$217 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 2/24. 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$393
Kahului
Kahului1 stop$422
Kailua-Kona
Kailua-Kona2 stops$462
Lihue
Lihue2 stops$367
Hilo
Hilo2 stops$665
Honolulu
Honolulu1 stop$393
Kahului
Kahului1 stop$422
Kailua-Kona
Kailua-Kona2 stops$462
Lihue
Lihue2 stops$367
Hilo
Hilo2 stops$665

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

Tue, Feb 24 - Tue, Mar 3
Southwest Logo
5:05 am - 4:25 pm
MDW
-
LIH
15h 20m
2 stops
Southwest Logo
9:15 pm - 2:45 pm
LIH
-
MDW
13h 30m
2 stops
$367Southwest
Thu, Feb 26 - Thu, Mar 5
Southwest Logo
5:00 am - 1:15 pm
MDW
-
HNL
12h 15m
1 stop
Southwest Logo
2:50 pm - 5:55 am
HNL
-
MDW
11h 05m
1 stop
$393Southwest
Thu, Feb 26 - Wed, Mar 4
Southwest Logo
10:15 pm - 11:15 am
MDW
-
HNL
17h 00m
1 stop
Southwest Logo
9:55 pm - 6:00 pm
HNL
-
MDW
16h 05m
2 stops
$399Southwest
Thu, Feb 26 - Thu, Mar 5
Southwest Logo
10:15 pm - 11:15 am
MDW
-
HNL
17h 00m
1 stop
Southwest Logo
2:50 pm - 11:05 am
HNL
-
MDW
16h 15m
1 stop
$403Southwest
Tue, Apr 14 - Tue, Apr 21
Southwest Logo
10:05 am - 9:00 pm
MDW
-
HNL
15h 55m
1 stop
Southwest Logo
1:00 pm - 5:50 am
HNL
-
MDW
11h 50m
1 stop
$413Southwest
Mon, Feb 23 - Tue, Mar 10
Southwest Logo
8:05 am - 9:00 pm
MDW
-
HNL
16h 55m
2 stops
Southwest Logo
8:10 am - 4:35 am
HNL
-
MDW
15h 25m
1 stop
$419Southwest
Thu, Feb 19 - Thu, Feb 26
Southwest Logo
8:00 am - 9:00 pm
MDW
-
HNL
17h 00m
1 stop
Southwest Logo
9:55 pm - 6:20 pm
HNL
-
MDW
16h 25m
1 stop
$421Southwest
Mon, Mar 2 - Mon, Mar 9
Southwest Logo
7:55 am - 4:30 pm
MDW
-
HNL
12h 35m
1 stop
Southwest Logo
11:25 am - 5:45 am
HNL
-
MDW
13h 20m
1 stop
$422Southwest
Sun, May 3 - Wed, May 6
Delta Logo
6:00 am - 1:45 pm
MDW
-
HNL
12h 45m
1 stop
Delta Logo
3:15 pm - 8:42 am
HNL
-
MDW
12h 27m
1 stop
$424Delta
Mon, Feb 23 - Tue, Mar 10
Delta Logo
6:00 am - 3:37 pm
MDW
-
OGG
13h 37m
1 stop
Delta Logo
12:59 pm - 8:53 am
OGG
-
MDW
14h 54m
2 stops
$428Delta
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 $913 and $868 respectively.

Good to know

Low seasonNovember
Cheapest flight$217
Best time to beat the crowds but there is an average 64% 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 4267 reviews
7.5Entertainment
7.0Food
8.6Crew
8.1Boarding
8.0Comfort
Airline reviews

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

10.0 ExcellentAnonymous, Jan 2026
PHX - MDW
Read more Southwest reviews

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

Everything went smoothly and we even arrived a little bit early.

Great vacation. Can't wait till next year for another one.

Great flight but super high price. Glad it was a business trip and not personal

On time. Friendly staff. Took to long to pre bord all the specialty groups. Cramped small plane

The seats were comfortable, and the boarding process was pretty smooth.

3 hour delay. Had to change plans and was still delayed.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

The crew canceled the complementary snack and drink in anticipation of turbulence that never materialized. I was counting on the drink (water) to take the the doses of medication - prescribed for my heart condition - that were due during the flight. Since no snack or meal was served on this flight, I cannot rate the food quality. Otherwise, this flight was excellent.

Departure was delayed more than 1/2 hour while we waited for luggage (only) transfer from another flight/plane. Once approved for takeoff, the flight was excellent.

Timing, quality of service, promptness and courtesy of the staff

It was last minute due to weather - considering - it was amazing! Good smiles, friendly staff and they were making sure we knew what was going on when and where.

delta last minute gave me a boarding pass for a different flight with no confirmation that they were changing it

The service from the flight attendants were of supreme quality. They greeted and treated everyone with a wide smile. This is totally absent nowadays. Kudos to them!!!!

Excellent flight and got us around tough weather. Only issue was seat TV did not work and crew tried to reboot.

Very large passenger too space from my own seat. Arm board couldn’t be lowered because of his size. It wads very uncomfortable trip, as the flight was full couldn’t move anywhere having back pain because of the position in which I was the entire flight.

was sitting in the jet bridge for 10 minutes in -20 degree weather waiting for my bag

Outdated equipment in disrepair, wifi inoperable. Broken seats, taped air vents, generally poor condition, the 717 showed its age and lack of upkeep.

My flight out of Baton Rouge to Atlanta was delayed by a half hour. This got us into Atlanta airport 30 minutes late. I ran through the airport to get to my connecting flight. As I approached the boarding gate, I saw the boarding door was still open and a passenger was being checked in. But when I got to the gate, the boarding agent told me they had already given away my seat and there were no empty seats on that flight. So I had to take a later flight. That has never happened to me before. Very frustrating.

Connection through Atlanta was difficult. Mechanical issue on plane caused a two hour delay. New gate was a mile away.

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

Information on your arrival and departure airports