MDW - HNL

$241 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 2/9. 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
Travelers love KAYAK
41.299.237 searches in the past 7 days on KAYAK

Save 23% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest round-trip
$428
Overall average: $680
Southwest
Mon 2/23Mon 3/2
MDW - HNL • 2 stops
Cheapest one-way
$245
Multiple Airlines
Mon 2/9
MDW - HNL • 3 stops
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, Feb 23 - Mon, Mar 2
Southwest Logo
8:05 am - 9:00 pm
MDW
-
HNL
16h 55m
2 stops
Southwest Logo
9:55 pm - 12:35 pm
HNL
-
MDW
10h 40m
1 stop
$428Southwest
Fri, Feb 6 - Fri, Feb 13
Southwest Logo
8:00 am - 9:00 pm
MDW
-
HNL
17h 00m
1 stop
Southwest Logo
8:05 am - 12:50 am
HNL
-
MDW
12h 45m
2 stops
$429Southwest
Sun, Feb 22 - Sun, Mar 1
Delta Logo
6:00 am - 3:11 pm
MDW
-
HNL
13h 11m
1 stop
Delta Logo
9:35 pm - 5:37 pm
HNL
-
MDW
16h 02m
2 stops
$430Delta
Tue, Mar 17 - Tue, Mar 24
Southwest Logo
10:05 am - 9:00 pm
MDW
-
HNL
15h 55m
1 stop
Southwest Logo
1:50 pm - 11:25 am
HNL
-
MDW
16h 35m
1 stop
$431Southwest
Sun, Feb 1 - Fri, Feb 6
Southwest Logo
8:10 am - 4:20 pm
MDW
-
HNL
12h 10m
1 stop
Southwest Logo
8:05 am - 12:25 am
HNL
-
MDW
12h 20m
1 stop
$432Southwest
Wed, Feb 25 - Wed, Mar 4
Delta Logo
9:34 am - 9:54 pm
MDW
-
HNL
16h 20m
2 stops
Delta Logo
4:50 pm - 1:05 pm
HNL
-
MDW
16h 15m
2 stops
$435Delta
Mon, Feb 23 - Thu, Feb 26
Multiple Airlines Logo
7:25 pm - 11:15 am
MDW
-
HNL
19h 50m
1 stop
Multiple Airlines Logo
11:50 am - 11:41 pm
HNL
-
MDW
31h 51m
2 stops
$438Multiple Airlines
Mon, Feb 23 - Wed, Feb 25
Multiple Airlines Logo
7:25 pm - 11:15 am
MDW
-
HNL
19h 50m
1 stop
Multiple Airlines Logo
8:11 am - 11:41 pm
HNL
-
MDW
35h 30m
2 stops
$443Multiple Airlines
Mon, Jan 26 - Thu, Jan 29
Delta Logo
6:00 am - 3:10 pm
MDW
-
HNL
13h 10m
1 stop
Delta Logo
4:44 pm - 8:52 am
HNL
-
MDW
12h 08m
1 stop
$444Delta
Mon, Feb 2 - Tue, Feb 3
Southwest Logo
5:05 am - 12:55 pm
MDW
-
HNL
11h 50m
1 stop
Southwest Logo
12:30 pm - 5:05 am
HNL
-
MDW
12h 35m
2 stops
$448Southwest
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.

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$245
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 $241 for a one-way ticket and $422 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 $768 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 $614 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
7.5Entertainment
8.0Comfort
7.0Food
8.6Crew
8.1Boarding
Airline reviews

The crew canceled the complementary snack and drink in anticipation of turbulence that never materialized. I was counting on the drink (water) to take the the doses of medication - prescribed for my heart condition - that were due during the flight. Since no snack or meal was served on this flight, I cannot rate the food quality. Otherwise, this flight was excellent.

10.0 ExcellentDaniel, Jan 2026
BWI - MHT
Read more Southwest reviews

The crew canceled the complementary snack and drink in anticipation of turbulence that never materialized. I was counting on the drink (water) to take the the doses of medication - prescribed for my heart condition - that were due during the flight. Since no snack or meal was served on this flight, I cannot rate the food quality. Otherwise, this flight was excellent.

Departure was delayed more than 1/2 hour while we waited for luggage (only) transfer from another flight/plane. Once approved for takeoff, the flight was excellent.

We got exit row seats both flights. Everything was running on time

The flight crew was extremely rude and especially not helpful when our flight was delayed.

Pretty seamless, just a tad bit late in taking off and landing.

Flight was fine other than there was a gate change that I was not notified of. By chance I happened to check my phone and saw the change, otherwise, we would have missed our connecting flight.

Haven’t flown on SW in years. Flight was on time departing and arriving. Served vegan butter onion flavored pretzels which were bad. Coke served was in a tiny paper cup. Crew was not engaging. Felt like they were going through the motions. Old plane, tight seats and no leg room.

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.

Food is basically Sun Chips, cookies or Cheezits. I had an exit row seat so I had plenty of room. The crew was very nice and efficient. Pilot kept us informed. Pretty good flight.

Air travel sucks. It continues to be awful for all airlines. No shame on delta alone.

It was Delta, but the flight attendants were stressful and disrespectful. I am a diamond member a travel weekly. I have not had a negative thing to share in quite some time. But this was noticeable.

Comfort Plus seat 11E seemed smaller than prior flights. The movie selection is good. Watched most of the most recent Tron movie. I'll watch the remaining part later as my movie is saved in the Delta Seatback Experience.

Flight was late from Newark to Atlanta, I asked flight attendant to please let my family of 3 out first when we landed to Atlanta because we were late for our connecting flight to Quito. She didn't and we were late for 5 minutes we couldn't board the plane and spend hours trying to get another flight with customer service for the next day.

I really liked the legroom. I am 6’4”.a at For some reason our seats were not together and using the app to fix it didn’t work. Passengers were nice enough to move for us but you should absolutely ensure a parent sits with their child.

Late delayed flight delays boarding and delays leaving and delays on arrival too. Cramped plane no room no food.

DTW line is too long. The flights from DTW to BWI are always delayed for unknown reasons.

Delta canceled our flight and we had to scramble to find another airline to get home. Phoenix is not a delta hub so they didn’t have another plane. It would have been a red eye though Salt Lake City. Getting in at 5am. No bueno.

This flight was no comparison to our prior flight. I'm thinking it all has to do with the age of the aircraft.

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

Information on your arrival and departure airports