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Find cheap flights from Chicago Midway Airport to O'ahu from $213

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 9/7. 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
0 bags
Thu 6/20
Thu 6/27

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Best O'ahu Flight Deals

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Honolulu
Honolulu1 stop$424

Good to know

Low season

April

High season

July

Cheapest flight

$213
Best time to beat the crowds with an average 16% drop in price.
Most popular time to fly with an average 52% 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 to O'ahu from Chicago Midway Airport 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 to O'ahu with an airline and back to Chicago Midway Airport 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 to O'ahu from Chicago Midway Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top airlines flying from Midway to O'ahu

 
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
DeltaOverall score based on 10595 reviews
8.2Boarding
8.0Entertainment
8.6Crew
7.9Comfort
7.4Food
Airline reviews

Rated entertainment as Mediocre as there were major problems with the Infotainment system that took probably a half hour for them to fix.

8.0 Excellentrghinftl, May 2024FLL - BOS
Read more about Delta reviews

Rated entertainment as Mediocre as there were major problems with the Infotainment system that took probably a half hour for them to fix.

Your crew could maybe answer the call bell at least one of the times I pressed it. I pressed it first time with 2.5 hours left in our flight bc my partner was hungry and wanted a sandwich. We finally got the sandwich with 40 mins left in the flight.

Delta crushed it. Flight attendant in first was attentive and just never stopped. Honestly one of the best domestic flights I’ve been on.

They were an hour late and they didn’t have my wheelchair for me

The Flight crew didn’t serve us until about 1.5 hours into the flight because of turbulence but after it ended it was fine to move around. They served us water only and snacks and then NEVER, NOT ONE TIME came through to collect trash until right before landing about 1.5 hours later. There was absolutely no need for that. They crew was just standing around talking and visiting with each other and really never tried to see if we might want something besides water or even try to come pick up trash. This is VERY unusual for a Delta flight but it was not what I would have expected for a 4 hour flight.

The 1st class male crew member was very pleasant - the short female with round glasses , maybe in 50’s had no personality- never spoke when delivering my food, drink, & never smiled the whole trip! In fact looked annoyed when the boarding proses was happening- I would never hire this woman - unfriendly . Have never dealt with a crew member like her-

5-hour delay due to storms in Tanoa and airspace restricted by Miami traffic controllers.

A regional sized plane was used for a cross country flight with no overhead bin space. I had to "pink check" my laptop and my medications. I was NOT pleased!!!!

Absolutely nothing flight was cancelled and delayed for 2 days. Barely a heads up I want a full refund

The plane from SNA wouldn’t start after 5 tries. The team gave me an option of flying direct from LAX and giving me a Lyft ride there! Perfect!

I’ve had a couple flights this week on United that were delayed by an hour or more

Great! The plane was decently sized and comfortable. The staff was nice and there was great in flight entertainment

Last minute gate change nearly caused us to miss our flight. Change was not announced or displayed in the main board at the old gate. Terrible communication. When we landed we had to wait 20 minutes because there was another plane at the assigned gate. Not the crew’s fault, but adding 20 minutes to a 45 minute flight sucked.

delay several times and wait extra long to board. no entertainment service because there are problem for some rows. always encounter some delays for the last flight of the day.

The flight experience was very good! Especially the United Club!

I was not able to buy food in the flight. They refer to include your Credit card in the APP, and if you are not from USA (i have a credit card form Canada) it is not possible

The flight from Ottawa to Chicago took a lot longer due to DC in Ottawa. We got to Chicago and went to our gate to catch our flight. We only had nine minutes I found that very stressful.

Good boarding. Crew started quick with drinks and food. They came around several times for trash which I really liked. Other than turbulence due to storms in the area, flight was great.

The control panel for the seat back screen did not work at all after takeoff.

Plane was so old it had cigarette butt trays in the seat

Book cheap flights from Chicago to O'ahu

Recent round-trip flight deals

8/29Thu
1 stopDelta
11h 18mMDW-HNL
9/5Thu
1 stopDelta
12h 24mHNL-MDW
$424
9/3Tue
1 stopDelta
11h 18mMDW-HNL
9/12Thu
1 stopDelta
12h 25mHNL-MDW
$426
9/3Tue
1 stopDelta
11h 18mMDW-HNL
9/12Thu
2 stopsDelta
15h 25mHNL-MDW
$431
9/5Thu
1 stopDelta
11h 18mMDW-HNL
9/9Mon
1 stopDelta
12h 25mHNL-MDW
$454
9/1Sun
1 stopDelta
11h 18mMDW-HNL
10/2Wed
2 stopsDelta
14h 33mHNL-MDW
$459
9/1Sun
2 stopsDelta
14h 26mMDW-HNL
10/2Wed
2 stopsDelta
14h 33mHNL-MDW
$464
9/14Sat
2 stopsDelta
15h 49mMDW-HNL
9/19Thu
1 stopDelta
12h 25mHNL-MDW
$487
8/29Thu
1 stopDelta
11h 18mMDW-HNL
9/5Thu
2 stopsDelta
14h 06mHNL-MDW
$507
9/11Wed
2 stopsDelta
15h 49mMDW-HNL
9/17Tue
1 stopDelta
12h 25mHNL-MDW
$509
9/17Tue
2 stopsDelta
16h 04mMDW-HNL
9/24Tue
2 stopsDelta
15h 25mHNL-MDW
$514

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Recent one-way flight deals

9/7Sat
1 stopDelta
11h 18mMDW-HNL
$213
9/7Sat
2 stopsDelta
15h 44mMDW-HNL
$218
5/30Thu
2 stopsDelta
15h 31mMDW-HNL
$266
8/14Wed
2 stopsDelta
15h 44mMDW-HNL
$296
9/10Tue
2 stopsDelta
22h 06mMDW-HNL
$300
5/31Fri
1 stopDelta
11h 15mMDW-HNL
$305
9/9Mon
2 stopsDelta
24h 20mMDW-HNL
$314
9/10Tue
1 stopDelta
12h 55mMDW-HNL
$321
6/5Wed
3 stopsWestJet
36h 50mMDW-HNL
$551
8/9Fri
3 stopsWestJet
32h 13mMDW-HNL
$707

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Last minute flights from Midway to O'ahu

Last minute flight, train and bus deals

5/26Sun
multi-stopDelta
15h 45mMDW-HNL
6/5Wed
multi-stopDelta
13h 01mHNL-MDW
$727
5/25Sat
multi-stopDelta
11h 15mMDW-HNL
6/5Wed
multi-stopDelta
13h 01mHNL-MDW
$749
5/25Sat
multi-stopDelta
15h 45mMDW-HNL
6/5Wed
multi-stopDelta
13h 01mHNL-MDW
$754
5/24Fri
multi-stopDelta
11h 15mMDW-HNL
5/31Fri
multi-stopDelta
15h 21mHNL-MDW
$777
5/25Sat
multi-stopDelta
11h 15mMDW-HNL
6/4Tue
multi-stopDelta
13h 01mHNL-MDW
$799
5/25Sat
multi-stopDelta
15h 45mMDW-HNL
6/4Tue
multi-stopDelta
13h 01mHNL-MDW
$804
5/25Sat
multi-stopDelta
15h 45mMDW-HNL
6/4Tue
multi-stopDelta
11h 45mHNL-MDW
$849
5/24Fri
multi-stopDelta
11h 15mMDW-HNL
5/31Fri
multi-stopDelta
15h 21mHNL-MDW
$853
5/24Fri
multi-stopDelta
11h 15mMDW-HNL
5/27Mon
multi-stopDelta
15h 16mHNL-MDW
$880
5/26Sun
multi-stopDelta
11h 15mMDW-HNL
6/5Wed
multi-stopDelta
13h 01mHNL-MDW
$882

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Chicago Midway Airport - O'ahu Flights

Departure:

Chicago Midway Airport (MDW)United States

Return flight deals:

O'ahu - Chicago Midway Airport

Cabin classes:

$650
$728
$477
$27

Browse destinations: