Find flights
Deals
Insights
When to book
FAQs & Tips
Direct Flights
Airlines

MDW - NYC

Find cheap flights from Chicago Midway Airport to New York from $53

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 4/24. 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
0 bags
Thu 4/18
Thu 4/25

Search hundreds of travel sites at once for deals on flights to New York

 
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
In the last 7 days travelers have searched 47,600,107 times on KAYAK, and here is why:

Save 20% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Bundle and saveSave money when you bundle your flight + hotel.

Cheap flight deals 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.
8:42 am - 8:59 pmMDW-LGA
11h 17m1 stop
10:00 pm - 8:21 amLGA-MDW
11h 21m1 stop
$102Frontier
Find Deal
Tue, Apr 9 - Wed, Apr 17
4:36 pm - 11:10 pmMDW-LGA
5h 34m1 stop
10:00 pm - 8:21 amLGA-MDW
11h 21m1 stop
$105Frontier
Find Deal
Wed, Apr 10 - Wed, Apr 17
8:42 am - 8:59 pmMDW-LGA
11h 17m1 stop
4:00 pm - 9:23 pmLGA-MDW
6h 23m1 stop
$106Frontier
Find Deal
Tue, Apr 9 - Wed, Apr 10
9:33 pm - 8:02 amMDW-LGA
9h 29m1 stop
8:52 am - 1:53 pmLGA-MDW
6h 01m1 stop
Tue, Apr 16 - Tue, Apr 23
9:33 pm - 8:02 amMDW-LGA
9h 29m1 stop
8:52 am - 1:53 pmLGA-MDW
6h 01m1 stop
Tue, Apr 16 - Tue, Apr 23
5:45 pm - 11:22 pmMDW-EWR
4h 37m1 stop
9:36 am - 12:41 pmEWR-MDW
4h 05m1 stop
$158Delta
Find Deal
Sat, May 11 - Tue, May 14
6:25 am - 9:30 amMDW-LGA
2h 05mnonstop
11:55 am - 1:10 pmLGA-MDW
2h 15mnonstop
$170Southwest
Find Deal
Sun, Apr 28 - Mon, Apr 29
5:45 pm - 11:00 pmMDW-EWR
4h 15m1 stop
4:00 pm - 9:47 pmEWR-MDW
6h 47m1 stop
$173Delta
Find Deal
Sat, Jul 27 - Sat, Aug 31
5:55 am - 9:00 amMDW-LGA
2h 05mnonstop
11:25 am - 12:55 pmLGA-MDW
2h 30mnonstop
$238Southwest
Find Deal
Mon, Apr 1 - Thu, Apr 4
9:08 pm - 9:05 amMDW-EWR
10h 57m1 stop
10:55 am - 8:18 pmEWR-MDW
10h 23m1 stop
$316Allegiant Air
Find Deal
Fri, Jun 14 - Mon, Jun 24

Flights from Midway to New York - Travel Insights & Trends

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 one-way flights from Chicago Midway Airport to New York.
Our data shows that the cheapest route for a one-way flight from Chicago Midway Airport to New York cost $215 and was between Chicago Midway Airport and New York LaGuardia Airport. On average, the best prices are found if you fly this route. The average price for a return flight for this route is $336.

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

The average price of all flights from Chicago Midway Airport to New York clicked on KAYAK for each day over the last 12 months.
For Chicago Midway Airport to New York, Tuesday is the cheapest day to fly on average and Sunday is the most expensive. Flying from New York back to Chicago Midway Airport, the best deals are generally found on Wednesday, with Sunday being the most expensive.

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 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 January, where tickets cost $189 on average. On the other hand, the most expensive months are June and July, where the average cost of tickets is $310 and $276 respectively.

How far in advance should I book a flight from Chicago Midway Airport to New York?

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from Chicago Midway Airport to New York, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
To get a below average price on the flight from Chicago Midway Airport to New York, you should book around 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 83 days before departure.

Which airlines provide the cheapest flights from Chicago Midway Airport to New York?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
In the last 72 hours, the best return deals on flights connecting Chicago Midway Airport to New York were found on Frontier ($102) and Delta ($158). Frontier proposed the cheapest one-way flight at $53.

Which airlines fly non-stop between Chicago Midway Airport and New York?

Airline and price data is aggregated from results in KAYAK’s search results from the last 2 weeks for flights from Chicago Midway Airport to New York.
There is just one airline that flies from Chicago Midway Airport to New York direct and that is Southwest. The best one-way deal found from Southwest for the route is $288.

How many flights are there between Chicago Midway Airport and New York per day?

Each day, there are between 6 and 16 nonstop flights that take off from Chicago Midway Airport and land in New York, with an average flight time of 2h 04m. The most common departure time is 5:00 pm and most flights take off in the afternoon, while the most flights land at New York LaGuardia Airport. Each week, there are 91 flights. The most frequent day of departure is Tuesday, when 18% of all weekly flights depart. The fewest flights depart on a Saturday.

Which cabin class options are there for flights between Chicago Midway Airport and New York?

The average price of flights for each cabin class for the route found by users searching on KAYAK over the last 2 weeks.
There is only one cabin class option available for the route, which is Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

How long does a flight from Chicago Midway Airport to New York take?

The average nonstop flight takes 2h 05m, covering a distance of 717 miles.

What’s the earliest departure time from Chicago Midway Airport to New York?

Early birds can take the earliest flight from Chicago Midway Airport at 5:55 am and will be landing in New York at 9:00 am.

What’s the latest departure time from Chicago Midway Airport to New York?

If you prefer to fly at night, the latest flight from Chicago Midway Airport to New York jets off at 8:25 pm and lands at 11:25 pm.

Good to know

Low season

April

High season

November

Cheapest flight

$53
Best time to beat the crowds with an average 2% drop in price.
Most popular time to fly and prices are also 13% lower on average.
Flight from Chicago Midway Airport to New York LaGuardia 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 $53 for a one-way ticket and $102 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?

    Delta, and American Airlines 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 737-700 Passenger/BBJ1 (winglets) 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.

  • 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

Top tips for finding a cheap flight from Chicago to New York

  • Looking for a cheap flight? 25% of our users found flights on this route for $404 or less round-trip.

Prefer to fly non-stop from Chicago Midway Airport to New York?

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

Nonstop 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

Nonstop 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 3 airlines serving from Midway to New York

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 KAYAK reviews.
8.0
DeltaOverall score based on 11551 reviews
75food
81overall
82boarding
79comfort
86crew
81entertainment
Airline reviews

Boarding was a sh!t show. JFK BOARDING was awful. The agent called three sections at a time Clogging the area then yelling at people to not block the walk way. How are you going to call delta one , premium select and comfort plus at once and the yell at highest paying passengers. Need to do a lot better and the flight attendants in the galley need to understand that their voices travel. They were talking about others and everyone in the cabin heard them

Read more about Delta

Boarding was a sh!t show. JFK BOARDING was awful. The agent called three sections at a time Clogging the area then yelling at people to not block the walk way. How are you going to call delta one , premium select and comfort plus at once and the yell at highest paying passengers. Need to do a lot better and the flight attendants in the galley need to understand that their voices travel. They were talking about others and everyone in the cabin heard them

The main person that was coordinating everything was a short white/light skin Spanish man and he was very rude. It honestly made me feel like it was everyone’s First day at work. His announcements were very not reasonable and they did not make sense. The stewardess on the flight that made the announcements she didn’t even know what she was talking about she sounded inebriated. There were no snacks or drinks on our flight there wasn’t even much turbulence. This flight was not enjoyable nor was it what a Delta flight should be and just this past week I flew with Delta 3 times.

Horrible. First delta flight was delayed. I ran to my connecting flight and arrived to the gate 13 mins before departure. I told the gate agent “I’m here”, she told me flight was closed while giving my already confirmed seat to an stand by passenger. I said again “madam, I’m here with my confirmed seat” and she said “no you’re not here@ and gave two stand by people a boarding pass and let them board. I asked “madam, why do you do that?”, and she repeated “you’re not here”. That was very rude. I’m disappointed of delta. It used to have a good customer service. Things have changed, but not for good.

full flihgt but crew and passengers all helped eachother we landed early! however we then had to wait 40 minutes on the tarmac to get into the gate there were people trying get connecting flights, assume its an airport issue but still frustrating

The crew was horrible. Cleo was the most unwelcoming flight attendant I’ve ever had.

Do not get fooled by the term “Delta One” flat bed! The seats were super narrow. The ottoman for the feet was so narrow that when you recline the seat in flat bed position, you can only fit one foot in the 8” width space. There was only 1 flight attendant for First Class. The breakfast took 2 hours to get served. Instead of offering French Toast, the served bread pudding. The champagne with orange juice or Mimosa tasted terrible. Almost all the movies offered were ridiculously old. For a long flight from San Francisco to NY, it was frustrating! I DO NOT RECOMMEND this flight!!!

Really big guy next to me Attendants moved him to an open row

the entertainment for the flight from DAL-LGA was not available.

It was a very smooth ride. Not sure on a flight departing at midnight can be much better but it was late arriving and I had an early day so really just the logistics.

The plane looks and feels like we are traveling in a 3rd world country airplane. Dirty bathrooms, horrible food, old and uncomfortable setting, my son’s little table was broken, the chair would stay recline, an so on.

I was not able to buy food in the flight. They refer to include your Credit card in the APP, and if you are not from USA (i have a credit card form Canada) it is not possible

Wheelchair assistance was not complete. The person left me at the departure gate without informing the groundstaff of my requirements. I had to walk to the departure counter to ask for help to reach the plane door. The crew informed me that in future they were not allowed to help passengers like me, senior citizen and Wheelchair passenger with placing their carry on bags in the overhead compartments!

The flight from Ottawa to Chicago took a lot longer due to DC in Ottawa. We got to Chicago and went to our gate to catch our flight. We only had nine minutes I found that very stressful.

Good boarding. Crew started quick with drinks and food. They came around several times for trash which I really liked. Other than turbulence due to storms in the area, flight was great.

The control panel for the seat back screen did not work at all after takeoff.

Plane was so old it had cigarette butt trays in the seat

Everything was good, hard to really comfortable on a flight that long.

Unfortunately our flight was delayed by 45 minutes due to Kate arriving aircraft. Once we stated everything was great.

For some strange reason I was put in zone 5 for boarding even though I had paid premium price for a premium seat right behind business class. This must have been a flaw because everyone else around me in the same zone (row) had been placed in zone 3.

Nothing bad to say about the actual crew or airline. It was nice to have a complimentary FULL can of soda, as well as a snack. Blankets and earbuds were also provided at no cost for this red eye flight. I especially appreciated the free WiFi and movie selection with the Bluetooth option. It helped the flight pass more quickly. No matter who you fly, boarding and disembarking are always SUCH a pain. As I mentioned, this is on the passengers and not the crew!!

Cut off carry ons, had to check, got on and there was plenty of bin space. Disappointing.

One of the worst flights I have ever taken Delayed over an hour without communication from the crew; very scary Entertainment not working Crew NASTY cabin cold

May never fly American again Delay in take off WITHOUT EXPLANATION Cabin freezing Crew NASTY entertainment did not work entire flight

The flight was so short that the lack of leg room didn't bother me for long. The plane was smaller so only two seats per row and there were chargers. However, they didn't serve any snacks.

Horrible trip. I won't fly AA again Boarding was a nightmare because they squeezed people into the waiting like sardines. My connection was 30 minutes and the run to the gate was horrible. Then the flight was canceled AFTER boarding. The Flight attendants did not know what to do and gave out the wrong instructions. They finally sent us to a different gate. Again, the waiting was like a sardine tin. The flight was okay and my baggage arrived fine.

My first time flying American Airlines, my first flight to CLT was wonderful and flight attendants was nice and had great customer service. My second flight from CLT to NY was very delayed due to whatever reason the crew was not greeting other than that I’m rate 8 .

Ther is no fly,over book .and they let out in San pedro sula ,antil Monday 2 of October 2023

it was a nightmare of a trip. multiple delays, dirty bathrooms, long wait in tarmac, ran out of fuel diverting flight. on and all over 4 hour delay!

19 hr delay requiring a change to red eye. No lounge access without paying. Loss of seat upgrade fee.

Check in was horrible in Miami. The woman was rude and not helpful with the questions. There was nothing to like at the check in and there were really slow even for First class passenger like me.

Book cheap flights from Chicago to New York

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Chicago to New York found on KAYAK in the last 72 hours.
4/24Wed
1 stopFrontier
5h 14mMDW-LGA
$53
4/9Tue
1 stopFrontier
5h 28mMDW-LGA
$54
5/8Wed
1 stopFrontier
5h 14mMDW-LGA
$57
4/16Tue
1 stop
18h 17mMDW-EWR
$62
4/17Wed
1 stop
12h 04mMDW-EWR
$65
5/18Sat
1 stopDelta
4h 37mMDW-EWR
$79
4/20Sat
1 stopDelta
4h 34mMDW-EWR
$94
7/12Fri
1 stopAllegiant Air
19h 51mMDW-EWR
$145
6/28Fri
1 stopAllegiant Air
19h 51mMDW-EWR
$164
3/28Thu
nonstopSouthwest
2h 05mMDW-LGA
$179

Search by stops

Search by airline

Search by price

Last minute flights from Midway to New York

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Chicago to New York that are departing in the next 10 days.
3/19Tue
multi-stopFrontier
7h 34mMDW-LGA
3/26Tue
multi-stopFrontier
10h 28mLGA-MDW
$249
3/19Tue
multi-stopFrontier
7h 34mMDW-LGA
3/25Mon
multi-stopFrontier
10h 19mLGA-MDW
$278
3/20Wed
multi-stopDelta
4h 31mMDW-JFK
3/27Wed
multi-stopDelta
6h 14mJFK-MDW
$382
3/22Fri
nonstopSouthwest
2h 05mMDW-LGA
3/28Thu
nonstopSouthwest
2h 25mLGA-MDW
$386
3/22Fri
multi-stopSouthwest
7h 45mMDW-LGA
3/28Thu
nonstopSouthwest
2h 25mLGA-MDW
$395
3/20Wed
multi-stopDelta
3h 16mMDW-EWR
3/31Sun
multi-stopDelta
3h 46mEWR-MDW
$401
3/22Fri
multi-stop
27h 12mMDW-LGA
3/26Tue
multi-stop
11h 41mLGA-MDW
$443
3/22Fri
multi-stop
20h 32mMDW-EWR
3/25Mon
multi-stop
7h 43mEWR-MDW
$497
3/23Sat
multi-stopPorter Airlines
5h 10mMDW-EWR
3/29Fri
multi-stopPorter Airlines
22h 25mEWR-MDW
$1,026
3/23Sat
multi-stopPorter Airlines
5h 10mMDW-EWR
3/29Fri
multi-stopPorter Airlines
26h 35mEWR-MDW
$1,052

Search by stops

Search by airline

Search by price

Chicago Midway Airport - New York Flights

Departure:

Chicago Midway Airport (MDW)United States

Return flight deals:

New York - Chicago Midway Airport

Cabin classes:

$377