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$73+ 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 10/30. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — JFK
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
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 August 14, 2025.

Round-trip from

$142
(Southwest)

One-way from

$73
(Priceline)

Popular in

December

Cheapest in

January

Average price

$218

Good round-trip deal

$169 or less

Good one-way deal

$99 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. 3% potential increase in price ($7 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($5 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 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 August 14, 2025.

This Southwest deal was found by Cheapflights users on 8/12. 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 9/37:05 pmMDW - LGA
Nonstop2h 10mSouthwest
Sat 9/67:30 amLGA - MDW
Nonstop2h 20mSouthwest
Deal found 8/12$142
This Mytrip deal was found by Cheapflights users on 8/14. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/85:15 pmMDW - LGA
1 stop5h 42mFrontier
Tue 9/166:30 amLGA - MDW
1 stop10h 28mFrontier
Deal found 8/14$143
This Priceline deal was found by Cheapflights users on 8/14. 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.
Thu 9/114:56 pmMDW - LGA
1 stop6h 01mFrontier
Mon 9/156:30 amLGA - MDW
1 stop10h 30mFrontier
Deal found 8/14$144
This Southwest deal was found by Cheapflights users on 8/12. 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 9/95:55 pmMDW - LGA
Nonstop2h 15mSouthwest
Tue 9/169:00 amLGA - MDW
Nonstop2h 25mSouthwest
Deal found 8/12$147
This Mytrip deal was found by Cheapflights users on 8/13. 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.
Wed 9/33:03 pmMDW - JFK
1 stop9h 10mFrontier
Fri 9/59:00 amJFK - MDW
1 stop8h 00mFrontier
Deal found 8/13$147
This Priceline deal was found by Cheapflights users on 8/13. 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.
Thu 9/114:56 pmMDW - JFK
1 stop7h 12mFrontier
Mon 9/159:00 amJFK - MDW
1 stop8h 00mFrontier
Deal found 8/13$148
This Southwest deal was found by Cheapflights users on 8/12. 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 9/37:05 pmMDW - LGA
Nonstop2h 10mSouthwest
Fri 10/34:30 pmLGA - MDW
Nonstop2h 25mSouthwest
Deal found 8/12$153
This Mytrip deal was found by Cheapflights users on 8/14. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/611:23 amMDW - LGA
1 stop7h 39mFrontier
Mon 9/811:30 amLGA - MDW
1 stop5h 30mFrontier
Deal found 8/14$154
This Mytrip deal was found by Cheapflights users on 8/14. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/2011:23 amMDW - LGA
1 stop7h 39mFrontier
Mon 9/2211:30 amLGA - MDW
1 stop5h 30mFrontier
Deal found 8/14$155
This Southwest deal was found by Cheapflights users on 8/13. 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 9/31:00 pmMDW - LGA
1 stop7h 30mSouthwest
Thu 9/49:40 pmLGA - MDW
Nonstop2h 20mSouthwest
Deal found 8/13$156
This Mytrip deal was found by Cheapflights users on 8/13. 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 9/55:15 pmMDW - JFK
1 stop6h 53mFrontier
Sun 9/76:59 amJFK - MDW
1 stop25h 24mFrontier
Deal found 8/13$156
This Southwest deal was found by Cheapflights users on 8/12. 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 9/48:15 pmMDW - LGA
Nonstop2h 10mSouthwest
Fri 9/59:40 pmLGA - MDW
Nonstop2h 20mSouthwest
Deal found 8/12$157

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 August 14, 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 9/3

7:05 pm-10:15 pm

Nonstop2h 10m

New York LaGuardia

Sat 9/6

7:30 am-8:50 am

Nonstop2h 20m

$142

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Wed 9/3

7:05 pm-10:15 pm

Nonstop2h 10m

New York LaGuardia

Wed 9/10

9:00 am-10:25 am

Nonstop2h 25m

$142

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Thu 9/4

8:15 pm-11:25 pm

Nonstop2h 10m

New York LaGuardia

Tue 9/9

9:00 am-10:25 am

Nonstop2h 25m

$142

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Thu 9/4

8:15 pm-11:25 pm

Nonstop2h 10m

New York LaGuardia

Sat 9/6

7:30 am-8:50 am

Nonstop2h 20m

$142

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Wed 9/3

3:03 pm-10:20 pm

1 stop6h 17m

New York LaGuardia

Fri 9/5

11:30 am-4:00 pm

1 stop5h 30m

$143

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Thu 9/11

4:56 pm-11:57 pm

1 stop6h 01m

New York LaGuardia

Mon 9/15

6:30 am-4:00 pm

1 stop10h 30m

$144

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Tue 9/9

2:32 pm-11:57 pm

1 stop8h 25m

New York LaGuardia

Fri 9/26

6:30 am-4:00 pm

1 stop10h 30m

$144

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Wed 10/22

8:05 am-5:02 pm

1 stop7h 57m

New York LaGuardia

Sat 10/25

6:14 pm-11:25 pm

1 stop6h 11m

$144

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Thu 9/11

4:56 pm-11:57 pm

1 stop6h 01m

New York LaGuardia

Thu 9/18

6:30 am-3:58 pm

1 stop10h 28m

$144

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Wed 10/15

8:05 am-5:02 pm

1 stop7h 57m

New York LaGuardia

Sat 10/18

6:14 pm-11:25 pm

1 stop6h 11m

$144

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/14

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 August 14, 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 August 14, 2025.
See what other customers who have flown with Southwest, Delta, and United 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
4,244 reviews

Comfort

8.0

Entertainment

7.5

Crew

8.6

Food

7.0

Boarding

8.1

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Southwest
8.0
Very good
4,244 reviews
Southwest
8.0
Very good
4,244 reviews

Comfort

8.0

Entertainment

7.5

Crew

8.6

Food

7.0

Boarding

8.1

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Delta
8.0
Very good
7,980 reviews
Southwest
8.0
Very good
4,244 reviews

Comfort

8.0

Entertainment

7.5

Crew

8.6

Food

7.0

Boarding

8.1

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
United Airlines
7.4
Good
8,916 reviews
Southwest
8.0
Very good
4,244 reviews

Comfort

8.0

Entertainment

7.5

Crew

8.6

Food

7.0

Boarding

8.1

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,244 reviews

Comfort

8.0

Entertainment

7.5

Crew

8.6

Food

7.0

Boarding

8.1

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Spirit Airlines
6.3
Okay
8,046 reviews
Southwest
8.0
Very good
4,244 reviews

Comfort

8.0

Entertainment

7.5

Crew

8.6

Food

7.0

Boarding

8.1

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

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.

  • 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 $73. 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 - Newark or Chicago Midway - New York John F Kennedy Intl, 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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O'Hare Intl to Charlotte flights
O'Hare Intl to George Bush Intcntl flights
O'Hare Intl to Cleveland 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 August 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$63Average$125FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$152Average$329FlexibilityNo cancel feeOn-time63%
DeltaCheapest$162Average$391FlexibilityNo cancel feeOn-timeN/A

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