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Find cheap flights from Chicago Midway Airport to New York from $58

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 New York departing on 8/21. 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
Mon 7/1
Mon 7/8

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Best New York Flight Deals

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

New York
New York1 stop$113
Buffalo
Buffalo1 stop$152
Syracuse
Syracuse1 stop$163
Rochester
Rochester1 stop$253
Albany
Albany1 stop$255
Ithaca
Ithaca2 stops$783
Binghamton
Binghamton1 stop$529
Burlington
Burlington1 stop$286

Good to know

Low season

May

High season

October

Cheapest flight

$58
Best time to beat the crowds with an average 21% drop in price.
Most popular time to fly with an average 10% increase in price.
Flight from Chicago Midway Airport to Syracuse

FAQs - booking New York State flights

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

    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 New York State.

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

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

    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 New York State 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 New York State?

    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 New York State 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 New York State

  • Morning departure is around 5% 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 New York

 
Need help choosing which airline to fly with from Midway to New York? 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 10419 reviews
8.6Crew
7.9Comfort
7.4Food
8.0Entertainment
8.2Boarding
Airline reviews

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

10.0 ExcellentBarb, Jun 2024MSP - JFK
Read more about Delta reviews

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

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.

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-

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!!!!

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!

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.

It was a crowded flight. They did the best they could.

Boarding was great. The flight landed early. It took the crew over an hour and a half to bring out drinks. I paid to upgrade my seat to Comfort+ only to be near a crying/screaming baby who was seldom quiet. Noise-cancelling earbuds didn’t even help. Waste of money to upgrade.

Boarding was a sh!t show. JFK BOARDING was awful. The agent called three sections at a time Clogging the area then yelling at people to not block the walk way. How are you going to call delta one , premium select and comfort plus at once and the yell at highest paying passengers. Need to do a lot better and the flight attendants in the galley need to understand that their voices travel. They were talking about others and everyone in the cabin heard them

The main person that was coordinating everything was a short white/light skin Spanish man and he was very rude. It honestly made me feel like it was everyone’s First day at work. His announcements were very not reasonable and they did not make sense. The stewardess on the flight that made the announcements she didn’t even know what she was talking about she sounded inebriated. There were no snacks or drinks on our flight there wasn’t even much turbulence. This flight was not enjoyable nor was it what a Delta flight should be and just this past week I flew with Delta 3 times.

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

Flight expected to leave at 6:40 pm ended leaving at 8:00 am the following day. I slept in a cold airport. Never again Spirit for me…

This was the return leg of my journey with Spirit Airlines. Despite its reputation, I found no issues as it got me from point A to B safely and without delay, especially with no mechanical delays, which is fantastic in my book! The staff, from ground crew to cabin crew, were all pleasant and hassle-free. The flight was smooth from takeoff to landing. I have absolutely no complaints about this no-frills airline!

It was the worst ever, i will be filing a lawsuit to get a refund. Our flight was delayed 4 hours so we would miss our connecting flight, we were not rebooked to our destination the same day, we were not offered any options to get home on the same day despite being clear that we absolutely cannot get stranded at night due to family, we were forced to book our own flights on a different airline to get home, and spririt is refusing a refund because our flight wasn't cancelled, only delayed. oh yeah, and they lost our luggage on the first part of the trip and you cannot get a hold of customer service when anything goes wrong, on hold for 30+ minutes. and their app breaks so you can't use that either.

My flight was cancelled!!! I had to spend 200.00 on another flight!!

Absolutely terrible. The boarding process had zero organization. Mobs of people trying to board. People were climbing over my child's stroller with her in it. No families were boarded first. Boarding was delayed with no reasoning or notification that it would be late. We were then stuck on the plane for 45 minutes after landing. Then waited over two hours for our luggage. There was zero communication with the travelers. Never have I experienced such I professionalism and disgrace of others. Extremely disappointed.

They didn’t let me get my boarding pass through the app because I have a lap infant. The ticket said to see a gate agent but there was no gate agent available. I was supposed to go to the kiosk. Ended up missing my flight and they said that I never checked in to my flight so there was nothing that could be done. I will never fly spirit again. Not even worth the hassle and poor customer service.

I like strict carry on policy. Quick to board, quick to leave. Less time at gate and get there quicker

The flight attendants were very personable, extremely friendly, and had a very good feeling of the energy around them not to mention they’re very funny and engaging. What made up for the discomfort of the seats and the fact that the plane sat for a long time on the Turmac. Not sure if the pilot was new, but the landing was very rough sort of like I was at a magic mountain theme park ride that was built in 1959

comfortable flight. not fond of the idea to pay for every little detail. baggage checkin or carry ons, basic snack, or some sort of basic entertainment/wifi. would be nice to offer these as perks and stop with the penny pinching.

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.

Frontier won’t help you at the airport without paying $25. Carry on was $75. Then you get on the plain and every beverage or snack is also a charge. Seats are hard and real packed in. I would never fly them again.

Worst experience I have seen. The flight was cancelled without any reason.

Book cheap flights from Chicago to New York State

Recent round-trip flight deals

9/14Sat
1 stopFrontier
11h 22mMDW-LGA
9/21Sat
1 stopFrontier
10h 53mLGA-MDW
$113
9/23Mon
1 stopFrontier
11h 22mMDW-LGA
9/25Wed
1 stopFrontier
5h 29mLGA-MDW
$116
9/14Sat
1 stopDelta
4h 09mMDW-EWR
9/21Sat
1 stopDelta
6h 44mEWR-MDW
$156
8/24Sat
1 stopDelta
4h 28mMDW-EWR
8/27Tue
1 stopDelta
5h 25mEWR-MDW
$187
7/12Fri
1 stopAllegiant Air
10h 58mMDW-EWR
7/15Mon
1 stopAllegiant Air
10h 22mEWR-MDW
$231
6/25Tue
nonstopSouthwest
2h 10mMDW-LGA
6/28Fri
nonstopSouthwest
2h 25mLGA-MDW
$232
6/14Fri
1 stopAllegiant Air
10h 57mMDW-EWR
6/21Fri
1 stopAllegiant Air
10h 23mEWR-MDW
$239
6/25Tue
1 stopSouthwest
8h 35mMDW-LGA
6/28Fri
1 stopSouthwest
10h 30mLGA-MDW
$250
6/14Fri
1 stop
10h 57mMDW-EWR
6/15Sat
2 stops
22h 50mEWR-MDW
$295
6/14Fri
2 stops
19h 00mMDW-EWR
6/17Mon
1 stop
10h 23mEWR-MDW
$297

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Recent one-way flight deals

8/21Wed
1 stopFrontier
5h 03mMDW-SYR
$58
8/28Wed
1 stopFrontier
10h 46mMDW-BUF
$64
6/12Wed
1 stopFrontier
9h 46mMDW-LGA
$64
9/9Mon
1 stopDelta
5h 14mMDW-EWR
$78
7/17Wed
1 stopDelta
5h 56mMDW-EWR
$83
6/24Mon
1 stopAllegiant Air
11h 57mMDW-EWR
$103
6/24Mon
1 stopAllegiant Air
11h 57mMDW-EWR
$106
6/27Thu
nonstopSouthwest
2h 10mMDW-LGA
$118
6/27Thu
1 stopSouthwest
6h 15mMDW-LGA
$131
6/19Wed
1 stopSpirit Airlines
6h 58mMDW-EWR
$196

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Last minute flights from Midway to New York

Last minute flight, train and bus deals

6/5Wed
multi-stopFrontier
9h 46mMDW-LGA
6/12Wed
multi-stopFrontier
17h 58mLGA-MDW
$157
6/5Wed
multi-stopFrontier
13h 35mMDW-SYR
6/12Wed
multi-stopFrontier
5h 24mSYR-MDW
$157
6/6Thu
multi-stopDelta
7h 24mMDW-JFK
6/11Tue
multi-stopDelta
7h 51mJFK-MDW
$306
6/4Tue
multi-stopDelta
6h 15mMDW-ROC
6/8Sat
multi-stopDelta
5h 00mROC-MDW
$355
6/3Mon
multi-stop
18h 48mMDW-EWR
6/10Mon
multi-stop
15h 29mEWR-MDW
$497
6/3Mon
multi-stop
18h 48mMDW-EWR
6/10Mon
multi-stop
9h 49mEWR-MDW
$508
6/5Wed
multi-stopPorter Airlines
19h 15mMDW-EWR
6/12Wed
multi-stopPorter Airlines
16h 42mEWR-MDW
$800
6/3Mon
multi-stopPorter Airlines
5h 20mMDW-EWR
6/3Mon
multi-stopPorter Airlines
16h 42mEWR-MDW
$865
6/4Tue
multi-stopWestJet
21h 38mMDW-JFK
6/7Fri
multi-stopWestJet
35h 00mJFK-MDW
$1,275
6/5Wed
multi-stopWestJet
26h 07mMDW-JFK
6/7Fri
multi-stopWestJet
35h 00mJFK-MDW
$1,281

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Chicago Midway Airport - New York State Flights