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Find cheap flights from Chicago Midway Airport to New York from $59

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 8/14. 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 New York Flight Deals

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

New York
New York1 stop$98
Buffalo
Buffalo1 stop$125
Syracuse
Syracuse1 stop$150
Rochester
Rochester1 stop$243
Albany
Albany1 stop$236
Ithaca
Ithaca2 stops$343
Binghamton
Binghamton1 stop$345
Burlington
Burlington1 stop$306

Good to know

Low season

May

High season

October

Cheapest flight

$59
Best time to beat the crowds with an average 23% drop in price.
Most popular time to fly with an average 9% increase in price.
Flight from Chicago Midway Airport to New York LaGuardia Airport

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 29% more expensive 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 10673 reviews
8.6Crew
7.4Food
8.2Boarding
7.9Comfort
8.0Entertainment
Airline reviews

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!!!!

4.0 OkayReginald, May 2024MCI - LGA
Read more about Delta reviews

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.

Horrible. Flight ORD to CGH was okay, but Paris was a nightmare. Old planes, delays, involuntary downgrades, broken planes, terrible communication. CGH to CPT was my worst flight ever.

Horrible. First delta flight was delayed. I ran to my connecting flight and arrived to the gate 13 mins before departure. I told the gate agent “I’m here”, she told me flight was closed while giving my already confirmed seat to an stand by passenger. I said again “madam, I’m here with my confirmed seat” and she said “no you’re not here@ and gave two stand by people a boarding pass and let them board. I asked “madam, why do you do that?”, and she repeated “you’re not here”. That was very rude. I’m disappointed of delta. It used to have a good customer service. Things have changed, but not for good.

full flihgt but crew and passengers all helped eachother we landed early! however we then had to wait 40 minutes on the tarmac to get into the gate there were people trying get connecting flights, assume its an airport issue but still frustrating

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 delayed 2+ hours missed a concert because of it…

The seats were larger & more roomy than the old planes. the crew was excellent. . overall a very good flight.

No water for handwashing and they charged $5 for water. Spirit up-charges for every little thing and the planes themselves are old and nauseating.

Seats could use more padding. Kind of hard on the tush.

Flying with Spirit is simple- it’s a minimalist airline that gets you from Point A to Point B. I have flown Spirit many times & have never had a problem with it, just don’t expect luxury or convenience. And know that, because the tickets are so affordable, the real charge comes in the bags, food, & extra purchases. The planes are simple, modern, and clean. They function in a way that moves large amounts of people in a more efficient manner, so the seats aren’t the most comfortable but I always bring a pillow and have no problem. I will continue to fly Spirit & would recommend to others

Check in online was easy. Seats aren’t very comfortable

Fecal matter in seat back pocket. Presumably from a kids diaper.

Worst airline to travel with. They treat you like a prisoner in a jailhouse barking out orders and threats. Nickle and dime you to the same price or higher than a respectable airline like one of the big 3 . Might as well fly with standard airlines

Well I mean u get what u pay for so 🤷‍♂️

Over an hour delay in departure but I was notified beforehand. Another delay on tarmac upon arrival at LGA. We ended up departing the plane almost 2 hours later than expected

I fly Frontier because it’s affordable. I understand that the seats are tight and not the most comfortable…but that’s part of it. The problem with this flight was that there was a group of travelers directly behind me at the back of the plane who were ridiculously loud and obnoxious the entire flight. I’m pretty sure they were drunk and I could periodically smell an odd odor that I believe was one of them using a smokeless vape pen. The stewards had to remind them to keep quiet during the pre-flight instruction, but that was it. They never said another thing to them for the rest of the flight. It was a miserable.

I checked a bag because it was $5 less than carry on. They managed to lose my bag on a 2.5 hr direct flight! Frontier has no airport staff at baggage claim to help. As soon as I got home around 11 pm I tried to use their online system to file the claim for lost bag - system wouldn't take the # on my baggage claim ticket - said it was not the correct number. Also said that I had not checked a bag, which wasn't true - even my online boarding pass showed that I had checked a bag. Wasted about an hour on that process with no luck. Tried again in the morning - same thing. So tried online chat with Frontier bot - waited 35-40" twice to be connected to a baggage agent and it never happened. Eventually drove to PDX after work and waited 2 hrs for the Frontier ticket agents to arrive prior to the next Frontier flight out of PDX and FINALLY got some help from one of them, to take me to lost luggage area where I was able to retrive my bag. Probably took 4-5 hrs. of my time and endless frustration to get my bag. This was my first -- and LAST -- experience flying Frontier Airlines. Check-in was also extremely difficult and time consuming. The flight itself (and staff) were fine but everything else about the experience was a total disaster! The fact that Frontier literally has NO WAY to connect to a human voice for customer service (in this case for lost luggage) is the WORST!!!!!

Frontier is a crappy airline nothing about it is honest

I didn't get to do this flight l, hard to review

Not good 😐 Over priced baggage fees Small hard seats No wifi or entertainment options 😕

Book cheap flights from Chicago to New York State

Recent round-trip flight deals

6/5Wed
1 stopFrontier
9h 46mMDW-LGA
6/12Wed
1 stopFrontier
17h 58mLGA-MDW
$98
8/14Wed
1 stopFrontier
10h 03mMDW-LGA
8/20Tue
1 stopFrontier
11h 14mLGA-MDW
$111
6/5Wed
1 stopFrontier
9h 46mMDW-LGA
6/11Tue
2 stopsFrontier
16h 20mLGA-MDW
$115
7/22Mon
1 stopDelta
5h 06mMDW-EWR
7/30Tue
1 stopDelta
5h 04mEWR-MDW
$188
7/24Wed
1 stopDelta
5h 56mMDW-EWR
7/30Tue
1 stopDelta
5h 04mEWR-MDW
$198
5/31Fri
1 stopAllegiant Air
19h 43mMDW-EWR
6/7Fri
1 stopAllegiant Air
9h 49mEWR-MDW
$220
7/1Mon
1 stopAllegiant Air
11h 57mMDW-EWR
7/5Fri
1 stopAllegiant Air
10h 22mEWR-MDW
$238
6/3Mon
3 stops
24h 41mMDW-EWR
6/7Fri
1 stop
9h 49mEWR-MDW
$257
6/4Tue
2 stopsSouthwest
13h 35mMDW-LGA
6/6Thu
1 stopSouthwest
10h 30mLGA-MDW
$280
6/14Fri
2 stops
14h 05mMDW-EWR
6/17Mon
1 stop
10h 23mEWR-MDW
$293

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Recent one-way flight deals

8/14Wed
1 stopFrontier
10h 03mMDW-LGA
$59
8/28Wed
1 stopFrontier
10h 46mMDW-BUF
$61
8/7Wed
1 stopDelta
5h 19mMDW-EWR
$94
6/7Fri
1 stopAllegiant Air
19h 51mMDW-EWR
$99
7/15Mon
1 stopAllegiant Air
11h 58mMDW-EWR
$102
8/31Sat
1 stopDelta
3h 54mMDW-ROC
$104
7/8Mon
nonstopSouthwest
2h 05mMDW-LGA
$114
6/17Mon
2 stops
26h 26mMDW-EWR
$137
7/24Wed
nonstopSouthwest
1h 25mMDW-BUF
$141
6/14Fri
2 stops
14h 05mMDW-EWR
$142

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Last minute flights from Midway to New York

Last minute flight, train and bus deals

5/20Mon
multi-stopFrontier
10h 04mMDW-LGA
5/29Wed
multi-stopFrontier
16h 53mLGA-MDW
$229
5/21Tue
multi-stopFrontier
12h 54mMDW-LGA
5/29Wed
multi-stopFrontier
16h 53mLGA-MDW
$238
5/20Mon
nonstopSouthwest
2h 05mMDW-LGA
5/23Thu
nonstopSouthwest
2h 25mLGA-MDW
$331
5/20Mon
multi-stopSouthwest
5h 45mMDW-LGA
5/23Thu
nonstopSouthwest
2h 25mLGA-MDW
$340
5/18Sat
multi-stopDelta
4h 37mMDW-EWR
5/29Wed
multi-stopDelta
8h 21mEWR-MDW
$366
5/18Sat
multi-stopDelta
4h 37mMDW-EWR
5/26Sun
multi-stopDelta
5h 48mEWR-MDW
$371
5/17Fri
multi-stop
24h 56mMDW-LGA
6/3Mon
multi-stop
14h 43mLGA-MDW
$505
5/20Mon
multi-stop
11h 58mMDW-LGA
6/3Mon
multi-stop
14h 43mLGA-MDW
$534
5/19Sun
multi-stopPorter Airlines
5h 50mMDW-EWR
5/27Mon
multi-stopPorter Airlines
16h 42mEWR-MDW
$739
5/19Sun
multi-stopPorter Airlines
6h 50mMDW-EWR
5/31Fri
multi-stopPorter Airlines
9h 27mEWR-MDW
$756

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Chicago Midway Airport - New York State Flights