$52 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 1/13. 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
Newark1 stop$103
Buffalo
Buffalo1 stop$144
Syracuse
Syracuse1 stop$229
Albany
Albany1 stop$177
Rochester
Rochesternonstop$155
Ithaca
Ithaca2 stops$1,700
Binghamton
Binghamton1 stop$347
New York
Newark1 stop$103
Buffalo
Buffalo1 stop$144
Syracuse
Syracuse1 stop$229
Albany
Albany1 stop$177
Rochester
Rochesternonstop$155
Ithaca
Ithaca2 stops$1,700
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

dom., ene. 11 - mar., ene. 13
Frontier Logo
12:41 pm - 1:10 am
MDW
-
EWR
11h 29m1 stop
Frontier Logo
10:30 pm - 12:02 am
EWR
-
MDW
2h 32mnonstop
$103Frontier
mié., ene. 14 - dom., ene. 18
Frontier Logo
11:39 am - 1:13 am
MDW
-
EWR
12h 34m1 stop
Frontier Logo
10:30 pm - 12:02 am
EWR
-
MDW
2h 32mnonstop
$104Frontier
vie., ene. 16 - dom., ene. 18
Frontier Logo
8:28 am - 1:13 am
MDW
-
EWR
15h 45m1 stop
Frontier Logo
10:30 pm - 12:02 am
EWR
-
MDW
2h 32mnonstop
$105Frontier
mar., mar. 17 - jue., mar. 19
Frontier Logo
7:44 am - 10:45 am
MDW
-
EWR
2h 01mnonstop
Frontier Logo
11:30 am - 1:01 pm
EWR
-
MDW
2h 31mnonstop
$106Frontier
lun., ene. 26 - mié., ene. 28
Southwest Logo
5:55 pm - 9:00 pm
MDW
-
LGA
2h 05mnonstop
Southwest Logo
6:00 am - 7:40 am
LGA
-
MDW
2h 40mnonstop
$114Southwest
mar., ene. 27 - mié., feb. 4
Southwest Logo
6:05 am - 9:10 am
MDW
-
LGA
2h 05mnonstop
Southwest Logo
9:45 pm - 11:15 pm
LGA
-
MDW
2h 30mnonstop
$116Southwest
mar., feb. 10 - mié., feb. 18
Delta Logo
10:48 am - 5:54 pm
MDW
-
BUF
6h 06m1 stop
Delta Logo
6:35 pm - 10:42 pm
BUF
-
MDW
5h 07m1 stop
$157Delta
mar., feb. 10 - mar., feb. 17
Delta Logo
10:48 am - 5:54 pm
MDW
-
BUF
6h 06m1 stop
Delta Logo
6:35 pm - 10:44 pm
BUF
-
MDW
5h 09m1 stop
$170Delta
vie., ene. 2 - vie., ene. 9
Multiple Airlines Logo
3:10 pm - 7:55 pm
MDW
-
SWF
27h 45m1 stop
Multiple Airlines Logo
11:09 am - 10:27 pm
SWF
-
MDW
36h 18m2 stops
$512Multiple Airlines
jue., dic. 25 - dom., dic. 28
Multiple Airlines Logo
3:10 pm - 11:44 am
MDW
-
SWF
19h 34m2 stops
Multiple Airlines Logo
11:43 am - 9:04 pm
SWF
-
MDW
10h 21m1 stop
$810Multiple Airlines
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.

How much is a round-trip flight from Chicago Midway Airport to State of New York?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago Midway Airport to State of New York departing in January.

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 $39 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 $39.

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 $379, 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 October, when tickets cost $167 (return) on average. On the other hand, the most expensive months are December and May, when the average cost of round-trip tickets is $342 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$52
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 in the evening, when round-trip flights cost $206 on average. Morning departures are around 20% 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 $263.

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 $65 one-way - $66 round-trip

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 4251 reviews
8.0Comfort
7.0Food
7.5Entertainment
8.1Boarding
8.6Crew
Airline reviews

Airline travel is always too cramped to really be pleasant, but the cabin crew on this flight did a pretty good job of making up for it by putting on some music during boarding and sprinkling a few funny remarks into the safety briefing and announcements, and just generally being friendly and helpful. It definitely reminded me of why I prefer the in-flight experience on Southwest!

10.0 ExcellentDavid, Nov 2025
BUF - PHX
Read more Southwest reviews

Airline travel is always too cramped to really be pleasant, but the cabin crew on this flight did a pretty good job of making up for it by putting on some music during boarding and sprinkling a few funny remarks into the safety briefing and announcements, and just generally being friendly and helpful. It definitely reminded me of why I prefer the in-flight experience on Southwest!

No delays and arrived to destination 30 min early. Staff was super friendly.

San Diego airport is brand new, spacious, airy and very smooth checkin at SW baggage drop.

It was rough. The staff was unprofessional, the choice of on board drinks terrible, it was cramped in space at every airport, they always ran out of overhead bin space so they pressured people to check bags for free or we couldn’t leave on the plane— so I did check my bag to help, and they nearly lost my bag. My bag did not arrive on the luggage belt, another man on my flight and I had to waste our time going to the baggage office to search for our bags. I would only fly southwest again if it was my last choice. Also, my flights were consistently delayed over and over again— at one point they straight up told us we were waiting for the pilot to arrive.

Crew could have been friendlier, maybe I'm spoiled by SW crews. In flight wifi was good. Would be nice to have more food offerings on a 4 plus hour flight

Had to get off plane from prior flight even though I had to reboard same plane to continue to my final destination.

Everything a cheap airline should be at normal airline rates.

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.

I fly Delta all the time, have Platinum Medallion status. But this route seems to have major problems with delays and seems to never leave on time! Have only taken it twice in the last two weeks, and each time it had delays of more than 1 hour... very disappointed!!!!

Staff was exceptional! Everyone was kind, professional and friendly making the trip very pleasant. Thank you!

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.

Flight got delayed for 5 hours no good explanation was offered ;(

Horrible. I would never fly Frontier again. The booking process is tricky at best, but fraudulent in my opinion. Frontier customer service did nothing to rectify my purchase -- I ended up paying more than double what I could have gotten from other airlines and nearly triple what I thought I was buying from Frontier. Their booking practices are unfair to the consumer.

Delayed. Text notifications were slow. Not much information o what was happening. Boarding was slow and confusing. Wasn’t even offered water other flight. Had to ask. No entertainment at all. Felt like.a Greyhound bus.

When I wanted to check in 3 hours prior to boarding time, the employees mentioned “a little over an hour delay” so I waited for an hour then I went to go look for food in the terminal and most people from that flight were in the same area looking for food. Finally I decided after food to check to see if it’s anytime closer and now it’s 2 mins until boarding closes?! What are you kidding me? I didn’t receive anything via sms about boarding now nor via email or on the intercom. I luckily made it through, barely, and then there’s no room for my carry on mind you I’m in the very first row so I had to place my purse in one further row back and my carry on sections down. Not sure who pays for better seats to get your stuff placed all over the plane but that was the worst experience I’ve ever had flying with anyone.

Better than expected. Staff were friendly and nice on both flights.

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.

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

Information on your arrival and departure airports