$240 Find Cheap Flights from Chicago Midway Airport to O'ahu

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to O'ahu departing on 11/11. 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

KAYAK searches hundreds of travel sites at once for deals on flights to O'ahu

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to O'ahu, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to O'ahu, as well as popular online travel agencies
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 22% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Midway to O'ahu

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Honolulu
Honolulu1 stop$471
Honolulu
Honolulu1 stop$471

Book Cheap Midway to O'ahu Plane Tickets

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

Sun, Jan 25 - Wed, Jan 28
Delta Logo
6:00 am - 3:12 pmMDW-HNL
13h 12m1 stop
Delta Logo
5:00 pm - 9:23 amHNL-MDW
12h 23m1 stop
$471Delta
Find Deal
Thu, Feb 5 - Tue, Feb 10
Southwest Logo
8:35 pm - 11:15 amMDW-HNL
18h 40m1 stop
Southwest Logo
9:55 pm - 12:35 pmHNL-MDW
10h 40m1 stop
$475Southwest
Find Deal
Tue, Jan 20 - Mon, Jan 26
Delta Logo
9:30 am - 9:50 pmMDW-HNL
16h 20m2 stops
Delta Logo
4:42 pm - 8:50 amHNL-MDW
12h 08m1 stop
$476Delta
Find Deal
Wed, Oct 29 - Wed, Nov 5
Southwest Logo
11:55 am - 9:00 pmMDW-HNL
14h 05m1 stop
Southwest Logo
9:55 pm - 4:40 pmHNL-MDW
14h 45m1 stop
$479Southwest
Find Deal
Sat, Jan 24 - Tue, Jan 27
Delta Logo
9:30 am - 8:33 pmMDW-HNL
15h 03m2 stops
Delta Logo
5:00 pm - 9:23 amHNL-MDW
12h 23m1 stop
$480Delta
Find Deal
Wed, Jan 21 - Tue, Jan 27
Delta Logo
9:30 am - 8:33 pmMDW-HNL
15h 03m2 stops
Delta Logo
11:15 pm - 6:08 pmHNL-MDW
14h 53m2 stops
$482Delta
Find Deal
Tue, Oct 21 - Fri, Oct 31
Delta Logo
9:20 am - 8:26 pmMDW-HNL
16h 06m2 stops
Delta Logo
4:50 pm - 8:40 amHNL-MDW
10h 50m1 stop
$484Delta
Find Deal
Sat, Jan 31 - Sun, Feb 8
Delta Logo
9:20 am - 8:33 pmMDW-HNL
15h 13m2 stops
Delta Logo
5:44 pm - 12:35 pmHNL-MDW
14h 51m2 stops
$486Delta
Find Deal
Sat, Oct 25 - Sat, Nov 1
Delta Logo
9:20 am - 8:26 pmMDW-HNL
16h 06m2 stops
Delta Logo
1:25 pm - 9:55 amHNL-MDW
15h 30m2 stops
$490Delta
Find Deal
Tue, Jan 20 - Mon, Jan 26
Delta Logo
6:00 am - 3:12 pmMDW-HNL
13h 12m1 stop
Delta Logo
5:00 pm - 9:23 amHNL-MDW
12h 23m1 stop
$497Delta
Find Deal
Booking Insights

KAYAK's insights & trends for Midway to O'ahu flights

Get data-powered insights and trends into flights from Midway to O'ahu to help you find the cheapest flights, the best time to fly and much more.

Can I save money by flying with a layover from Chicago Midway Airport to O'ahu?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $321, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Chicago Midway Airport to O'ahu?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago Midway Airport to O'ahu, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago Midway Airport to O'ahu is January, when tickets cost $465 (return) on average. On the other hand, the most expensive months are July and June, when the average cost of round-trip tickets is $913 and $863 respectively.

What’s the cheapest day of the week to fly from Chicago Midway Airport to O'ahu?

The average price of all round-trip flights from Chicago Midway Airport to O'ahu clicked on KAYAK for each day over the last 12 months.

Your flight ticket price will generally be cheaper if you fly to O'ahu on a Tuesday and more expensive on a Saturday. On your return trip to Chicago Midway Airport, you should consider flying back on a Tuesday, and avoid Fridays for better deals.

Good to know

Low seasonJuly
Cheapest flight$240
Best time to beat the crowds but there is an average 23% increase in price.
Most popular time to fly with an average 17% increase in price.
Flight from Chicago Midway Airport to Honolulu

FAQs - booking O'ahu flights

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

    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 Chicago Midway Airport to O'ahu.

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

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

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

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

    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 from Chicago Midway Airport to O'ahu up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to O'ahu?

    The cheapest time of day to fly to O'ahu is generally in the morning, when round-trip flights cost $775 on average. The most expensive time of day to fly to O'ahu is generally at night, which is peak travel time and where the average cost of a ticket is $782.

Reviews of the top airlines flying from Midway to O'ahu

 
See real verified KAYAK customer reviews for airlines flying from Chicago to O'ahu. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Midway to O'ahu? 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
8.1Boarding
8.6Crew
7.5Entertainment
7.0Food
8.0Comfort
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..,

Everything you need to know for your flight to O'ahu

Information on your arrival and departure airports

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.