$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 8/11. 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 Yorknonstop$129
Buffalo
Buffalo1 stop$136
Syracuse
Syracuse1 stop$289
Albany
Albany1 stop$238
Rochester
Rochester1 stop$277
Ithaca
Ithaca2 stops$437
Binghamton
Binghamton1 stop$417
New York
New Yorknonstop$129
Buffalo
Buffalo1 stop$136
Syracuse
Syracuse1 stop$289
Albany
Albany1 stop$238
Rochester
Rochester1 stop$277
Ithaca
Ithaca2 stops$437
Binghamton
Binghamton1 stop$417

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

Selasa, Mei 12 - Rabu, Mei 13
Southwest Logo
12:40 pm - 3:45 pm
MDW
-
LGA
2h 05mnonstop
Southwest Logo
3:55 pm - 5:40 pm
LGA
-
MDW
2h 45mnonstop
$129Southwest
Rabu, Mei 20 - Rabu, Mei 27
Southwest Logo
5:15 am - 8:15 am
MDW
-
LGA
2h 00mnonstop
Southwest Logo
1:25 pm - 2:50 pm
LGA
-
MDW
2h 25mnonstop
$130Southwest
Rabu, Mei 20 - Selasa, Mei 26
Southwest Logo
5:15 am - 8:15 am
MDW
-
LGA
2h 00mnonstop
Southwest Logo
10:55 am - 12:20 pm
LGA
-
MDW
2h 25mnonstop
$131Southwest
Rabu, Mei 27 - Rabu, Jun 3
Frontier Logo
6:00 am - 1:54 pm
MDW
-
BUF
6h 54m
1 stop
Frontier Logo
2:49 pm - 10:02 pm
BUF
-
MDW
8h 13m
1 stop
$136Frontier
Rabu, Mei 13 - Selasa, Mei 19
Frontier Logo
6:00 am - 1:54 pm
MDW
-
BUF
6h 54m
1 stop
Frontier Logo
11:36 am - 10:02 pm
BUF
-
MDW
11h 26m
1 stop
$140Frontier
Selasa, Mei 12 - Khamis, Mei 14
Frontier Logo
12:24 pm - 11:14 pm
MDW
-
LGA
9h 50m
1 stop
Frontier Logo
10:45 pm - 3:57 pm
LGA
-
MDW
18h 12m
1 stop
$140Frontier
Jumaat, Mei 15 - Ahad, Mei 17
Frontier Logo
4:52 pm - 4:11 pm
MDW
-
LGA
22h 19m
1 stop
Frontier Logo
10:45 pm - 3:57 pm
LGA
-
MDW
18h 12m
1 stop
$141Frontier
Rabu, Mei 27 - Selasa, Jun 2
Multiple Airlines Logo
12:04 pm - 11:36 am
MDW
-
EWR
22h 32m
1 stop
Multiple Airlines Logo
10:29 pm - 10:02 pm
EWR
-
MDW
24h 33m
1 stop
$175Multiple Airlines
Khamis, Jun 4 - Selasa, Jun 9
Delta Logo
12:53 pm - 8:35 pm
MDW
-
EWR
6h 42m
1 stop
Delta Logo
7:00 am - 12:00 pm
EWR
-
MDW
6h 00m
1 stop
$177Delta
Selasa, Mei 19 - Selasa, Mei 26
Delta Logo
6:36 pm - 11:18 pm
MDW
-
ALB
3h 42m
1 stop
Delta Logo
6:00 am - 8:43 am
ALB
-
MDW
3h 43m
1 stop
$241Delta
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 $56 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 $177.

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

The average price for all round-trip flights from Chicago Midway Airport to New York State depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to New York State is generally in the evening, when round-trip flights cost $207 on average. Morning departures are around 13% 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 $323.

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 2 stops layover the cheapest option at $311 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 January, when tickets cost $29 (return) on average. On the other hand, the most expensive months are February and August, when the average cost of round-trip tickets is $158 and $143 respectively.

Good to know

Low seasonFebruary
Cheapest flight$65
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly and prices are also 5% lower on average.
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.

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 $69 one-way - $65 round-trip; New York $124 one-way - $246 round-trip

Reviews of the top airlines flying 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 4313 reviews
8.6Crew
7.5Entertainment
7.0Food
8.0Comfort
8.1Boarding
Airline reviews

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

10.0 Excellentlarry, Apr 2026
LGB - PHX
Read more Southwest reviews

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

First time I've had to use the disabled accommodations. And I could not have had a better experience with Southwest, i was having trouble getting from one terminal to another due to my heart failure. And the next thing I know a Southwest agent had made sure. I had a wheelchair at all my flights. Can't thank them enough.

Delayed flight, lack of information, boarding process is a mess as is the carryon luggage causing issues when leaving the plane….just a poor experience.

Comfortable. Easy. No problems. Just wish they had gf options for snacks.

The crew was very kind and made going to Hawaii relaxing and fun to look forward to! Thank you Southwest for a pleasant flight!

This leg was much better, but we did have to have a 3 hour lay o er after coming from a very exhausting hiccup with our flight from BNA to Den

We waited in the airplane for over 45 min for a southwest employee to make the flight. This cause over half the plane to miss their connecting flight in Denver. When we confronted the desk upon arrival, they told us the only flight they had was the next day leaving at 8:50 pm!!! Or they offered to get us to Burbank or LA, but after that we were on our own to get back to Santa Barbara. I paid for a flight from sba to bna bna to sba. My re entry into mom mode has been 💯 rough because of southwest mistake with my flight. And now I’m leaving to Reno tomorrow for a vballl tournament and just discovered that my leg in Vegas has me and my 3 kids on a stand by flight even though I had booked these ticket last year November!! Do better southwest!

Southwest is kind of a slum airline. It’s gotten more expensive over the years for less and less service. I am a Southwest Chase Visa card holder and was forced to choose a seat in the 26th row in the middle seat. However my wife who is a rewards member but doesn’t hold a card or anything else, gets randomly assigned a normally paid seat in row 6! How does that work?

For the first time in a long time, the Wi-Fi actually worked the entire flight! The flight crew was amazing as usual.

Plane was hot and miserable and the crew was rude!

12 hour delay required getting on and off plane 3 times - would have at least liked to have been offered a snack or drink

They didn’t offer a water, even after I asked

They switched our terminal 3 times and we were delayed for four plus hours!!!

It was an early flight and most people napped/slept and the crew let us which was nice.

The crew acted like they had never done this and kept barking passive aggressive orders at people. + the security line + the delay + sitting on the tarmac for 2 hours + none of the apps or signage updating with correct times

More inflight connection. And leg space is horrible. And the paying for baggage I'd ridiculous!!!

My flight was originally from SAT to MCO connecting from MCO to ORD. We got diverted to ATL and than Frontier staff there was sooo un helpful first they said they couldn’t give us any accommodation since our flight first got delayed that cancelled and now it’s 221am and I am still in ATL since they said they need to create a new flight my final destination is ORD and I have been delayed twice and cancelled. With no real help the frontier app didn’t work no email updates over all such a horrible experience

There's no seats that lean back with little leg space i wad uncomfortable the entire flight. Your charges for extra baggage is despicable and costly!!

Remind customers of the need to have passport or new ID for boarding.

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

Information on your arrival and departure airports