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$77+ Cheap flights from New York State to Midway (MDW)

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 9/17. Fares are subject to change and may not be available on all flights or dates of travel.
JFK — MDW
Aug 22 — Aug 291
Fri 8/22
Fri 8/29
1 adult, Economy
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Cheap flight deals from New York to Midway

Keep the following information in mind while searching for New York to Midway flight deals. Data was last updated August 17, 2025.

Round-trip from

$147
(Gotogate)

One-way from

$77
(Mytrip)

Popular in

June

Cheapest in

September

Average price

$269

Good round-trip deal

$202 or less

Good one-way deal

$151 or less
From New York to Chicago Midway
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One-way flight from New York to Chicago Midway
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Highest demand for flights based on searches. 11% potential increase in price ($32 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 August 2025
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Price to beat on a round-trip flight from New York to Chicago Midway.
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Price to beat on a one-way flight from New York to Chicago Midway.
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Find flight deals from New York to Midway

Cheapest flights from New York to Midway
Explore the most affordable flight options available from New York to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 17, 2025.

This Flightnetwork deal was found by Cheapflights users on 8/17. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/46:15 amJFK - MDW
1 stop10h 43mFrontier
Mon 9/85:15 pmMDW - JFK
1 stop6h 53mFrontier
Deal found 8/17$147
This Southwest deal was found by Cheapflights users on 8/17. 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.
Fri 12/59:10 amLGA - MDW
Nonstop2h 30mSouthwest
Sun 12/76:15 pmMDW - LGA
Nonstop2h 10mSouthwest
Deal found 8/17$147
This Priceline deal was found by Cheapflights users on 8/15. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/229:00 amJFK - MDW
1 stop5h 38mFrontier
Tue 10/281:56 pmMDW - JFK
1 stop9h 37mFrontier
Deal found 8/15$148
This Booking.com deal was found by Cheapflights users on 8/17. 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.
Mon 10/69:00 amJFK - MDW
1 stop8h 25mFrontier
Thu 10/99:26 pmMDW - JFK
1 stop9h 02mFrontier
Deal found 8/17$149
This Booking.com deal was found by Cheapflights users on 8/16. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/151:01 pmJFK - MDW
1 stop11h 19mFrontier
Mon 9/225:15 pmMDW - JFK
1 stop6h 53mFrontier
Deal found 8/16$151
This Mytrip deal was found by Cheapflights users on 8/17. 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.
Fri 9/191:01 pmJFK - MDW
1 stop11h 19mFrontier
Mon 9/225:15 pmMDW - JFK
1 stop6h 53mFrontier
Deal found 8/17$152
This Southwest deal was found by Cheapflights users on 8/17. 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.
Thu 9/49:10 amLGA - MDW
Nonstop2h 25mSouthwest
Mon 9/88:15 pmMDW - LGA
Nonstop2h 10mSouthwest
Deal found 8/17$152
This Mytrip deal was found by Cheapflights users on 8/17. 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.
Fri 9/511:30 amLGA - MDW
1 stop5h 30mFrontier
Sun 9/710:13 amMDW - LGA
1 stop24h 48mFrontier
Deal found 8/17$153
This Booking.com deal was found by Cheapflights users on 8/17. 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 9/1211:30 amLGA - MDW
1 stop5h 30mFrontier
Sun 9/1410:13 amMDW - LGA
1 stop24h 48mFrontier
Deal found 8/17$154
This Priceline deal was found by Cheapflights users on 8/17. 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.
Wed 9/106:30 amLGA - MDW
1 stop10h 28mFrontier
Sat 9/1311:23 amMDW - LGA
1 stop7h 39mFrontier
Deal found 8/17$155
This Mytrip deal was found by Cheapflights users on 8/17. 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.
Fri 9/121:01 pmJFK - MDW
1 stop11h 19mFrontier
Sun 9/1410:13 amMDW - JFK
1 stop23h 13mFrontier
Deal found 8/17$156
This Booking.com deal was found by Cheapflights users on 8/17. 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.
Thu 10/21:01 pmJFK - MDW
1 stop11h 19mFrontier
Sun 10/510:13 amMDW - JFK
1 stop23h 13mFrontier
Deal found 8/17$157

Cheapflights Fare Finder

 
Customize your flight search to find flights from New York to Midway 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 August 17, 2025.
Use the filters below to find and compare flights from New York State to Chicago Midway Airport that are best for you.

Fly from

New York

Fly to

Midway

Route

Depart

Return

Price

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Fri 9/5

1:01 pm-11:20 pm

1 stop11h 19m

Chicago Midway

Tue 9/9

2:32 pm-1:08 am

1 stop9h 36m

$147

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Fri 9/5

9:40 pm-11:00 pm

Nonstop2h 20m

Chicago Midway

Sat 9/6

5:40 pm-8:50 pm

Nonstop2h 10m

$147

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Thu 9/4

1:01 pm-11:20 pm

1 stop11h 19m

Chicago Midway

Mon 9/8

5:15 pm-1:08 am

1 stop6h 53m

$147

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Wed 9/3

9:00 am-10:25 am

Nonstop2h 25m

Chicago Midway

Sat 9/6

5:40 pm-8:50 pm

Nonstop2h 10m

$147

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Tue 9/16

9:00 am-3:58 pm

1 stop7h 58m

Chicago Midway

Tue 9/23

2:32 pm-1:08 am

1 stop9h 36m

$147

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Tue 9/16

6:00 am-7:20 am

Nonstop2h 20m

Chicago Midway

Tue 9/23

7:05 pm-10:15 pm

Nonstop2h 10m

$147

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Sat 9/20

1:01 pm-11:17 pm

1 stop11h 16m

Chicago Midway

Tue 9/23

2:32 pm-1:08 am

1 stop9h 36m

$147

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Tue 9/2

6:00 am-7:20 am

Nonstop2h 20m

Chicago Midway

Sat 9/6

5:40 pm-8:50 pm

Nonstop2h 10m

$147

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Wed 10/1

9:00 am-3:58 pm

1 stop7h 58m

Chicago Midway

Fri 10/3

5:15 pm-1:08 am

1 stop6h 53m

$147

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Wed 10/8

9:00 am-10:35 am

Nonstop2h 35m

Chicago Midway

Tue 10/14

7:20 pm-10:25 pm

Nonstop2h 05m

$147

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/16

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

Have a flexible travel schedule? Discover the best time to fly to Midway from New York 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 New York State to Chicago Midway Airport

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

Currently, April is the cheapest month in which you can book a flight from State of New York to Chicago Midway Airport (average of $160). Flying from State of New York to Chicago Midway Airport in November is currently the most expensive (average of $249). 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 NY to MDW?

Find hourly flight availability from New York to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 17, 2025.

When flying from State of New York to Chicago Midway Airport, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Related info for your journey

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

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

    To fly one-way, consider booking your trip with Frontier, which is currently one of the cheapest options available, starting at $77. Southwest flights start at $79 while deals on Delta start at $144 one-way.

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

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

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

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

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

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

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

    Yes. Cheapflights offers flight deals from New York to Midway 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 State of New York to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from State of New York to Chicago Midway Airport (average of $160). Flying from State of New York to Chicago Midway Airport in November is currently the most expensive (average of $249). 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

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for New York to Midway

See prices for flight routes from nearby airports that may be better suited for you.
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Top 3 airlines flying from New York to Midway

Discover the top 3 airlines that operate flights from New York to Midway. 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 August 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$92Average$171FlexibilityNo cancel feeOn-time65%
DeltaCheapest$134Average$380FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$153Average$324FlexibilityNo cancel feeOn-time63%

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