$53 Find Cheap Flights from Chicago Midway Airport to New York State

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
1 adult, Economy

KAYAK searches hundreds of travel sites at once for deals on flights to New York State

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to New York State, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to New York State, as well as popular online travel agencies
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Flights Deals

Best New York Flight Deals from Midway

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
New York
New York1 stop$105
Buffalo
Buffalononstop$137
Syracuse
Syracuse1 stop$229
Rochester
Rochesternonstop$303
Albany
Albanynonstop$211
Binghamton
Binghamton1 stop$347
New York
New York1 stop$105
Buffalo
Buffalononstop$137
Syracuse
Syracuse1 stop$229
Rochester
Rochesternonstop$303
Albany
Albanynonstop$211
Binghamton
Binghamton1 stop$347

Cheap Flights from Midway to New York

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to New York that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Midway to New York

Thu, Sep 4 - Mon, Sep 8
Frontier Logo
5:04 pm - 11:31 pmMDW-LGA
5h 27m1 stop
Frontier Logo
6:30 am - 3:58 pmLGA-MDW
10h 28m1 stop
$105Frontier
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Thu, Sep 4 - Mon, Sep 8
Frontier Logo
5:04 pm - 12:34 amMDW-EWR
6h 30m1 stop
Frontier Logo
11:15 am - 3:58 pmEWR-MDW
5h 43m1 stop
$105Frontier
Find Deal
Thu, Aug 14 - Mon, Aug 18
Southwest Logo
9:00 pm - 11:30 pmMDW-BUF
1h 30mnonstop
Southwest Logo
12:35 pm - 1:10 pmBUF-MDW
1h 35mnonstop
$137Southwest
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Thu, Aug 7 - Mon, Aug 11
Southwest Logo
9:00 pm - 11:30 pmMDW-BUF
1h 30mnonstop
Southwest Logo
5:35 pm - 10:45 pmBUF-MDW
6h 10m1 stop
$147Southwest
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Wed, Aug 13 - Wed, Aug 20
Delta Logo
10:31 am - 6:10 pmMDW-BUF
6h 39m1 stop
Delta Logo
6:00 am - 9:36 amBUF-MDW
4h 36m1 stop
$177Delta
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Sat, Sep 13 - Sat, Sep 20
Delta Logo
4:25 pm - 11:00 pmMDW-EWR
5h 35m1 stop
Delta Logo
9:40 am - 12:32 pmEWR-MDW
3h 52m1 stop
$177Delta
Find Deal
Thu, Aug 14 - Thu, Aug 21
Allegiant Air Logo
10:53 am - 6:34 pmMDW-ALB
6h 41m1 stop
Allegiant Air Logo
10:12 am - 8:42 amALB-MDW
23h 30m2 stops
$287Allegiant Air
Find Deal
Thu, Aug 14 - Thu, Aug 21
Allegiant Air Logo
10:53 am - 6:34 pmMDW-ALB
6h 41m1 stop
Allegiant Air Logo
10:12 am - 8:42 amALB-MDW
23h 30m2 stops
$289Allegiant Air
Find Deal
Fri, Jul 18 - Sun, Jul 20
 Logo
10:31 am - 9:33 amMDW-SYR
22h 02m2 stops
 Logo
11:46 am - 9:41 amSYR-MDW
22h 55m2 stops
Fri, Jul 18 - Sun, Jul 20
 Logo
10:31 am - 9:33 amMDW-SYR
22h 02m2 stops
 Logo
11:46 am - 8:22 amSYR-MDW
21h 36m3 stops
Useful Info

KAYAK's insights & trends for Midway to New York flights

Get data-powered insights and trends into flights from Midway to New York to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Chicago Midway Airport to New York State flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Chicago Midway Airport to New York State.

The cheapest ticket to New York State from Chicago Midway Airport found in the last 72 hours was to New York, at $120 round-trip. The most popular route is from Chicago Midway Airport (MDW) to New York LaGuardia Airport (LGA), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $120.

Can I save money by flying with a layover from Chicago Midway Airport to New York State?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $365, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Chicago Midway Airport to New York State?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago Midway Airport to New York State, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago Midway Airport to New York State is September, when tickets cost $207 (return) on average. On the other hand, the most expensive months are December and August, when the average cost of round-trip tickets is $379 and $307 respectively.

What’s the cheapest day of the week to fly from Chicago Midway Airport to New York State?

The average price of all round-trip flights from Chicago Midway Airport to New York State clicked on KAYAK for each day over the last 12 months.

If your flying dates are flexible, you should consider flying to New York State on a Saturday, as we generally find the cheapest rates on that day for this route. On the other hand, Thursday is the most expensive day to fly from Chicago Midway Airport to New York State. For your return ticket, we recommend flying on a Tuesday and avoiding Sundays for the best deals.


Good to know

Low seasonFebruary
High seasonMarch
Cheapest flight$53
Best time to beat the crowds with an average 38% drop in price.
Most popular time to fly with an average 9% increase in price.
Flight from Chicago Midway Airport to Buffalo

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 from Chicago Midway Airport to New York State 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 from Chicago Midway Airport to New York State with an airline and back 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 from Chicago Midway Airport to New York State up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to New York State?

    The cheapest time of day to fly to New York State is generally at night, when round-trip flights cost $239 on average. Morning departures are around 4% cheaper than evening flights, on average. The most expensive time of day to fly to New York State is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $269.

Top tips for finding cheap flights to New York State

  • Looking for a cheap flight? 25% of our users found tickets from Chicago Midway Airport to the following destinations at these prices or less: New York $123 one-way - $191 round-trip

Reviews of the top 4 airlines serving from Midway to New York

 
See real verified KAYAK customer reviews for airlines flying from Chicago to New York State. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
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
SouthwestOverall score based on 4278 reviews
8.0Comfort
8.2Boarding
7.0Food
8.6Crew
7.6Entertainment
Airline reviews

Delayed flight. Nicest crew member was a SW pilot flying seated next to me who kindly move to seat the final passenger. Flight extra delayed. My cup of refreshment of ginger ale was so packed with ice it was literally 2 sips.

4.0 OkayTraci, Jun 2025OAK - SEA
Read more Southwest reviews

Delayed flight. Nicest crew member was a SW pilot flying seated next to me who kindly move to seat the final passenger. Flight extra delayed. My cup of refreshment of ginger ale was so packed with ice it was literally 2 sips.

For my birthday trip this was my second time ever flying, this trip was the best.

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

No trays in our seats, we sat in first row, purchased a business class fare. Had to hold our drinks and snack in our hands. No plugs for our cell phones. Had to pay for it a drink cocktail each. Seats so uncomfortable.

Flight wasn’t even full, but too many carry-ons caused us to run out of bin space. New bag fee has folks who would usually check their bags carrying on. Watching Southwest morph into Spirit/Frontier is so sad to watch

Sat on tarmac for 2 hours and then missed my connecting flight

First time traveling on Southwest since bag fees were implemented. Usual good service. Just more expensive now.

Everything was on time. I was disappointed by the front section female, African American flight attendant. I did not see her name tag or would have identified by name not race. As passengers moved to the bathroom early in flight, she would say with a disdainful tone “I have to say the seat belt light is on” then go back to her book. Better trained flight attendants say something like be careful the seat belt light is on.

Cluster mess boarding. Can't wait for SWA reserved seating. Internet didn't seem to work on the plane.

Flights delayed by 4-6 hours. Boarding was a mess and unclear. Bags were not at arrival airport and had never even been put on the plane. No idea when I’ll get them. Don’t fly into Denver!

I like for how they process during check in. It was very smoothly.

Most aspects were good however if they assign boarding zones they ought to enforce them or why bother? My luggage from SAN-JFK-MAD was lost in NY so I without my main bag for two days upon arrival in Spain. They were helpful in tracking it and eventually delivered it to my hotel. The flub was because of a delay upon arrival in NYC. I had booked 2 1/2 hours between flights but we had to hold on the taxiway for an hour after landing while waiting for a clear gate which likely caused the baggage error.

Great overall. There was a bit of turbulence so they could only serve water because too much turbulence for the carts. Was glad they prioritized safety though

Delayed take-off. Very small plane so very scary with lots of bumps during the flight. Would never fly Delta on short flights in small 80 seaters plane again! Felt relieved when landed.

The plane was old with small storage areas that had problems closing/latching and not enough storage for everyone, and worn, damaged seats. Service was great but feel a little unsafe on such well used planes.

Great staff. Wifi is terrible. Signing up for skylines is a painstaking process. Had to call customer service just to get my flight itinerary and confirmation sent to me. Consistent delays. A well staffed company that is run so poorly. Upper management needs to be renewed.

Boarding is, as it always is… horrible. Gate lice. Slow moving zones. Too many people with carry ons

I sat in comfort plus. It was fine. Seats were comfortable. I got drinks and snacks.

Good and consistent Printer in lounge did not work for me :(

Flight heavily delayed. No food available despite purchasing an upgrade. No in cabin service.

I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

You were more on time than United. I'm so over united delays.

The meals were mediocre and the alcohol selection was poor. I enjoyed the selection of movies and other entertainment.

I chatted with the captain before the flight, and similarly during the welcome announcement, he warned of a turbulent flight that may impact the in-flight service. However, once at altitude, he announced that the weather changed and he immediately turned off the seatbelt sign. But it appeared the cabin crew had already decided to take off this flight. They remained seated and then just chatted in the galley. The flight was fully catered, but only first class received service.

My flight attendant was attentive! The elderly person next to me was flatulent and the flight attendant could see that I was in distress and brought me some face masks

My boarding pass wouldn't pull up in the app very easily and had to really dig through my email. That caused a delay in TSA..

The flight times got delayed multiple times due to weather which is understandable, but later the time got prepared 30min. Made to the flight barely but got stressed too much.

Onboarding was an easy process. Staff waa friendly and courteous. Should have a complimentary snack and drink. We paid $900 round trip for two to myrtle from New York, which is an expensive fare. Going to the seats were not in good shape but our return home, the air plane seemed to be new with comfortable seating with slightly more space. If traveling again, we will still consider flying SpIrit.

It was absolutely awesome. The crew was welcoming to all, not just the first class. They were full of energy. The in-cabin music was an excellent choice, not boring like most airlines. We were ready for takeoff ahead of time. Pilots were great. Smooth takeoff and landing. The plane was beautiful and nicely cleaned. This was truly a fantastic flight. I fly Delta and American all the time. I was apprehensive about Spirit. I will definitely be looking for Spirit first. Thanks for a great experience.

Tell them to chose a better, less bumpy route :( my seat had no window all the way at the end 😔

All was good expecting the seats need a bit of cushion. Besides that I can’t complain.

The only positive is that the flight made it both ways. Getting charged for every little thing after the cost of the ticket itself is comical, considering how the plane and services are as bottom-tier as possible. The self check-in kiosks are useless. It’s nice to think that you can print your boarding pass, tag your checked bag, and then just drop it off. But no, they still make you go through the line once you finish- what’s the point of the self check-in then? Any questions for the staff seem like the biggest inconvenience and were met with condescending responses. This was my first and now last time ever flying with Spirit. After all the extra costs, subpar plane and staff, I see no value. I’d rather drive the 13 hours than give Spirit another dime.

Worst airline ever! The guy weighing my bag had his foot on the metal plate and when I called him out on it, I got this stupid little smirk. La is a scam and so is Spirit Airlines. All the flight attendants looked like they hated our flight just as much as we did.

Very dissatisfied with spirit airlines after buying my ticket's they cancelled our flights with no reasoning.

Spirit is awful. Too expensive for what you get. Stop nickel and diming.

Seats are poor. They do not lean back. They do not even have pockets on the back, making it impossible to store a phone or a coke bottle. If you opt for basic economy cheap seats, they stick you always in the middle or window seat, even though there are unoccupied seats on the aisle. And then there is the nickel and diming. No carry-ons. And checking your carry-on is $70. At the end there is no price advantage but there is plenty of aggravation.

Everything you need to know for your flight from Midway to New York

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