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NYC - MDW

$55 Find cheap flights from New York to Chicago Midway Airport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from New York to Midway departing on 5/11. 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
0 bags
Sun 5/26
Sun 6/2

Search hundreds of travel sites at once for deals on flights to Chicago Midway Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from New York to Chicago, 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 New York to Chicago, as well as popular online travel agencies
In the last 7 days travelers have searched 44,979,812 times on KAYAK, and here is why:

Save 22% or moreCompare multiple travel sites with one search.

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Cheap flight deals from New York to Midway (NYC-MDW)

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from New York to Midway 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 and deals for you by selecting your travel dates.
Choose your dates
6:00 am - 9:53 pmLGA-MDW
16h 53m1 stop
12:09 pm - 11:19 pmMDW-LGA
10h 10m1 stop
$116Frontier
Find Deal
Wed, May 22 - Wed, May 29
6:00 am - 9:53 pmLGA-MDW
16h 53m1 stop
6:00 am - 8:59 pmMDW-LGA
13h 59m1 stop
$122Frontier
Find Deal
Wed, May 22 - Wed, May 29
10:00 pm - 9:22 amLGA-MDW
12h 22m1 stop
12:08 pm - 8:59 pmMDW-LGA
7h 51m1 stop
$123Frontier
Find Deal
Tue, May 14 - Sat, May 18
10:00 pm - 8:31 amLGA-MDW
11h 31m1 stop
4:56 pm - 11:10 pmMDW-LGA
5h 14m1 stop
$124Frontier
Find Deal
Sat, May 11 - Wed, May 15
9:40 pm - 11:05 pmLGA-MDW
2h 25mnonstop
5:15 pm - 10:55 pmMDW-LGA
4h 40m1 stop
$181Southwest
Find Deal
Mon, Jun 3 - Wed, Jun 5
6:00 am - 9:06 amEWR-MDW
4h 06m1 stop
5:00 pm - 11:37 pmMDW-EWR
5h 37m1 stop
$192Delta
Find Deal
Wed, May 29 - Sat, Jun 1
6:00 am - 9:51 amEWR-MDW
4h 51m1 stop
5:45 pm - 11:01 pmMDW-EWR
4h 16m1 stop
$206Delta
Find Deal
Wed, Jun 12 - Wed, Jun 19
7:30 pm - 9:00 pmLGA-MDW
2h 30mnonstop
8:15 pm - 11:20 pmMDW-LGA
2h 05mnonstop
$231Southwest
Find Deal
Wed, May 15 - Fri, May 17
6:50 am - 4:17 pmEWR-MDW
10h 27m1 stop
11:05 am - 8:55 pmMDW-EWR
8h 50m1 stop
$451Porter Airlines
Find Deal
Thu, May 23 - Tue, May 28
12:10 pm - 9:37 pmEWR-MDW
10h 27m1 stop
8:00 am - 2:20 pmMDW-EWR
5h 20m1 stop
$452Porter Airlines
Find Deal
Wed, May 22 - Wed, May 29

Flights from New York to Midway - Travel Insights & Trends

Get data-powered insights and trends into flights from New York to Midway to help you find the cheapest flights, the best time to fly and much more.

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

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for one-way flights from New York to Chicago Midway Airport.
Our data shows that the cheapest route for a one-way flight from New York to Chicago Midway Airport cost $119 and was between New York LaGuardia Airport and Chicago Midway Airport. On average, the best prices are found if you fly this route. The average price for a return flight for this route is $398.

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

The average price of all flights from New York to Chicago Midway Airport clicked on KAYAK for each day over the last 12 months.
If your flying dates are flexible, you should consider flying to Chicago Midway Airport on a Wednesday, as we generally find the cheapest rates on that day for this route. On the other hand, Sunday is the most expensive day to fly from New York to Chicago Midway Airport. For your return ticket, we recommend flying on a Wednesday and avoiding Sundays for the best deals.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from New York to Chicago Midway Airport, 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 New York to Chicago Midway Airport is April, where tickets cost $205 on average. On the other hand, the most expensive months are May and July, where the average cost of tickets is $488 and $438 respectively.

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

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from New York to Chicago Midway Airport, 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 New York to Chicago Midway Airport, you should book around 5 days before departure. For the absolute cheapest price, our data suggests you should book 88 days before departure.

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

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
The best deals for a one-way ticket found by KAYAK users over the last 3 days were on Frontier ($55) and Delta ($79). The cheapest round-trip tickets were found on Frontier ($116) and Southwest ($181).

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

Each day, there are between 3 and 8 nonstop flights that take off from New York and land in Chicago Midway Airport, with an average flight time of 2h 27m. The most common departure time is 11:00 am and most flights take off in the morning. Each week, there are 44 flights. The most frequent day of departure is Wednesday, when 18% of all weekly flights depart. The fewest flights depart on a Saturday.

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

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 New York to Chicago Midway Airport take?

Direct flights take on average 2h 20m to travel the 717 miles between New York and Chicago Midway Airport.

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

Early birds can take the earliest flight from New York at 6:30 am and will be landing in Chicago Midway Airport at 7:55 am.

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

If you prefer to fly at night, the latest flight from New York to Chicago Midway Airport jets off at 9:55 pm and lands at 11:15 pm.

Good to know

Low season

January

High season

October

Cheapest flight

$55
Best time to beat the crowds with an average 27% drop in price.
Most popular time to fly and prices are also 27% lower on average.
Flight from New York LaGuardia Airport to Chicago Midway Airport

When to book flights from New York to Midway

Are your dates flexible? Find out the best times to travel from New York to Midway 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 New York to Chicago Midway Airport flights

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

    In the last 3 days, the lowest price for a flight from New York to Chicago Midway Airport was $55 for a one-way ticket and $116 for a round-trip.

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

    No

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

    New York is served by 3 major airports and there is only 1 main airport in Chicago Midway Airport. You will leave New York from one of these airports: Newark, New York John F Kennedy Intl, or New York LaGuardia. You will be arriving at Chicago Midway.

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

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

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

    The Boeing 737-800 is the aircraft model that flies most regularly on the New York to Chicago Midway Airport flight route.

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

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

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

    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 New York to Chicago Midway Airport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from New York to Chicago Midway Airport?

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

    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 Chicago Midway Airport with an airline and back to New York with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from New York to Chicago Midway Airport?

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

See more FAQs

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

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

Nonstop departures

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

Nonstop returns

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
See more direct flights

Top 3 airlines serving from New York to Midway

 
See real verified KAYAK customer reviews for airlines flying from New York to Chicago. 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 New York to Midway? 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
DeltaOverall score based on 10975 reviews
8.2boarding
8.6crew
8.0entertainment
7.4food
7.9comfort
Airline reviews

I'm a larger, athletic guy (6'2", 260lbs powerlifter) and I found the seats incredibly uncomfortable with minimal leg room, especially in a window seat. Now, I full understand that being smaller may change my view but even if I was 80lbs less, my legs would be the same size and I was sandwiched between my seat and the seat in front of me.

6.0 GoodDan, Apr 2024LGA - DEN
Read more about Delta reviews

I'm a larger, athletic guy (6'2", 260lbs powerlifter) and I found the seats incredibly uncomfortable with minimal leg room, especially in a window seat. Now, I full understand that being smaller may change my view but even if I was 80lbs less, my legs would be the same size and I was sandwiched between my seat and the seat in front of me.

Seat back monitors and outlets were dead and not working.

I usually have a positive experience with Delta. Complimentary upgrades are always nice!

Service was good for such a short flight. Small plane but smooth flight.

The flight was delayed but we got to our final destination.

Uncomfortable seats on 14 hour flight. Mediocre food. On time and great crew.

The helpful attitude of the staff, and being a wheelchair passenger everyone was helpful and understanding. The trip was made comfortable by the upgraded seat which was given without my request, that was a great surprise. Thank you Delta.

Everything went well with the flight. But one of the flight attendants had on inappropriate pants. She had on an old worn out pair of sweat pants. The back seam was unrivaled and should not have been worn for work. If I had not seen her in the airport with the standard type of luggage, I certainly would not have thought she was working for Delta. Not a good look at all for representation.

Great!! I haven’t had a bad experience with them.

The plane was one hour late cause they were doing some reparations with us on the plane no mention I was in the first seat and the door was open the entire time with 8 degrees! The plane was totally dirty no mention old ! The staff was nice but no put together, the attention to details and passenger experience is missing and i always travel first !!! Is better the lounge than the plane! KLM/air France every details is taken care maybe you need a creative creator or experience client need asap was terrible and not memorable for the price that I payed very dissatisfied

The delays (5 hrs) were a comedy of errors, and the multiple safety issues encountered were very concerning.

The flight was delayed instead of leaving at 11 it left at 12.20

United WiFi is consistently unusable (it can take 10 mins to load a single web page). If you need Wifi to do work, be prepared to lose half a day of productivity.

Good movies, iffy pay WiFi, food ok- on time though and that was great!

Awful…flight was delayed more than 12hrs, missed all connections to Fort Wayne, IN, had to get flight to another city 2 hours from my destination, flight was again delayed by 40 mins because they did not have enough fuel, again missed a connection, finally arrived in Indiana at 11pm…but before my 2 hour drive home, ay, no Five That Our Luggage Never Made On The plane and Still In Chicago

Boarding was friendly and quick. While the plane model was older with no live tv, the entertainment was full of movies and tv shows. All food was available. Pilots were very communicative with status of the flight. Flight landed on time.

The Palm Springs to Chicago O’Hare was on Time and Palm Springs airport is easier navigate. As our connection was only an approximately 50 minutes, we asked staff for insights for the Chicago airport in terms of transferring into the other terminal from which our flight left, and they were unhelpful. However, the United App was very helpful in terms of notifications and even providing directions. The Chicago to Detroit flight was significantly delayed which we all know does happen. However, there were very few updates or notifications as to why this was happening when we would actually arrive. It took nearly 30 minutes for bags to make it to baggage claim. We arrived nearly 1 hour late on a 40 minute flight.

Flight cancelled due to fog. No other flights available for 36 hours. Directed by United to book passage on another carrier, and submit receipts for reimbursement. Did that. United now states they will not reimburse. Currently out 2 grand.

The flight was delayed by 4 hours !!!!! It was very uncomfortable , and they told us only one our before departure

The flights from Ottawa to Albuquerque went smoothly enough though on on flight they didn't have how water for coffee or tea and on another there there was no ice. The return flights from Albuquerque were delayed by mechanical problems on both flights. Ottawa was a ground crew maintenance issue.

This flight is frequently delayed. The connections seemingly are more frequently delayed. I’ve missed connections as a result twice on the same route to charlotte then Charleston. Final destination arrival has been the next day, twice in a row. No pilots, no crew. Too many excuses. Unfortunately, my days with American are over.

Entertainment was okay not because anything was wrong but it is a short flight so having no wifi is annoying but understandable. Crew was outstanding as usual

Those seats were way too narrow. I had the middle seat, one person was a very skinny person and we still couldn’t avoid touching each other anytime one of us moved. The other person was larger and we were basically sitting in each others lap the entire flight. There was zero entertainment. The flight was long enough to justify tvs, but no. Gotta sit there in your infant seat and twiddle your thumbs.

Flight was fine. It took an unusually long time to have baggage delivered to the carousel in ORD.

Average - flew with Jet Blue internal and it was far more comfortable and better food and entertainment. Notable difference

The flight got canceled due to mechanical issues, and he to be rebooked and missed my appointments for that day

The flight was scheduled to depart DCA at 12:30 pm but was delayed twice on the ground so that we were finally scheduled to depart at around 4:00 pm. Once we boarded, it was announced that takeoff would be delayed again to fix a hydraulic problem which delayed our eventual takeoff until around 5:00 pm. Once we departed, it was a smooth flight back to ORD. We did not get any explanation about what caused the original significant delay. In my experience, this happens frequently with AA.

The only problem experienced was a ground stop in Chicago due to weather. But the crew handled everything professionally. They prioritized rebooking those passengers who had connecting flights and then deplaning the other passengers. When the hold was lifted, they efficiently re-boarded all the passengers so that we could depart before our departure limit expired.

Our second leg to Jackson WY was unable to land due to weather. We were flown back to Dallas after stopping in SLC. We were given hotel rooms and vouchers. We were told that we would be back on the same plane in the morning. Instead we were given a different flight with different seats. Not a good experience. No one knew what was going on.

Turn on the heat. Flight was way too cold from Arizona to Chicago.

Book cheap flights from New York to Chicago

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from New York to Chicago found on KAYAK in the last 72 hours.
5/11Sat
1 stopFrontier
11h 31mLGA-MDW
$55
5/11Sat
1 stopFrontier
11h 31mLGA-MDW
$56
5/21Tue
1 stop
9h 54mEWR-MDW
$70
5/21Tue
2 stops
17h 59mLGA-MDW
$75
5/26Sun
1 stopDelta
5h 48mEWR-MDW
$79
6/12Wed
1 stopDelta
4h 51mEWR-MDW
$89
5/22Wed
nonstopSouthwest
2h 30mLGA-MDW
$113
5/23Thu
1 stopSouthwest
4h 55mLGA-MDW
$142
5/25Sat
2 stopsSpirit Airlines
13h 54mLGA-MDW
$149
5/24Fri
3 stopsSpirit Airlines
21h 58mEWR-MDW
$248

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Last minute flights from New York to Midway

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 New York to Chicago that are departing in the next 10 days.
4/29Mon
multi-stopFrontier
11h 51mLGA-MDW
5/8Wed
multi-stopFrontier
5h 14mMDW-LGA
$194
4/28Sun
multi-stopFrontier
13h 07mLGA-MDW
5/8Wed
multi-stopFrontier
5h 14mMDW-LGA
$204
4/30Tue
multi-stopFrontier
12h 22mLGA-MDW
5/6Mon
multi-stopFrontier
8h 59mMDW-LGA
$217
4/30Tue
multi-stopFrontier
12h 22mLGA-MDW
5/4Sat
multi-stopFrontier
13h 28mMDW-LGA
$218
4/29Mon
multi-stopSouthwest
6h 05mLGA-MDW
5/2Thu
nonstopSouthwest
2h 05mMDW-LGA
$330
4/29Mon
multi-stopSouthwest
12h 00mLGA-MDW
5/2Thu
nonstopSouthwest
2h 05mMDW-LGA
$335
4/30Tue
multi-stopDelta
7h 15mEWR-MDW
5/3Fri
multi-stopDelta
5h 32mMDW-EWR
$336
4/27Sat
multi-stopDelta
7h 43mEWR-MDW
5/4Sat
multi-stopDelta
6h 16mMDW-EWR
$362
4/30Tue
multi-stopPorter Airlines
7h 37mEWR-MDW
5/1Wed
multi-stopPorter Airlines
5h 20mMDW-EWR
$748
4/27Sat
multi-stopPorter Airlines
6h 52mEWR-MDW
5/5Sun
multi-stopPorter Airlines
9h 55mMDW-EWR
$756

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Flights to Chicago Midway Airport