MDW

$221 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 6/5. 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.
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Flights 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.

Recent round-trip flight deals from O'ahu to Midway

KAYAK's recommended round-trip deals from the most popular airlines that fly from O'ahu to Midway.
Discover the best prices for you by selecting your travel dates on KAYAK.
Delta Logo
12:35 pm - 8:36 amHNL-MDW
15h 01m2 stops
Delta Logo
6:00 am - 1:30 pmMDW-HNL
12h 30m1 stop
$548Delta
Find Deal
Thu, Aug 21 - Tue, Aug 26
Delta Logo
12:35 pm - 8:36 amHNL-MDW
15h 01m2 stops
Delta Logo
9:30 am - 7:12 pmMDW-HNL
14h 42m2 stops
$554Delta
Find Deal
Thu, Aug 21 - Tue, Aug 26
Delta Logo
1:20 pm - 8:36 amHNL-MDW
14h 16m2 stops
Delta Logo
9:16 am - 8:44 pmMDW-HNL
16h 28m2 stops
$558Delta
Find Deal
Fri, May 23 - Fri, May 30
Delta Logo
3:45 pm - 8:40 amHNL-MDW
11h 55m1 stop
Delta Logo
9:20 am - 7:50 pmMDW-HNL
15h 30m2 stops
$560Delta
Find Deal
Thu, Sep 4 - Thu, Sep 11
Southwest Logo
8:10 am - 11:25 pmHNL-MDW
10h 15m1 stop
Southwest Logo
9:10 pm - 10:20 amMDW-HNL
18h 10m1 stop
$563Southwest
Find Deal
Thu, Sep 4 - Thu, Sep 11
Delta Logo
4:10 pm - 12:30 pmHNL-MDW
15h 20m2 stops
Delta Logo
9:20 am - 7:50 pmMDW-HNL
15h 30m2 stops
$566Delta
Find Deal
Thu, Sep 4 - Thu, Sep 11
Delta Logo
1:20 pm - 8:40 amHNL-MDW
14h 20m2 stops
Delta Logo
9:16 am - 8:44 pmMDW-HNL
16h 28m2 stops
$598Delta
Find Deal
Wed, May 28 - Wed, Jun 4
Delta Logo
12:00 pm - 8:46 amHNL-MDW
15h 46m2 stops
Delta Logo
9:20 am - 7:50 pmMDW-HNL
15h 30m2 stops
$614Delta
Find Deal
Fri, Oct 17 - Wed, Oct 22
Delta Logo
3:45 pm - 8:45 amHNL-MDW
12h 00m1 stop
Delta Logo
9:20 am - 7:50 pmMDW-HNL
15h 30m2 stops
$618Delta
Find Deal
Wed, Oct 15 - Wed, Oct 22
Southwest Logo
8:05 am - 12:25 amHNL-MDW
11h 20m1 stop
Southwest Logo
9:00 pm - 10:20 amMDW-HNL
18h 20m1 stop
$663Southwest
Find Deal
Wed, Oct 22 - Sat, Oct 25
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Good to know

Low seasonJanuary
High seasonMay
Cheapest flight$221
Best time to beat the crowds with an average 5% drop in price.
Most popular time to fly and prices are also 4% 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.

Top airlines 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 4294 reviews
8.2Boarding
8.6Crew
7.1Food
7.6Entertainment
8.0Comfort
Airline reviews

It is southwest seat was ok. Not the most comfortable seat

8.0 ExcellentJohn, Apr 2025PVD - FLL
Read more Southwest reviews

It is southwest seat was ok. Not the most comfortable seat

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

Plz don't take away free bags and free seating

The seats were a bit cramped and worn, but otherwise okay.

I would have liked to arrive on time - not 5 hours late!

After a 3 hour layover in Denver my flight was delayed over 5 hours! No explanation; no assistance; no offer to provide compensation; no one at Southwest was willing to offer any assistance. 8 hours in the Denver airport - ridiculous!

It was a perfect flight in all aspects! Both legs!

Only one drink pass through the cabin for a 4 hour flight. Quite rough and bumpy landing.

Boarding process, crew were good. But the seats were so uncomfortable that was all I could focus on. I literally had to sit forward so that all 3 of us could fit in row. I will try to avoid Southwest in the future for any flights over 60 minutes.

Delta is my preferred airline. I've traveled with them for years. On time in most cases, good communication, easy to use app. Most planes are pretty nice. I was on a CRJ 700/900 however, which was pretty badly aged inside and needed a refresh. No infotainment, unreliable wifi, best to download before boarding or bring a book. Food choices are really just snacks on this flight, nice variety but about what you'd expect. Great staff and prompt in departure and early arrival too. Overall quite satisfied.

Crew was friendly Love the entertainment in the seat head rest.

Delta flight was on time, seats were comfortable, and crew was nice.

This had nothing to do with Delta… The flights were on time and flawless. The service was excellent. We purchased seats in (aisle/middle) comfort plus since this was a cross country flight. Unfortunately, the woman seated at the window was 300+ pounds and, as might be expected, covered up about a third of the middle seat also. there was absolutely nothing that Delta could have done about that… I just don’t know what the answer should be. If you purchase a seat, you should should be able to use the entire seat and not just the portion that someone else is not sitting/oozing in. Disappointing…there should be something that could be done….I'm just not sure what solution could be.

Delayed take-off. Very small plane so very scary with lots of bumps during the flight. Would never fly Delta on short flights in small 80 seaters plane again! Felt relieved when landed.

The worst part was I was NOT allowed in the lounge even though I was holding a first class ticket and have a premium American Express card. I have flown Business or First Class with many airlines. Delta is the ONLY one who does not extend this courtesy to anyone except people who hold the very expensive American Express card. As a result, I won’t fly Delta if I have any other choice.

A little bumpy ride . No food was being provided due the the turbulence. That was ok it was a short flight to my standards.

Simply outstanding. Their new lounge for Delta One customers is a cut above the rest.

The Dekta Rep that checked us in was great. She's very personable, pleasant, and can tell she enjoys her job.

The plane was old with small storage areas that had problems closing/latching and not enough storage for everyone, and worn, damaged seats. Service was great but feel a little unsafe on such well used planes.

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