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$65+ 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 1/6. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — JFK
Nov 22 — Nov 291
Sat 11/22
Sat 11/29
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 October 23, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$117
(Southwest)

One-way from

$65
(Southwest)

Popular in

December

Cheapest in

January

Average price

$201

Good round-trip deal

$157 or less

Good one-way deal

$173 or less
Provider with most accurate pricing for Chicago (CHI)-New York (NYC) flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-New York (NYC) flights.
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From Chicago Midway to New York
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One-way flight from Chicago Midway to New York
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High demand for flights, 2% potential price rise
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Cheapest flight prices on average. 1% potential price decrease ($3 potential savings vs. average RT price).
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Average for round-trip flights in October 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 October 23, 2025.

This Southwest deal was found by Cheapflights users on 10/21. 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 11/117:15 pmMDW - LGA
Nonstop2h 05mSouthwest
Thu 11/139:00 amLGA - MDW
Nonstop2h 25mSouthwest
Deal found 10/21$117
This Southwest deal was found by Cheapflights users on 10/22. 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 12/97:15 pmMDW - LGA
Nonstop2h 05mSouthwest
Fri 12/127:15 amLGA - MDW
Nonstop2h 30mSouthwest
Deal found 10/22$122
This Southwest deal was found by Cheapflights users on 10/22. 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 11/117:15 pmMDW - LGA
Nonstop2h 05mSouthwest
Wed 11/126:00 amLGA - MDW
Nonstop2h 30mSouthwest
Deal found 10/22$127
This Southwest deal was found by Cheapflights users on 10/22. 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.
Mon 12/87:15 pmMDW - LGA
Nonstop2h 05mSouthwest
Tue 12/99:10 amLGA - MDW
Nonstop2h 30mSouthwest
Deal found 10/22$128
This eDestinos deal was found by Cheapflights users on 10/22. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/66:00 amMDW - JFK
1 stop17h 59mFrontier
Sat 12/136:25 amJFK - MDW
1 stop15h 57mFrontier
Deal found 10/22$128
This eDestinos deal was found by Cheapflights users on 10/22. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/216:00 amMDW - JFK
1 stop17h 55mFrontier
Sun 1/116:10 amJFK - MDW
1 stop18h 15mFrontier
Deal found 10/22$131
This Kiwi.com deal was found by Cheapflights users on 10/21. 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.
Sat 11/152:05 pmMDW - JFK
1 stop10h 10mFrontier
Tue 11/186:20 amJFK - MDW
1 stop6h 18mFrontier
Deal found 10/21$132
This Southwest deal was found by Cheapflights users on 10/23. 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 11/47:15 pmMDW - LGA
Nonstop2h 05mSouthwest
Thu 11/69:00 amLGA - MDW
Nonstop2h 25mSouthwest
Deal found 10/23$133
This Kiwi.com deal was found by Cheapflights users on 10/23. 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 11/122:06 pmMDW - JFK
1 stop9h 27mFrontier
Tue 11/186:20 amJFK - MDW
1 stop6h 18mFrontier
Deal found 10/23$133
This Kiwi.com deal was found by Cheapflights users on 10/22. 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.
Tue 11/111:56 pmMDW - JFK
1 stop9h 37mFrontier
Sat 11/1510:00 amJFK - MDW
1 stop9h 39mFrontier
Deal found 10/22$134
This Southwest deal was found by Cheapflights users on 10/21. 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 12/1012:25 pmMDW - LGA
1 stop6h 50mSouthwest
Wed 12/109:55 pmLGA - MDW
Nonstop2h 25mSouthwest
Deal found 10/21$136
This Southwest deal was found by Cheapflights users on 10/22. 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 11/117:15 pmMDW - LGA
Nonstop2h 05mSouthwest
Sat 11/152:15 pmLGA - MDW
Nonstop2h 30mSouthwest
Deal found 10/22$137

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 October 23, 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

Thu 11/13

6:10 am-9:15 am

Nonstop2h 05m

New York LaGuardia

Tue 11/18

9:10 am-10:40 am

Nonstop2h 30m

$117

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Sat 1/10

6:00 am-1:00 pm

1 stop6h 00m

New York LaGuardia

Sat 1/17

11:55 am-1:30 pm

Nonstop2h 35m

$135

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Tue 11/11

7:15 pm-10:20 pm

Nonstop2h 05m

New York LaGuardia

Sat 11/15

2:15 pm-3:45 pm

Nonstop2h 30m

$137

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Tue 11/18

6:00 am-9:00 am

Nonstop2h 00m

New York LaGuardia

Sun 11/23

9:00 am-10:25 am

Nonstop2h 25m

$143

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Tue 12/9

5:15 pm-11:20 pm

1 stop5h 05m

New York LaGuardia

Fri 12/12

11:00 am-7:15 pm

1 stop9h 15m

$153

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Tue 11/4

5:15 pm-11:20 pm

1 stop5h 05m

New York LaGuardia

Wed 11/12

6:00 am-7:30 am

Nonstop2h 30m

$163

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Tue 11/11

12:25 pm-8:20 pm

1 stop6h 55m

New York LaGuardia

Tue 11/18

9:10 am-10:40 am

Nonstop2h 30m

$167

ChicagoBuffalo

MDW - BUF

MDWBUF

Chicago Midway

Sat 12/6

4:29 pm-11:59 pm

1 stop6h 30m

Buffalo

Sun 12/7

6:12 am-8:54 am

1 stop3h 42m

$170

ChicagoNew York

MDW - JFK

MDWJFK

Chicago Midway

Sat 11/8

1:37 pm-12:33 am

1 stop9h 56m

New York John F Kennedy Intl

Mon 11/10

10:00 am-6:39 pm

1 stop9h 39m

$170

ChicagoRochester

MDW - ROC

MDWROC

Chicago Midway

Wed 12/10

3:15 pm-5:50 pm

Nonstop1h 35m

Greater Rochester Intl

Sat 12/13

3:20 pm-6:30 pm

1 stop4h 10m

$172

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/23

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, October is the cheapest month in which you can book a flight from Chicago Midway Airport to State of New York (average of $54). Flying from Chicago Midway Airport to State of New York in August is currently the most expensive (average of $227). 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 October 23, 2025.

One of the essential ways to save on airfare from Chicago Midway Airport to State of New York is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the afternoon could potentially save you up to 31% on airfare.

What is the cheapest day to fly from Chicago Midway Airport to State of New York?

Use this chart to determine the cheapest time to fly round-trip from Midway to New York. Price data was last updated on October 19, 2025.

Travelers seeking maximum savings on their Chicago Midway Airport to State of New York flight should consider departing on Tuesday mornings when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

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 October 23, 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
4,237 reviews

Comfort

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Overall

8.0

Boarding

8.1

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
4,237 reviews
Southwest
8.0
Very good
4,237 reviews

Comfort

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Overall

8.0

Boarding

8.1

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
7.9
Good
7,981 reviews
Southwest
8.0
Very good
4,237 reviews

Comfort

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Overall

8.0

Boarding

8.1

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
8,098 reviews
Southwest
8.0
Very good
4,237 reviews

Comfort

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Overall

8.0

Boarding

8.1

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
Frontier
5.8
Fair
3,128 reviews
Southwest
8.0
Very good
4,237 reviews

Comfort

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Overall

8.0

Boarding

8.1

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, Delta, and Frontier 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 51m. 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 $68. 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 LaGuardia or Chicago Midway - Newark, Chicago Midway - New York John F Kennedy Intl 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, October is the cheapest month in which you can book a flight from Chicago Midway Airport to State of New York (average of $54). Flying from Chicago Midway Airport to State of New York in August is currently the most expensive (average of $227). 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.

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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 Portland flights
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Top 4 airlines flying from Midway to New York

Discover the top 4 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 October 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$80Average$128FlexibilityNo cancel feeOn-time65%
FrontierCheapest$88Average$162FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$157Average$343FlexibilityNo cancel feeOn-time63%
DeltaCheapest$162Average$369FlexibilityNo cancel feeOn-timeN/A

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