HNL - MDW

$247 Find Cheap Flights from Honolulu to Chicago Midway Airport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Honolulu to Midway departing on 9/9. 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 Chicago Midway Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Honolulu to Chicago, 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 Honolulu to Chicago, as well as popular online travel agencies
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Everything you should know

Cheapest round-trip
$500
Southwest
Wed 9/23Wed 9/30
HNL - MDW • 1 stop
Cheapest one-way
$247
Delta
Wed 9/9
HNL - MDW • 1 stop
Top airlines
Southwest
Cheapest • from $500 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Not available
There are currently no direct flights between Honolulu and Midway. You'll need at least 1 connection.
Insights
Insights
Insights
Insights
Top layover airports
Los Angeles (LAX)
Cheapest • Avg $799 (round-trip)
Las Vegas (LAS)
Shortest trip • 10h 20m (one-way)
Insights
Insights
Insights
Insights
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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 Midway!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Honolulu to Midway (HNL-MDW)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Honolulu to Midway 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 Honolulu to Midway

Wed, Sep 23 - Wed, Sep 30
Southwest Logo
10:20 pm - 5:00 pm
HNL
-
MDW
13h 40m
1 stop
Southwest Logo
10:20 am - 9:10 pm
MDW
-
HNL
15h 50m
1 stop
$500Southwest
Wed, Sep 23 - Wed, Sep 30
Southwest Logo
10:20 pm - 3:15 pm
HNL
-
MDW
11h 55m
2 stops
Southwest Logo
10:20 am - 9:10 pm
MDW
-
HNL
15h 50m
1 stop
$506Southwest
Wed, Sep 23 - Wed, Sep 30
Southwest Logo
9:25 pm - 3:15 pm
HNL
-
MDW
12h 50m
2 stops
Southwest Logo
12:00 pm - 9:20 pm
MDW
-
HNL
14h 20m
2 stops
$551Southwest
Fri, Aug 28 - Tue, Sep 8
Southwest Logo
8:15 am - 5:00 am
HNL
-
MDW
15h 45m
1 stop
Southwest Logo
10:20 am - 9:10 pm
MDW
-
HNL
15h 50m
1 stop
$554Southwest
Wed, Sep 9 - Sun, Sep 13
Southwest Logo
8:10 am - 4:30 am
HNL
-
MDW
15h 20m
1 stop
Southwest Logo
12:15 pm - 9:15 pm
MDW
-
HNL
14h 00m
2 stops
$560Southwest
Wed, Aug 19 - Thu, Aug 27
Southwest Logo
11:55 am - 5:45 am
HNL
-
MDW
12h 50m
1 stop
Southwest Logo
10:15 am - 9:10 pm
MDW
-
HNL
15h 55m
1 stop
$583Southwest
Wed, Aug 19 - Thu, Aug 27
Southwest Logo
11:55 am - 5:45 am
HNL
-
MDW
12h 50m
1 stop
Southwest Logo
12:15 pm - 9:20 pm
MDW
-
HNL
14h 05m
2 stops
$589Southwest
Fri, Aug 28 - Tue, Sep 8
Delta Logo
4:10 pm - 12:30 pm
HNL
-
MDW
15h 20m
2 stops
Delta Logo
6:00 am - 1:15 pm
MDW
-
HNL
12h 15m
1 stop
$603Delta
Wed, Aug 19 - Thu, Aug 27
Southwest Logo
8:55 pm - 2:35 pm
HNL
-
MDW
12h 40m
2 stops
Southwest Logo
11:10 am - 9:15 pm
MDW
-
HNL
15h 05m
2 stops
$619Southwest
Wed, Sep 9 - Sun, Sep 13
Southwest Logo
8:15 am - 5:55 am
HNL
-
MDW
16h 40m
2 stops
Southwest Logo
12:15 pm - 9:15 pm
MDW
-
HNL
14h 00m
2 stops
$625Southwest
Booking Insights

KAYAK's insights & trends for Honolulu to Midway flights

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

Which airlines provide the cheapest flights from Honolulu to Chicago Midway Airport?

The cheapest round-trip price for the route for each airline clicked by KAYAK users in the last 72 hours.

In the past 3 days, the cheapest round-trip tickets from Honolulu to Chicago Midway Airport were found on Southwest ($500) and Delta ($603).

Find deals

Good to know

Cheapest flight$247
Flight from Honolulu to Chicago Midway Airport

When to book flights from Honolulu to Midway

Are your dates flexible? Find out the best times to travel from Honolulu to Midway 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 Honolulu to Chicago Midway Airport flights

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

    In the last 3 days, the lowest price for a flight from Honolulu to Chicago Midway Airport was $247 for a one-way ticket and $500 for a round-trip.

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

    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 Honolulu to Chicago Midway Airport?

    When flying out of Honolulu you will be using Honolulu. You will be landing at Chicago Midway Airport, also known as Chicago Midway.

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

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

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

    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 Honolulu to Chicago Midway Airport.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport from Honolulu 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 Honolulu to Chicago Midway Airport?

    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 Chicago Midway Airport with an airline and back to Honolulu with another airline. Booking your flights between Honolulu and MDW 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 Honolulu to Chicago Midway Airport?

    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 Chicago Midway Airport from Honolulu up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airline flying from Honolulu to Midway

 
See real verified KAYAK customer reviews for airlines flying from Honolulu to Chicago. 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 Honolulu to Midway? 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 4314 reviews
8.6Crew
7.0Food
8.1Boarding
8.0Comfort
7.5Entertainment
Airline reviews

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

10.0 Excellentlarry, Apr 2026
LGB - PHX
Read more Southwest reviews

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

First time I've had to use the disabled accommodations. And I could not have had a better experience with Southwest, i was having trouble getting from one terminal to another due to my heart failure. And the next thing I know a Southwest agent had made sure. I had a wheelchair at all my flights. Can't thank them enough.

Delayed flight, lack of information, boarding process is a mess as is the carryon luggage causing issues when leaving the plane….just a poor experience.

Comfortable. Easy. No problems. Just wish they had gf options for snacks.

The crew was very kind and made going to Hawaii relaxing and fun to look forward to! Thank you Southwest for a pleasant flight!

This leg was much better, but we did have to have a 3 hour lay o er after coming from a very exhausting hiccup with our flight from BNA to Den

We waited in the airplane for over 45 min for a southwest employee to make the flight. This cause over half the plane to miss their connecting flight in Denver. When we confronted the desk upon arrival, they told us the only flight they had was the next day leaving at 8:50 pm!!! Or they offered to get us to Burbank or LA, but after that we were on our own to get back to Santa Barbara. I paid for a flight from sba to bna bna to sba. My re entry into mom mode has been 💯 rough because of southwest mistake with my flight. And now I’m leaving to Reno tomorrow for a vballl tournament and just discovered that my leg in Vegas has me and my 3 kids on a stand by flight even though I had booked these ticket last year November!! Do better southwest!

Southwest is kind of a slum airline. It’s gotten more expensive over the years for less and less service. I am a Southwest Chase Visa card holder and was forced to choose a seat in the 26th row in the middle seat. However my wife who is a rewards member but doesn’t hold a card or anything else, gets randomly assigned a normally paid seat in row 6! How does that work?

For the first time in a long time, the Wi-Fi actually worked the entire flight! The flight crew was amazing as usual.

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

Information on your arrival and departure airports

Honolulu (HNL)
Midway (MDW)