MDW

$181 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 3/6. 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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Everything you should know

Cheapest round-trip
$360
Southwest
Thu 2/26Thu 3/5
HNL - MDW • 1 stop
Cheapest one-way
$181
Southwest
Fri 3/6
HNL - MDW • 1 stop
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We hope you love your trip to Midway!
Flight Deals
Useful Info
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, Feb 26 - Thu, Mar 5
Southwest Logo
9:55 pm - 6:20 pm
HNL
-
MDW
16h 25m
1 stop
Southwest Logo
9:30 pm - 11:00 am
MDW
-
HNL
17h 30m
1 stop
$360Southwest
Thu, Feb 26 - Thu, Mar 5
Southwest Logo
9:55 pm - 1:40 pm
HNL
-
MDW
11h 45m
2 stops
Southwest Logo
8:50 am - 10:10 pm
MDW
-
HNL
17h 20m
1 stop
$366Southwest
Mon, May 11 - Mon, May 18
Southwest Logo
11:55 am - 5:25 am
HNL
-
MDW
12h 30m
1 stop
Southwest Logo
9:45 pm - 9:50 am
MDW
-
HNL
17h 05m
1 stop
$422Southwest
Wed, Apr 1 - Wed, Apr 8
Delta Logo
3:30 pm - 8:53 am
HNL
-
MDW
12h 23m
1 stop
Delta Logo
9:30 am - 8:53 pm
MDW
-
HNL
16h 23m
2 stops
$430Delta
Mon, May 11 - Mon, May 18
Southwest Logo
11:55 am - 5:00 am
HNL
-
MDW
12h 05m
2 stops
Southwest Logo
9:45 pm - 9:50 am
MDW
-
HNL
17h 05m
1 stop
$456Southwest
Mon, Feb 23 - Mon, Mar 2
Southwest Logo
9:55 pm - 12:35 pm
HNL
-
MDW
10h 40m
1 stop
Southwest Logo
8:00 am - 9:00 pm
MDW
-
HNL
17h 00m
1 stop
$470Southwest
Wed, Feb 25 - Wed, Mar 4
Delta Logo
1:55 pm - 9:06 am
HNL
-
MDW
15h 11m
2 stops
Delta Logo
6:00 am - 3:11 pm
MDW
-
HNL
13h 11m
1 stop
$488Delta
Mon, Feb 23 - Mon, Mar 2
Delta Logo
4:45 pm - 8:54 am
HNL
-
MDW
12h 09m
1 stop
Delta Logo
9:34 am - 9:28 pm
MDW
-
HNL
15h 54m
2 stops
$490Delta
Sun, May 10 - Thu, May 14
Southwest Logo
9:25 pm - 12:35 pm
HNL
-
MDW
10h 10m
1 stop
Southwest Logo
9:45 pm - 9:50 am
MDW
-
HNL
17h 05m
1 stop
$492Southwest
Wed, Feb 18 - Sun, Feb 22
Southwest Logo
9:00 pm - 12:10 pm
HNL
-
MDW
11h 10m
1 stop
Southwest Logo
10:50 am - 9:00 pm
MDW
-
HNL
14h 10m
1 stop
$493Southwest
Useful Info

Good to know

Low seasonDecember
Cheapest flight$181
Best time to beat the crowds but there is an average 11% increase in price.
Most popular time to fly with an average 3% increase in price.
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 4268 reviews
7.0Food
7.5Entertainment
8.1Boarding
8.0Comfort
8.6Crew
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.

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
Griffith
Saint John

Everything you need to know for your flight to Midway

Information on your arrival and departure airports

Chicago Midway Airport (MDW)