MDW - HNL

$240 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 11/11. 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

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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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

Sun, Jan 25 - Mon, Jan 26
Delta Logo
6:00 am - 3:12 pmMDW-HNL
13h 12m1 stop
Delta Logo
4:42 pm - 8:50 amHNL-MDW
12h 08m1 stop
$471Delta
Find Deal
Fri, Jan 23 - Thu, Jan 29
Delta Logo
6:00 am - 3:12 pmMDW-HNL
13h 12m1 stop
Delta Logo
4:42 pm - 8:50 amHNL-MDW
12h 08m1 stop
$472Delta
Find Deal
Thu, Feb 5 - Tue, Feb 10
Southwest Logo
8:35 pm - 11:15 amMDW-HNL
18h 40m1 stop
Southwest Logo
9:55 pm - 12:35 pmHNL-MDW
10h 40m1 stop
$475Southwest
Find Deal
Tue, Jan 20 - Wed, Jan 28
Delta Logo
9:30 am - 8:33 pmMDW-HNL
15h 03m2 stops
Delta Logo
5:00 pm - 9:23 amHNL-MDW
12h 23m1 stop
$476Delta
Find Deal
Wed, Oct 29 - Wed, Nov 5
Southwest Logo
11:55 am - 9:00 pmMDW-HNL
14h 05m1 stop
Southwest Logo
9:55 pm - 4:40 pmHNL-MDW
14h 45m1 stop
$479Southwest
Find Deal
Sat, Jan 24 - Sun, Jan 25
Delta Logo
9:30 am - 8:33 pmMDW-HNL
15h 03m2 stops
Delta Logo
4:42 pm - 8:50 amHNL-MDW
12h 08m1 stop
$480Delta
Find Deal
Tue, Jan 20 - Tue, Jan 27
Delta Logo
9:30 am - 8:33 pmMDW-HNL
15h 03m2 stops
Delta Logo
1:35 pm - 8:50 amHNL-MDW
15h 15m2 stops
$482Delta
Find Deal
Sun, Feb 1 - Sat, Feb 7
Southwest Logo
8:35 pm - 11:15 amMDW-HNL
18h 40m1 stop
Southwest Logo
8:10 am - 5:05 amHNL-MDW
16h 55m1 stop
$501Southwest
Find Deal
Mon, Oct 27 - Thu, Oct 30
Southwest Logo
9:25 pm - 10:20 amMDW-HNL
17h 55m1 stop
Southwest Logo
9:05 pm - 2:00 pmHNL-MDW
11h 55m1 stop
$511Southwest
Find Deal
Mon, Oct 27 - Fri, Oct 31
 Logo
10:56 pm - 11:53 amMDW-HNL
17h 57m1 stop
 Logo
1:34 pm - 12:37 pmHNL-MDW
18h 03m2 stops

Everything you should know

Top airlines
Delta
Cheapest • from $471 (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
Cheapest round-trip
$471
Overall average: $465
Delta
Sun 1/25Mon 1/26
MDW - HNL • 1 stop
Cheapest one-way
$240
Typical prices: $396-502
Delta
Tue 11/11
MDW - HNL • 1 stop
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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!
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$240
Best time to beat the crowds but there is an average 23% increase in price.
Most popular time to fly with an average 17% 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 $240 for a one-way ticket and $471 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 $763 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 4242 reviews
8.6Crew
8.1Boarding
7.5Entertainment
7.0Food
8.0Comfort
Airline reviews

I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!

10.0 ExcellentG, Sep 2025LAS - ATL
Read more Southwest reviews

I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!

As always, the entire Southwest experience was wonderful, from online booking to flight to baggage retrieval. Very grateful.

The weather could have been better. There was a 40 minute ATC delay in SFO because of marine fog and a micro cell storm delayed landing and take-off at Nashville. The gate was changed 5 minutes from boarding from gate B3 to gate C23 at Nashville airport.

After being assaulted by a flight attendant I was then brushed off as oh well because he long braids didn’t mean to whip me in the eye. I have filed complaints and will see. But like any other issue I’ve had with kayak involved it’s been trash. Last time I’ll be using your app

AC sub par. WiFi not working correctly. Ac sucked. Seats very narrow.

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

Southwest's seats are the least comfortable I have ever sat in.

The cabin was quiet for the redeye flight. The area was clean. The staff was great. The 787 Max was in good condition. Drawbacks were that the seat widths were tight for some passengers. The seat padding was at best average and for a long flight uncomfortable.

Southwest like most American domestic airlines, is a mediocre airline. But it is among the cheapest. Oh well.

My flight was delayed 50 minutes and we were rushed to board to then sit for 15 minutes until the pilot arrived. Unacceptable since we could have waited to board. Also the delayed flight was updated AFTER we boarded to more than the 10 minutes as originally stated.

Perfect flight both ways. On time, courteous staff, plane comfortable and cool. Best domestic flights I’ve had in awhile.

Really low quality food especially for an international flight. The crew also was surprisingly unpleasant except couple of ladies. I know we were not in first class but that’s no reason to treat customers as less.

Flight delayed for two and half hours and then canceled altogether due to mechanical issues. No mechanic onsite to fix so had to send one from LAX.

Crew was good. The reservation got mixed up and they didn't have my TSA number. I am also a Silver Medallion and wasn't able to use Sky Priority.

Delta made it easy, comfortable and timely. The crew was fantastic.

This route with Delta always has delays or is cancelled. Aircrafts seem smaller and older. I fly Delta quite a bit - haven’t had issues with the international flights. But this route has always been the troublesome one

Three seats in first class were broken and while they were able to still acommodate us it was looking very touch and go and they had others they could not acommodate

Mechanic delay in addition to a 2 hour change in takeoff time was frustrating.

Delayed due to thunderstorms and no in-flight service due to rough weather — both of which are out of Delta’s control. Flight was good overall.

The flight attendants in SLC were rude. I arrived 40 minutes early to gate. Ticket said I needed check in for seat assignments and tried check in and attendants said they weren’t doing it. And proceeded to never call me to give me a ticket so when time to board I received the very last seat. Please relay to employees to do their job better..,

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

Information on your arrival and departure airports

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