Find flights
When to book
FAQs & Tips
Direct Flights
Airlines
Deals

MDW

$375 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 7/4. 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
dj. 5/30
dj. 6/6

Search hundreds of travel sites at once for deals on flights to Chicago Midway Airport

In the last 7 days travelers have searched 43,983,279 times on KAYAK, and here is why:

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

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

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

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

Good to know

Low season

January

High season

October

Cheapest flight

$375
Best time to beat the crowds but there is an average 6% increase in price.
Most popular time to fly and prices are also 16% 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.

See more FAQs

Prefer to fly non-stop from O'ahu to Chicago Midway Airport?

Find which airlines fly direct from O'ahu to Midway, which days they fly and book direct flights.

Nonstop departures

O'ahu to Chicago Midway

Monday

Aeromexico, Air France, Allegiant Air, +11 more

Aeromexico, Air France, +12 more

Tuesday

Aeromexico, Air France, Delta, +9 more

Aeromexico, Air France, +10 more

Wednesday

Aeromexico, Air France, Delta, +9 more

Aeromexico, Air France, +10 more

Thursday

Aeromexico, Air France, Allegiant Air, +10 more

Aeromexico, Air France, +11 more

Friday

Aeromexico, Air France, Allegiant Air, +11 more

Aeromexico, Air France, +12 more

Saturday

Aeromexico, Air France, Delta, +9 more

Aeromexico, Air France, +10 more

Sunday

Aeromexico, Air France, Allegiant Air, +10 more

Aeromexico, Air France, +11 more

See more direct flights

Nonstop returns

Chicago Midway to O'ahu

Monday

Aeromexico, Air France, Allegiant Air, +11 more

Aeromexico, Air France, +12 more

Tuesday

Aeromexico, Air France, Delta, +9 more

Aeromexico, Air France, +10 more

Wednesday

Aeromexico, Air France, Delta, +9 more

Aeromexico, Air France, +10 more

Thursday

Aeromexico, Air France, Allegiant Air, +10 more

Aeromexico, Air France, +11 more

Friday

Aeromexico, Air France, Allegiant Air, +11 more

Aeromexico, Air France, +12 more

Saturday

Aeromexico, Air France, Delta, +9 more

Aeromexico, Air France, +10 more

Sunday

Aeromexico, Air France, Allegiant Air, +10 more

Aeromexico, Air France, +11 more

See more direct flights
See more direct flights

Top airline 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
DeltaOverall score based on 10913 reviews
8.0Entertainment
8.2Boarding
7.9Comfort
8.6Crew
7.4Food
Airline reviews

From Atlanta to Cabo I would have hoped on a plane that size I would have been able to breathe and wiggle my feet a little! The leg room in that plane is non existent and I am only 5”4’. And the air vent either wasn’t working very well or just could not blow air from the ceiling to the seat area as I was suffocating through the entire flight! And please don’t say I would have been more comfortable in first class because I cannot afford those rates and have always travelled Main Cabin without issues !

8.0 ExcellentCynthia, Apr 2024TYS - ATL
Read more about Delta reviews

From Atlanta to Cabo I would have hoped on a plane that size I would have been able to breathe and wiggle my feet a little! The leg room in that plane is non existent and I am only 5”4’. And the air vent either wasn’t working very well or just could not blow air from the ceiling to the seat area as I was suffocating through the entire flight! And please don’t say I would have been more comfortable in first class because I cannot afford those rates and have always travelled Main Cabin without issues !

The pilots were good. Disappointing when planes don't have electrical ports

I liked the piloting of the aircraft. Very disappointed about lack of electrical ports. Also, although a short flight. there was enough time to hand out snacks to comfort + seats as was done for first class.

I had a wonderful experience flying with delta. The gentleman taking care of us on our flight was so nice, accommodating, and attentive. He always was smiling and giving pins to the kids which made me smile. The flight was quick too and without turbulence. Thank you for the great flying experience.

Delta is one of the best airlines I have flown

Made the Atlanta to Pittsburgh trip many times, with Delta no issues

I always fly with Delta. My friends tell me their horror stories of flying with other airlines. I just smile and say, “You should fly Delta”

I'm a larger, athletic guy (6'2", 260lbs powerlifter) and I found the seats incredibly uncomfortable with minimal leg room, especially in a window seat. Now, I full understand that being smaller may change my view but even if I was 80lbs less, my legs would be the same size and I was sandwiched between my seat and the seat in front of me.

Horrible. This was not first class. This was a connecting flight whi h was late. My original flight never came. I hated the fact that delta gave me a connecting flight from New York to Orlando Florida. No meals and the television screens were not working. There wasn't even any power to charge your phones. This is NOT FIRST CLASS DELTA!!! Do better next time!

This flight was ridiculous. I had to have a connecting flight from New York to orlando Florida??? The flight left late and because it was a short flight there was no first class amenities. I had one alcohol drink. The flight crew was fine, but it sure did not feel like first class. Delta to me dropped the ball by giving me a connecting flight. By the time we got to Raleigh we would have missed the next flight. Lucky for me the flight never came so now I was stuck waiting for a later flight that came in late also.

Book cheap flights from O'ahu to Chicago

Recent round-trip flight deals

9/18dc.
1 stopDelta
12h 25mHNL-MDW
9/30dl.
2 stopsDelta
16h 04mMDW-HNL
$755
9/18dc.
2 stopsDelta
14h 37mHNL-MDW
9/30dl.
2 stopsDelta
16h 04mMDW-HNL
$760
8/5dl.
1 stopDelta
12h 24mHNL-MDW
8/13dt.
1 stopDelta
11h 18mMDW-HNL
$776
7/10dc.
1 stopDelta
12h 15mHNL-MDW
7/23dt.
1 stopDelta
11h 25mMDW-HNL
$802
7/10dc.
2 stopsDelta
15h 10mHNL-MDW
7/23dt.
1 stopDelta
11h 25mMDW-HNL
$807
5/29dc.
2 stopsDelta
15h 17mHNL-MDW
6/5dc.
1 stopDelta
11h 14mMDW-HNL
$827
5/29dc.
2 stopsDelta
15h 17mHNL-MDW
6/5dc.
2 stopsDelta
15h 45mMDW-HNL
$832
7/10dc.
1 stopDelta
12h 15mHNL-MDW
7/15dl.
1 stopDelta
11h 25mMDW-HNL
$862
7/19dv.
1 stopDelta
12h 15mHNL-MDW
7/24dc.
1 stopDelta
11h 25mMDW-HNL
$863
8/5dl.
1 stopDelta
12h 24mHNL-MDW
8/13dt.
2 stopsDelta
15h 44mMDW-HNL
$867

Search by stops

Search by airline

Search by price

Recent one-way flight deals

7/4dj.
1 stopDelta
12h 29mHNL-MDW
$375
7/4dj.
2 stopsDelta
15h 08mHNL-MDW
$380
5/5dg.
2 stopsDelta
14h 33mHNL-MDW
$386
5/28dt.
1 stopDelta
13h 01mHNL-MDW
$391
6/4dt.
2 stopsDelta
15h 16mHNL-MDW
$396
7/1dl.
1 stopDelta
12h 29mHNL-MDW
$401
7/21dg.
1 stopSouthwest
16h 25mHNL-MDW
$419
7/20ds.
1 stopSouthwest
10h 00mHNL-MDW
$430
7/20ds.
2 stops
13h 48mHNL-MDW
$622
5/13dl.
2 stopsAlaska Airlines
21h 43mHNL-MDW
$920

Search by stops

Search by airline

Search by price

Flights to Chicago Midway Airport

Destination:

Chicago Midway Airport (MDW)United States

Return flight deals:

Chicago Midway Airport - O'ahu

Cabin classes:

$408
$513
$219
$38