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$251+ 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 12/4. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — HNL
Nov 13 — Nov 201
Thu 11/13
Thu 11/20
1 adult, Economy
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Find 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 October 14, 2025.

This Delta deal was found by Cheapflights users on 10/13. 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 12/69:29 amMDW - HNL
2 stops15h 00mDelta
Sun 12/142:26 pmHNL - MDW
2 stops14h 28mDelta
Deal found 10/13$474
This Delta deal was found by Cheapflights users on 10/13. 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 11/136:00 amMDW - HNL
2 stops18h 15mDelta
Sun 11/2311:25 pmHNL - MDW
2 stops14h 53mDelta
Deal found 10/13$484
This Delta deal was found by Cheapflights users on 10/13. 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.
Mon 11/106:00 amMDW - HNL
1 stop13h 01mDelta
Wed 11/192:19 pmHNL - MDW
2 stops14h 42mDelta
Deal found 10/13$506
This Delta deal was found by Cheapflights users on 10/13. 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 11/189:34 amMDW - HNL
2 stops16h 15mDelta
Sun 11/232:19 pmHNL - MDW
2 stops14h 42mDelta
Deal found 10/13$521
This Delta deal was found by Cheapflights users on 10/14. 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.
Mon 11/36:00 amMDW - HNL
1 stop12h 32mDelta
Thu 11/132:19 pmHNL - MDW
2 stops14h 42mDelta
Deal found 10/14$522
This Kiwi.com deal was found by Cheapflights users on 10/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/99:00 amMDW - HNL
1 stop30h 53mMultiple Airlines
Sun 11/1611:13 pmHNL - MDW
2 stops32h 25mMultiple Airlines
Deal found 10/12$529
This Southwest deal was found by Cheapflights users on 10/14. 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 12/158:20 amMDW - HNL
1 stop16h 40mSouthwest
Fri 1/168:05 amHNL - MDW
1 stop12h 20mSouthwest
Deal found 10/14$548

Cheap 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 October 14, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$473
(Delta)

One-way from

$251
(Kiwi.com)

Popular in

July

Cheapest in

January

Average price

$703
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. 13% potential increase in price ($118 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 October 2025
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 October 14, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Honolulu that are best for you.

Fly from

Midway

Fly to

Honolulu

Route

Depart

Return

Price

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Tue 11/11

6:00 am-8:15 pm

2 stops18h 15m

Honolulu

Tue 11/18

2:19 pm-8:54 am

2 stops14h 35m

$554

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Thu 11/13

6:00 am-8:15 pm

2 stops18h 15m

Honolulu

Tue 11/18

2:19 pm-9:01 am

2 stops14h 42m

$554

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Mon 11/3

6:00 am-2:32 pm

1 stop12h 32m

Honolulu

Thu 11/13

2:19 pm-9:01 am

2 stops14h 42m

$562

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Mon 11/3

6:00 am-2:32 pm

1 stop12h 32m

Honolulu

Wed 11/12

2:19 pm-8:54 am

2 stops14h 35m

$562

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Fri 12/5

8:55 pm-3:00 pm

2 stops22h 05m

Honolulu

Fri 12/12

8:00 am-1:30 am

1 stop13h 30m

$594

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Fri 11/14

9:41 am-9:49 pm

2 stops16h 08m

Honolulu

Mon 11/17

2:19 pm-9:52 am

2 stops15h 33m

$597

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Fri 12/5

9:59 am-9:48 pm

2 stops15h 49m

Honolulu

Mon 12/15

2:26 pm-9:19 am

2 stops14h 53m

$597

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Sun 11/9

6:00 am-3:01 pm

1 stop13h 01m

Honolulu

Wed 11/19

2:19 pm-8:54 am

2 stops14h 35m

$599

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Mon 12/15

5:15 am-4:10 pm

2 stops14h 55m

Honolulu

Fri 1/16

9:55 pm-4:40 pm

2 stops14h 45m

$603

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Thu 12/4

9:59 am-9:48 pm

2 stops15h 49m

Honolulu

Sun 12/14

5:37 pm-12:34 pm

2 stops14h 57m

$610

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/14

Showing 1-10 of 20 results
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 October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice 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 $362). Flying from Chicago Midway Airport to Honolulu in July is currently the most expensive (average of $886). 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 October 14, 2025.
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
4,238 reviews

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,238 reviews
Southwest
8.0
Very good
4,238 reviews

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
8.0
Very good
7,975 reviews
Southwest
8.0
Very good
4,238 reviews

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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 18h 15m. 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 $427, 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 41% 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 $362). Flying from Chicago Midway Airport to Honolulu in July is currently the most expensive (average of $886). 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?

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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 October 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$427Average$596FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$553Average$760FlexibilityNo cancel feeOn-time63%

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