$71 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 10/8. 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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Flight Deals

Cheap Flights from Midway to New York

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
New York
New Yorknonstop$137
Buffalo
Buffalo1 stop$176
Syracuse
Syracuse1 stop$229
Albany
Albanynonstop$237
Rochester
Rochester1 stop$245
Ithaca
Ithaca2 stops$269
Binghamton
Binghamton1 stop$347
New York
New Yorknonstop$137
Buffalo
Buffalo1 stop$176
Syracuse
Syracuse1 stop$229
Albany
Albanynonstop$237
Rochester
Rochester1 stop$245
Ithaca
Ithaca2 stops$269
Binghamton
Binghamton1 stop$347

Book Cheap Midway to New York Plane Tickets

 
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

Tue, Oct 7 - Wed, Oct 8
Southwest Logo
8:25 am - 11:30 amMDW-LGA
2h 05mnonstop
Southwest Logo
6:05 am - 7:30 amLGA-MDW
2h 25mnonstop
$137Southwest
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Thu, Oct 30 - Thu, Nov 6
Frontier Logo
1:37 pm - 10:44 pmMDW-LGA
8h 07m1 stop
Frontier Logo
12:30 pm - 6:39 pmLGA-MDW
7h 09m1 stop
$138Frontier
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Wed, Oct 8 - Wed, Oct 15
Frontier Logo
8:05 am - 4:29 pmMDW-LGA
7h 24m1 stop
Frontier Logo
6:30 am - 1:38 pmLGA-MDW
8h 08m1 stop
$141Frontier
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Wed, Nov 19 - Sat, Nov 22
Southwest Logo
12:55 pm - 3:55 pmMDW-LGA
2h 00mnonstop
Southwest Logo
6:10 am - 7:35 amLGA-MDW
2h 25mnonstop
$142Southwest
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Tue, Oct 28 - Wed, Oct 29
Frontier Logo
1:56 pm - 10:21 pmMDW-LGA
7h 25m1 stop
Frontier Logo
6:29 am - 12:41 pmLGA-MDW
7h 12m1 stop
$143Frontier
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Sat, Oct 4 - Mon, Oct 6
Frontier Logo
11:23 am - 8:02 pmMDW-LGA
7h 39m1 stop
Frontier Logo
6:30 am - 4:25 pmLGA-MDW
10h 55m1 stop
$144Frontier
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Sun, Sep 28 - Sat, Oct 4
Frontier Logo
10:13 am - 12:01 pmMDW-LGA
24h 48m1 stop
Frontier Logo
12:59 pm - 9:18 amLGA-MDW
21h 19m1 stop
$145Frontier
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Fri, Oct 24 - Sun, Oct 26
Frontier Logo
5:28 pm - 12:04 pmMDW-LGA
17h 36m1 stop
Frontier Logo
10:00 pm - 11:08 amLGA-MDW
14h 08m1 stop
$146Frontier
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Tue, Oct 7 - Wed, Oct 15
Delta Logo
5:04 pm - 12:59 amMDW-EWR
6h 55m1 stop
Delta Logo
6:00 am - 8:40 amEWR-MDW
3h 40m1 stop
$177Delta
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Sat, Oct 18 - Wed, Oct 22
Delta Logo
6:23 pm - 11:10 pmMDW-EWR
3h 47m1 stop
Delta Logo
5:56 pm - 10:14 pmEWR-MDW
5h 18m1 stop
$178Delta
Find Deal
Booking Insights

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?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to New York State from Chicago Midway Airport found in the last 72 hours was to New York, at $66 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 $162.

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 $352, 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 August, when tickets cost $202 (return) on average. On the other hand, the most expensive months are December and May, when the average cost of round-trip tickets is $353 and $277 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 seasonJuly
Cheapest flight$71
Best time to beat the crowds with an average 2% drop in price.
Most popular time to fly with an average 8% 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 $240 on average. On average, there is no price difference when choosing to fly in the morning or the evening on this flight route. 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 $278.

Reviews of the top 3 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 4242 reviews
8.0Comfort
8.1Boarding
7.0Food
8.6Crew
7.5Entertainment
Airline reviews

I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!

10.0 ExcellentG, Sep 2025LAS - ATL
Read more Southwest reviews

I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!

As always, the entire Southwest experience was wonderful, from online booking to flight to baggage retrieval. Very grateful.

The weather could have been better. There was a 40 minute ATC delay in SFO because of marine fog and a micro cell storm delayed landing and take-off at Nashville. The gate was changed 5 minutes from boarding from gate B3 to gate C23 at Nashville airport.

After being assaulted by a flight attendant I was then brushed off as oh well because he long braids didn’t mean to whip me in the eye. I have filed complaints and will see. But like any other issue I’ve had with kayak involved it’s been trash. Last time I’ll be using your app

AC sub par. WiFi not working correctly. Ac sucked. Seats very narrow.

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

Southwest's seats are the least comfortable I have ever sat in.

The cabin was quiet for the redeye flight. The area was clean. The staff was great. The 787 Max was in good condition. Drawbacks were that the seat widths were tight for some passengers. The seat padding was at best average and for a long flight uncomfortable.

Southwest like most American domestic airlines, is a mediocre airline. But it is among the cheapest. Oh well.

My flight was delayed 50 minutes and we were rushed to board to then sit for 15 minutes until the pilot arrived. Unacceptable since we could have waited to board. Also the delayed flight was updated AFTER we boarded to more than the 10 minutes as originally stated.

Delta made it easy, comfortable and timely. The crew was fantastic.

On this flight I felt the food offering was not as complete as on previous flights. The tomato salad was a bit off and there was nothing additional such a bread or butter. The breakfast was only one option, so you either ate what they had or ate nothing. The crew was efficient, but most seemed frustrated throughout the flight. The flight arrived early and was obstacle-free, so I’m overall quite happy, but the shine in the rest of the experience just wasn’t there.

Great flight with Delta! Boarding was quick and easy, the amenities were solid, and the plane was in great shape. The flight attendants had a fun, lively energy while staying professional. All in all, a smooth trip — even managed to catch up on some rest. Thanks, Delta!

De planning was an absolute mess. We were never told that we weren’t at the gate and that we had to go down unstable stairs and then hop on a bus. People were falling, we couldn’t tell who was in charge. Overall terrible communication that ended up leaving a bad impression at the very end of the experience.

For a 69 year old with health problems I had the worse experience, no wheelchair when I entered a lady told me to sit and wait while a gentleman told me I had to walk to the Delta station, which I did. I had a carry on and a bag, and I was traveling with my service dog, which was on his carrier and the lady charged me for my carry on luggage, beside all the waiting cause of the delay, I had to walk to get my luggage cause no wheelchair showed up, I am so disappointed. I will get in touch with the company. I got home at 3:00 am, not good for my health situation.

Did not know my son and I had different seating arrangements. He was fine, but it was disappointing.

My flight was canceled after being rescheduled for four days canceling my trip. Kayak and everyone affiliated with it I.e the airlines, and just fly have been excruciating to deal with. My trip to visit family had to be canceled as there was no way to make it. I am furious at all of you.

They delayed our flight because of bad weather in NY which was completely understandable. Then they cancelled our flight and a later flight that evening. The earliest we could fly was the next morning. We ended up buying last minute tickets on another airline and made it home slightly delayed but safely that evening. Delta kept saying it was weather related but if that was the case how did we make it back on another airline? The weather in NY was cloudy but not bad.

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.

No Tumberlence smooth flight. Try to change the menu on Snacks.

Spirit is low fare air line. Food also cost you. No free food.

The flight was delayed twice with minimal explanation. The terminal and airplane were filthy. The food voucher didn’t even cover a tiny pizza from a kiosk in the terminal. All in all, a pretty miserable experience for a flight to attend a funeral

Everyone was kind for the most part. I did travel with children and paid for seats and even then it was not as suitable. I tried calling their customer service prior to check in and I was told they couldn't help me because I didn't purchase my tickets with them.

It was very bad it got delayed by 2 hours.Never going to travel with spirit airlines in future.

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.

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

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