MDW - HNL

$277 Find Cheap Flights from Chicago Midway Airport to Honolulu - Compare and Save

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 8/19. 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

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Everything you should know

Cheapest round-trip
$667
Typical prices: $621-$763
Southwest
Sat 8/22Tue 8/25
MDW - HNL • 1 stop
Cheapest one-way
$277
Southwest
Wed 8/19
MDW - HNL • 1 stop
Top airlines
Southwest
Cheapest • from $667 (round-trip)
Southwest
Best reviews • 7.9 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 • 42% price drop
April
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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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 - Tue, Aug 25
Southwest Logo
6:55 am - 1:20 pm
MDW
-
HNL
11h 25m
1 stop
Southwest Logo
9:55 pm - 5:05 pm
HNL
-
MDW
14h 10m
1 stop
$667Southwest
Thu, Aug 13 - Wed, Aug 19
Southwest Logo
10:15 am - 9:10 pm
MDW
-
HNL
15h 55m
1 stop
Southwest Logo
8:15 am - 5:00 am
HNL
-
MDW
15h 45m
1 stop
$669Southwest
Wed, Sep 2 - Thu, Sep 3
Southwest Logo
12:20 pm - 9:15 pm
MDW
-
HNL
13h 55m
1 stop
Southwest Logo
8:10 am - 11:45 pm
HNL
-
MDW
10h 35m
1 stop
$672Southwest
Wed, Sep 9 - Wed, Sep 16
Southwest Logo
11:00 am - 9:15 pm
MDW
-
HNL
15h 15m
2 stops
Southwest Logo
9:55 pm - 3:15 pm
HNL
-
MDW
12h 20m
2 stops
$675Southwest
Sat, Sep 5 - Sun, Sep 13
Delta Logo
9:24 am - 9:20 pm
MDW
-
HNL
16h 56m
2 stops
Delta Logo
2:50 pm - 9:07 am
HNL
-
MDW
13h 17m
1 stop
$677Delta
Fri, Sep 11 - Wed, Sep 16
Southwest Logo
1:50 pm - 9:15 pm
MDW
-
HNL
12h 25m
2 stops
Southwest Logo
9:55 pm - 3:15 pm
HNL
-
MDW
12h 20m
2 stops
$678Southwest
Thu, Aug 6 - Thu, Aug 13
Southwest Logo
10:15 am - 9:10 pm
MDW
-
HNL
15h 55m
1 stop
Southwest Logo
11:55 am - 5:45 am
HNL
-
MDW
12h 50m
1 stop
$681Southwest
Sat, Sep 5 - Fri, Sep 11
Delta Logo
9:24 am - 9:20 pm
MDW
-
HNL
16h 56m
2 stops
Delta Logo
1:00 pm - 8:48 am
HNL
-
MDW
14h 48m
2 stops
$682Delta
Thu, Sep 17 - Wed, Sep 30
Delta Logo
9:59 am - 9:13 pm
MDW
-
HNL
16h 14m
2 stops
Delta Logo
3:10 pm - 9:50 am
HNL
-
MDW
13h 40m
1 stop
$683Delta
Thu, Aug 20 - Sat, Aug 29
Southwest Logo
10:10 am - 9:15 pm
MDW
-
HNL
16h 05m
1 stop
Southwest Logo
11:00 am - 5:45 am
HNL
-
MDW
13h 45m
1 stop
$685Southwest
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 June and July, where the average cost of round-trip tickets is $1,011 and $909 respectively.

Find deals

Good to know

Low seasonNovember
Cheapest flight$277
Best time to beat the crowds but there is an average 20% increase in price.
Most popular time to fly and prices are also 12% 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 $277 for a one-way ticket and $667 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.
7.9
SouthwestOverall score based on 4250 reviews
8.6Crew
8.1Boarding
8.0Comfort
7.0Food
7.5Entertainment
Airline reviews

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

6.0 GoodAnonymous, Jun 2026
MDW - BDL
Read more Southwest reviews

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

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

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

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

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

I recently flew Southwest from San Jose to Honolulu. I was very impressed with the flight crew, especially the flight attendant in charge of the front of the plane. She came through the aisle at least five times for drinks and water, and two times for snacks. I have not seen such service since I flew first class. Also, for the first time, they gave us the correct baggage claim number, and the luggage came out quickly. I can't wait for Southwest to have assigned seating! I absolutely hate the Cattle Call boarding procedure and the mad dash to get seats and overhead bins. However, the boarding was efficient.

Unfortunately it was not a good experience. There was a rude stewardess.

Boarding was well explained and smooth. The flight was short, so there was no time for snacks. They did offer water or juice, though.

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)