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Find cheap flights from Chicago Midway Airport to O'ahu from $216

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 8/20. 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
Sat 6/15
Sat 6/22

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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$437

Good to know

Low season

April

High season

July

Cheapest flight

$216
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 10673 reviews
7.4Food
8.6Crew
7.9Comfort
8.2Boarding
8.0Entertainment
Airline reviews

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

6.0 GoodGary, May 2024MSP - TPA
Read more about Delta reviews

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!

Best airline! Always friendly and welcoming. Skyclub was great and loved the fast free wifi on board. I also love that you can pre-order your meal on the app!

Atlanta boarding crew at gate were filled with arrogance and were disrespectful. In flight crew showed indifference to the needs of passengers. This is about the flight from ATL to BDL.

Boarding was somewhat chaotic. Unable to evaluate crew or food/drink because captain kept them seated due to turbulence. Have no idea if entertainment was offered.

The gate area was incredibly short staffed, with one representative manning 4-5 flights, which caused a 3 hr delay in boarding even though the plane was all ready to leave. Other flights also were delayed because of this. The flight crew was awesome and I feel bad for the only gate worker on call, but Delta needs to hire more employees.

Very frustrated with boarding gate crew. She announced the plane was small and they would be limiting us to one item to carry on. Not a problem for me as I understand the tiny planes have limited space!! Not the case here! It was a rather large plane and had plenty of room for bags! So because I don’t want to be one of “those people” who ignores the request to check a carry on I did so asking if I would be able to pick it up at the bottom of the ramp on arrival in Knoxville to which she responded “yes”! Then I watched as every other passenger held onto their 2 items and boarded!! Then when we arrived in Knoxville our 2 carry ons had been put with all the other luggage and we had to go to baggage pick up and wait for all the big checked bags to come off the carousel! So she lied!! Frustrating. Next time I won’t be so nice!

It was a good experience except when boarding a female flight attendant did not go out of her way to assist my teenage daughters in finding space for their carry-ons after their compartments were full.

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
9/3Tue
1 stopDelta
12h 24mHNL-MDW
$437
8/29Thu
1 stopDelta
11h 18mMDW-HNL
9/3Tue
2 stopsDelta
14h 08mHNL-MDW
$442
9/6Fri
1 stopDelta
11h 18mMDW-HNL
9/11Wed
1 stopDelta
12h 25mHNL-MDW
$444
8/29Thu
1 stopDelta
11h 18mMDW-HNL
9/6Fri
2 stopsDelta
15h 24mHNL-MDW
$449
9/6Fri
1 stopDelta
11h 18mMDW-HNL
9/11Wed
1 stopDelta
12h 25mHNL-MDW
$452
9/6Fri
1 stopDelta
11h 18mMDW-HNL
9/11Wed
2 stopsDelta
14h 33mHNL-MDW
$457
9/11Wed
2 stopsDelta
15h 49mMDW-HNL
9/17Tue
2 stopsDelta
15h 25mHNL-MDW
$462
8/29Thu
1 stopDelta
11h 18mMDW-HNL
9/6Fri
1 stopDelta
12h 24mHNL-MDW
$472
9/6Fri
1 stopDelta
11h 18mMDW-HNL
9/11Wed
2 stopsDelta
15h 25mHNL-MDW
$477
8/30Fri
1 stopDelta
11h 18mMDW-HNL
9/6Fri
2 stopsDelta
16h 18mHNL-MDW
$479

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Recent one-way flight deals

8/20Tue
2 stopsDelta
15h 44mMDW-HNL
$216
8/20Tue
1 stopDelta
11h 18mMDW-HNL
$241
9/21Sat
2 stopsDelta
15h 49mMDW-HNL
$246
5/30Thu
1 stopDelta
11h 15mMDW-HNL
$261
9/17Tue
2 stopsDelta
16h 04mMDW-HNL
$296
5/30Thu
2 stopsDelta
14h 26mMDW-HNL
$315
8/19Mon
1 stopDelta
11h 18mMDW-HNL
$321
6/4Tue
2 stopsDelta
15h 45mMDW-HNL
$346
5/31Fri
1 stopDelta
11h 15mMDW-HNL
$361
5/30Thu
2 stopsDelta
15h 31mMDW-HNL
$366

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Last minute flights from Midway to O'ahu

Last minute flight, train and bus deals

5/17Fri
multi-stopDelta
11h 15mMDW-HNL
5/25Sat
multi-stopDelta
15h 16mHNL-MDW
$527
5/18Sat
multi-stopDelta
11h 15mMDW-HNL
5/25Sat
multi-stopDelta
15h 05mHNL-MDW
$571
5/18Sat
multi-stopDelta
15h 05mMDW-HNL
5/25Sat
multi-stopDelta
15h 05mHNL-MDW
$576
5/17Fri
multi-stopDelta
15h 05mMDW-HNL
5/25Sat
multi-stopDelta
15h 21mHNL-MDW
$612
5/17Fri
multi-stopDelta
11h 15mMDW-HNL
5/25Sat
multi-stopDelta
12h 46mHNL-MDW
$642
5/18Sat
multi-stopDelta
11h 15mMDW-HNL
5/28Tue
multi-stopDelta
13h 01mHNL-MDW
$646
5/19Sun
multi-stopDelta
11h 15mMDW-HNL
5/26Sun
multi-stopDelta
15h 12mHNL-MDW
$647
5/18Sat
multi-stopDelta
15h 05mMDW-HNL
5/28Tue
multi-stopDelta
13h 01mHNL-MDW
$651
5/18Sat
multi-stopDelta
11h 15mMDW-HNL
5/31Fri
multi-stopDelta
15h 21mHNL-MDW
$674
5/18Sat
multi-stopDelta
15h 05mMDW-HNL
5/31Fri
multi-stopDelta
15h 21mHNL-MDW
$679

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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:

$636
$598
$477
$27

Browse destinations: