HNL - MDW

$218 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 5/13. 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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41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$362
Southwest
Thu 4/23Mon 4/27
HNL - MDW • 1 stop
Cheapest one-way
$218
Typical prices: $281-$411
Delta
Wed 5/13
HNL - MDW • 2 stops
Top airlines
Southwest
Cheapest • from $362 (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

Thu, Apr 23 - Mon, Apr 27
Southwest Logo
9:25 pm - 1:05 pm
HNL
-
MDW
10h 40m
1 stop
Southwest Logo
9:45 pm - 9:50 am
MDW
-
HNL
17h 05m
1 stop
$362Southwest
Thu, Apr 23 - Mon, Apr 27
Southwest Logo
9:25 pm - 1:05 pm
HNL
-
MDW
10h 40m
1 stop
Southwest Logo
8:35 am - 9:05 pm
MDW
-
HNL
17h 30m
2 stops
$368Southwest
Thu, Apr 23 - Mon, Apr 27
Southwest Logo
9:25 pm - 5:55 pm
HNL
-
MDW
15h 30m
1 stop
Southwest Logo
9:45 pm - 9:50 am
MDW
-
HNL
17h 05m
1 stop
$438Southwest
Thu, Apr 23 - Mon, Apr 27
Southwest Logo
9:25 pm - 5:55 pm
HNL
-
MDW
15h 30m
1 stop
Southwest Logo
8:35 am - 9:05 pm
MDW
-
HNL
17h 30m
2 stops
$444Southwest
Thu, Apr 16 - Wed, Apr 29
Delta Logo
3:15 pm - 8:47 am
HNL
-
MDW
12h 32m
1 stop
Delta Logo
9:29 am - 9:45 pm
MDW
-
HNL
17h 16m
2 stops
$460Delta
Thu, Apr 23 - Mon, Apr 27
Southwest Logo
8:55 pm - 2:20 pm
HNL
-
MDW
12h 25m
2 stops
Southwest Logo
8:35 am - 9:05 pm
MDW
-
HNL
17h 30m
2 stops
$464Southwest
Thu, Apr 16 - Wed, Apr 29
Delta Logo
3:15 pm - 8:47 am
HNL
-
MDW
12h 32m
1 stop
Delta Logo
9:29 am - 9:45 pm
MDW
-
HNL
17h 16m
2 stops
$480Delta
Wed, Apr 29 - Wed, May 6
Southwest Logo
9:25 pm - 5:55 pm
HNL
-
MDW
15h 30m
1 stop
Southwest Logo
10:05 am - 9:00 pm
MDW
-
HNL
15h 55m
1 stop
$485Southwest
Wed, Apr 29 - Wed, May 6
Southwest Logo
9:25 pm - 1:05 pm
HNL
-
MDW
10h 40m
1 stop
Southwest Logo
11:45 am - 9:00 pm
MDW
-
HNL
14h 15m
2 stops
$491Southwest
Fri, Apr 24 - Sun, Apr 26
Southwest Logo
8:15 am - 5:00 am
HNL
-
MDW
15h 45m
1 stop
Southwest Logo
9:55 am - 9:05 pm
MDW
-
HNL
16h 10m
1 stop
$514Southwest
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 ($362) and Delta ($460).

Find deals

Good to know

Cheapest flight$218
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 $218 for a one-way ticket and $362 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 4320 reviews
8.0Comfort
7.5Entertainment
7.0Food
8.6Crew
8.1Boarding
Airline reviews

We had a 5 hour delay on the tarmac in Baltimore

2.0 MediocreDavid, Mar 2026
ALB - BWI
Read more Southwest reviews

We had a 5 hour delay on the tarmac in Baltimore

Long layover between flights to Long Island from BWI - need better coordination between flights

I elected to pay for the upgrades and found very little difference

The new seating arrangement is so over priced for what you get.

The problem with the seat assignments is that there were a lot of rows in the front that were empty but my row at the back was full. Just not so pleasant.

No food or entertainment, just a quick 40 minute flight. A little bumpy due to Santa Ana winds but pilot has no control over that. Good flight and landing!

Good but I prefer choose your own seat. With the new assigned seats they should board from the back I see no advantage to this new boarding. Just like every other airline

I realize they are still working out kinks with the new boarding process, but by the time I boarded in group 5, most of the bins were full. All airlines should better enforce small bags and jackets going under the seats until everyone has boarded.

WiFi was not working and didn’t have a beverage service

Snacks are always pretzels. Why can't you also offer peanuts ?

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

Information on your arrival and departure airports

Honolulu (HNL)
Midway (MDW)