$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 7/2. 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 Yorknonstop$140
Buffalo
Buffalo1 stop$210
Syracuse
Syracuse1 stop$224
Albany
Albanynonstop$249
Rochester
Rochesternonstop$281
Ithaca
Ithaca2 stops$508
Binghamton
Binghamton1 stop$407
New York
New Yorknonstop$140
Buffalo
Buffalo1 stop$210
Syracuse
Syracuse1 stop$224
Albany
Albanynonstop$249
Rochester
Rochesternonstop$281
Ithaca
Ithaca2 stops$508
Binghamton
Binghamton1 stop$407

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

Wed, Sep 3 - Tue, Sep 9
Southwest Logo
5:55 pm - 9:10 pmMDW-LGA
2h 15mnonstop
Southwest Logo
6:00 am - 7:20 amLGA-MDW
2h 20mnonstop
$140Southwest
Find Deal
Tue, Jul 1 - Tue, Jul 8
Southwest Logo
7:20 pm - 10:30 pmMDW-LGA
2h 10mnonstop
Southwest Logo
9:35 pm - 10:55 pmLGA-MDW
2h 20mnonstop
$141Southwest
Find Deal
Tue, Jul 8 - Wed, Jul 9
Frontier Logo
11:39 am - 12:44 amMDW-EWR
12h 05m1 stop
Frontier Logo
5:59 am - 10:40 amEWR-MDW
5h 41m1 stop
$159Frontier
Find Deal
Tue, Jul 1 - Tue, Jul 8
Frontier Logo
11:39 am - 12:44 amMDW-EWR
12h 05m1 stop
Frontier Logo
5:59 am - 10:40 amEWR-MDW
5h 41m1 stop
$160Frontier
Find Deal
Wed, Oct 8 - Tue, Oct 14
Delta Logo
1:00 pm - 7:28 pmMDW-EWR
5h 28m1 stop
Delta Logo
1:00 pm - 6:36 pmEWR-MDW
6h 36m1 stop
$177Delta
Find Deal
Tue, Jul 15 - Tue, Jul 22
Delta Logo
6:20 pm - 11:13 pmMDW-EWR
3h 53m1 stop
Delta Logo
7:00 am - 11:58 amEWR-MDW
5h 58m1 stop
$179Delta
Find Deal
Fri, Aug 1 - Sun, Aug 3
Allegiant Air Logo
1:11 pm - 9:05 amMDW-EWR
18h 54m1 stop
Allegiant Air Logo
9:55 am - 12:21 pmEWR-MDW
27h 26m1 stop
$203Allegiant Air
Find Deal
Fri, Jul 11 - Sun, Jul 20
Allegiant Air Logo
10:31 am - 9:05 amMDW-EWR
21h 34m1 stop
Allegiant Air Logo
9:55 am - 9:41 amEWR-MDW
24h 46m1 stop
$209Allegiant Air
Find Deal
Fri, Jul 4 - Sun, Jul 20
 Logo
10:31 am - 8:59 amMDW-EWR
21h 28m2 stops
 Logo
9:55 am - 9:41 amEWR-MDW
24h 46m1 stop
Thu, Jul 31 - Thu, Aug 7
 Logo
2:55 pm - 12:44 amMDW-EWR
8h 49m1 stop
 Logo
9:55 am - 12:21 pmEWR-MDW
27h 26m1 stop
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 $145 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 $145.

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 $345, 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 $308 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 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 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 $242 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 $267.

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 $118 one-way - $208 round-trip

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
8.6Crew
7.6Entertainment
8.2Boarding
7.1Food
8.0Comfort
Airline reviews

Southwest is Southwest. No frills. If you're luck enough to get a happy crew (we did), then it makes for a nicer flight.

10.0 ExcellentMichael, Jun 2025SMF - SEA
Read more Southwest reviews

Southwest is Southwest. No frills. If you're luck enough to get a happy crew (we did), then it makes for a nicer flight.

Southwest is typically delayed, and it gets wearisome. It is no longer a discount airline and you get way less than you pay for when it comes to comfort and Ce.

We sat on the plane on the tarmac for 4 hours.

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

Flight crew and cabin crew were great. I had to rearrange flights because my original flight was 3hrs delayed for weather, the rub is the flight I moved to boarded on time then we sat at the gate for 2 hours because scheduling stole our first officer for another flight, TWICE. Then our actual FO was an hour delayed. To make it worse my original flight went from a 3 hour delay to departing 15min EARLY. Just poor scheduling operations all around.

Bring back peanuts Take our drink orders when were all seated, especially after you switch to assigned seating.

Staff was far less than helpful at all times. Departure and arrival times mean nothing to Southwest. Extremely disappointed, will never fly with them again, and I’ll be sure to share my experience with all.

It is southwest seat was ok. Not the most comfortable seat

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

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.

It was not in Delta's control, but when we landed, we ended up parking at the wrong gate, and so everyone was already ready to deplane and had their carryon bags, ready to leave. But we had to sit down and move to the proper gate. This process took over 30 minutes. Again, not Delta's fault - more so on the staff at JFK

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..

I had a TERRIBLE experience with the AA crew. I believe it was disability-related. It’s unlikely I will fly AA again.

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.

Good crew and safe. However, comfort and being nickeled-and-dimed are my issues. $75 each way for luggage is exhortation. The space to the next seat is so close you cannot open a laptop. The magazine rack doesn’t hold your items. Not a fan.

Everything on the flight was OK. However, the price is very deceiving the way that it is marketed. It seems like it’s going to be very low cost, but when you add in the charges for luggage, choosing a seat, food & drink, etc., that are already included in other competitors fares, it really is no cheaper, and possibly even more expensive than the other carriers. It actually makes your carrier seem dishonest.

The seats were comfortable and not as tight as i would have expected. Would have been nice to be able to recline my seat, which was not available. Some form of free snacks and drink option would be appreciated as well, even just a water and small bag of crackers would have been better than nothing at all.

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