$94 Find Cheap Flights from Chicago Midway Airport to New York State - Compare and Save

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 8/4. 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.
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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 York2 stops$185
Buffalo
Buffalo1 stop$203
Syracuse
Syracuse1 stop$289
Albany
Albany2 stops$308
Rochester
Rochester1 stop$255
Ithaca
Ithaca2 stops$335
Binghamton
Binghamton1 stop$427
New York
New York2 stops$185
Buffalo
Buffalo1 stop$203
Syracuse
Syracuse1 stop$289
Albany
Albany2 stops$308
Rochester
Rochester1 stop$255
Ithaca
Ithaca2 stops$335
Binghamton
Binghamton1 stop$427

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, Aug 5 - Sat, Sep 19
Southwest Logo
8:50 am - 5:05 pm
MDW
-
LGA
7h 15m
2 stops
Southwest Logo
7:00 am - 1:20 pm
LGA
-
MDW
7h 20m
2 stops
$185Southwest
Thu, Aug 20 - Sat, Aug 22
Southwest Logo
7:15 am - 1:55 pm
MDW
-
LGA
5h 40m
1 stop
Southwest Logo
8:20 am - 2:05 pm
LGA
-
MDW
6h 45m
1 stop
$186Southwest
Sat, Aug 8 - Mon, Aug 10
Southwest Logo
7:45 am - 5:05 pm
MDW
-
LGA
8h 20m
1 stop
Southwest Logo
6:00 am - 7:15 am
LGA
-
MDW
2h 15mnonstop
$187Southwest
Fri, Jul 31 - Wed, Aug 5
Southwest Logo
7:45 pm - 11:00 pm
MDW
-
LGA
2h 15mnonstop
Southwest Logo
7:10 am - 1:55 pm
LGA
-
MDW
7h 45m
1 stop
$188Southwest
Thu, Sep 17 - Sun, Sep 20
Delta Logo
1:19 pm - 7:30 pm
MDW
-
EWR
5h 11m
1 stop
Delta Logo
6:00 am - 9:07 am
EWR
-
MDW
4h 07m
1 stop
$202Delta
Thu, Aug 6 - Tue, Aug 11
Frontier Logo
11:06 am - 1:53 pm
MDW
-
BUF
25h 47m
1 stop
Frontier Logo
11:29 am - 10:03 pm
BUF
-
MDW
11h 34m
1 stop
$203Frontier
Fri, Aug 7 - Tue, Aug 11
Frontier Logo
6:05 am - 1:53 pm
MDW
-
BUF
6h 48m
1 stop
Frontier Logo
11:29 am - 10:03 pm
BUF
-
MDW
11h 34m
1 stop
$204Frontier
Sat, Aug 15 - Tue, Sep 15
Delta Logo
6:42 pm - 11:25 pm
MDW
-
EWR
3h 43m
1 stop
Delta Logo
1:00 pm - 6:33 pm
EWR
-
MDW
6h 33m
1 stop
$227Delta
Thu, Oct 29 - Sun, Nov 1
Multiple Airlines Logo
10:08 am - 10:29 am
MDW
-
SWF
23h 21m
1 stop
Multiple Airlines Logo
11:58 am - 10:58 am
SWF
-
MDW
24h 00m
2 stops
$313Multiple Airlines
Sun, Dec 6 - Sun, Dec 13
Multiple Airlines Logo
6:10 pm - 8:52 am
MDW
-
SWF
13h 42m
1 stop
Multiple Airlines Logo
9:36 am - 7:02 pm
SWF
-
MDW
10h 26m
1 stop
$427Multiple 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.

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 5 days was to New York, at $187 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 5 days was $187.

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 $212 on average. Morning departures are around 17% 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 $352.

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 July and June, when the average cost of round-trip tickets is $177 and $169 respectively.

Good to know

Low seasonFebruary
Cheapest flight$94
Best time to beat the crowds but there is an average 6% increase in price.
Most popular time to fly with an average 35% 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.

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 $163 one-way - $234 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.
7.9
SouthwestOverall score based on 4250 reviews
8.1Boarding
8.0Comfort
7.0Food
8.6Crew
7.5Entertainment
Airline reviews

Overall good, just screaming kids in the area the whole flight.

8.0 ExcellentAnonymous, Jul 2026
MDW - MHT
Read more Southwest reviews

Overall good, just screaming kids in the area the whole flight.

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

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

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

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

My flight to Chicago left and landed early. My return flight left two minutes late and arrived 2 minutes late. My seat selections were ideal! There were no snacks going to Chicago and no snacks on the return trip. There are no charging outlets on board.

It good. Just not that plane didn’t have power outlets to charge devices etc.

Flight was canceled. Most upsetting was message from Kayak, stating that the flight was canceled and click with Kayak for details regarding rebook, refund details. THERE'S NO INFORMATION PROVIDED BY KAYAK EXCEPT THAT FLIGHT IS CANCELED. AND NOW THIS SURVEY TO FIND OUT HOW WAS THE FLIGHT !!!!!!!

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

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.

Great for the price. No wifi or entertainment, but gate agents and crew were fantastic and we boarded quickly and left on time.

Our flight was canceled for no known reason. We weren’t told until we were checking in at 5:00 am. This was after our last flight with Frontier where we sat on the plane for three hours (not an exaggeration) before we took off because of a mechanical issue. We won’t be flying Frontier again.

I didn’t have enough time to catch my connecting flight and had to use a different Airline. I will be requesting a refund.

I brought a ticket and car rental through Travelocity. There was no where to add a KTN. So I thought i’d add it by looking up ticket on frontier website. I tried 3 times with the frontier chat bot to add my KTN it never updated my boarding pass. So then I tried showing up early to do it in person at the airport. The first employee update my ktn in the system and gave me a new boarding pass. I was sent back by tsa to join regular line. Then I was told to add my Ktn. It would cost me $25 extra. Given the length of the cue I did pay. Congratulations! BUT I will NEVER fly frontier again. Plus the plane was very old. It had actual ashtrays and old looking tray backs. Worst travel experience ever. Im warning my friends and family not to use frontier ever.

It was delayed 9 hours for operational reasons, despite the plane arriving to the airport on time.

Was just ok with over selling I guess. A lot of people in a short space and when we finally arrive i20 minutes, waiting to get out from the plain because we were waiting authorization for out boarding? Something like that.

They changed my flight and did not want to accommodate me or try to help me in any way. They do not care about their customers.

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

Information on your arrival and departure airports