midway

$639

Delta flights from Chicago Midway Airport to Honolulu

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

Delta

Sep 15

MDW9:29 amChicago Midway

16h 43m

2 stops

HNL9:12 pmHonolulu

Sep 22

HNL12:35 pmHonolulu

15h 13m

2 stops

MDW8:48 amChicago Midway

$636

Delta

Sep 1

MDW9:24 amChicago Midway

16h 56m

2 stops

HNL9:20 pmHonolulu

Sep 9

HNL2:50 pmHonolulu

13h 17m

1 stop

MDW9:07 amChicago Midway

$656

Delta

Sep 1

MDW9:24 amChicago Midway

16h 56m

2 stops

HNL9:20 pmHonolulu

Sep 9

HNL1:00 pmHonolulu

14h 48m

2 stops

MDW8:48 amChicago Midway

$661

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 9/21

10:15 am-9:15 pm

1 stop16h 00m

Honolulu

Mon 10/5

8:55 pm-3:45 pm

1 stop13h 50m

$629

ChicagoHonolulu

MDW Chicago Midway - HNL Honolulu

MDWHNL

Chicago Midway

Mon 9/21

10:15 am-9:15 pm

1 stop16h 00m

Honolulu

Mon 10/5

12:05 pm-5:40 am

1 stop12h 35m

$629

Quickest round-trip

ChicagoHonolulu

MDW Chicago Midway - HNL Honolulu

MDWHNL

Chicago Midway

Mon 11/9

10:05 am-7:45 pm

1 stop13h 40m

Honolulu

Mon 11/16

10:15 pm-2:10 pm

1 stop11h 55m

$629

ChicagoHonolulu

MDW Chicago Midway - HNL Honolulu

MDWHNL

Chicago Midway

Thu 9/17

10:15 am-9:15 pm

1 stop16h 00m

Honolulu

Thu 9/24

8:15 am-5:00 am

1 stop15h 45m

$629

ChicagoHonolulu

MDW Chicago Midway - HNL Honolulu

MDWHNL

Chicago Midway

Thu 9/17

10:15 am-9:15 pm

1 stop16h 00m

Honolulu

Tue 9/22

9:25 pm-4:35 pm

1 stop14h 10m

$629

ChicagoHonolulu

MDW Chicago Midway - HNL Honolulu

MDWHNL

Chicago Midway

Thu 10/22

2:55 pm-9:25 pm

1 stop11h 30m

Honolulu

Fri 10/23

8:15 am-5:00 am

1 stop15h 45m

$629

ChicagoHonolulu

MDW Chicago Midway - HNL Honolulu

MDWHNL

Chicago Midway

Mon 1/18

10:20 am-7:45 pm

1 stop13h 25m

Honolulu

Mon 1/25

10:00 pm-4:15 pm

1 stop14h 15m

$629

ChicagoHonolulu

MDW Chicago Midway - HNL Honolulu

MDWHNL

Chicago Midway

Wed 11/18

5:50 am-1:25 pm

1 stop11h 35m

Honolulu

Tue 12/1

10:05 pm-5:15 pm

1 stop15h 10m

$629

ChicagoHonolulu

MDW Chicago Midway - HNL Honolulu

MDWHNL

Chicago Midway

Tue 9/15

9:29 am-9:12 pm

2 stops16h 43m

Honolulu

Tue 9/22

12:35 pm-8:48 am

2 stops15h 13m

$636

ChicagoHonolulu

MDW Chicago Midway - HNL Honolulu

MDWHNL

Chicago Midway

Tue 9/1

9:24 am-9:20 pm

2 stops16h 56m

Honolulu

Wed 9/9

2:50 pm-9:07 am

1 stop13h 17m

$656

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 typical for flights on this route.

Typical prices usually range from $621 to $728.
The lowest price recently found on this route was $629.

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 August is your next best option. Flight prices from Chicago Midway Airport to Honolulu during August average around $639.

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 $747. 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 $1,087.

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

You could potentially save up to 41% 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.

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 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 1 as of August 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 $553	Free Cancellation	Rating 8.0 4,216 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.