Find flights
Deals
When to book
FAQs & Tips
Airlines

Find cheap flights from Chicago Midway Airport to Hawaii from $209

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 Hawaii departing on 8/29. 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 7/6
Sat 7/13

Search hundreds of travel sites at once for deals on flights to Hawaii

In the last 7 days travelers have searched 43,995,393 times on KAYAK, and here is why:

Save 21% 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.

Best Hawaii Flight Deals

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

Honolulu
Honolulu1 stop$597
Kahului
Kahului2 stops$546
Kailua-Kona
Kailua-Kona2 stops$462
Lihue
Lihue2 stops$522
Hilo
Hilo2 stops$981

Good to know

Low season

April

High season

February

Cheapest flight

$209
Best time to beat the crowds with an average 22% drop in price.
Most popular time to fly and prices are also 35% lower on average.
Flight from Chicago Midway Airport to Kahului

FAQs - booking Hawaii flights

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

    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 Hawaii.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Hawaii 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 Hawaii?

    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 Hawaii 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 Hawaii?

    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 Hawaii 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 tips for finding cheap flights to Hawaii

  • Morning departure is around 20% cheaper than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

Top 3 airlines serving from Midway to Hawaii

Need help choosing which airline to fly with from Midway to Hawaii? 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 10347 reviews
8.2Boarding
7.9Comfort
8.0Entertainment
7.4Food
8.6Crew
Airline reviews

Really bad baggage handling. Had my Rimowa bag badly damaged at the latches.

4.0 OkayDavwinder Singh, Jun 2024SEA - ATL
Read more about Delta reviews

Really bad baggage handling. Had my Rimowa bag badly damaged at the latches.

It was pretty good I was worried with the short Layover that I might not catch my connection but the gate was there

It was good until there was a 3 hour delay because there was not any pilots to fly the plane.

There was plenty of overhead room but half of the passengers were told they had to check their carryon bags. My partner and I checked in as early as possible and our seats were split across the aisle.

Friendly flight attendants. Comfort plus seats were very comfortable and had lots of leg room. 10A and 10 B.

Flew first class so everything was great. But maybe because the flights were red eye, no meals were served, just chips. I flew Alaska Air 1st class at 9PM (2 hour flight) and they served beef short rib sliders!

Had to change aircraft due to a faulty door. Surprisingly it only caused about an hour and a half of delay. Delta handled this situation as well as can be expected.

Awful. Flight was continuously getting delayed and gates kept changing without any reason. Flight was delayed for more then 3 hours

Paid premium for Delta only to be on safe but tired old 767 with ancient cabin in mediocre condition. Poor wifi and horrible inflight entertainment. Hardly a premium experience. Should have flown SW and had fun flight crew and no pretense

Our flight to Zurich was delayed by almost 3 hours, so we missed our next flight. There was no indication it would be delayed this much. We were told the gate had changed and then it apparently took over 2 hours to load the "catering" on the plane. We were not compensated in any way for the trouble.

Terrible legroom, seats do not recline, tray table the size of an iPhone, delayed flight, have to pay 5$ to get a cup of water onboard.

Could have TV/Movie and some water ou soda free

Flight was good and clean but delayed over an hour on the return flight.

The non stop flight and able to go into Atlantic City airport. They could lower the prices. It starts out low but then if you want to bring luggage and pick your seat the price goes up quite a bit.

Flight got diwngraded last minute and left us stranded. I was told I’ll be given credit for my luggage and seat upgrades but haven’t got anything yet

We can’t predict circumstances like this ahead of time, but I give your staff a hats off for immediately giving us updated informations.

It was nice! There was a very unhappy child in front of us and the flight attendant did a great job calming the child. I was impressed.

The plane was not on time for boarding or departure or arrivals.

EVERYTHING WAS WONDERFUL HOSPITALITY THE HELP.THE SEATING FRIENDLY ALWAYS HAVE A GOOD RIDE NOT ONE BAD EXPERIENCE WITH THEM

This was the smoothest flight I have had in awhile. I was also offered an exit row seat for a great upgrade cost and was able to sleep almost thr whole flight due to comfort and a smooth flight. We left on time and arrived on time.

FRONTIER SUCKS! The agent downstairs tricked me into booking, just to get to the gate. At the gate, they told me they couldn't help. I then called Customer Service. They and the gate attendants kept blaming each other. Neither side was willing to help the customer.

The agent at check-in was strident, unwelcoming, and condescending to customers ahead of me.

Flight was delay 9hrs and nothing was provided at airport, had to go and get a room to sleep in, paid for Uber back and fort with no offers until we landed back home a 1hr later for a $75 voucher for a future flight.

Didn't like anything..entire crew was very rude to everyone on the flight. Plane old and the trays fall down on you the while time you're flying. Charged more for a carry on bag than for the plane ticket itself. Did make it from point a to point b, but worth the extra money to fly with another airline

9 hours of delay!! Was not able to check my luggage that I paid for!!!

It was delayed 9 hours for operational reasons, despite the plane arriving to the airport on time.

I am very disappointed with Frontier Airlines. They cancelled our flight because they couldn't find a crew member, and then didn't get us to our connecting flight. We had to cancel our whole vacation. We were promised flight and hotel vouchers, but they never sent them.

9hrs delay and didn’t provided anything until after flight landed $75 voucher for fiuture travel no meals or anything.

It was ridiculously hard to check in for the flight, and Frontier charged us a LOT of money to have a carry on suitcase, and then told everyone we could not carry on bags and had to check them through at the gate, and didn't refund the extra money we paid to have the suitcase as carry on.

I had a terrible experience with Frontier. I arrived before the 60 minute cut off and was told that Frontier has a two hour window for bags. I was then told the next available flight wasn’t until the end of the day (I had booked a 6am flight). I took a look around and saw other people being told that they could not board their flights or that they had to pay additional fees. I opted to rebook on American Airlines. There’s absolutely no straightforward way to contact Frontier, so this ticket was a complete waste of money. Oh - and the kicker is that the lady lied about the two hour cut off.

Book cheap flights from Chicago to Hawaii

Recent round-trip flight deals

8/28Wed
2 stopsDelta
14h 00mMDW-KOA
9/4Wed
2 stopsDelta
16h 08mKOA-MDW
$462
9/20Fri
2 stopsDelta
14h 18mMDW-KOA
9/27Fri
2 stopsDelta
16h 39mKOA-MDW
$512
11/5Tue
2 stopsDelta
14h 45mMDW-LIH
11/12Tue
2 stopsDelta
15h 45mLIH-MDW
$522
9/6Fri
2 stopsDelta
14h 00mMDW-KOA
9/9Mon
2 stopsDelta
16h 39mKOA-MDW
$545
9/8Sun
2 stopsDelta
15h 17mMDW-OGG
9/17Tue
2 stopsDelta
14h 55mOGG-MDW
$546
8/12Mon
2 stopsDelta
15h 17mMDW-OGG
8/19Mon
2 stopsDelta
16h 38mOGG-MDW
$580
8/20Tue
1 stopDelta
11h 28mMDW-HNL
8/27Tue
2 stopsDelta
15h 03mHNL-MDW
$597
8/29Thu
1 stopDelta
11h 28mMDW-HNL
9/5Thu
1 stopDelta
12h 03mHNL-MDW
$602
7/6Sat
3 stops
42h 55mMDW-LIH
7/13Sat
3 stops
27h 02mLIH-MDW
$1,322
7/6Sat
2 stops
20h 05mMDW-LIH
7/13Sat
3 stops
27h 02mLIH-MDW
$1,360

Search by stops

Search by airline

Search by price

Recent one-way flight deals

8/29Thu
2 stopsDelta
15h 17mMDW-OGG
$209
8/20Tue
2 stopsDelta
14h 15mMDW-KOA
$216
9/9Mon
2 stopsDelta
14h 18mMDW-KOA
$296
9/12Thu
2 stopsDelta
14h 18mMDW-KOA
$315
9/1Sun
2 stopsDelta
14h 41mMDW-HNL
$336
6/11Tue
2 stopsDelta
13h 56mMDW-KOA
$366
7/24Wed
1 stopDelta
11h 28mMDW-HNL
$371
7/10Wed
2 stopsDelta
14h 15mMDW-KOA
$381
7/11Thu
3 stopsWestJet
31h 39mMDW-HNL
$881
6/9Sun
3 stopsWestJet
30h 42mMDW-OGG
$970

Search by stops

Search by airline

Search by price

Last minute flights from Midway to Hawaii

Last minute flight, train and bus deals

6/8Sat
multi-stopDelta
15h 06mMDW-OGG
6/15Sat
multi-stopDelta
15h 34mOGG-MDW
$862
6/8Sat
multi-stopDelta
16h 27mMDW-HNL
6/13Thu
multi-stopDelta
15h 04mHNL-MDW
$872
6/7Fri
multi-stopDelta
12h 32mMDW-HNL
6/10Mon
multi-stopDelta
14h 34mHNL-MDW
$947
6/7Fri
multi-stopDelta
16h 26mMDW-HNL
6/10Mon
multi-stopDelta
14h 34mHNL-MDW
$952
6/8Sat
multi-stopDelta
16h 27mMDW-HNL
6/13Thu
multi-stopDelta
11h 19mHNL-MDW
$957
6/7Fri
multi-stopDelta
16h 21mMDW-LIH
6/10Mon
multi-stopDelta
15h 34mLIH-MDW
$1,025
6/9Sun
multi-stopDelta
15h 05mMDW-OGG
6/15Sat
multi-stopDelta
15h 34mOGG-MDW
$1,027
6/8Sat
multi-stopDelta
11h 27mMDW-HNL
6/13Thu
multi-stopDelta
11h 19mHNL-MDW
$1,042
6/8Sat
multi-stopDelta
11h 27mMDW-HNL
6/15Sat
multi-stopDelta
14h 34mHNL-MDW
$1,087
6/10Mon
multi-stopDelta
11h 21mMDW-HNL
6/24Mon
multi-stopDelta
11h 19mHNL-MDW
$1,132

Search by stops

Search by airline

Search by price

Chicago Midway Airport - Hawaii Flights

Departure:

Chicago Midway Airport (MDW)United States

Return flight deals:

Hawaii - Chicago Midway Airport

Cabin classes: