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$71+ Cheap flights from Midway (MDW) to New York State

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/26. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — JFK
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
1 adult, Economy
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Cheap flight deals from Midway to New York

Keep the following information in mind while searching for Midway to New York flight deals. Data was last updated September 16, 2025.

Round-trip from

$137
(Southwest)

One-way from

$71
(Kiwi.com)

Popular in

December

Cheapest in

January

Average price

$187

Good round-trip deal

$217 or less

Good one-way deal

$129 or less
From Chicago Midway to New York
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One-way flight from Chicago Midway to New York
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Highest demand for flights based on searches. 0% potential increase in price ($2 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Chicago Midway to New York.
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Price to beat on a one-way flight from Chicago Midway to New York.
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Find flight deals from Midway to New York

Cheapest flights from Midway to New York
Explore the most affordable flight options available from Midway to New York. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 16, 2025.

This Southwest deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/182:45 pmMDW - LGA
Nonstop2h 00mSouthwest
Wed 11/199:55 pmLGA - MDW
Nonstop2h 25mSouthwest
Deal found 9/15$137
This SmartFares deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/301:37 pmMDW - LGA
1 stop8h 07mFrontier
Thu 11/612:30 pmLGA - MDW
1 stop7h 09mFrontier
Deal found 9/14$138
This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/88:05 amMDW - LGA
1 stop7h 24mFrontier
Wed 10/156:30 amLGA - MDW
1 stop8h 08mFrontier
Deal found 9/14$141
This Southwest deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1912:55 pmMDW - LGA
Nonstop2h 00mSouthwest
Sat 11/226:10 amLGA - MDW
Nonstop2h 25mSouthwest
Deal found 9/15$142
This Priceline deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/295:15 pmMDW - LGA
1 stop5h 42mFrontier
Fri 10/311:30 amLGA - MDW
1 stop5h 30mFrontier
Deal found 9/14$143
This Frontier deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/411:23 amMDW - LGA
1 stop7h 39mFrontier
Mon 10/66:30 amLGA - MDW
1 stop10h 55mFrontier
Deal found 9/14$144
This Booking.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/105:28 pmMDW - LGA
1 stop17h 36mFrontier
Tue 10/146:30 amLGA - MDW
1 stop8h 08mFrontier
Deal found 9/14$145
This Mytrip deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/301:37 pmMDW - JFK
1 stop9h 56mFrontier
Tue 11/46:20 amJFK - MDW
1 stop6h 18mFrontier
Deal found 9/15$147
This Southwest deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/58:25 amMDW - LGA
Nonstop2h 05mSouthwest
Sat 11/82:15 pmLGA - MDW
Nonstop2h 30mSouthwest
Deal found 9/16$148
This Booking.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/35:15 pmMDW - JFK
1 stop6h 53mFrontier
Mon 10/66:15 amJFK - MDW
1 stop11h 10mFrontier
Deal found 9/14$148
This Trip.com deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/411:23 amMDW - LGA
1 stop7h 39mFrontier
Wed 10/86:30 amLGA - MDW
1 stop8h 08mFrontier
Deal found 9/15$150
This Trip.com deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/301:37 pmMDW - LGA
1 stop8h 07mFrontier
Sat 11/81:20 pmLGA - MDW
1 stop6h 19mFrontier
Deal found 9/15$151

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to New York that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 16, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to New York State that are best for you.

Fly from

Midway

Fly to

New York

Route

Depart

Return

Price

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Wed 10/8

7:20 pm-10:25 pm

Nonstop2h 05m

New York LaGuardia

Sat 10/18

8:15 am-9:40 am

Nonstop2h 25m

$142

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Wed 11/5

7:15 pm-10:20 pm

Nonstop2h 05m

New York LaGuardia

Mon 11/10

7:15 am-8:45 am

Nonstop2h 30m

$142

ChicagoNew York

MDW - JFK

MDWJFK

Chicago Midway

Wed 10/29

2:06 pm-12:33 am

1 stop9h 27m

New York John F Kennedy Intl

Wed 11/5

6:20 am-12:41 pm

1 stop7h 21m

$147

ChicagoNew York

MDW - JFK

MDWJFK

Chicago Midway

Mon 10/6

5:33 pm-1:08 am

1 stop6h 35m

New York John F Kennedy Intl

Wed 10/8

9:00 am-1:38 pm

1 stop5h 38m

$147

ChicagoNew York

MDW - JFK

MDWJFK

Chicago Midway

Thu 10/23

9:26 pm-7:28 am

1 stop9h 02m

New York John F Kennedy Intl

Mon 10/27

1:01 pm-11:46 pm

1 stop11h 45m

$148

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Wed 11/19

8:25 am-4:10 pm

1 stop6h 45m

New York LaGuardia

Sun 11/23

7:15 am-8:45 am

Nonstop2h 30m

$152

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Wed 10/1

6:00 am-9:00 am

Nonstop2h 00m

New York LaGuardia

Wed 10/8

9:00 am-10:35 am

Nonstop2h 35m

$152

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Tue 11/18

10:00 am-5:05 pm

2 stops6h 05m

New York LaGuardia

Wed 11/19

7:15 am-3:55 pm

1 stop9h 40m

$162

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Sat 10/25

2:15 pm-10:05 pm

1 stop6h 50m

New York LaGuardia

Mon 11/3

9:55 pm-11:20 pm

Nonstop2h 25m

$163

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Tue 10/7

5:04 pm-11:06 pm

1 stop5h 02m

Newark

Wed 10/8

6:00 am-8:40 am

1 stop3h 40m

$177

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/16

Showing 1-10 of 60 results
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Best time to book a flight from Midway to New York

Have a flexible travel schedule? Discover the best time to fly to New York from Midway with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago Midway Airport to New York State

What is the cheapest month to book a flight from Chicago Midway Airport to State of New York?

Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to State of New York (average of $236). Flying from Chicago Midway Airport to State of New York in June is currently the most expensive (average of $313). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from MDW to NY?

Find hourly flight availability from Midway to New York. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 16, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago Midway Airport to State of New York as you normally would.

Reviews of airlines servicing New York

Get insights into the airlines that provide service to New York. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to New York. Reviews last updated September 16, 2025.
See what other customers who have flown with Southwest, Delta, and Spirit Airlines from Chicago Midway Airport to New York State have to say. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Entertainment

7.5

Crew

8.6

Overall

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Entertainment

7.5

Crew

8.6

Overall

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
8.0
Very good
7,957 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Entertainment

7.5

Crew

8.6

Overall

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Spirit Airlines
6.3
Okay
8,019 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Entertainment

7.5

Crew

8.6

Overall

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Related info for your journey

Find useful and relevant information for your journey from Midway to New York. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Chicago Midway Airport to State of New York?

    Airlines like Southwest, Frontier, and Delta fly from Chicago Midway Airport to State of New York in about 2h 05m. The time it takes to get you to your destination can typically vary by up to 7h 22m. The distance between Chicago Midway Airport and State of New York is about 722 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines to fly from Chicago Midway Airport to State of New York one-way?

    The cheapest airline one-way is Frontier, with whom users have recently found tickets for as low as $72. However, be on the lookout for offers from Southwest and Delta, as they are both options that can get you from Chicago Midway Airport to State of New York for a low price.

  • What are the most popular routes from Chicago Midway Airport to State of New York?

    While some choose either Chicago Midway - New York John F Kennedy Intl or Chicago Midway - Newark, Chicago Midway - New York LaGuardia is the most popular route from Chicago Midway Airport to State of New York.

  • Can I find deals for flights from Midway to New York that include hotel bookings?

    Yes. In addition to deals on Midway to New York flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to New York?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to New York.

  • Can I find deals for business class flights from Midway to New York?

    Yes. Cheapflights offers flight deals from Midway to New York by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago Midway Airport to State of New York?

    Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to State of New York (average of $236). Flying from Chicago Midway Airport to State of New York in June is currently the most expensive (average of $313). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Alternative routes for Midway to New York

See prices for flight routes from nearby airports that may be better suited for you.
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Midway to Dallas/Fort Worth flights
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Midway to Miami flights
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Midway to Seattle flights
Midway to Denver flights
O'Hare Intl to George Bush Intcntl flights

Top 3 airlines flying from Midway to New York

Discover the top 3 airlines that operate flights from Midway to New York. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$63Average$125FlexibilityNo cancel feeOn-time65%
DeltaCheapest$162Average$369FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$162Average$346FlexibilityNo cancel feeOn-time63%

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