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$277+ 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 8/24. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — HNL
Jun 26 — Jul 31
Fri 6/26
Fri 7/3
1 adult, Economy
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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 May 27, 2026.

This Delta deal was found by Cheapflights users on 5/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/39:59 am
MDW
-
HNL
2 stops16h 21m
Delta
Wed 9/161:00 pm
HNL
-
MDW
2 stops14h 50m
Delta
Deal found 5/27$661
This Delta deal was found by Cheapflights users on 5/25. 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 10/296:00 am
MDW
-
HNL
1 stop13h 14m
Delta
Sun 11/14:30 pm
HNL
-
MDW
1 stop12h 15m
Delta
Deal found 5/25$665
This Delta deal was found by Cheapflights users on 5/24. 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 8/139:59 am
MDW
-
HNL
2 stops16h 21m
Delta
Thu 8/2010:45 pm
HNL
-
MDW
2 stops14h 16m
Delta
Deal found 5/24$666
This Delta deal was found by Cheapflights users on 5/26. 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.
Sat 9/59:24 am
MDW
-
HNL
2 stops16h 56m
Delta
Sun 9/132:50 pm
HNL
-
MDW
1 stop13h 17m
Delta
Deal found 5/26$667
This Southwest deal was found by Cheapflights users on 5/24. 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.
Tue 8/1812:00 pm
MDW
-
HNL
2 stops14h 15m
Southwest
Sun 8/239:25 pm
HNL
-
MDW
2 stops12h 50m
Southwest
Deal found 5/24$668
This Southwest deal was found by Cheapflights users on 5/26. 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 9/2412:15 pm
MDW
-
HNL
2 stops14h 05m
Southwest
Fri 10/210:25 pm
HNL
-
MDW
2 stops14h 50m
Southwest
Deal found 5/26$670
This Southwest deal was found by Cheapflights users on 5/22. 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.
Fri 8/1410:15 am
MDW
-
HNL
1 stop15h 55m
Southwest
Tue 8/259:25 pm
HNL
-
MDW
2 stops12h 20m
Southwest
Deal found 5/22$673
This Southwest deal was found by Cheapflights users on 5/22. 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.
Tue 12/810:00 am
MDW
-
HNL
1 stop13h 30m
Southwest
Tue 12/223:15 pm
HNL
-
MDW
1 stop10h 25m
Southwest
Deal found 5/22$674
This Delta deal was found by Cheapflights users on 5/25. 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 9/109:20 am
MDW
-
HNL
2 stops16h 27m
Delta
Sun 9/1312:45 pm
HNL
-
MDW
2 stops15h 05m
Delta
Deal found 5/25$676

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 May 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$666
(Delta)

One-way from

$277
(Southwest)

Popular in

July

Cheapest in

January

Average price

$720
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 ($99 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($17 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 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 May 27, 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

Cheapest round-trip

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Thu 10/29

9:30 am-7:24 pm

2 stops14h 54m

Honolulu

Sun 11/1

3:30 pm-9:52 am

1 stop14h 22m

$671

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Thu 9/10

9:20 am-8:47 pm

2 stops16h 27m

Honolulu

Sun 9/13

4:05 pm-12:30 pm

2 stops15h 25m

$676

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Tue 9/1

6:00 am-1:15 pm

1 stop12h 15m

Honolulu

Wed 9/9

12:45 pm-8:42 am

2 stops14h 57m

$685

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Sun 8/30

7:10 am-9:10 pm

2 stops19h 00m

Honolulu

Sun 9/6

8:10 am-4:30 am

1 stop15h 20m

$695
Quickest round-trip

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Sat 9/5

6:05 am-1:10 pm

1 stop12h 05m

Honolulu

Sun 9/13

2:50 pm-9:07 am

1 stop13h 17m

$782

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Sat 7/4

9:17 am-9:14 pm

2 stops16h 57m

Honolulu

Tue 7/14

9:30 pm-6:25 pm

2 stops15h 55m

$797

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Sat 7/4

6:00 am-1:41 pm

1 stop12h 41m

Honolulu

Thu 7/9

9:30 pm-6:25 pm

2 stops15h 55m

$819

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Sat 6/6

11:20 am-9:00 pm

2 stops14h 40m

Honolulu

Fri 6/12

8:10 am-4:40 am

1 stop15h 30m

$832

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Thu 7/30

2:15 pm-9:30 pm

1 stop12h 15m

Honolulu

Sun 8/9

9:30 pm-4:10 pm

2 stops13h 40m

$862

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Mon 8/3

6:05 am-1:20 pm

1 stop12h 15m

Honolulu

Fri 8/7

2:50 pm-9:17 am

1 stop13h 27m

$865

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/25

Showing 1-10 of 19 resultsSorted by cheapest first
1
2

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 May.
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 $429). Flying from Chicago Midway Airport to Honolulu in July is currently the most expensive (average of $909). 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.

How much does it cost to fly round-trip from Chicago Midway Airport to Honolulu?

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 May 27, 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
7.9
Good
4,265 reviews

Entertainment

7.5

Overall

7.9

Crew

8.6

Food

7.0

Comfort

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
7.9
Good
4,265 reviews
Southwest
7.9
Good
4,265 reviews

Entertainment

7.5

Overall

7.9

Crew

8.6

Food

7.0

Comfort

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Delta
7.9
Good
8,423 reviews
Southwest
7.9
Good
4,265 reviews

Entertainment

7.5

Overall

7.9

Crew

8.6

Food

7.0

Comfort

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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 14h 54m. 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 40% 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 $429). Flying from Chicago Midway Airport to Honolulu in July is currently the most expensive (average of $909). 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
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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 May 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$429Average$733FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$553Average$744FlexibilityNo cancel feeOn-time63%

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