MDW - NYC

$65 Find Cheap Flights from Chicago Midway Airport to New York

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 4/30. 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

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These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to New York, 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, as well as popular online travel agencies
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Cheap Flights from Midway to New York

 
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.

Recent round-trip flight deals from Midway to New York

KAYAK's recommended round-trip deals from the most popular airlines that fly from Midway to New York.
Discover the best prices for you by selecting your travel dates on KAYAK.
Choose your dates
Southwest Logo
6:05 am - 9:05 amMDW-LGA
2h 00mnonstop
Southwest Logo
9:45 pm - 11:00 pmLGA-MDW
2h 15mnonstop
$153Southwest
Find Deal
Tue, May 20 - Tue, May 27
Southwest Logo
6:05 am - 9:05 amMDW-LGA
2h 00mnonstop
Southwest Logo
9:45 pm - 11:00 pmLGA-MDW
2h 15mnonstop
$158Southwest
Find Deal
Wed, May 28 - Fri, May 30
Frontier Logo
9:34 am - 4:29 pmMDW-LGA
5h 55m1 stop
Frontier Logo
6:30 am - 11:26 amLGA-MDW
5h 56m1 stop
$176Frontier
Find Deal
Tue, May 13 - Wed, May 14
Frontier Logo
2:12 pm - 11:03 pmMDW-LGA
7h 51m1 stop
Frontier Logo
6:30 am - 11:26 amLGA-MDW
5h 56m1 stop
$178Frontier
Find Deal
Wed, May 14 - Wed, May 21
Delta Logo
4:15 pm - 11:07 pmMDW-EWR
5h 52m1 stop
Delta Logo
1:01 pm - 6:41 pmEWR-MDW
6h 40m1 stop
$179Delta
Find Deal
Wed, Jun 4 - Tue, Jun 10
Delta Logo
9:24 am - 3:59 pmMDW-EWR
5h 35m1 stop
Delta Logo
6:00 am - 11:55 amEWR-MDW
6h 55m1 stop
$189Delta
Find Deal
Fri, Jul 4 - Wed, Jul 9
Allegiant Air Logo
8:04 pm - 11:05 amMDW-EWR
14h 01m1 stop
Allegiant Air Logo
11:55 am - 3:37 pmEWR-MDW
28h 42m1 stop
$228Allegiant Air
Find Deal
Fri, May 30 - Tue, Jun 3
Allegiant Air Logo
8:36 pm - 11:05 amMDW-EWR
13h 29m1 stop
Allegiant Air Logo
9:55 am - 2:03 pmEWR-MDW
5h 08m1 stop
$238Allegiant Air
Find Deal
Fri, Jun 6 - Fri, Jun 13
 Logo
10:31 am - 9:05 amMDW-EWR
21h 34m1 stop
 Logo
11:01 am - 10:40 amEWR-MDW
24h 39m1 stop
Fri, Aug 1 - Mon, Aug 4
 Logo
8:36 pm - 11:05 amMDW-EWR
13h 29m1 stop
 Logo
5:15 am - 7:46 pmEWR-MDW
15h 31m2 stops
Fri, Jun 13 - Mon, Jun 16

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 flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Chicago Midway Airport to New York.
Our data shows that the cheapest route for a return flight from Chicago Midway Airport to New York cost $149 and was between Chicago Midway Airport (MDW) and New York LaGuardia Airport (LGA). On average, the best prices are found if you fly this route. The average price for a return flight for this route is $149.

What’s the cheapest day of the week to fly from Chicago Midway Airport to New York?

The average price of all round-trip flights from Chicago Midway Airport to New York clicked on KAYAK for each day over the last 12 months.
When flying from Chicago Midway Airport to New York, you should consider leaving on a Saturday and avoid Thursdays if you are looking for the best rates. For your return to Chicago Midway Airport, you’ll find the best rates on Tuesdays and the most expensive ones on Sundays.

What is the cheapest month to fly from Chicago Midway Airport to New York?

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, 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 is September, where tickets cost $207 (return) on average. On the other hand, the most expensive months are July and December, where the average cost of round-trip tickets is $397 and $351 respectively.

Good to know

Low season

July

High season

March

Cheapest flight

$65
Best time to beat the crowds but there is an average 48% increase in price.
Most popular time to fly and prices are also 9% lower on average.
Flight from Chicago Midway Airport to New York John F Kennedy Airport

When to book flights from Midway to New York

Are your dates flexible? Find out the best times to travel from Midway to New York based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Chicago Midway Airport to New York flights

  • What is the cheapest flight from Chicago Midway Airport to New York?

    In the last 3 days, the lowest price for a flight from Chicago Midway Airport to New York was $65 for a one-way ticket and $153 for a round-trip.

  • Do I need a passport to fly between Chicago Midway Airport and New York?

    Even though you are not required to have a passport, keep in mind that an official ID is needed to board the airplane.

  • Which airports will I be using when flying from Chicago Midway Airport to New York?

    On your way to New York, you’ll fly out from Chicago Midway. You’ll be landing in one of New York’s 3 airports: Newark, New York John F Kennedy Intl, or New York LaGuardia.

  • Which airlines offer Wi-Fi service onboard planes from Chicago Midway Airport to New York?

    American Airlines, Delta, and JetBlue offer inflight Wi-Fi service on the Chicago Midway Airport to New York flight route.

  • Which aircraft models fly most regularly from Chicago Midway Airport to New York?

    The Boeing 737 MAX 8 is the aircraft model that flies most regularly on the Chicago Midway Airport to New York flight route.

  • On which days can I fly direct from Chicago Midway Airport to New York?

    There are nonstop flights from Chicago Midway Airport to New York on a daily basis.

  • Which is the best airline for flights from Chicago to New York, Southwest or Delta?

    The two airlines most popular with KAYAK users for flights from Chicago to New York are Southwest and Delta. With an average price for the route of $248 and an overall rating of 8.0, Southwest is the most popular choice. Delta is also a great choice for the route, with an average price of $442 and an overall rating of 8.0.

  • How does KAYAK find such low prices on flights from Chicago Midway Airport to New York?

    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.

  • 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?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to New York from Chicago Midway Airport 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?

    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 to New York with an airline and back to Chicago Midway Airport 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?

    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 to New York from Chicago Midway Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

KAYAK’s top tips for finding a cheap flight from Chicago Midway Airport to New York

  • Looking for a cheap flight? 25% of our users found flights on this route for $96 or less one-way and $189 or less round-trip.

Prefer to fly direct from Chicago Midway Airport to New York?

Find which airlines fly direct from Chicago Midway Airport to New York, which days they fly and book direct flights.

Direct departures

Chicago Midway to New York

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Direct returns

New York to Chicago Midway

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights
See more direct flights

Top 5 airlines serving from Midway to New York

 
See real verified KAYAK customer reviews for airlines flying from Chicago to New York. 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 4287 reviews
7.6Entertainment
8.6Crew
8.0Comfort
7.1Food
8.2Boarding
Airline reviews

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

8.0 ExcellentJonathan, Apr 2025AUS - MSY
Read more Southwest reviews

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

Plz don't take away free bags and free seating

The seats were a bit cramped and worn, but otherwise okay.

I would have liked to arrive on time - not 5 hours late!

After a 3 hour layover in Denver my flight was delayed over 5 hours! No explanation; no assistance; no offer to provide compensation; no one at Southwest was willing to offer any assistance. 8 hours in the Denver airport - ridiculous!

It was a perfect flight in all aspects! Both legs!

Only one drink pass through the cabin for a 4 hour flight. Quite rough and bumpy landing.

Boarding process, crew were good. But the seats were so uncomfortable that was all I could focus on. I literally had to sit forward so that all 3 of us could fit in row. I will try to avoid Southwest in the future for any flights over 60 minutes.

1.5 hour delay, poor service, no compassion from the crew. Terrible experience

Delayed take-off. Very small plane so very scary with lots of bumps during the flight. Would never fly Delta on short flights in small 80 seaters plane again! Felt relieved when landed.

third trip overseas with delta recently where the TV did not work- not acceptable for a 8 hour flight! your food really has declined crew great and I am loyal to delta

The plane was old with small storage areas that had problems closing/latching and not enough storage for everyone, and worn, damaged seats. Service was great but feel a little unsafe on such well used planes.

Great staff. Wifi is terrible. Signing up for skylines is a painstaking process. Had to call customer service just to get my flight itinerary and confirmation sent to me. Consistent delays. A well staffed company that is run so poorly. Upper management needs to be renewed.

Boarding is, as it always is… horrible. Gate lice. Slow moving zones. Too many people with carry ons

Everything was ok!! Just bags came up a little be late.

Tasty snacks. On-time departure and early arrival. Luggage arrived quickly at the carrousel. The only negative was a man behind us that was heavily inebriated. He was served 3 double drinks during the flight. There was no telling how much he had before the flight. He was so out of it that he spilled a drink and broke the heavy liquor glass on the floor. I don't believe he should have been served so much alcohol on a two-hour flight.

It was terrible, I sat next to a person with a cat, I'm allergic to animal dander, my discomfort was extreme

I sat in comfort plus. It was fine. Seats were comfortable. I got drinks and snacks.

Good and consistent Printer in lounge did not work for me :(

Boarding took forever, the plane was cramped and cold, and the seatbelt song came on constantly throughout the red eye flight with a loud pre-recorded message playing each time

Cabin felt crammed Snacks are lame But crew was super efficient getting us out on time despite delay

Flight was delayed bc of mechanical issue. New plane had different configuration so some seats had to be switched. They called all passengers who needed new boarding cards. They did not call us so we thought our seats were the same and fine. When we boarded they informed us our receipts had changed and we are now all sitting separate and in the back row. Both my daughters had meltdowns and started to cry and once we got on the flight, we figured out how we could sit closer to each other, but this was very upsetting.

You ant watch TV if you don't have a device, the seats have more space, and the snacks are different.

Flight was empty so had a whole row to myself. Still had to wait to get the bag due to the negligence at Palm Springs departure.

Amazingly comfy flight - I had upgraded for a reasonable price and it was worth it. The food also was good.

Random carry-on baggage inspection before boarding for NO REASON. The crew kept talking loudly the entire time, making it impossible to rest. When I asked the crew for something, they said they would come back later but never did. It was an EXTREMELY UNPLEASANT and UNCOMFORTABLE flight.

Only thing that I liked it that I got to my destination safely, otherwise American Airlines stinks.

Ok. Got us there safely and a bit early. Need food available on this long flight. Almost 3 hours.

It was good overall but the prices of snacks are ridiculous.

Worst airline ever! The guy weighing my bag had his foot on the metal plate and when I called him out on it, I got this stupid little smirk. La is a scam and so is Spirit Airlines. All the flight attendants looked like they hated our flight just as much as we did.

Spirit is awful. Too expensive for what you get. Stop nickel and diming.

Seats are poor. They do not lean back. They do not even have pockets on the back, making it impossible to store a phone or a coke bottle. If you opt for basic economy cheap seats, they stick you always in the middle or window seat, even though there are unoccupied seats on the aisle. And then there is the nickel and diming. No carry-ons. And checking your carry-on is $70. At the end there is no price advantage but there is plenty of aggravation.

Good crew and safe. However, comfort and being nickeled-and-dimed are my issues. $75 each way for luggage is exhortation. The space to the next seat is so close you cannot open a laptop. The magazine rack doesn’t hold your items. Not a fan.

The seats were comfortable and not as tight as i would have expected. Would have been nice to be able to recline my seat, which was not available. Some form of free snacks and drink option would be appreciated as well, even just a water and small bag of crackers would have been better than nothing at all.

Bad seats. Very uncomfortable. Crew was fine. Too much upcsharging

WiFi could have been a little more consistent - otherwise a phenomenal and positive experience. The 1000 mile giveaway was awesome!!!

Your employees need to learn how to talk to people as creations of Yah. We are not their children nor are we lower than them.

Fast check-in. Went through security quickly enough. Got their early. And the crew took care of my seating at the gate. The cost for 1 checked bag is ridiculous! $79!? Cmon!! The seating on the plane was very cramped, like sardines. I did not want to pay extra just to pick a seat. Might have to next time.

Helpful attendants at check-in is very good. The $70 charge for a checked bags I didn't care for.and the constant charges for picking a seat and faster check-in are too much. Please cut the prices by at least 50% would be fantastic!

Not very good. Paid in excess of $400 for assigned seating for my family and that was not provided. I want that money back.

The seats were hard molded plastic covered in plastic vinyl. And the scam to charge people extra to sit together. Don’t they know we can just ask someone to trade seats. And watching the staff separate young children from parents… super classy. We had to guilt them into offering up our seats. This companies policies suck. Don’t give them your money.

The seats were awful, hard plastic covered in sheet vinyl. The airline tries to scam you into paying extra to get seat together when the flight wasn’t full. They were going to separate a family with young children but my wife who had a row to herself gave up her seat so the young mom could be with her young boys. I’m never giving this airline my money again.

It was a short flight so no food or entertainment….

Seats are uncomfortable but price is good. Guess I can put up with misery for four hours.

I’ve never traveled on Frontier before. If you want basic, no frills, friendly service at great prices then give them a fly!

I guess you get what you pay for. The seats are very uncomfortable and very little space. The snacks were pricey.

Cancelled and declined to find alternatives Earlier flight is 2 days later Sent the cancellation notification very late, wish I knew earlier would have stayed to watch the Miami open final game Very disappointing service

The worst flight of my life. Never will I fly frontier again

Landing in terminal 2, but my luggage is terminal 3. We (and others) were looking for it in terminal 1. We probably missed the crew broadcast, but the communication could have been clearer for non native (or elderly) passengers.

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