MDW

$218 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 5/13. 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

Thu, Apr 23 - Mon, Apr 27
Southwest Logo
9:25 pm - 1:05 pm
HNL
-
MDW
10h 40m
1 stop
Southwest Logo
9:45 pm - 9:50 am
MDW
-
HNL
17h 05m
1 stop
$362Southwest
Thu, Apr 23 - Mon, Apr 27
Southwest Logo
9:25 pm - 1:05 pm
HNL
-
MDW
10h 40m
1 stop
Southwest Logo
8:35 am - 9:05 pm
MDW
-
HNL
17h 30m
2 stops
$368Southwest
Thu, Apr 23 - Mon, Apr 27
Southwest Logo
9:25 pm - 5:55 pm
HNL
-
MDW
15h 30m
1 stop
Southwest Logo
9:45 pm - 9:50 am
MDW
-
HNL
17h 05m
1 stop
$438Southwest
Thu, Apr 23 - Mon, Apr 27
Southwest Logo
9:25 pm - 5:55 pm
HNL
-
MDW
15h 30m
1 stop
Southwest Logo
8:35 am - 9:05 pm
MDW
-
HNL
17h 30m
2 stops
$444Southwest
Thu, Apr 16 - Wed, Apr 29
Delta Logo
3:15 pm - 8:47 am
HNL
-
MDW
12h 32m
1 stop
Delta Logo
9:29 am - 9:45 pm
MDW
-
HNL
17h 16m
2 stops
$460Delta
Thu, Apr 23 - Mon, Apr 27
Southwest Logo
8:55 pm - 2:20 pm
HNL
-
MDW
12h 25m
2 stops
Southwest Logo
8:35 am - 9:05 pm
MDW
-
HNL
17h 30m
2 stops
$464Southwest
Thu, Apr 16 - Wed, Apr 29
Delta Logo
3:15 pm - 8:47 am
HNL
-
MDW
12h 32m
1 stop
Delta Logo
9:29 am - 9:45 pm
MDW
-
HNL
17h 16m
2 stops
$480Delta
Wed, Apr 29 - Wed, May 6
Southwest Logo
9:25 pm - 5:55 pm
HNL
-
MDW
15h 30m
1 stop
Southwest Logo
10:05 am - 9:00 pm
MDW
-
HNL
15h 55m
1 stop
$485Southwest
Wed, Apr 29 - Wed, May 6
Southwest Logo
9:25 pm - 1:05 pm
HNL
-
MDW
10h 40m
1 stop
Southwest Logo
11:45 am - 9:00 pm
MDW
-
HNL
14h 15m
2 stops
$491Southwest
Fri, Apr 24 - Sun, Apr 26
Southwest Logo
8:15 am - 5:00 am
HNL
-
MDW
15h 45m
1 stop
Southwest Logo
9:55 am - 9:05 pm
MDW
-
HNL
16h 10m
1 stop
$514Southwest
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$218
Best time to beat the crowds with an average 2% drop in price.
Most popular time to fly and prices are also 2% 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.
8.0
SouthwestOverall score based on 4320 reviews
7.0Food
8.6Crew
8.1Boarding
7.5Entertainment
8.0Comfort
Airline reviews

We had a 5 hour delay on the tarmac in Baltimore

2.0 MediocreDavid, Mar 2026
ALB - BWI
Read more Southwest reviews

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 problem with the seat assignments is that there were a lot of rows in the front that were empty but my row at the back was full. Just not so pleasant.

No food or entertainment, just a quick 40 minute flight. A little bumpy due to Santa Ana winds but pilot has no control over that. Good flight and landing!

Good but I prefer choose your own seat. With the new assigned seats they should board from the back I see no advantage to this new boarding. Just like every other airline

I realize they are still working out kinks with the new boarding process, but by the time I boarded in group 5, most of the bins were full. All airlines should better enforce small bags and jackets going under the seats until everyone has boarded.

WiFi was not working and didn’t have a beverage service

Snacks are always pretzels. Why can't you also offer peanuts ?

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
Chesterton
Schererville
Munster
Porter
Monticello
Saint John
Griffith

Everything you need to know for your flight to Midway

Information on your arrival and departure airports

Chicago Midway Airport (MDW)