$258 Find Cheap Flights from Chicago Midway Airport to O'ahu

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 O'ahu departing on 4/29. 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 O'ahu

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to O'ahu, 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 O'ahu, as well as popular online travel agencies
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Flight Deals

Book Cheap Midway to O'ahu 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 O'ahu 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 O'ahu

Wed, Aug 19 - Wed, Aug 26
Southwest Logo
10:20 am - 9:10 pm
MDW
-
HNL
15h 50m
1 stop
Southwest Logo
8:10 am - 4:30 am
HNL
-
MDW
15h 20m
1 stop
$428Southwest
Wed, Aug 19 - Wed, Aug 26
Southwest Logo
10:20 am - 9:10 pm
MDW
-
HNL
15h 50m
1 stop
Southwest Logo
8:55 pm - 2:35 pm
HNL
-
MDW
12h 40m
2 stops
$434Southwest
Wed, Apr 29 - Wed, May 6
Delta Logo
9:29 am - 9:45 pm
MDW
-
HNL
17h 16m
2 stops
Delta Logo
2:45 pm - 8:43 am
HNL
-
MDW
12h 58m
1 stop
$470Delta
Wed, Apr 29 - Wed, May 6
Delta Logo
9:29 am - 9:45 pm
MDW
-
HNL
17h 16m
2 stops
Delta Logo
12:25 pm - 8:43 am
HNL
-
MDW
15h 18m
2 stops
$475Delta
Tue, Sep 1 - Tue, Sep 15
Southwest Logo
10:20 am - 9:10 pm
MDW
-
HNL
15h 50m
1 stop
Southwest Logo
11:55 am - 5:45 am
HNL
-
MDW
12h 50m
1 stop
$496Southwest
Tue, Sep 1 - Tue, Sep 15
Southwest Logo
11:10 am - 9:20 pm
MDW
-
HNL
15h 10m
2 stops
Southwest Logo
8:00 am - 11:00 pm
HNL
-
MDW
10h 00m
1 stop
$502Southwest
Wed, Apr 22 - Wed, Apr 29
Southwest Logo
10:20 am - 5:40 pm
MDW
-
HNL
12h 20m
1 stop
Southwest Logo
8:15 am - 5:00 am
HNL
-
MDW
15h 45m
1 stop
$504Southwest
Tue, Sep 1 - Tue, Sep 15
Southwest Logo
11:10 am - 9:20 pm
MDW
-
HNL
15h 10m
2 stops
Southwest Logo
8:15 am - 5:55 am
HNL
-
MDW
16h 40m
2 stops
$507Southwest
Mon, Apr 27 - Thu, Apr 30
Southwest Logo
8:35 am - 9:05 pm
MDW
-
HNL
17h 30m
2 stops
Southwest Logo
8:50 pm - 5:55 pm
HNL
-
MDW
16h 05m
2 stops
$512Southwest
Mon, Apr 13 - Wed, Apr 22
Delta Logo
1:24 pm - 9:45 pm
MDW
-
HNL
13h 21m
2 stops
Delta Logo
12:25 pm - 8:47 am
HNL
-
MDW
15h 22m
2 stops
$515Delta
Booking Insights

KAYAK's insights & trends for Midway to O'ahu flights

Get data-powered insights and trends into flights from Midway to O'ahu 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 O'ahu?

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 $384, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Chicago Midway Airport to O'ahu?

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 O'ahu, 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 O'ahu 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 $909 and $868 respectively.

Good to know

Low seasonNovember
Cheapest flight$258
Best time to beat the crowds but there is an average 19% increase in price.
Most popular time to fly and prices are also 4% lower on average.
Flight from Chicago Midway Airport to Honolulu

FAQs - booking O'ahu flights

  • How does KAYAK find such low prices on flights from Chicago Midway Airport to O'ahu?

    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 O'ahu.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago Midway Airport to O'ahu 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 O'ahu?

    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 O'ahu 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 O'ahu?

    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 O'ahu 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 O'ahu

 
See real verified KAYAK customer reviews for airlines flying from Chicago to O'ahu. 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 O'ahu? 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 4331 reviews
8.0Comfort
7.0Food
7.5Entertainment
8.1Boarding
8.6Crew
Airline reviews

Great flight. Good snacks and drinks. Grateful it was free. The flight from Nashville to louisville, i think her name was Tracy (not sure that's right) super awesome, nice and cheerful. She really enjoyed being at work today! She was the person who scanned the boarding pass on flight wn941. She should be recommended for a raise !

10.0 ExcellentGwen, Mar 2026
DAL - BNA
Read more Southwest reviews

Great flight. Good snacks and drinks. Grateful it was free. The flight from Nashville to louisville, i think her name was Tracy (not sure that's right) super awesome, nice and cheerful. She really enjoyed being at work today! She was the person who scanned the boarding pass on flight wn941. She should be recommended for a raise !

I liked it better when you were truer to your roots Am paying more for less fun

Southwest was greaat! The most expensive but the least upsetting for those we were flying to see.

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

Boarding was easy. The seats are small and fairly uncomfortable

I was supposed to be on a later flight. When I showed up at the gate, the woman working there was extremely helpful getting moved up to this earlier flight.

We had a 5 hour delay on the tarmac in Baltimore

Long layover between flights to Long Island from BWI - need better coordination between flights

I elected to pay for the upgrades and found very little difference

The new seating arrangement is so over priced for what you get.

The cabin temperature was nice and cool. The wifi was not working.

Flight late, the waited for a long time for “personal” to arrive at gate to dock the plane in Rochester. So annoying. This flight was expected, why aren’t personel available for the jet bridge?

As previously noted, this flight was great: departure was timely, the crew was friendly and attentive, and wifi connectivity was seamless. In particular, I appreciated that the flight attendant just told me to stow the laptop right before takeoff/landing, and trusted me to do so (which I did!).

Kayak botched up the booking, i had to call delta and fix. In the process Delta failed to honor my comfort plus seat assignment that i had previously.

Entertainment is ok! Boarding and seat with zone is terrible. I paid for the seats but you didn’t give me what I paid for which is exit isles.

the crew cancel the morning service due to the weather. Then the flight got deverted to Nashville . we were on the ground for over two hours the only gave us water once... no food or any snacks.... the crew should have handled better and offered something to passengers.

My recent experience was excellent on Delta! I flew with Delta Comfort and I was really comfortable in my seat. I enjoyed the in-flight service. The flight attendants were so friendly and hospitable. I love the snack on the flight as well. This was my first time flying on Delta and I will definitely consider flying with them again.

My flight was cencaled due with the bad weather on Sunday the crew was poorly mistaken my luggage supposed depart with my flight instead I didn’t have my luggage for almost 3 days the website is poorly respond to my complain until I have someone to do it my connection smooth their not even respon or email me even the have my luggage

Delta needs to step its game up get a more reliable internet service. Internet service was non-existent for this flight.

Mechanical Delay of over an hour with multiple gate changes. Entertainment system down for rejuvenation.

Everything you need to know for your flight to O'ahu

Information on your arrival and departure airports