MDW - HNL

$280 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 2/20. 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
1 adult, Economy, 0 bags

KAYAK searches 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
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Everything you should know

Cheapest round-trip
$456
Typical prices: $472-$600
Delta
Mon 1/26Fri 2/6
MDW - HNL • 1 stop
Cheapest one-way
$280
Delta
Fri 2/20
MDW - HNL • 1 stop
When to travel
January
Cheapest • 42% price drop
June
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Honolulu!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Midway to Honolulu (MDW-HNL)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to Honolulu that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Midway to Honolulu

Mon, Jan 26 - Fri, Feb 6
Delta Logo
6:00 am - 3:10 pm
MDW
-
HNL
13h 10m1 stop
Delta Logo
4:45 pm - 11:05 am
HNL
-
MDW
14h 20m2 stops
$456Delta
Sun, Feb 8 - Sun, Mar 8
Delta Logo
6:00 am - 3:10 pm
MDW
-
HNL
13h 10m1 stop
Delta Logo
4:20 pm - 8:50 am
HNL
-
MDW
11h 30m1 stop
$460Delta
Mon, Jan 26 - Fri, Feb 6
Delta Logo
9:33 am - 9:28 pm
MDW
-
HNL
15h 55m2 stops
Delta Logo
9:35 pm - 4:16 pm
HNL
-
MDW
14h 41m2 stops
$462Delta
Sun, Feb 8 - Thu, Feb 12
Multiple Airlines Logo
7:30 am - 12:48 pm
MDW
-
HNL
33h 18m2 stops
Multiple Airlines Logo
10:15 am - 8:00 pm
HNL
-
MDW
29h 45m1 stop
$465Multiple Airlines
Sun, Feb 8 - Thu, Feb 12
Multiple Airlines Logo
7:30 am - 8:51 pm
MDW
-
HNL
41h 21m2 stops
Multiple Airlines Logo
10:15 am - 8:00 pm
HNL
-
MDW
29h 45m1 stop
$466Multiple Airlines
Tue, Jan 20 - Thu, Jan 29
Delta Logo
6:00 am - 9:28 pm
MDW
-
HNL
19h 28m2 stops
Delta Logo
4:44 pm - 8:52 am
HNL
-
MDW
12h 08m1 stop
$467Delta
Tue, Jan 20 - Mon, Jan 26
Delta Logo
6:00 am - 9:28 pm
MDW
-
HNL
19h 28m2 stops
Delta Logo
4:44 pm - 8:52 am
HNL
-
MDW
12h 08m1 stop
$468Delta
Thu, Feb 19 - Mon, Feb 23
Delta Logo
6:00 am - 3:11 pm
MDW
-
HNL
13h 11m1 stop
Delta Logo
4:45 pm - 8:54 am
HNL
-
MDW
12h 09m1 stop
$470Delta
Sat, Jan 31 - Sun, Feb 8
Delta Logo
11:45 am - 9:28 pm
MDW
-
HNL
13h 43m2 stops
Delta Logo
1:55 pm - 8:52 am
HNL
-
MDW
14h 57m2 stops
$471Delta
Sun, Feb 8 - Sun, Mar 8
Delta Logo
6:00 am - 3:10 pm
MDW
-
HNL
13h 10m1 stop
Delta Logo
4:20 pm - 8:50 am
HNL
-
MDW
11h 30m1 stop
$472Delta
Booking Insights

KAYAK's insights & trends for Midway to Honolulu flights

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.

How much is a round-trip flight from Chicago Midway Airport to Honolulu?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago Midway Airport to Honolulu departing in January.

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 round-trip 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 $429 (return) on average. On the other hand, the most expensive months are July and June, where the average cost of round-trip tickets is $913 and $863 respectively.

Good to know

Low seasonNovember
Cheapest flight$280
Best time to beat the crowds but there is an average 12% increase in price.
Most popular time to fly with an average 15% increase in price.
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 $280 for a one-way ticket and $456 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 $765 and an overall rating of 8.0, Southwest is the most popular choice. Delta is also a great choice for the route, with an average price of $613 and an overall rating of 7.9.

  • 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.

Reviews of the 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.
8.0
SouthwestOverall score based on 4256 reviews
8.0Comfort
7.5Entertainment
8.1Boarding
8.6Crew
7.0Food
Airline reviews

Check-in, Boarding and flight were smooth. All the employees and crew was very nice and funny. They gave the kids crayons and workbooks to keep them occupied which was a big win. I’ve flown Southwest many times and that’s the first time I’ve seen that and it is a great addition.

10.0 ExcellentAnonymous, Dec 2025
DAL - CHS
Read more Southwest reviews

Check-in, Boarding and flight were smooth. All the employees and crew was very nice and funny. They gave the kids crayons and workbooks to keep them occupied which was a big win. I’ve flown Southwest many times and that’s the first time I’ve seen that and it is a great addition.

Flight was on time. Wi-fi was a little spotty/slow. Boarding and exit were efficient.

Okay, not wonderful. Short flight. Wi-fi didn't work properly. Stuck waiting for a gate to open upon arrival for 20 or so minutes.

They sent a notice that they were boarding an hour early. We had to leave the club and run to the gate. They said sorry, that came from corporate and was a mistake. They did not have enough seating because the flight before it had not taken off on time. They moved our gate and delayed it for an hour.

The boarding and seat assignment system no longer works for me, but I know it is being replaced. Otherwise, I am good with the overall experience.

The lead steward kept singing about "San Francisco" and hotel California---more annoying than humorous....needs work. Flight was smooth and on time.

Still a fan of open seating. Flight was on schedule and arrived on time. The 737 MAX is very comfortable.

Airline travel is always too cramped to really be pleasant, but the cabin crew on this flight did a pretty good job of making up for it by putting on some music during boarding and sprinkling a few funny remarks into the safety briefing and announcements, and just generally being friendly and helpful. It definitely reminded me of why I prefer the in-flight experience on Southwest!

No delays and arrived to destination 30 min early. Staff was super friendly.

San Diego airport is brand new, spacious, airy and very smooth checkin at SW baggage drop.

Did not realize internet screen was hidden between seats and no info printed!!!!

2 of the seats in row 31 the entertainment system was not working, and one seat the tray table did not go all the way down. Flight arrived early and departed on time which was great.

Very good flight crew and very nice people staff were incredible especially the gate agent

Waited at the usual crowded gate at DCA where one ends up standing up because there aren't enough seats.

The flight was delayed for about 2 hrs. Other than it, it was good.

Advertised fruit trays with cheese, but only snacks handed out!

The plant way delayed departing by 3 hours. It was an old airplane with broken seats and armrests. The bathroom made a hollering sound. A really crappy flight experience and travel day all around.

Flight delays both to Detroits and return flight . The flight to Detroit was associated with mechanical difficulty

I am extremely disappointed that delta internal pilot manuals now refer to the Gulf of Mexico as the “gulf of America”. You can bow down to the Orange turd on your own. I will never fly delta again

Wasn't a Delta issue I don't think, but seems there was a Delta flight at each of the 2 Dallas airports at the same exact time, both to Atlanta. I was evidently booked on the one at Love Airport, but the Carey transport shuttle took me to DFW instead and I ended up missing the flight by just a few minutes. Was able to book a Southwest flight from Love Airport, but was a big loss of time and an inconvenience.

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

Information on your arrival and departure airports