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NYC - MDW

$46 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 9/17. 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 7/11
Thu 7/18

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 43,795,805 times on KAYAK, and here is why:

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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
10:56 am - 9:10 pmLGA-MDW
11h 14m1 stop
12:15 pm - 11:18 pmMDW-LGA
10h 03m1 stop
$99Frontier
Find Deal
Tue, Aug 20 - Wed, Aug 28
10:56 am - 8:49 pmLGA-MDW
10h 53m1 stop
9:44 pm - 10:06 amMDW-LGA
11h 22m1 stop
$100Frontier
Find Deal
Tue, Sep 10 - Sat, Sep 14
1:00 pm - 5:04 pmEWR-MDW
5h 04m1 stop
5:45 pm - 11:19 pmMDW-EWR
4h 34m1 stop
$156Delta
Find Deal
Tue, Sep 10 - Sat, Sep 14
1:00 pm - 5:04 pmEWR-MDW
5h 04m1 stop
1:08 pm - 7:28 pmMDW-EWR
5h 20m1 stop
$167Delta
Find Deal
Tue, Sep 10 - Wed, Sep 11
6:10 am - 7:30 amLGA-MDW
2h 20mnonstop
1:20 pm - 4:25 pmMDW-LGA
2h 05mnonstop
$232Southwest
Find Deal
Wed, Jul 10 - Thu, Jul 11
7:35 pm - 9:10 pmLGA-MDW
2h 35mnonstop
5:55 am - 9:00 amMDW-LGA
2h 05mnonstop
$235Southwest
Find Deal
Tue, Jul 9 - Thu, Jul 11
10:55 am - 1:24 pmEWR-MDW
27h 29m1 stop
9:07 pm - 10:05 amMDW-EWR
11h 58m1 stop
$246Allegiant Air
Find Deal
Sun, Jul 14 - Mon, Jul 15
10:55 am - 8:18 pmEWR-MDW
10h 23m1 stop
9:08 pm - 10:05 amMDW-EWR
11h 57m1 stop
$278Allegiant Air
Find Deal
Fri, Jun 21 - Mon, Jun 24
10:55 am - 1:24 pmEWR-MDW
27h 29m1 stop
9:07 pm - 11:10 pmMDW-EWR
25h 03m3 stops
Sun, Jul 14 - Mon, Jul 15
10:55 am - 8:18 pmEWR-MDW
10h 23m1 stop
9:08 pm - 12:34 amMDW-EWR
26h 26m2 stops
Fri, Jun 21 - Mon, Jun 24

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 $288.

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 Tuesday, 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 Tuesday and avoiding Mondays 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 January, where tickets cost $235 on average. On the other hand, the most expensive months are June and July, where the average cost of tickets is $500 and $447 respectively.

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 ($46) and Delta ($78). The cheapest round-trip tickets were found on Frontier ($99) and Delta ($156).

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

Each day, there are between 5 and 11 nonstop flights that take off from New York and land in Chicago Midway Airport, with an average flight time of 2h 28m. The most common departure time is 7:00 pm and most flights take off in the morning. Each week, there are 53 flights. The most frequent day of departure is Friday, when 21% of all weekly flights depart. The fewest flights depart on a Sunday.

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 6:10 am and will be landing in Chicago Midway Airport at 7:30 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 9:50 pm and lands at 11:15 pm.

Good to know

Low season

December

High season

July

Cheapest flight

$46
Best time to beat the crowds but there is an average 4% increase in price.
Most popular time to fly with an average 25% increase in price.
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 $46 for a one-way ticket and $99 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 MAX 8 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 4 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 10000 reviews
8.6Crew
7.9Comfort
8.0Entertainment
8.2Boarding
7.4Food
Airline reviews

Awful. Flight was continuously getting delayed and gates kept changing without any reason. Flight was delayed for more then 3 hours

2.0 MediocreNairan, May 2024JFK - FLL
Read more about Delta reviews

Awful. Flight was continuously getting delayed and gates kept changing without any reason. Flight was delayed for more then 3 hours

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.

It is a modern tragedy that any airline expects you to travel for 14 hours in such discomfort and that the only way to add comfort is exorbitant prices. I was in pain by the time we landed. Shameful.

After the morning frenzy of 35 min wait through CLT security at 4;30 AM, it was nice to have a smooth pleasant boarding experience. This 6:30 AM flight was not full. We were able to get seated swiftly and took off promptly. Nice touch they distributed the old fashioned headsets with 8 mm jacks. Snacks were decent and arrival was uneventful.

I had a great flight. Everything went smoothly and the flight arrived early.

The flight and boarding were easy peasy. I was traveling with my 4-year-old, so a smooth boarding experience was especially appreciated. My only piece of feedback is really about where our gate was in O'Hare. They've shoved four gates into a tiny corner of the B terminal and there isn't early enough room or seating for everyone. Not United's problem, but did dent the overall experience.

I was told we'd have a hot breakfast option in first class, so I chose not get a hot breakfast. It was a very strange meal, but the fresh fruit was very good quality. Service was excellent from ORD to ELP. No service from MBS to ORD, not even water. However, when flying American from FNT to ORD, which is a shorter flight, they at least pass out snacks and offer water.

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

Internet service was erratic. Crew service was poor and slow. My luggage on this non-stop flight was lost and not recovered

The CX617 from HK to BKK was delayed more than 1.5 hours.

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.

Flight got diwngraded last minute and left us stranded. I was told I’ll be given credit for my luggage and seat upgrades but haven’t got anything yet

This recognisable no-frills airline gets me from point-A to point-B. I was able to get to Chicago without stress. The checked baggage collection and reclaim could be improved.

Crew was nice, explained emergency protocol very well. Flight took off and arrived on time. Pilot explained the small delay that occurred with docking and providing updates. I would definitely fly spirit again.

The seat are terrible. Don’t even think of sleeping on a Spirit flight. The kids that run the plane aka flight attendants are pretty rude and straight forward. They get the job done but without class.

I had a death in my family and booked my flight on Spirit. My flight was cancelled the morning of my flight, no explanation, no help to rebook, nobody to talk to. The next available flight was 2days later !!!! Terrible airline, will NEVER fly with them again!

They took a horrible route with a lot of turbulence and I eneded up getting sick. Even if the flight takes longer. Don't put people life at risk just to get to the airport on time.

Every thing was fine ,low price,easy on time ,clean, good staff, really no issues

Had to board plan 2x due to lack of security check after 1st boarding

Miserable. The crew was rude, the flight was delayed 5 hours for mechanical reasons and then “weather” even though other planes were leaving.

They kept Changing the flight times. It was delayed several times and at one point it was supposed to depart at 3.40am! At which point we ended up staying overnight and booked long a separate United flight for early morning departure. The spirit flight then got moved up and left at 1.30 in the morning when it was supposed to leave at 9.40pm the night before.

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.
9/17Tue
1 stopFrontier
5h 29mLGA-MDW
$46
9/10Tue
1 stopFrontier
5h 29mLGA-MDW
$47
9/14Sat
1 stopDelta
5h 14mEWR-MDW
$78
9/1Sun
1 stopDelta
6h 44mEWR-MDW
$94
8/9Fri
1 stopAllegiant Air
9h 45mEWR-MDW
$111
8/9Fri
1 stopAllegiant Air
9h 45mEWR-MDW
$112
9/9Mon
2 stopsSouthwest
10h 10mLGA-MDW
$137
9/9Mon
3 stopsSouthwest
11h 15mLGA-MDW
$142
8/15Thu
2 stops
19h 00mEWR-MDW
$167
9/6Fri
2 stops
11h 26mEWR-MDW
$177

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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.
6/12Wed
multi-stopFrontier
17h 58mLGA-MDW
6/19Wed
multi-stopFrontier
9h 46mMDW-LGA
$166
6/12Wed
multi-stopFrontier
17h 58mLGA-MDW
6/19Wed
multi-stopFrontier
9h 46mMDW-LGA
$170
6/14Fri
multi-stopAllegiant Air
10h 23mEWR-MDW
7/1Mon
multi-stopAllegiant Air
11h 57mMDW-EWR
$301
6/16Sun
nonstopSouthwest
2h 25mLGA-MDW
6/19Wed
nonstopSouthwest
2h 10mMDW-LGA
$304
6/16Sun
multi-stopDelta
4h 51mJFK-MDW
6/17Mon
multi-stopDelta
4h 41mMDW-JFK
$306
6/16Sun
multi-stopSouthwest
11h 50mLGA-MDW
6/19Wed
nonstopSouthwest
2h 05mMDW-LGA
$313
6/14Fri
multi-stop
10h 23mEWR-MDW
6/17Mon
multi-stop
19h 01mMDW-EWR
$351
6/14Fri
multi-stopAllegiant Air
10h 23mEWR-MDW
6/21Fri
multi-stopAllegiant Air
10h 57mMDW-EWR
$367
6/14Fri
multi-stopDelta
3h 43mEWR-MDW
7/1Mon
multi-stopDelta
6h 01mMDW-EWR
$371
6/14Fri
multi-stop
6h 12mEWR-MDW
6/14Fri
multi-stop
10h 57mMDW-EWR
$661

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Flights to Chicago Midway Airport