$55 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 1/15. 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, 0 bags

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 York1 stop$110
Buffalo
Buffalo1 stop$152
Syracuse
Syracuse1 stop$209
Albany
Albany1 stop$233
Rochester
Rochester2 stops$264
Ithaca
Ithaca2 stops$462
Binghamton
Binghamton1 stop$289
New York
New York1 stop$110
Buffalo
Buffalo1 stop$152
Syracuse
Syracuse1 stop$209
Albany
Albany1 stop$233
Rochester
Rochester2 stops$264
Ithaca
Ithaca2 stops$462
Binghamton
Binghamton1 stop$289

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

Wed, Dec 3 - Sat, Dec 6
Frontier Logo
2:49 pm - 11:05 pmMDW-LGA
7h 16m1 stop
Frontier Logo
10:55 pm - 11:08 amLGA-MDW
13h 13m1 stop
$110Frontier
Find Deal
Wed, Dec 3 - Sat, Dec 6
Frontier Logo
2:49 pm - 12:59 amMDW-JFK
9h 10m1 stop
Frontier Logo
6:25 am - 1:59 pmJFK-MDW
8h 34m1 stop
$110Frontier
Find Deal
Wed, Dec 3 - Sat, Dec 6
Frontier Logo
2:49 pm - 11:05 pmMDW-LGA
7h 16m1 stop
Frontier Logo
6:20 am - 1:59 pmLGA-MDW
8h 39m1 stop
$111Frontier
Find Deal
Wed, Dec 3 - Sat, Dec 6
Frontier Logo
2:49 pm - 12:59 amMDW-JFK
9h 10m1 stop
Frontier Logo
6:00 am - 10:30 pmJFK-MDW
17h 30m1 stop
$111Frontier
Find Deal
Mon, Dec 8 - Sat, Dec 13
Southwest Logo
5:55 pm - 9:00 pmMDW-LGA
2h 05mnonstop
Southwest Logo
8:35 am - 10:00 amLGA-MDW
2h 25mnonstop
$115Southwest
Find Deal
Tue, Dec 16 - Wed, Dec 17
Multiple Airlines Logo
7:44 am - 10:45 amMDW-EWR
2h 01mnonstop
Multiple Airlines Logo
10:00 pm - 5:38 pmEWR-MDW
20h 38m1 stop
$115Multiple Airlines
Find Deal
Sat, Nov 22 - Tue, Dec 2
Multiple Airlines Logo
6:05 am - 1:33 pmMDW-EWR
6h 28m1 stop
Multiple Airlines Logo
11:30 am - 1:01 pmEWR-MDW
2h 31mnonstop
$126Multiple Airlines
Find Deal
Tue, Dec 9 - Fri, Dec 12
Southwest Logo
7:15 pm - 10:20 pmMDW-LGA
2h 05mnonstop
Southwest Logo
9:00 am - 10:25 amLGA-MDW
2h 25mnonstop
$132Southwest
Find Deal
Sat, Dec 6 - Wed, Dec 10
Delta Logo
1:14 pm - 6:45 pmMDW-JFK
4h 31m1 stop
Delta Logo
6:00 am - 11:55 amJFK-MDW
6h 55m1 stop
$159Delta
Find Deal
Wed, Nov 26 - Mon, Dec 1
Delta Logo
6:48 pm - 11:10 pmMDW-SYR
3h 22m1 stop
Delta Logo
7:01 pm - 11:40 pmSYR-MDW
5h 39m1 stop
$229Delta
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 $29 round-trip. The most popular route is from Chicago Midway Airport (MDW) to Newark Airport (EWR), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $29.

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.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $354 on average.

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 $366 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$55
Best time to beat the crowds with an average 1% 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 in the evening, when round-trip flights cost $214 on average. Morning departures are around 19% more expensive 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 $279.

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: Newark $56 one-way - $88 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 4241 reviews
8.1Boarding
7.0Food
8.0Comfort
8.6Crew
7.5Entertainment
Airline reviews

Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.

2.0 MediocreAnonymous, Nov 2025ORD - LAS
Read more Southwest reviews

Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

Full cans of soda would be nice. A choice between two snacks would be appreciated.

Tried watching free movie and it kept freezing so I couldn’t finish.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

Sacrament staff are always polite and helpful. Airport is easy to maneuver and boarding is straightforward.

Great flight. Outstanding Service. Southwest was able to put us on a direct flight to Denver when the connection could have been affected by a later arrival to Baltimore. The direct flight was less expensive that the flight with the connection in Baltimore.

Delays delays delays. Late taking off, late landing, wait for a gate, etc.

Boarded on time but once we were ready for take off, the crew determined that, although every seat was taken, somehow someone was on the wrong flight. Delay, delay delay, announcements and ended up with one person checking EVERY ID against their passenger Manifest only to figure out it was a "clerical error." We departed 54 minutes late causing me to run in the St. Louis Airport to make my connection and lose the priority boarding spot I had paid for. Unnecessary delay.

I was re-booked onto another flight because my original flight was delayed and I would have missed my connector. I ended up in the “C” group after paying extra to be in the “A “ group on the original flight. At least if you’re going to re-book people, re-book them into the same group.

The flight used a B767 with a very old interior from before 2014. The entertainment system did not work at all during the flight despite attempts to reset the system. It was like they flew this route just to be competitive.

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.

My experience was terrible. They cancelled my flight twice. They kept delaying it and leading me on, acting like the flight was going to go when it never had a chance. I missed out on valuable family time because of spirit and I won’t be flying with them again.

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 😔

There was no one at the counter to assist with our check in. The app didn’t work, so I arrived at the airport with time to check in and I couldn’t because no employees were there. When I finally got someone on the phone, it was inside the 60min rule and they said I could no longer check in and they could sell me another ticket. We had to scramble and pay an additional $800 for tickets and THEN AFTER (about 60 min from my original convo with customer service and 10min after original departure time) I had boarded my new flight, there was email saying my original flight from Frontier was delayed and leaving 2hr 50min later, but I STILL wouldn’t have been able to check in. Which means customer service should have been able to see it and let me check in because I was well within my check in time. When I call Frontier, they hang up on me. So their app didn’t work and they employees left and they take zero responsibility or assistance with their “customer service”

Terrible. Flight cancelled with no reasoning and no flights to rebook. Employees were useless and did nothing to help. Did not even know where to retrieve luggage from the cancelled flight. Flyers beware.

No fault of Frontier staff: plane was very late, reached Orlando at 1 am, took a while to get luggage. Weather, gov financial shutdown impact on TSA, air controllers seemed to have multiple flights backed up. Frontier staff seemed to cope as gracefully as possible. It did reassure me that I and my new hip could adapt to travel challenges. Food/entertainment were irrelevant to my trip.

Terrible. The canceled my entire flight when I requested a refund for a trip frontier canceled trip one way.

Boarding was on time and plane departed as scheduled. There are obviously no amenities (food, drink, entertainment) on Frontier, but there also didn't seem to be any issues with luggage space either.

Inbound plane was on time and flight departed on time with no issues while boarding.

I knew going into this that Frontier, being a low cost carrier, would be pretty bare bones and charge for most extras but this was made up for by the fact that the airplane was a reasonably new Airbus, every employee was great and best of all, Everett Washington is an amazing airport - thanks Frontier for flying there!!!

i was unable to check in the flight. refund requested

It was well done. It was my first time flying with them and I was nervous b/c I have heard of many cancelled and/or delray flights. Everything went smoothly.

Just know that everything, and I mean everything is “ala cart”. 60$ just to put something in the overhead bin. I will never fly Frontier again nor do I recommend them to anyone else.

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

Information on your arrival and departure airports