MDW

$277 Find Cheap Flights from O'ahu to Chicago Midway Airport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Midway departing on 9/10. 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

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Flight Deals

Cheap Flights from O'ahu to Midway

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from O'ahu to Midway 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 O'ahu to Midway

Wed, Sep 2 - Wed, Sep 9
Southwest Logo
8:10 am - 4:30 am
HNL
-
MDW
15h 20m
1 stop
Southwest Logo
10:15 am - 9:15 pm
MDW
-
HNL
16h 00m
1 stop
$554Southwest
Thu, Aug 27 - Wed, Sep 9
Southwest Logo
9:25 pm - 3:15 pm
HNL
-
MDW
12h 50m
2 stops
Southwest Logo
12:20 pm - 9:15 pm
MDW
-
HNL
13h 55m
1 stop
$560Southwest
Thu, Sep 10 - Mon, Sep 14
Southwest Logo
9:25 pm - 3:15 pm
HNL
-
MDW
12h 50m
2 stops
Southwest Logo
10:20 am - 9:15 pm
MDW
-
HNL
15h 55m
2 stops
$565Southwest
Thu, Aug 20 - Tue, Aug 25
Southwest Logo
8:10 am - 4:30 am
HNL
-
MDW
15h 20m
1 stop
Southwest Logo
12:20 pm - 9:15 pm
MDW
-
HNL
13h 55m
1 stop
$584Southwest
Thu, Aug 20 - Tue, Aug 25
Southwest Logo
8:10 am - 11:45 pm
HNL
-
MDW
10h 35m
1 stop
Southwest Logo
11:00 am - 9:20 pm
MDW
-
HNL
15h 20m
2 stops
$590Southwest
Wed, Sep 2 - Wed, Sep 9
Southwest Logo
8:55 pm - 2:35 pm
HNL
-
MDW
12h 40m
2 stops
Southwest Logo
10:20 am - 9:10 pm
MDW
-
HNL
15h 50m
1 stop
$598Southwest
Wed, Aug 26 - Tue, Sep 8
Southwest Logo
9:55 pm - 5:00 pm
HNL
-
MDW
14h 05m
1 stop
Southwest Logo
10:20 am - 9:10 pm
MDW
-
HNL
15h 50m
1 stop
$602Southwest
Wed, Sep 2 - Wed, Sep 9
Delta Logo
4:18 pm - 12:39 pm
HNL
-
MDW
15h 21m
2 stops
Delta Logo
9:20 am - 8:47 pm
MDW
-
HNL
16h 27m
2 stops
$603Delta
Wed, Aug 26 - Tue, Sep 8
Southwest Logo
9:55 pm - 3:15 pm
HNL
-
MDW
12h 20m
2 stops
Southwest Logo
10:20 am - 9:10 pm
MDW
-
HNL
15h 50m
1 stop
$608Southwest
Mon, Aug 3 - Mon, Aug 17
Southwest Logo
12:15 pm - 5:40 am
HNL
-
MDW
12h 25m
1 stop
Southwest Logo
10:10 am - 9:15 pm
MDW
-
HNL
16h 05m
1 stop
$622Southwest
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$277
Best time to beat the crowds but there is an average 7% increase in price.
Most popular time to fly and prices are also 1% lower on average.
Flight from Honolulu to Chicago Midway Airport

FAQs for booking O'ahu to Chicago Midway Airport flights

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

    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 O'ahu to Chicago Midway Airport.

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

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

    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 to Chicago Midway Airport with an airline and back to O'ahu with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from O'ahu to Chicago Midway Airport?

    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 to Chicago Midway Airport from 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 airline flying from O'ahu to Midway

 
Need help choosing which airline to fly with from O'ahu to Midway? 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.
7.9
SouthwestOverall score based on 4235 reviews
8.1Boarding
8.6Crew
7.5Entertainment
8.0Comfort
7.0Food
Airline reviews

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

2.0 MediocreMatthew, Jun 2026
CVG - MDW
Read more Southwest reviews

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

It was great. The gate staff were very helpful in Portland when my son forgot his rolling bag and had to go back to get it just in time to make it on the plane. We really appreciate that. Great job!

Airline is not very senior friendly. Flights are late, forcing us to run to the connecting flight. Food is awful. Wish they would go back to pretzels and peanuts. During flight, pressurization isn’t quite right and all of our ears get plugged. Everything is nickel and dime, charging for boarding, seat selection and legroom. While a screen at the desk in the gate area says check your roll on bag now for free due to space limitation, the employee at the desk will not check the bag without a $100 fee. Insane.

Kayak could’ve posted the correct gate number. Almost missed my flight.

Slow boarding, limited food and drink portions. Bad delays and turbulence

there were two flight attendants that were up front...that were the best! They get KUDOs for making my trip only fantastic. Tell them Jeff said that!

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

Flight coming out of Buffalo was delayed, so we had to be rescheduled on another flight from Baltimore to Phoenix which means we had a long layover and got home 3.5 hours late. Shuttle to parking stopped at 10pm, so we had to pay for an Uber to the parking lot and got charged an extra day of parking since it was after midnight. Not the best experience. Long day!

Was fine, delayed and feels like southwest is always late

I don't know why flying out of Sarasota requires two plane changes.

Traveling to a place near Midway?

Book flights to Midway if you plan to visit one of these locations
Merrillville
Saint Joseph
Hammond
Portage
Lansing
Valparaiso
Schererville
Munster
Chesterton
Porter
Monticello
Saint John
Griffith

Everything you need to know for your flight to Midway

Information on your arrival and departure airports