MDW - HNL

$274 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 8/27. 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 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
$668
Typical prices: $771-$603
Southwest
Sat 8/22Fri 8/28
MDW - HNL • 2 stops
Cheapest one-way
$274
Delta
Thu 8/27
MDW - HNL • 2 stops
Top airlines
Southwest
Cheapest • from $668 (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 Midway and Honolulu. You'll need at least 1 connection.
Insights
Insights
Insights
Insights
Top layover airports
San Jose (SJC)
Cheapest • Avg $563 (round-trip)
Phoenix (PHX)
Shortest trip • 11h 25m (one-way)
Insights
Insights
Insights
Insights
When to travel
January
Cheapest • 41% price drop
April
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

Sat, Aug 22 - Fri, Aug 28
Southwest Logo
1:45 pm - 9:20 pm
MDW
-
HNL
12h 35m
2 stops
Southwest Logo
9:55 pm - 5:35 pm
HNL
-
MDW
14h 40m
2 stops
$668Southwest
Wed, Oct 7 - Wed, Oct 14
Southwest Logo
12:25 pm - 9:15 pm
MDW
-
HNL
13h 50m
2 stops
Southwest Logo
9:30 pm - 5:40 pm
HNL
-
MDW
15h 10m
2 stops
$670Southwest
Sat, Jul 4 - Thu, Jul 9
Southwest Logo
10:35 am - 9:05 pm
MDW
-
HNL
15h 30m
1 stop
Southwest Logo
11:00 am - 5:25 am
HNL
-
MDW
13h 25m
2 stops
$671Southwest
Tue, Jul 14 - Thu, Jul 23
Southwest Logo
10:10 am - 9:25 pm
MDW
-
HNL
16h 15m
1 stop
Southwest Logo
12:15 pm - 5:40 am
HNL
-
MDW
12h 25m
1 stop
$672Southwest
Tue, Jul 14 - Wed, Jul 29
Southwest Logo
3:05 pm - 9:25 pm
MDW
-
HNL
11h 20m
1 stop
Southwest Logo
12:15 pm - 5:40 am
HNL
-
MDW
12h 25m
1 stop
$674Southwest
Sat, Jul 4 - Thu, Jul 9
Southwest Logo
12:50 pm - 9:05 pm
MDW
-
HNL
13h 15m
2 stops
Southwest Logo
11:00 am - 5:25 am
HNL
-
MDW
13h 25m
2 stops
$676Southwest
Wed, Sep 9 - Sun, Sep 13
Southwest Logo
12:00 pm - 9:20 pm
MDW
-
HNL
14h 20m
2 stops
Southwest Logo
8:55 pm - 2:35 pm
HNL
-
MDW
12h 40m
2 stops
$678Southwest
Wed, Aug 19 - Tue, Aug 25
Delta Logo
5:10 pm - 4:43 pm
MDW
-
HNL
28h 33m
2 stops
Delta Logo
2:50 pm - 9:17 am
HNL
-
MDW
13h 27m
1 stop
$679Delta
Fri, Aug 14 - Tue, Aug 25
Southwest Logo
2:50 pm - 9:20 pm
MDW
-
HNL
11h 30m
1 stop
Southwest Logo
9:25 pm - 2:20 pm
HNL
-
MDW
11h 55m
2 stops
$680Southwest
Fri, Jul 3 - Mon, Jul 6
Southwest Logo
10:05 am - 9:15 pm
MDW
-
HNL
16h 10m
1 stop
Southwest Logo
11:00 am - 5:00 am
HNL
-
MDW
13h 00m
1 stop
$682Southwest
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.

How much is a round-trip flight from Chicago Midway Airport to Honolulu?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago Midway Airport to Honolulu departing in August.

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 $429 (return) on average. On the other hand, the most expensive months are July and November, where the average cost of round-trip tickets is $909 and $868 respectively.

Find deals

Good to know

Low seasonNovember
Cheapest flight$274
Best time to beat the crowds but there is an average 19% increase in price.
Most popular time to fly and prices are also 10% lower on average.
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 5 days, the lowest price for a flight from Chicago Midway Airport to Honolulu was $274 for a one-way ticket and $668 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.

  • 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 airline 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 4255 reviews
7.5Entertainment
8.1Boarding
7.0Food
8.0Comfort
8.6Crew
Airline reviews

Flight coming out of Buffalo was delayed, so we had to be rescheduled on another flight from Baltimore to Phoenix which means we had a long layover and got home 3.5 hours late. Shuttle to parking stopped at 10pm, so we had to pay for an Uber to the parking lot and got charged an extra day of parking since it was after midnight. Not the best experience. Long day!

2.0 MediocreDawn, Jun 2026
BUF - BWI
Read more Southwest reviews

Flight coming out of Buffalo was delayed, so we had to be rescheduled on another flight from Baltimore to Phoenix which means we had a long layover and got home 3.5 hours late. Shuttle to parking stopped at 10pm, so we had to pay for an Uber to the parking lot and got charged an extra day of parking since it was after midnight. Not the best experience. Long day!

Was fine, delayed and feels like southwest is always late

I don't know why flying out of Sarasota requires two plane changes.

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

The flight was smooth. The Southwest experience has degraded overall, but this one was okay.

No gluten free snacks. Seats felt worn or bare bones even though it was a new 737 MAX 8.

One major problem that was very unprofessional and uncalled for. Plane landed and we had to wait 20 minutes to get off the plane since they were waiting for someone to come to the gate to drive the jetway. Southwest couldn't have someone available and waiting for the plane to land? Is there only one person in Hobby airport who knows to drive the jetway? Was he at lunch? In the bar? Uncomfortable and uncalled for!

The checking experience in Orlando was terrible, almost missed the flight. Too many travelers and Southwest completely understaffed.

I'm glad it wasn't only 75% full because I could get a good seat

if I was good. Not happy that I have to pay extra money to get the seat I need for lake room, but I guess that’s a sign of the times.

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

Information on your arrival and departure airports

Chicago Midway Airport (MDW)
Honolulu (HNL)