$296 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 6/7. 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.
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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
Honolulu2 stops$478
Kahului
Kahului2 stops$641
Kailua-Kona
Kailua-Kona2 stops$478
Lihue
Lihue2 stops$594
Hilo
Hilo2 stops$1,124
Honolulu
Honolulu2 stops$478
Kahului
Kahului2 stops$641
Kailua-Kona
Kailua-Kona2 stops$478
Lihue
Lihue2 stops$594
Hilo
Hilo2 stops$1,124

Cheap Flight Deals from Midway to Hawaii (MDW-USHI)

 
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.

Recent round-trip flight deals from Midway to Hawaii

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Midway to Hawaii.
Discover the best prices for you by selecting your travel dates on KAYAK.
Delta Logo
9:20 am - 9:20 pmMDW-HNL
17h 00m2 stops
Delta Logo
12:35 pm - 8:46 amHNL-MDW
15h 11m2 stops
$478Delta
Find Deal
Wed, Sep 3 - Thu, Sep 11
Delta Logo
9:20 am - 6:40 pmMDW-KOA
14h 20m2 stops
Delta Logo
8:40 pm - 6:07 pmKOA-MDW
16h 27m2 stops
$478Delta
Find Deal
Mon, Sep 8 - Mon, Sep 15
Southwest Logo
9:10 pm - 10:20 amMDW-HNL
18h 10m1 stop
Southwest Logo
8:05 am - 12:30 amHNL-MDW
11h 25m1 stop
$479Southwest
Find Deal
Wed, Sep 3 - Thu, Sep 11
Southwest Logo
9:10 pm - 10:20 amMDW-HNL
18h 10m1 stop
Southwest Logo
11:35 am - 10:30 amHNL-MDW
17h 55m2 stops
$497Southwest
Find Deal
Wed, Sep 3 - Thu, Sep 11
Delta Logo
9:20 am - 8:44 pmMDW-HNL
16h 24m2 stops
Delta Logo
1:20 pm - 8:36 amHNL-MDW
14h 16m2 stops
$498Delta
Find Deal
Tue, May 27 - Mon, Jun 2
Southwest Logo
9:10 pm - 10:20 amMDW-HNL
18h 10m1 stop
Southwest Logo
9:05 pm - 12:20 pmHNL-MDW
10h 15m1 stop
$524Southwest
Find Deal
Wed, Sep 10 - Wed, Sep 17
Delta Logo
9:16 am - 8:44 pmMDW-HNL
16h 28m2 stops
Delta Logo
1:10 pm - 8:36 amHNL-MDW
14h 26m2 stops
$528Delta
Find Deal
Thu, May 29 - Thu, Jun 5
Southwest Logo
9:10 pm - 10:20 amMDW-HNL
18h 10m1 stop
Southwest Logo
11:35 am - 5:10 amHNL-MDW
12h 35m2 stops
$529Southwest
Find Deal
Mon, Sep 8 - Fri, Sep 12
Delta Logo
9:20 am - 7:50 pmMDW-HNL
15h 30m2 stops
Delta Logo
4:10 pm - 12:32 pmHNL-MDW
15h 22m2 stops
$536Delta
Find Deal
Thu, Sep 25 - Tue, Sep 30
Delta Logo
9:20 am - 6:40 pmMDW-KOA
14h 20m2 stops
Delta Logo
8:40 pm - 6:07 pmKOA-MDW
16h 27m2 stops
$546Delta
Find Deal
Sun, Sep 21 - Tue, Sep 30
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 June and July, when the average cost of round-trip tickets is $963 and $957 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 seasonOctober
Cheapest flight$296
Best time to beat the crowds but there is an average 10% increase in price.
Most popular time to fly and prices are also 16% lower on average.
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 4294 reviews
7.1Food
8.2Boarding
8.6Crew
7.6Entertainment
8.0Comfort
Airline reviews

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

8.0 ExcellentJohn, Apr 2025PVD - FLL
Read more Southwest reviews

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

The seats were a bit cramped and worn, but otherwise okay.

I would have liked to arrive on time - not 5 hours late!

After a 3 hour layover in Denver my flight was delayed over 5 hours! No explanation; no assistance; no offer to provide compensation; no one at Southwest was willing to offer any assistance. 8 hours in the Denver airport - ridiculous!

It was a perfect flight in all aspects! Both legs!

Only one drink pass through the cabin for a 4 hour flight. Quite rough and bumpy landing.

Boarding process, crew were good. But the seats were so uncomfortable that was all I could focus on. I literally had to sit forward so that all 3 of us could fit in row. I will try to avoid Southwest in the future for any flights over 60 minutes.

Delta is my preferred airline. I've traveled with them for years. On time in most cases, good communication, easy to use app. Most planes are pretty nice. I was on a CRJ 700/900 however, which was pretty badly aged inside and needed a refresh. No infotainment, unreliable wifi, best to download before boarding or bring a book. Food choices are really just snacks on this flight, nice variety but about what you'd expect. Great staff and prompt in departure and early arrival too. Overall quite satisfied.

Crew was friendly Love the entertainment in the seat head rest.

Delta flight was on time, seats were comfortable, and crew was nice.

This had nothing to do with Delta… The flights were on time and flawless. The service was excellent. We purchased seats in (aisle/middle) comfort plus since this was a cross country flight. Unfortunately, the woman seated at the window was 300+ pounds and, as might be expected, covered up about a third of the middle seat also. there was absolutely nothing that Delta could have done about that… I just don’t know what the answer should be. If you purchase a seat, you should should be able to use the entire seat and not just the portion that someone else is not sitting/oozing in. Disappointing…there should be something that could be done….I'm just not sure what solution could be.

Delayed take-off. Very small plane so very scary with lots of bumps during the flight. Would never fly Delta on short flights in small 80 seaters plane again! Felt relieved when landed.

The worst part was I was NOT allowed in the lounge even though I was holding a first class ticket and have a premium American Express card. I have flown Business or First Class with many airlines. Delta is the ONLY one who does not extend this courtesy to anyone except people who hold the very expensive American Express card. As a result, I won’t fly Delta if I have any other choice.

A little bumpy ride . No food was being provided due the the turbulence. That was ok it was a short flight to my standards.

Simply outstanding. Their new lounge for Delta One customers is a cut above the rest.

The Dekta Rep that checked us in was great. She's very personable, pleasant, and can tell she enjoys her job.

The plane was old with small storage areas that had problems closing/latching and not enough storage for everyone, and worn, damaged seats. Service was great but feel a little unsafe on such well used planes.

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

Information on your arrival and departure airports

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