$219 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 8/12. 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
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Flights Deals

Best Hawaii Flight Deals from Midway

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Honolulu
Honolulu1 stop$437
Kahului
Kahului2 stops$454
Kailua-Kona
Kailua-Kona1 stop$560
Lihue
Lihue1 stop$518
Hilo
Hilo2 stops$644
Honolulu
Honolulu1 stop$437
Kahului
Kahului2 stops$454
Kailua-Kona
Kailua-Kona1 stop$560
Lihue
Lihue1 stop$518
Hilo
Hilo2 stops$644

Cheap Flights from Midway to Hawaii

 
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 10 - Thu, Sep 18
Delta Logo
6:00 am - 1:15 pmMDW-HNL
12h 15m1 stop
Delta Logo
3:45 pm - 8:45 amHNL-MDW
12h 00m1 stop
$437Delta
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Tue, Sep 9 - Thu, Sep 18
Delta Logo
9:15 am - 8:28 pmMDW-HNL
16h 13m2 stops
Delta Logo
3:45 pm - 8:45 amHNL-MDW
12h 00m1 stop
$442Delta
Find Deal
Tue, Sep 9 - Wed, Sep 17
Delta Logo
9:15 am - 8:28 pmMDW-HNL
16h 13m2 stops
Delta Logo
12:35 pm - 8:46 amHNL-MDW
15h 11m2 stops
$448Delta
Find Deal
Wed, Sep 3 - Mon, Sep 8
Southwest Logo
6:10 am - 4:30 pmMDW-OGG
15h 20m2 stops
Southwest Logo
8:30 pm - 6:30 pmOGG-MDW
17h 00m1 stop
$454Southwest
Find Deal
Wed, Sep 3 - Mon, Sep 8
Southwest Logo
6:10 am - 4:30 pmMDW-OGG
15h 20m2 stops
Southwest Logo
8:30 pm - 3:55 pmOGG-MDW
14h 25m2 stops
$460Southwest
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Wed, Sep 3 - Mon, Sep 8
Southwest Logo
6:10 am - 12:25 pmMDW-OGG
11h 15m1 stop
Southwest Logo
8:30 pm - 12:15 pmOGG-MDW
10h 45m1 stop
$469Southwest
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Mon, Oct 27 - Mon, Nov 10
Southwest Logo
5:45 am - 1:00 pmMDW-OGG
12h 15m1 stop
Southwest Logo
9:35 pm - 11:35 amOGG-MDW
10h 00m1 stop
$481Southwest
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Mon, Oct 27 - Mon, Nov 10
Southwest Logo
7:45 am - 4:30 pmMDW-OGG
13h 45m1 stop
Southwest Logo
9:35 pm - 3:00 pmOGG-MDW
13h 25m2 stops
$486Southwest
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Wed, Sep 10 - Fri, Sep 19
Delta Logo
6:00 am - 1:15 pmMDW-HNL
12h 15m1 stop
Delta Logo
12:35 pm - 8:46 amHNL-MDW
15h 11m2 stops
$488Delta
Find Deal
Tue, Sep 9 - Fri, Sep 19
Delta Logo
9:15 am - 8:28 pmMDW-HNL
16h 13m2 stops
Delta Logo
12:35 pm - 8:46 amHNL-MDW
15h 11m2 stops
$494Delta
Find Deal
Useful Info

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 $858 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
High seasonJune
Cheapest flight$219
Best time to beat the crowds but there is an average 5% 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.

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 4287 reviews
8.2Boarding
8.0Comfort
7.1Food
7.6Entertainment
8.6Crew
Airline reviews

Southwest is typically delayed, and it gets wearisome. It is no longer a discount airline and you get way less than you pay for when it comes to comfort and Ce.

6.0 GoodDavid, Jun 2025BWI - COS
Read more Southwest reviews

Southwest is typically delayed, and it gets wearisome. It is no longer a discount airline and you get way less than you pay for when it comes to comfort and Ce.

We sat on the plane on the tarmac for 4 hours.

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

Flight crew and cabin crew were great. I had to rearrange flights because my original flight was 3hrs delayed for weather, the rub is the flight I moved to boarded on time then we sat at the gate for 2 hours because scheduling stole our first officer for another flight, TWICE. Then our actual FO was an hour delayed. To make it worse my original flight went from a 3 hour delay to departing 15min EARLY. Just poor scheduling operations all around.

Bring back peanuts Take our drink orders when were all seated, especially after you switch to assigned seating.

Staff was far less than helpful at all times. Departure and arrival times mean nothing to Southwest. Extremely disappointed, will never fly with them again, and I’ll be sure to share my experience with all.

It is southwest seat was ok. Not the most comfortable seat

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

Plz don't take away free bags and free seating

Great overall. There was a bit of turbulence so they could only serve water because too much turbulence for the carts. Was glad they prioritized safety though

Excellent flight, the planes were newer, they did a nice job with boarding, great service overall.

Great service. Flight was delayed while we sat on the runway for a couple of hours. Weather related. Staff made is very bearable. The steward servicing the first class cabin was exceptional. Thank you! 💗

5 hours of delay that could've been much shorter if Delta had taken the 1 hour delay they imposed on the flight before boarding to run any of the plane checks required for flight to find the hydraulic issue that required nearly 3 hours to fix. $24 of meal credit buys a sandwich and a soft drink. Poor communication within the terminal about what gate we'd be re-boarding from and when we'd be re-boarding.

Amazing flight! I have never noticed the uniforms of the attendants before in twenty years of flying except today when one female had the most amazing dress on. It was beautifully designed and showed she was in charge. I never dreamed I would google who designed Delta uniforms . The ultimate compliment is when another woman admires your outfit. . I hope your designer puts it on the market

It would be nice if was given wires ear buds. Overall was a good experience was able to sleep on the plane

My flight was 6 pm 6/6. Every hour they delayed it again - air condition issues then no pilot then the crew had worked too many hours and cancelled the flight at 11 pm. Sent customers to NJ a 45 minutes uber ride to a hotel. Had to be back by 5 am for a 7 am flight and again no pilot etc with another three hours of delays.

The entertainment and wifi mostly didn't work on this flight.

Terrible entertainment system - kept freezing and audio kept cutting out. Snacks were mediocre at best for a 5 hour flight.

The check in and bag drop off for Sky Priority members is slow. The Clear security was also slow - a TSA issue.

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

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