$205 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 8/26. 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

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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 22% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flights Deals
Booking Insights
Flights 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$409
Kahului
Kahului1 stop$480
Kailua-Kona
Kailua-Kona1 stop$508
Lihue
Lihue2 stops$491
Hilo
Hilo2 stops$714
Honolulu
Honolulu1 stop$409
Kahului
Kahului1 stop$480
Kailua-Kona
Kailua-Kona1 stop$508
Lihue
Lihue2 stops$491
Hilo
Hilo2 stops$714

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

Wed, Sep 17 - Wed, Sep 24
Southwest Logo
1:35 pm - 9:00 pmMDW-HNL
12h 25m1 stop
Southwest Logo
8:10 am - 5:10 amHNL-MDW
16h 00m1 stop
$409Southwest
Find Deal
Wed, Sep 17 - Wed, Sep 24
Southwest Logo
1:35 pm - 9:00 pmMDW-HNL
12h 25m1 stop
Southwest Logo
11:35 am - 5:10 amHNL-MDW
12h 35m2 stops
$414Southwest
Find Deal
Fri, Aug 29 - Fri, Sep 5
Southwest Logo
7:55 am - 4:05 pmMDW-HNL
13h 10m1 stop
Southwest Logo
8:05 am - 12:30 amHNL-MDW
11h 25m1 stop
$416Southwest
Find Deal
Fri, Aug 29 - Fri, Sep 5
Southwest Logo
7:55 am - 4:05 pmMDW-HNL
13h 10m2 stops
Southwest Logo
8:05 am - 12:30 amHNL-MDW
11h 25m1 stop
$421Southwest
Find Deal
Mon, Aug 25 - Thu, Sep 4
Delta Logo
6:00 am - 1:15 pmMDW-HNL
12h 15m1 stop
Delta Logo
3:00 pm - 8:35 amHNL-MDW
12h 35m1 stop
$423Delta
Find Deal
Mon, Aug 25 - Thu, Sep 4
Delta Logo
6:00 am - 1:15 pmMDW-HNL
12h 15m1 stop
Delta Logo
1:20 pm - 8:50 amHNL-MDW
14h 30m2 stops
$429Delta
Find Deal
Tue, Sep 16 - Fri, Sep 26
Delta Logo
9:20 am - 8:30 pmMDW-HNL
16h 10m2 stops
Delta Logo
1:00 pm - 8:53 amHNL-MDW
14h 53m2 stops
$434Delta
Find Deal
Tue, Aug 19 - Wed, Aug 27
Southwest Logo
1:35 pm - 9:00 pmMDW-HNL
12h 25m1 stop
Southwest Logo
8:10 am - 5:10 amHNL-MDW
16h 00m1 stop
$442Southwest
Find Deal
Thu, Oct 23 - Tue, Oct 28
Southwest Logo
11:00 am - 9:00 pmMDW-HNL
15h 00m1 stop
Southwest Logo
9:00 pm - 2:05 pmHNL-MDW
12h 05m1 stop
$449Southwest
Find Deal
Tue, Sep 30 - Wed, Oct 15
Southwest Logo
6:40 am - 1:00 pmMDW-HNL
11h 20m1 stop
Southwest Logo
9:10 pm - 12:35 pmHNL-MDW
10h 25m1 stop
$454Southwest
Find Deal
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 February, when tickets cost $598 (return) on average. On the other hand, the most expensive months are July and June, when the average cost of round-trip tickets is $898 and $863 respectively.

What’s the cheapest day of the week to fly from Chicago Midway Airport to Hawaii?

The average price of all round-trip flights from Chicago Midway Airport to Hawaii clicked on KAYAK for each day over the last 12 months.

Your flight ticket price will generally be cheaper if you fly to Hawaii on a Tuesday and more expensive on a Saturday. On your return trip to Chicago Midway Airport, you should consider flying back on a Tuesday, and avoid Fridays for better deals.


Good to know

Low seasonJuly
Cheapest flight$205
Best time to beat the crowds but there is an average 7% increase in price.
Most popular time to fly with an average 5% increase in price.
Flight from Chicago Midway Airport to Honolulu

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.

  • What is the cheapest time of day to fly to Hawaii?

    The cheapest time of day to fly to Hawaii is generally in the morning, when round-trip flights cost $775 on average. The most expensive time of day to fly to Hawaii is generally at night, which is peak travel time and where the average cost of a ticket is $782.

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 4241 reviews
8.0Comfort
8.1Boarding
7.0Food
8.6Crew
7.5Entertainment
Airline reviews

Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.

10.0 ExcellentKevin, Jul 2025MDW - PUJ
Read more Southwest reviews

Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.

southwest just starting charging for luggage. hadnt realized it until it was too late. now out $70 when i couldve bought a carry on if i wouldve known. free bags was one of the only reasons i chose southwest over another airline (the other being no assigned seats, which is apparently also being changed). stupid business decision. wont be flying southwest anymore.

The quality of Southwest Airlines continues to degrade each time I fly with them. If it were not for the free luggage, I would probably choose another airline. Their prices are a little bit competitive, but way too high for the quality of the service. Southwest is not unique in this way. Domestic flight in the United States of America has continued to be a lower and lower quality product. Very sad when you compare the quality of domestic airlines to that of many international airlines around the world.

Very smooth checking in our luggage with a super pleasant SW agent. I enjoyed a fun entertaining movie.

WiFi did not work. For as outrageous as these flights cost, when they’re advertised with certain services/ features they should be in working order

Worst experience I had on Southwest. Still better than most, but the seating was barely tolerable.

The Southwest employees (all two of them) were very nice and cheerful despite the fact the line to self-check a bag (simply drop it off) was hundreds of people long. Thank God I arrived early to the airport because I stood in this line for at least an hour. Once on the flight that had been delayed by an hour, we had no Wi-Fi and thus no entertainment. Finally, I hope the investor strong arm tactics against Southwest pay off in a short-term windfall to your C-Suite because the rest of you are screwed. I have been a faithful Southwest customer for 15 years due to everything you just got rid of. I'm flying to Idaho and Washington in October, both places I used to simply book with Southwest without a second thought now with Frontier (Washington) and United (Idaho) because they offer everything the "new" Southwest does but cheaper and at better times, destinations, etc. This really makes me sad...

It was okay. The plane was delayed from earlier in the day, but they kept updating the departure time, sometimes later, sometimes earlier. That was stressful. Once we finally got on and took off, it was fine. I was supposed to have a connection in Chicago to Los Angeles, and the time for so late I was rebooked to arrive in LA 3 hours late. The departure time to Chicago later became early enough to have taken my original connection and arrive earlier but that wasn't an option.

It was one and half hour late... Not sure if any other experience matters.

Delayed flight. Nicest crew member was a SW pilot flying seated next to me who kindly move to seat the final passenger. Flight extra delayed. My cup of refreshment of ginger ale was so packed with ice it was literally 2 sips.

My experience on any Delta flight is always overshadowed by the time Delta removed me from a flight for no apparent reason.

Delayed and took off even later than the scheduled delay time

For a 69 year old with health problems I had the worse experience, no wheelchair when I entered a lady told me to sit and wait while a gentleman told me I had to walk to the Delta station, which I did. I had a carry on and a bag, and I was traveling with my service dog, which was on his carrier and the lady charged me for my carry on luggage, beside all the waiting cause of the delay, I had to walk to get my luggage cause no wheelchair showed up, I am so disappointed. I will get in touch with the company. I got home at 3:00 am, not good for my health situation.

Great experience on Delta. Staff from baggage check to flight attendants were very courteous and professional. My only issue was a personal preference for pretzels instead of the chips and cookies that were offered.

There was no problems, just a little uncomfortable with seats that do not lay back a little

Always good but we must do something about people in rows ahead of you that don't put their seats back up when they are suppose to. And It's rough to not be able to even lean over to get something out of my purse.

Flight was delayed, 30+ bags had to be gate checked. Crew were very friendly!

Everything was good until we were boarding our connection flight in Atlanta, we were told to gate check our carry-on, but when we got inside the plane, there was plenty of room in the overhead.

Did not know my son and I had different seating arrangements. He was fine, but it was disappointing.

Flight was canceled, and no effort was made to help with rebooking, no hotel vouchers, no car transportation and minimal food voucher and most places for food were closed by the time the voucher was given. Waited for 3 hours for bags. Simply the worst travel experience I have ever had

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

Information on your arrival and departure airports

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.