HNL - MDW

$171 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 2/27. 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
$342
Southwest
Thu 2/19Wed 2/25
HNL - MDW • 1 stop
Cheapest one-way
$218
Delta
Fri 2/27
HNL - MDW • 2 stops
Top airlines
Southwest
Cheapest • from $342 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
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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, Feb 19 - Wed, Feb 25
Southwest Logo
8:05 am - 12:25 am
HNL
-
MDW
12h 20m
1 stop
Southwest Logo
8:25 am - 4:30 pm
MDW
-
HNL
12h 05m
1 stop
$342Southwest
Thu, Feb 26 - Sun, Mar 1
Southwest Logo
9:55 pm - 1:40 pm
HNL
-
MDW
11h 45m
2 stops
Southwest Logo
10:15 pm - 11:15 am
MDW
-
HNL
17h 00m
1 stop
$348Southwest
Thu, May 14 - Mon, May 18
Southwest Logo
8:10 am - 4:35 am
HNL
-
MDW
15h 25m
1 stop
Southwest Logo
9:45 pm - 9:50 am
MDW
-
HNL
17h 05m
1 stop
$413Southwest
Sun, Mar 1 - Wed, Mar 4
Southwest Logo
8:05 am - 12:35 am
HNL
-
MDW
12h 30m
1 stop
Southwest Logo
8:15 am - 9:00 pm
MDW
-
HNL
16h 45m
1 stop
$422Southwest
Mon, Mar 2 - Mon, Mar 9
Southwest Logo
11:55 am - 5:05 am
HNL
-
MDW
13h 10m
2 stops
Southwest Logo
8:50 am - 9:10 pm
MDW
-
HNL
17h 20m
1 stop
$428Southwest
Thu, Feb 26 - Sun, Mar 1
Southwest Logo
9:55 pm - 1:40 pm
HNL
-
MDW
11h 45m
2 stops
Southwest Logo
7:50 am - 9:00 pm
MDW
-
HNL
17h 10m
2 stops
$443Southwest
Wed, Mar 11 - Wed, Mar 18
Southwest Logo
9:05 pm - 6:00 pm
HNL
-
MDW
15h 55m
2 stops
Southwest Logo
11:50 am - 9:00 pm
MDW
-
HNL
14h 10m
2 stops
$451Southwest
Wed, Mar 11 - Thu, Mar 19
Southwest Logo
9:05 pm - 5:30 pm
HNL
-
MDW
15h 25m
1 stop
Southwest Logo
8:50 am - 9:10 pm
MDW
-
HNL
17h 20m
1 stop
$462Southwest
Thu, Feb 19 - Wed, Feb 25
Southwest Logo
8:05 am - 12:25 am
HNL
-
MDW
12h 20m
1 stop
Southwest Logo
11:15 am - 9:00 pm
MDW
-
HNL
13h 45m
2 stops
$466Southwest
Wed, Mar 11 - Thu, Mar 19
Southwest Logo
9:05 pm - 6:00 pm
HNL
-
MDW
15h 55m
2 stops
Southwest Logo
8:50 am - 9:10 pm
MDW
-
HNL
17h 20m
1 stop
$468Southwest
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 ($342) and Delta ($474).

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 $171 for a one-way ticket and $342 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 4267 reviews
8.6Crew
7.0Food
8.0Comfort
7.5Entertainment
8.1Boarding
Airline reviews

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

10.0 ExcellentAnonymous, Jan 2026
PHX - MDW
Read more Southwest reviews

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

Everything went smoothly and we even arrived a little bit early.

Great vacation. Can't wait till next year for another one.

Great flight but super high price. Glad it was a business trip and not personal

On time. Friendly staff. Took to long to pre bord all the specialty groups. Cramped small plane

The seats were comfortable, and the boarding process was pretty smooth.

3 hour delay. Had to change plans and was still delayed.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

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.

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

Information on your arrival and departure airports

Honolulu (HNL)
Midway (MDW)