$218 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 4/13. 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

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
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Flight Deals

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

Mon, Mar 2 - Mon, Mar 9
Southwest Logo
7:55 am - 4:30 pm
MDW
-
HNL
12h 35m
1 stop
Southwest Logo
11:55 am - 5:55 am
HNL
-
MDW
13h 00m
1 stop
$391Southwest
Tue, Mar 3 - Tue, Mar 10
Southwest Logo
8:15 am - 9:00 pm
MDW
-
HNL
16h 45m
1 stop
Southwest Logo
8:10 am - 4:35 am
HNL
-
MDW
15h 25m
1 stop
$413Southwest
Mon, May 4 - Fri, May 8
Southwest Logo
8:35 am - 9:05 pm
MDW
-
HNL
17h 30m
2 stops
Southwest Logo
8:15 am - 5:00 am
HNL
-
MDW
15h 45m
1 stop
$419Southwest
Tue, Mar 10 - Mon, Mar 16
Southwest Logo
10:30 am - 5:40 pm
MDW
-
HNL
12h 10m
1 stop
Southwest Logo
11:55 am - 5:55 am
HNL
-
MDW
13h 00m
1 stop
$423Southwest
Mon, Mar 2 - Tue, Mar 10
Delta Logo
6:00 am - 3:11 pm
MDW
-
HNL
13h 11m
1 stop
Delta Logo
3:46 pm - 8:53 am
HNL
-
MDW
12h 07m
1 stop
$424Delta
Wed, Apr 29 - Wed, May 6
Delta Logo
9:31 am - 9:45 pm
MDW
-
HNL
17h 14m
2 stops
Delta Logo
3:15 pm - 8:43 am
HNL
-
MDW
12h 28m
1 stop
$430Delta
Sun, Mar 1 - Thu, Mar 5
Southwest Logo
10:50 am - 9:00 pm
MDW
-
HNL
14h 10m
1 stop
Southwest Logo
9:15 am - 5:00 am
HNL
-
MDW
15h 45m
1 stop
$431Southwest
Mon, Mar 2 - Mon, Mar 9
Delta Logo
6:00 am - 3:11 pm
MDW
-
HNL
13h 11m
1 stop
Delta Logo
3:46 pm - 8:53 am
HNL
-
MDW
12h 07m
1 stop
$432Delta
Mon, Apr 27 - Thu, Apr 30
Delta Logo
1:23 pm - 9:45 pm
MDW
-
HNL
13h 22m
2 stops
Delta Logo
12:31 pm - 8:51 am
HNL
-
MDW
15h 20m
2 stops
$435Delta
Mon, Apr 13 - Thu, Apr 16
Southwest Logo
8:35 am - 9:05 pm
MDW
-
HNL
17h 30m
2 stops
Southwest Logo
1:00 pm - 5:50 am
HNL
-
MDW
11h 50m
1 stop
$437Southwest
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 $374, 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 $429 (return) on average. On the other hand, the most expensive months are July and November, when the average cost of round-trip tickets is $913 and $868 respectively.

Good to know

Low seasonNovember
Cheapest flight$218
Best time to beat the crowds but there is an average 16% increase in price.
Most popular time to fly with an average 14% 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.

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 4280 reviews
8.6Crew
7.0Food
8.1Boarding
8.0Comfort
7.5Entertainment
Airline reviews

My flight from Denver to Minneapolis was excellent. My flight from Minneapolis to Denver was one of the worst I flights I have ever experienced. I had a window seat, the gentleman in the middle seat was morbidly obese and SW should have made him purchase two seats. His elbow dug into my arm most of the way even after I asked to please be careful. I was literally squashed between the him and the window with no wiggle room. The plane was full so it was not possible to ask for a different seat. I realize I should have complained to the flight attendant but I didn't feel anything could be done to rectify the situation. I fly SW often, I will continue to do so as this was my first negative experience.

10.0 ExcellentCarol, Feb 2026
DEN - MSP
Read more Southwest reviews

My flight from Denver to Minneapolis was excellent. My flight from Minneapolis to Denver was one of the worst I flights I have ever experienced. I had a window seat, the gentleman in the middle seat was morbidly obese and SW should have made him purchase two seats. His elbow dug into my arm most of the way even after I asked to please be careful. I was literally squashed between the him and the window with no wiggle room. The plane was full so it was not possible to ask for a different seat. I realize I should have complained to the flight attendant but I didn't feel anything could be done to rectify the situation. I fly SW often, I will continue to do so as this was my first negative experience.

I was assigned seat 7E, yet my boarding was Group 5, which caused me to have to put my luggage in the back of the plance above `19 or 20 aisle, as passengers who had boarded earlier took the overhead bins in the front. SW needs to monitor bin space and ensure that bin space above the seat are aligned to those sitting near their seats. Also the seating assignments needs to align with group number. Maybe board those last first and so on? Having said the ALL the passengers on the plane were gracious enough to allow me and other passengers in this dilema to retrieve our luggage and helped us along the way. I always love the flight staff, as always their fantastic and I can't rave about them enough!

I appreciate the staff who allowed me to board though I arrived a little late! Regarding the assigned seating, I had booked my flight before this change and wasn't aware of the change at the time, and so I didn't select a seat at booking as I didn't realize it was relevant. Better communication about the change would have been helpful for preparing.

Flight attendants very hospitable and friendly. Pilot flew a smooth take off and landing.

Paid for premium extra leg room but the bin space for rows 1-3 had to go in rows 4-6 and 4-6 had to go to 7-9 because flight attendants have snacks and their luggage upfront. So we pay extra to have to fight thru traffic to get our bags. Only 2nd day of new seating so hope they fix this.

WIFI was great. My selection for seating is an aisle, but during my trip, I never had an aisle seat. If we can get that corrected, I will be thrilled. No snack or drink on this flight.

WIFI was great. My selection for seating is an aisle, but during my trip, I never had an aisle seat. If we can get that corrected, I will be thrilled.

The wifi on the plane is great. The only issue that I have is that I prefer an aisle seat and on my trips this week, I was either in the middle or window. If we can work to secure aisle seating, I will be thrilled. Nice trip.

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.

First class and monitors weren’t working for mine & my husbands. Eventually fixed, but quite annoyed as we bought first class. Also, No foot rests.

Prior to takeoff, the pilot told us there was a possibility of not being able to land and going to Portland. Well that happened, we took off and then did 8 loops around Spokane before the pilot told us we ran out of fuel and had to go to Portland. So for a 35 minute flight we have now been on the plane for 3 hours (boarded at 6:50 am and landed in Portland at 10:30). Then, we just sat in Portland's airport with no updates of when we can start heading back. All of a sudden, our pilots and crew just left, leaving us stranded in a different city and state. We continued to sit in Portland until we finally got a new crew assigned and boarded the plane (This was from 10:30-2). We then sat on the plane for an additional hour before take off because they had to count us multiple times. We finally landed in Spokane at 3:55 PM. So a flight that should have taken at max an hour took us 10 hours and we missed the majority of the recruiting event we went for.

It was delayed but other than that it was great.

Got on the plane and sat there for an hour before departure.

Second flight in a row where the entertainment system is broken. 5 hour long flight with no entertainment and flight attendants did not seem interested in resolving the matter. Very shocked to be treated this poorly considering I paid for a first class experience and have Diamond Medallion status.

They double booked seats, the gate staff changed my ticket as I was boarding she went over to the computer and changed it without telling me. She messed up an entire three row section for me and others. Other travelers were outraged but the gate staff were so rude, so condescending saying it wasn't their problem to solve. I would rate this a zero if I could. Will not fly Delta again I'll stick with United and American.

Comfort seating was on the tight side. Maybe it was a smaller plane(?)

I didn't take this flight. I changed the flight. Why am I getting surveys and notifications on flights that I change. Seems like a defect with Kayak.

Delta One is extraordinary. I fly business when somebody hires me. I just wonder why there is such a chasm between business class and the insanely inhumane and nonsensical coach. The seats are not large enough to fit even my tiny wife. We fly 10% of what we did because we don’t want to pay 5-10 k but for $400 it’s unbearable. It seems like the accountants took over and made stupid decisions. Screw in 20 extra seats and make it so unbearable that people fly 90% less. Just put the damn price up and put some proper chairs in. But business, yay.

Timing, quality of service, promptness and courtesy of the staff

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

Information on your arrival and departure airports