HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Honolulu

$222+ Cheap flights from Midway (MDW) to Honolulu (HNL)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 4/15. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — HNL
Apr 1 — Apr 81
Wed 4/1
Wed 4/8
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Midway to Honolulu with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Midway to Honolulu

Cheapest flights from Midway to Honolulu
Explore the most affordable flight options available from Midway to Honolulu. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 2, 2026.

This Southwest deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/1510:20 am
MDW
-
HNL
1 stop12h 20m
Southwest
Wed 4/229:25 pm
HNL
-
MDW
1 stop10h 40m
Southwest
Deal found 3/1$411
This Southwest deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/95:25 am
MDW
-
HNL
1 stop11h 50m
Southwest
Wed 4/2211:10 am
HNL
-
MDW
1 stop13h 15m
Southwest
Deal found 2/27$420
This Delta deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/76:00 am
MDW
-
HNL
1 stop13h 00m
Delta
Thu 4/233:15 pm
HNL
-
MDW
1 stop12h 32m
Delta
Deal found 3/1$424
This Delta deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/149:27 am
MDW
-
HNL
2 stops16h 53m
Delta
Tue 4/213:15 pm
HNL
-
MDW
1 stop12h 32m
Delta
Deal found 3/1$430
This Southwest deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/209:45 pm
MDW
-
HNL
1 stop17h 05m
Southwest
Mon 5/411:55 am
HNL
-
MDW
1 stop12h 30m
Southwest
Deal found 2/28$431
This Southwest deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/1610:05 am
MDW
-
HNL
2 stops12h 35m
Southwest
Thu 4/239:25 pm
HNL
-
MDW
1 stop15h 30m
Southwest
Deal found 3/2$437
This Delta deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/99:30 am
MDW
-
HNL
2 stops16h 23m
Delta
Thu 4/163:15 pm
HNL
-
MDW
1 stop12h 32m
Delta
Deal found 3/1$448
This Southwest deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/79:45 pm
MDW
-
HNL
1 stop17h 05m
Southwest
Tue 5/121:00 pm
HNL
-
MDW
1 stop11h 50m
Southwest
Deal found 2/27$450

Find flight deals from Midway to Honolulu

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Honolulu (HNL). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated March 2, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$411
(Southwest)

One-way from

$222
(Delta)

Popular in

July

Cheapest in

January

Average price

$778
Provider with most accurate pricing for Chicago Midway-Honolulu flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago Midway-Honolulu flights.
Search Deals
From Chicago Midway to Honolulu
Search Deals
One-way flight from Chicago Midway to Honolulu
Search Deals
Highest demand for flights based on searches. 12% potential increase in price ($108 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Honolulu that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated March 2, 2026.
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

Tue 5/12

9:22 am-9:06 pm

2 stops16h 44m

Honolulu

Tue 5/19

4:06 pm-12:42 pm

2 stops15h 36m

$435

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Thu 4/9

8:35 am-9:05 pm

2 stops17h 30m

Honolulu

Wed 4/22

11:10 am-5:00 am

2 stops12h 50m

$442

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Thu 4/9

9:30 am-8:53 pm

2 stops16h 23m

Honolulu

Thu 4/16

3:15 pm-8:47 am

1 stop12h 32m

$448

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Fri 5/1

9:45 pm-9:50 am

1 stop17h 05m

Honolulu

Mon 5/4

1:00 pm-11:15 am

1 stop17h 15m

$537

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Thu 5/28

9:45 pm-9:50 am

1 stop17h 05m

Honolulu

Mon 6/1

8:15 am-5:00 am

1 stop15h 45m

$574

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Thu 3/12

11:50 am-9:00 pm

2 stops14h 10m

Honolulu

Wed 3/18

11:25 am-5:00 am

2 stops12h 35m

$727

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Tue 3/10

9:30 am-8:53 pm

2 stops16h 23m

Honolulu

Tue 3/17

4:20 pm-12:29 pm

2 stops15h 09m

$729

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Fri 3/6

10:05 am-10:00 pm

1 stop15h 55m

Honolulu

Wed 3/11

8:10 am-4:35 am

1 stop15h 25m

$741

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Sun 4/12

9:35 am-8:53 pm

2 stops16h 18m

Honolulu

Thu 4/16

12:25 pm-8:47 am

2 stops15h 22m

$765

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Sun 4/26

9:27 am-9:45 pm

2 stops17h 18m

Honolulu

Sun 5/3

4:10 pm-12:43 pm

2 stops15h 33m

$832

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/26

Showing 1-10 of 21 resultsSorted by cheapest first
1
2
3

Compare providers for flights from Midway to Honolulu

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Midway to Honolulu in March.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago Midway Airport-Honolulu flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-Honolulu flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Honolulu flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago Midway Airport-Honolulu flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago Midway Airport-Honolulu flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Midway to Honolulu

Have a flexible travel schedule? Discover the best time to fly to Honolulu from Midway with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago Midway Airport to Honolulu

What is the cheapest month to book a flight from Chicago Midway Airport to Honolulu?

Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Honolulu (average of $310). Flying from Chicago Midway Airport to Honolulu in November is currently the most expensive (average of $843). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

Reviews of airlines servicing Honolulu

Get insights into the airlines that provide service to Honolulu. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Honolulu. Reviews last updated March 2, 2026.
Read reviews from past customers who have flown Southwest and Delta from Chicago Midway Airport to Honolulu. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,306 reviews

Crew

8.6

Overall

8.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Feb 2026

DEN - BDL

Weird they cancelled a direct and rerouted me on a connecting flight to get in 10 hours later. What was the point? Crew and flight were great, but not sure what's going on with Southwest.
Southwest
8.0
Very good
4,306 reviews
Southwest
8.0
Very good
4,306 reviews

Crew

8.6

Overall

8.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Feb 2026

DEN - BDL

Weird they cancelled a direct and rerouted me on a connecting flight to get in 10 hours later. What was the point? Crew and flight were great, but not sure what's going on with Southwest.
Delta
7.9
Good
8,237 reviews
Southwest
8.0
Very good
4,306 reviews

Crew

8.6

Overall

8.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Feb 2026

DEN - BDL

Weird they cancelled a direct and rerouted me on a connecting flight to get in 10 hours later. What was the point? Crew and flight were great, but not sure what's going on with Southwest.

Related info for your journey

Find useful and relevant information for your journey from Midway to Honolulu. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Honolulu from Chicago Midway?

    Honolulu (HNL), located 4.4 mi from the city center, is the airport you fly into when you book flights from Chicago Midway to Honolulu. 2 airlines have flights to Honolulu from Chicago Midway on a regular basis. Booking flights from Chicago Midway to Honolulu should not be difficult; the airport handles an average of 0 inbound flights from Chicago Midway per day.

  • How long is the flight from Chicago Midway Airport to Honolulu?

    Departing from Chicago Midway Airport to Honolulu will take you 16h 44m. Chicago Midway Airport and Honolulu are separated by a distance of 4243 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines flying from Chicago Midway Airport to Honolulu round-trip?

    Delta, at $429, was found to be the cheapest airline from Chicago Midway Airport to Honolulu. An alternate airline flying to your destination would be Southwest. Delta is currently priced 42% below the average price you’ll pay for this route.

  • Can I find deals for flights from Midway to Honolulu that include hotel bookings?

    Yes. In addition to deals on Midway to Honolulu flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Honolulu?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Honolulu.

  • Can I find deals for business class flights from Midway to Honolulu?

    Yes. Cheapflights offers flight deals from Midway to Honolulu by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago Midway Airport to Honolulu?

    Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Honolulu (average of $310). Flying from Chicago Midway Airport to Honolulu in November is currently the most expensive (average of $843). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Honolulu?

Book flights to Honolulu if you plan to visit one of these locations
Aiea

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Midway to Honolulu

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Honolulu flights
O'Hare Intl to Kahului flights
O'Hare Intl to Kailua-Kona flights
O'Hare Intl to Lihue flights
Midway to Lihue flights

Top 2 airlines flying from Midway to Honolulu

Discover the top 2 airlines that operate flights from Midway to Honolulu. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated March 2, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$429Average$614FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$553Average$758FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.
Site
©2026 Cheapflights