MDW - HNL

$216 Find Cheap Flights from Chicago Midway Airport to Honolulu

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to Honolulu departing on 1/19. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags

Search hundreds of travel sites at once for deals on flights to Honolulu

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Honolulu, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Honolulu, as well as popular online travel agencies
In the last 7 days travelers have searched 46,646,933 times on KAYAK, and here is why:

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Cheap Flight Deals from Chicago Midway Airport to Honolulu (MDW-HNL)

 
These are the cheapest deals for flights from Midway to Honolulu currently on KAYAK along with options from the most popular airlines KAYAK users selected for this route. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Recent round-trip flight deals from Midway to Honolulu

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Midway to Honolulu.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
8:40 am - 5:30 pmMDW-HNL
12h 50m1 stop
10:30 am - 10:35 amHNL-MDW
20h 05m2 stops
$409Southwest
Find Deal
Mon, Feb 3 - Fri, Feb 7
10:19 am - 10:01 pmMDW-HNL
15h 42m2 stops
4:50 pm - 8:54 amHNL-MDW
12h 04m1 stop
$427Delta
Find Deal
Sun, Jan 12 - Wed, Jan 22
9:34 am - 9:55 pmMDW-HNL
16h 21m2 stops
1:54 pm - 8:54 amHNL-MDW
15h 00m2 stops
$432Delta
Find Deal
Tue, Jan 21 - Wed, Jan 29
6:00 am - 2:56 pmMDW-HNL
12h 56m1 stop
4:50 pm - 8:54 amHNL-MDW
12h 04m1 stop
$433Delta
Find Deal
Tue, Jan 21 - Wed, Jan 29
9:34 am - 7:21 pmMDW-HNL
13h 47m2 stops
4:50 pm - 8:54 amHNL-MDW
12h 04m1 stop
$438Delta
Find Deal
Mon, Jan 13 - Mon, Jan 20
9:34 am - 9:55 pmMDW-HNL
16h 21m2 stops
4:50 pm - 12:46 pmHNL-MDW
15h 56m2 stops
$443Delta
Find Deal
Mon, Jan 13 - Mon, Jan 20
9:34 am - 10:01 pmMDW-HNL
16h 27m2 stops
4:50 pm - 8:54 amHNL-MDW
12h 04m1 stop
$449Delta
Find Deal
Sat, Jan 11 - Mon, Jan 20
6:00 am - 2:56 pmMDW-HNL
12h 56m1 stop
4:50 pm - 8:54 amHNL-MDW
12h 04m1 stop
$462Delta
Find Deal
Tue, Jan 28 - Fri, Feb 7
7:00 am - 6:45 pmMDW-HNL
15h 45m2 stops
8:20 am - 10:40 pmHNL-MDW
10h 20m1 stop
$469Southwest
Find Deal
Thu, Jan 16 - Thu, Jan 23
8:41 pm - 2:15 pmMDW-HNL
21h 34m2 stops
9:40 pm - 8:14 pmHNL-MDW
18h 34m2 stops
Sun, Jan 5 - Sun, Jan 12

Flights from Midway to Honolulu - Travel Insights & Trends

Get data-powered insights and trends into flights from Midway to Honolulu to help you find the cheapest flights, the best time to fly and much more.

What’s the cheapest day of the week to fly from Chicago Midway Airport to Honolulu?

The average price of all flights from Chicago Midway Airport to Honolulu clicked on KAYAK for each day over the last 12 months.
If your flying dates are flexible, you should consider flying to Honolulu on a Thursday, as we generally find the cheapest rates on that day for this route. On the other hand, Saturday is the most expensive day to fly from Chicago Midway Airport to Honolulu. For your return ticket, we recommend flying on a Monday and avoiding Fridays for the best deals.

What is the cheapest month to fly from Chicago Midway Airport to Honolulu?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from Chicago Midway Airport to Honolulu, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.
The cheapest month for flights from Chicago Midway Airport to Honolulu is January, where tickets cost $590 on average. On the other hand, the most expensive months are December and June, where the average cost of tickets is $1,043 and $1,000 respectively.

How far in advance should I book a flight from Chicago Midway Airport to Honolulu?

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from Chicago Midway Airport to Honolulu, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
To get a below average price on the flight from Chicago Midway Airport to Honolulu, you should book around 3 days before departure. For the absolute cheapest price, our data suggests you should book 131 days before departure.

Good to know

Low season

April

High season

January

Cheapest flight

$216
Best time to beat the crowds with an average 14% drop in price.
Most popular time to fly and prices are also 34% lower on average.
Flight from Chicago Midway Airport to Honolulu

When to book flights from Midway to Honolulu

Are your dates flexible? Find out the best times to travel from Midway to Honolulu based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Chicago Midway Airport to Honolulu flights

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

    In the last 3 days, the lowest price for a flight from Chicago Midway Airport to Honolulu was $216 for a one-way ticket and $409 for a round-trip.

  • Do I need a passport to fly between Chicago Midway Airport and Honolulu?

    Even though you are not required to have a passport, keep in mind that an official ID is needed to board the airplane.

  • Which airports will I be using when flying from Chicago Midway Airport to Honolulu?

    Chicago Midway Airport and Honolulu are both served by 1 main airport. You will leave Chicago Midway Airport from Chicago Midway and will be arriving at Honolulu.

  • Which aircraft models fly most regularly from Chicago Midway Airport to Honolulu?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Chicago Midway Airport to Honolulu?

    SkyTeam is the only airline alliance operating flights between Chicago Midway Airport and Honolulu.

  • Which is the best airline for flights from Chicago to Honolulu, Southwest or Delta?

    The two airlines most popular with KAYAK users for flights from Chicago to Honolulu are Southwest and Delta. With an average price for the route of $651 and an overall rating of 8.1, Southwest is the most popular choice. Delta is also a great choice for the route, with an average price of $902 and an overall rating of 8.0.

  • How does KAYAK find such low prices on flights from Chicago Midway Airport to Honolulu?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago Midway Airport to Honolulu.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago Midway Airport to Honolulu?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Honolulu from Chicago Midway Airport is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago Midway Airport to Honolulu?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Honolulu with an airline and back to Chicago Midway Airport with another airline. Booking your flights between Chicago Midway Airport and HNL can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago Midway Airport to Honolulu?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Honolulu from Chicago Midway Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top airlines flying from Midway to Honolulu

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Honolulu. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Midway to Honolulu? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.1
SouthwestOverall score based on 5005 reviews
7.2Food
7.7Entertainment
8.2Boarding
8.7Crew
8.1Comfort
Airline reviews

This was a nicer flight - not fully booked and so we were able to spread out.

10.0 ExcellentJohn, Nov 2024LAS - IND
Read more Southwest reviews

This was a nicer flight - not fully booked and so we were able to spread out.

We had a nice flight. Boarding was easy, our seats were comfortable and the on board service was pleasant.

Planes are aged. The wifi is unreliable and on many fights, no-existent. The flight attendants were very good.

I had a wonderful flight, but the only thing that annoyed me was how crowded TSA was. I still believe airports and all planes work together to bunch everyone together to drive up cost.

Easy to book and to get check in and get on and off.

The last 30 min or so, they put the heat on full. We thought we were being basted.

Excellent experience. WiFi worked on this leg of My trip

Flight was great, but golf bag never made it until later in the day. Even though I had a nonstop flight it was placed on a different one. They made it right with flight credits and I was able to get it the same day.

It seems as though the provisions are even less. Although SWA used to be an economy Airline, that isn't really the case anymore. I paid over $700. for a round trip to Denver and I could have flown just about any airline for the price. The drinks are now in a 6-ounce cup and with ice I'm sure a can would fill more than 2 cups. However, I am very proud of SWA for using paper rather than continuing to contribute to the millions of plastic cups being used each day. I've thought of this fr many years and am so glad to see it come to fruition, if not by only SWA so far.

Exceptional crew! Friendly and professional. Pleasant attitude and treated everyone with respect.

I sat in comfort plus. It was fine. Seats were comfortable. I got drinks and snacks.

Crew was nice. Flight was timely. Seats could be better as well as the food considering it’s first class.

Left on time and arrived early this extending our 31 minute transfer. Bags made it also!

Good and consistent Printer in lounge did not work for me :(

Most of my discomfort was going through TSA. However, the Delta seats had inadequate leg room and I tried my very best to connect to the wi-fi and it was a cumbersome process that finally gave me the info that I needed to sign in AFTER I had completed the flight...Why make it so difficult to use? That said I really really appreciate the pilot taking a little extra time to avoid a bad storm area and both landings in Atlanta and Orlando were flawless to my delight!!!

Delayed in taking off because no flight crew. The in seat entertainment was working properly.

I upgraded to first class only to find out that I still had no access to the sky lounge without a sky miles card or AmEx (something that should be emphasized outside of the fine print!) Also, no food or drink service provided during the flight, so I basically paid 4x more just for “free” checked baggage and a bigger seat. Not worth it.

Delta was really good about being transparent with why we were delayed it’s just that’s the plane was really old and outdated and a lot of the comfort and amenities we know Delta to have did not shine through

Bottom seat cushion is almost non existent. Very uncomfortable seat.

Delta was great the entertainment was outdated. Screen was very small and didn’t work.

Book cheap flights from Chicago to Honolulu

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Chicago to Honolulu found on KAYAK in the last 72 hours.
1/19Sun
2 stopsDelta
16h 21mMDW-HNL
$216
1/10Fri
1 stopSouthwest
18h 45mMDW-HNL
$222
1/24Fri
2 stopsDelta
15h 42mMDW-HNL
$227
1/19Sun
1 stopSouthwest
13h 00mMDW-HNL
$232
1/24Fri
2 stopsSouthwest
16h 20mMDW-HNL
$237
1/4Sat
1 stopSouthwest
13h 25mMDW-HNL
$251
2/20Thu
2 stopsDelta
15h 42mMDW-HNL
$256
1/14Tue
1 stopSouthwest
13h 00mMDW-HNL
$272
1/20Mon
3 stopsWestJet
40h 23mMDW-HNL
$463
1/18Sat
3 stopsWestJet
38h 05mMDW-HNL
$464

Search by stops

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Last minute flights from Midway to Honolulu

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Chicago to Honolulu that are departing in the next 10 days.
11/25Mon
multi-stopSouthwest
13h 00mMDW-HNL
11/27Wed
multi-stopSouthwest
12h 30mHNL-MDW
$664
11/25Mon
multi-stopSouthwest
17h 10mMDW-HNL
11/27Wed
multi-stopSouthwest
13h 00mHNL-MDW
$669
11/25Mon
multi-stopSouthwest
17h 20mMDW-HNL
11/27Wed
multi-stopSouthwest
11h 35mHNL-MDW
$674
11/23Sat
multi-stopSouthwest
16h 25mMDW-HNL
11/25Mon
multi-stopSouthwest
12h 30mHNL-MDW
$678
11/23Sat
multi-stopSouthwest
16h 30mMDW-HNL
11/25Mon
multi-stopSouthwest
12h 30mHNL-MDW
$703
11/22Fri
multi-stopDelta
13h 14mMDW-HNL
12/12Thu
multi-stopDelta
10h 11mHNL-MDW
$997
11/22Fri
multi-stopDelta
16h 20mMDW-HNL
12/12Thu
multi-stopDelta
10h 11mHNL-MDW
$1,002
11/22Fri
multi-stopDelta
17h 13mMDW-HNL
12/12Thu
multi-stopDelta
14h 11mHNL-MDW
$1,011
11/22Fri
multi-stopDelta
13h 14mMDW-HNL
11/29Fri
multi-stopDelta
11h 55mHNL-MDW
$1,364
11/23Sat
multi-stopWestJet
35h 07mMDW-HNL
11/25Mon
multi-stopWestJet
22h 52mHNL-MDW
$1,845

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Everything you need to know for your flight from Midway to Honolulu

Information on your arrival and departure airports

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