$305 Find Cheap Flights from Chicago Midway Airport to The Big Island

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 The Big Island departing on 9/11. 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 The Big Island

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to The Big Island, 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 The Big Island, as well as popular online travel agencies
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Cheap Flights from Midway to The Big Island

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Kailua-Kona
Kailua-Kona1 stop$508
Hilo
Hilo2 stops$714
Kailua-Kona
Kailua-Kona1 stop$508
Hilo
Hilo2 stops$714

Book Cheap Midway to The Big Island 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 The Big Island 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 The Big Island

Wed, Dec 3 - Wed, Dec 10
Southwest Logo
5:15 am - 1:40 pmMDW-KOA
12h 25m1 stop
Southwest Logo
9:15 pm - 11:35 amKOA-MDW
10h 20m1 stop
$508Southwest
Find Deal
Wed, Dec 3 - Wed, Dec 10
Southwest Logo
5:15 am - 1:40 pmMDW-KOA
12h 25m1 stop
Southwest Logo
10:00 am - 5:05 amKOA-MDW
15h 05m2 stops
$513Southwest
Find Deal
Mon, Nov 10 - Mon, Nov 24
Southwest Logo
5:25 am - 1:40 pmMDW-KOA
12h 15m1 stop
Southwest Logo
9:15 pm - 3:40 pmKOA-MDW
14h 25m1 stop
$522Southwest
Find Deal
Thu, Nov 13 - Tue, Nov 18
Southwest Logo
7:55 am - 6:10 pmMDW-KOA
14h 15m2 stops
Southwest Logo
9:15 pm - 11:35 amKOA-MDW
10h 20m1 stop
$529Southwest
Find Deal
Thu, Nov 13 - Tue, Nov 18
Southwest Logo
7:55 am - 6:10 pmMDW-KOA
14h 15m2 stops
Southwest Logo
6:55 pm - 12:45 pmKOA-MDW
13h 50m2 stops
$535Southwest
Find Deal
Mon, Nov 10 - Mon, Nov 24
Southwest Logo
5:25 am - 1:40 pmMDW-KOA
12h 15m1 stop
Southwest Logo
9:15 pm - 2:35 pmKOA-MDW
13h 20m2 stops
$559Southwest
Find Deal
Thu, Nov 13 - Tue, Nov 18
Southwest Logo
5:25 am - 1:40 pmMDW-KOA
12h 15m1 stop
Southwest Logo
9:15 pm - 11:35 amKOA-MDW
10h 20m1 stop
$577Southwest
Find Deal
Sat, Sep 13 - Tue, Sep 23
Southwest Logo
8:25 am - 6:10 pmMDW-KOA
14h 45m2 stops
Southwest Logo
8:30 pm - 11:45 amKOA-MDW
10h 15m1 stop
$579Southwest
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Tue, Nov 4 - Thu, Nov 6
Delta Logo
6:00 am - 7:53 pmMDW-KOA
17h 53m2 stops
Delta Logo
9:30 pm - 8:40 amKOA-MDW
31h 10m2 stops
$613Delta
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Wed, Oct 29 - Tue, Nov 11
Delta Logo
9:35 am - 5:30 pmMDW-KOA
36h 55m2 stops
Delta Logo
9:35 pm - 6:36 pmKOA-MDW
17h 01m2 stops
$614Delta
Find Deal
Booking Insights

KAYAK's insights & trends for Midway to The Big Island flights

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

Can I save money by flying with a layover from Chicago Midway Airport to The Big Island?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $310, prices are generally cheapest when you fly direct.


Good to know

Low seasonNovember
Cheapest flight$305
Best time to beat the crowds with an average 37% drop in price.
Most popular time to fly and prices are also 25% lower on average.
Flight from Chicago Midway Airport to Kailua-Kona

FAQs - booking The Big Island flights

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

    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 The Big Island.

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

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

    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 The Big Island 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 The Big Island?

    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 The Big Island 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 The Big Island?

    The cheapest time of day to fly to The Big Island is generally in the morning, when round-trip flights cost $741 on average. The most expensive time of day to fly to The Big Island is generally in the morning, which is peak travel time and where the average cost of a ticket is $741.

Reviews of the top airline flying from Midway to The Big Island

 
See real verified KAYAK customer reviews for airlines flying from Chicago to The Big Island. 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 The Big Island? 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.

Everything you need to know for your flight to The Big Island

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