MDW - HNL

$278 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 1/31. 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
$497
Overall average: $465
Southwest
Fri 1/9Fri 1/16
MDW - HNL • 2 stops
Cheapest one-way
$278
Typical prices: $336-$426
Southwest
Sat 1/31
MDW - HNL • 1 stop
Top airlines
Southwest
Cheapest • from $509 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to travel
January
Cheapest • 37% price drop
June
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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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

Fri, Jan 9 - Fri, Jan 16
Southwest Logo
10:30 am - 9:00 pmMDW-HNL
14h 30m2 stops
Southwest Logo
11:55 am - 5:05 amHNL-MDW
13h 10m2 stops
$497Southwest
Find Deal
Tue, Jan 13 - Sun, Jan 25
Delta Logo
9:32 am - 9:28 pmMDW-HNL
15h 56m2 stops
Delta Logo
5:15 pm - 12:46 pmHNL-MDW
15h 31m2 stops
$498Delta
Find Deal
Sun, Jan 11 - Mon, Jan 19
Southwest Logo
8:10 am - 4:20 pmMDW-HNL
12h 10m1 stop
Southwest Logo
8:05 am - 12:25 amHNL-MDW
12h 20m1 stop
$499Southwest
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Mon, Jan 12 - Mon, Jan 19
Southwest Logo
11:15 am - 9:00 pmMDW-HNL
13h 45m2 stops
Southwest Logo
8:05 am - 12:25 amHNL-MDW
12h 20m1 stop
$504Southwest
Find Deal
Fri, Jan 30 - Mon, Feb 9
Delta Logo
6:00 am - 9:28 pmMDW-HNL
19h 28m2 stops
Delta Logo
4:50 pm - 9:53 amHNL-MDW
13h 03m1 stop
$505Delta
Find Deal
Mon, Jan 5 - Thu, Jan 15
Southwest Logo
9:45 pm - 11:15 amMDW-HNL
17h 30m1 stop
Southwest Logo
9:00 pm - 12:10 pmHNL-MDW
11h 10m1 stop
$509Southwest
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Wed, Feb 25 - Tue, Mar 3
Delta Logo
6:00 am - 3:11 pmMDW-HNL
13h 11m1 stop
Delta Logo
5:15 pm - 9:06 amHNL-MDW
11h 51m1 stop
$510Delta
Find Deal
Sun, Feb 22 - Sun, Mar 1
Southwest Logo
10:15 pm - 12:45 pmMDW-HNL
18h 30m1 stop
Southwest Logo
9:55 pm - 12:30 pmHNL-MDW
10h 35m1 stop
$512Southwest
Find Deal
Mon, Jan 5 - Wed, Jan 14
Southwest Logo
9:45 pm - 11:15 amMDW-HNL
17h 30m1 stop
Southwest Logo
12:30 pm - 5:05 amHNL-MDW
12h 35m2 stops
$514Southwest
Find Deal
Mon, Feb 2 - Mon, Feb 9
Delta Logo
6:00 am - 3:10 pmMDW-HNL
13h 10m1 stop
Delta Logo
9:35 pm - 6:36 pmHNL-MDW
17h 01m2 stops
$515Delta
Find Deal
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’s the cheapest day of the week to fly from Chicago Midway Airport to Honolulu?

The average price of all round-trip flights from Chicago Midway Airport to Honolulu clicked on KAYAK for each day over the last 12 months.

Your flight ticket price will generally be cheaper if you fly to Honolulu on a Tuesday and more expensive on a Saturday. On your return trip to Chicago Midway Airport, you should consider flying back on a Tuesday, and avoid Fridays for better 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 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 $465 (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 seasonJuly
Cheapest flight$278
Best time to beat the crowds but there is an average 23% increase in price.
Most popular time to fly with an average 16% 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 $278 for a one-way ticket and $497 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 $776 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 4254 reviews
8.1Boarding
8.6Crew
7.0Food
8.0Comfort
7.5Entertainment
Airline reviews

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!

10.0 ExcellentDavid, Nov 2025BUF - PHX
Read more Southwest reviews

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.

It was rough. The staff was unprofessional, the choice of on board drinks terrible, it was cramped in space at every airport, they always ran out of overhead bin space so they pressured people to check bags for free or we couldn’t leave on the plane— so I did check my bag to help, and they nearly lost my bag. My bag did not arrive on the luggage belt, another man on my flight and I had to waste our time going to the baggage office to search for our bags. I would only fly southwest again if it was my last choice. Also, my flights were consistently delayed over and over again— at one point they straight up told us we were waiting for the pilot to arrive.

Crew could have been friendlier, maybe I'm spoiled by SW crews. In flight wifi was good. Would be nice to have more food offerings on a 4 plus hour flight

Had to get off plane from prior flight even though I had to reboard same plane to continue to my final destination.

Everything a cheap airline should be at normal airline rates.

Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

Full cans of soda would be nice. A choice between two snacks would be appreciated.

I fly Delta all the time, have Platinum Medallion status. But this route seems to have major problems with delays and seems to never leave on time! Have only taken it twice in the last two weeks, and each time it had delays of more than 1 hour... very disappointed!!!!

Good seats in Main cabin, excellent service and excellent landing

My flight was cancelled with no explanation after I had already cleared security. I was given 4 options to rebook, only one being non-stop like I had paid for. I grabbed it. It was 4 plus hours later and then took off even later. Biggest complaint is that I booked early and had an aisle seat. They gave me a "window" seat in front of the exit row, so the seat did not decline. I weigh all of 103 #s and it was tight for me! For what I paid, I feel I was kind of ripped off. I think they should have given me the empty comfort seat for the inconvenience. There was no apology nor any explanation as to why the flight was cancelled. My guess is it benefitted Delta in some way.

Very smooth, on-time, and pleasantly uneventful flight. The team at the gate and on board were professional and genuinely courteous. The pilot kept us well updated throughout, and both takeoff and landing were steady and enjoyable without any drama. Just a good, solid flight. Thank you! 💗

Staff was exceptional! Everyone was kind, professional and friendly making the trip very pleasant. Thank you!

No lunch on a x-country flight scheduled for 10:50 am departure, arrived 5+ hrs later. That requires a black box label before you pay for the tickets. Worst, when I checked in online, it's specifically said that lunch was served on his flight for economy Plus passengers.

We had a lot of really rough weather but that was not Delta's fault. Pilot was amazing.

First, Delta needs more flights to/from Miami. Second, a 1000pm leaving at 1230pm is unacceptable from their biggest airport world hub. Another aircraft could have been used such as the aircraft scheduled to be used in the morning for that exact same route. Yes, I did get me there but the lack of sleep the next day didn't help me enjoy my entire trip since I was busy with activities during the weekend. This can be and is expected from Spirit (going bankrupt) and Frontier (despite they're nickel and dimers). But from Delta's World Hub? That's totally unacceptable!

This flight was straightforward and without difficulty. Service was OK, but I continue to be underwhelmed by level of attention given to Sky Priority passengers.

It would’ve been nice for all that money to have a more substantial snack for free. I remember once upon a time getting a very nice turkey sandwich with Swiss cheese on whole wheat bread for no charge along with a drink. I guess those days are gone. it’s a little insulting being given a cookie or a bag of baked chips Going forward I’ll just bring my own.

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

Information on your arrival and departure airports