$221 Find Cheap Flights from Chicago Midway Airport to Hawaii

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 Hawaii departing on 4/20. 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 Hawaii

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Hawaii, 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 Hawaii, as well as popular online travel agencies
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Flight Deals

Cheap Flights from Midway to Hawaii

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Honolulu
Honolulu1 stop$407
Kahului
Kahului1 stop$498
Kailua-Kona
Kailua-Kona1 stop$531
Lihue
Lihue1 stop$488
Hilo
Hilo2 stops$1,095
Honolulu
Honolulu1 stop$407
Kahului
Kahului1 stop$498
Kailua-Kona
Kailua-Kona1 stop$531
Lihue
Lihue1 stop$488
Hilo
Hilo2 stops$1,095

Book Cheap Midway to Hawaii Plane Tickets

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

Thu, Apr 9 - Wed, Apr 22
Southwest Logo
9:45 pm - 9:50 am
MDW
-
HNL
17h 05m
1 stop
Southwest Logo
9:05 pm - 5:55 pm
HNL
-
MDW
15h 50m
2 stops
$407Southwest
Tue, Apr 28 - Mon, May 4
Southwest Logo
10:05 am - 9:00 pm
MDW
-
HNL
15h 55m
1 stop
Southwest Logo
11:55 am - 5:25 am
HNL
-
MDW
12h 30m
1 stop
$411Southwest
Wed, Apr 8 - Mon, Apr 20
Southwest Logo
10:10 am - 9:05 pm
MDW
-
HNL
15h 55m
1 stop
Southwest Logo
8:15 am - 5:00 am
HNL
-
MDW
15h 45m
1 stop
$421Southwest
Wed, Apr 8 - Wed, Apr 15
Delta Logo
6:00 am - 2:00 pm
MDW
-
HNL
13h 00m
1 stop
Delta Logo
3:15 pm - 8:47 am
HNL
-
MDW
12h 32m
1 stop
$424Delta
Tue, Apr 28 - Tue, May 5
Southwest Logo
10:40 am - 9:05 pm
MDW
-
HNL
15h 25m
2 stops
Southwest Logo
11:05 am - 5:45 am
HNL
-
MDW
13h 40m
1 stop
$427Southwest
Wed, Apr 15 - Wed, Apr 22
Southwest Logo
10:00 am - 4:05 pm
MDW
-
HNL
11h 05m
1 stop
Southwest Logo
11:55 am - 6:00 am
HNL
-
MDW
13h 05m
1 stop
$431Southwest
Mon, Aug 24 - Tue, Sep 1
Southwest Logo
7:10 am - 1:05 pm
MDW
-
HNL
10h 55m
1 stop
Southwest Logo
8:15 am - 5:55 am
HNL
-
MDW
16h 40m
2 stops
$434Southwest
Wed, Apr 15 - Wed, Apr 22
Southwest Logo
7:30 am - 9:00 pm
MDW
-
HNL
18h 30m
2 stops
Southwest Logo
11:55 am - 6:00 am
HNL
-
MDW
13h 05m
1 stop
$437Southwest
Tue, Apr 21 - Tue, Apr 28
Southwest Logo
10:10 am - 9:05 pm
MDW
-
HNL
15h 55m
1 stop
Southwest Logo
11:55 am - 6:00 am
HNL
-
MDW
13h 05m
1 stop
$438Southwest
Sun, May 10 - Sun, May 17
Delta Logo
9:23 am - 7:35 pm
MDW
-
OGG
15h 12m
2 stops
Delta Logo
10:00 pm - 6:33 pm
OGG
-
MDW
15h 33m
2 stops
$534Delta
Booking Insights

KAYAK's insights & trends for Midway to Hawaii flights

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

What is the cheapest month to fly from Chicago Midway Airport to Hawaii?

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

Good to know

Low seasonNovember
Cheapest flight$221
Best time to beat the crowds but there is an average 66% increase in price.
Most popular time to fly with an average 9% increase in price.
Flight from Chicago Midway Airport to Kahului

FAQs - booking Hawaii flights

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

    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 Hawaii.

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

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

    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 from Chicago Midway Airport to Hawaii with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago Midway Airport to Hawaii?

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

Reviews of the top airlines flying from Midway to Hawaii

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Hawaii. 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 Hawaii? 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 4318 reviews
7.0Food
8.0Comfort
7.5Entertainment
8.6Crew
8.1Boarding
Airline reviews

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

4.0 OkayKenny, Mar 2026
TPA - BWI
Read more Southwest reviews

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 ?

Flight boarded late after announcing on time boarding. Flight arrived only a little late despite late departure. Had trouble connecting to WiFi

First class is comfortable. Enjoyed a movie and was able to relax compared to coach.

Loved flying First Class. Very comfortable. The seat was amazing. Enjoyed a movie and was able to relax so much better than in coach.

We landed and sat on the tarmac for 45 minutes because they only have one gate at the airport and there was another plane running late so we had to wait

The WiFi was not working. That made for a long flight.

Absolutely no communication on why there's a delay and multiple flight time reschedules. I would have canceled the flight and drove back home if I known it was going to be rescheduled 3 or 4 times.

Another late night flight and MORE men belligerently drinking and yelling. I had to move from first to economy because they were so obnoxious and disruptive. Crazy to go from a cozy chair to cardboard when you were supposed to be in first. Delta allows was too much drinking which leads to belligerent behavior.

I was in first class and literally the men behind me were so aggressively loud I moved myself to economy. This has become so common on Delta - people using audio without headphones, and men on 12am / late night flights drinking and yelling to talk to each other which prevents anyone around them from resting. Pretty crazy to have to move from first to economy (poorer service, less comfort...). Wild wild. Looking into other airlines.

Love delta smaller commuter plane so no entertainment and paid wifi on MKE-LGA leg was extremely unreliable and slow

Stop changing gates. Stop cancelling flights Stop moving my seat.

Extremely disappointed with Delta. They canceled flight last minute and then I rebooked the other flights and with which were delayed as well

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

Information on your arrival and departure airports