MDW

$265 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 10/8. 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

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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

Mon, Nov 17 - Mon, Jan 12
Delta Logo
4:45 pm - 8:52 amHNL-MDW
12h 07m1 stop
Delta Logo
6:00 am - 3:12 pmMDW-HNL
13h 12m1 stop
$475Delta
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Mon, Nov 17 - Mon, Jan 12
Delta Logo
4:45 pm - 1:07 pmHNL-MDW
16h 22m2 stops
Delta Logo
6:00 am - 3:12 pmMDW-HNL
13h 12m1 stop
$480Delta
Find Deal
Mon, Nov 17 - Mon, Jan 12
Delta Logo
4:45 pm - 11:52 amHNL-MDW
15h 07m2 stops
Delta Logo
9:30 am - 8:33 pmMDW-HNL
15h 03m2 stops
$486Delta
Find Deal
Mon, Nov 17 - Mon, Jan 5
Delta Logo
4:45 pm - 8:52 amHNL-MDW
12h 07m1 stop
Delta Logo
6:00 am - 3:12 pmMDW-HNL
13h 12m1 stop
$511Delta
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Thu, Oct 23 - Mon, Oct 27
Delta Logo
2:50 pm - 8:40 amHNL-MDW
12h 50m1 stop
Delta Logo
9:35 am - 8:26 pmMDW-HNL
15h 51m2 stops
$516Delta
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Mon, Oct 27 - Mon, Nov 3
Southwest Logo
9:05 pm - 3:15 pmHNL-MDW
13h 10m2 stops
Southwest Logo
8:20 am - 9:00 pmMDW-HNL
16h 40m1 stop
$539Southwest
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Mon, Oct 13 - Mon, Oct 20
Multiple Airlines Logo
3:01 pm - 11:25 pmHNL-MDW
27h 24m1 stop
Multiple Airlines Logo
5:28 pm - 11:10 amMDW-HNL
46h 42m2 stops
$669Multiple Airlines
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Sun, Sep 28 - Sat, Oct 4
Southwest Logo
12:25 pm - 10:35 amHNL-MDW
17h 10m2 stops
Southwest Logo
9:00 pm - 10:20 amMDW-HNL
18h 20m1 stop
$718Southwest
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Mon, Oct 6 - Thu, Oct 9
Southwest Logo
9:05 pm - 12:25 pmHNL-MDW
10h 20m1 stop
Southwest Logo
9:25 pm - 10:20 amMDW-HNL
17h 55m1 stop
$719Southwest
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Sun, Oct 5 - Wed, Oct 8
Southwest Logo
9:05 pm - 1:20 pmHNL-MDW
11h 15m1 stop
Southwest Logo
7:10 am - 4:25 pmMDW-HNL
14h 15m2 stops
$736Southwest
Find Deal

Everything you should know

Cheapest round-trip
$475
Delta
Mon 11/17Mon 1/12
HNL - MDW • 1 stop
Cheapest one-way
$265
Typical prices: $307-350
Multiple Airlines
Wed 10/8
HNL - MDW • 2 stops
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Midway!
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$265
Best time to beat the crowds with an average 12% drop in price.
Most popular time to fly and prices are also 11% 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 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 4242 reviews
8.0Comfort
7.5Entertainment
7.0Food
8.6Crew
8.1Boarding
Airline reviews

I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!

10.0 ExcellentG, Sep 2025LAS - ATL
Read more Southwest reviews

I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!

As always, the entire Southwest experience was wonderful, from online booking to flight to baggage retrieval. Very grateful.

The weather could have been better. There was a 40 minute ATC delay in SFO because of marine fog and a micro cell storm delayed landing and take-off at Nashville. The gate was changed 5 minutes from boarding from gate B3 to gate C23 at Nashville airport.

After being assaulted by a flight attendant I was then brushed off as oh well because he long braids didn’t mean to whip me in the eye. I have filed complaints and will see. But like any other issue I’ve had with kayak involved it’s been trash. Last time I’ll be using your app

AC sub par. WiFi not working correctly. Ac sucked. Seats very narrow.

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

Southwest's seats are the least comfortable I have ever sat in.

The cabin was quiet for the redeye flight. The area was clean. The staff was great. The 787 Max was in good condition. Drawbacks were that the seat widths were tight for some passengers. The seat padding was at best average and for a long flight uncomfortable.

Southwest like most American domestic airlines, is a mediocre airline. But it is among the cheapest. Oh well.

My flight was delayed 50 minutes and we were rushed to board to then sit for 15 minutes until the pilot arrived. Unacceptable since we could have waited to board. Also the delayed flight was updated AFTER we boarded to more than the 10 minutes as originally stated.

Perfect flight both ways. On time, courteous staff, plane comfortable and cool. Best domestic flights I’ve had in awhile.

Really low quality food especially for an international flight. The crew also was surprisingly unpleasant except couple of ladies. I know we were not in first class but that’s no reason to treat customers as less.

Flight delayed for two and half hours and then canceled altogether due to mechanical issues. No mechanic onsite to fix so had to send one from LAX.

Crew was good. The reservation got mixed up and they didn't have my TSA number. I am also a Silver Medallion and wasn't able to use Sky Priority.

Delta made it easy, comfortable and timely. The crew was fantastic.

This route with Delta always has delays or is cancelled. Aircrafts seem smaller and older. I fly Delta quite a bit - haven’t had issues with the international flights. But this route has always been the troublesome one

Three seats in first class were broken and while they were able to still acommodate us it was looking very touch and go and they had others they could not acommodate

Mechanic delay in addition to a 2 hour change in takeoff time was frustrating.

Delayed due to thunderstorms and no in-flight service due to rough weather — both of which are out of Delta’s control. Flight was good overall.

The flight attendants in SLC were rude. I arrived 40 minutes early to gate. Ticket said I needed check in for seat assignments and tried check in and attendants said they weren’t doing it. And proceeded to never call me to give me a ticket so when time to board I received the very last seat. Please relay to employees to do their job better..,

Traveling to a place near Midway?

Book flights to Midway if you plan to visit one of these locations
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Schererville
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Griffith

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