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$56+ 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 2/10. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — JFK
Feb 5 — Feb 121
Thu 2/5
Thu 2/12
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 January 6, 2026.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$104
(Frontier)

One-way from

$56
(Southwest)

Popular in

June

Cheapest in

January

Average price

$148

Good round-trip deal

$219 or less

Good one-way deal

$146 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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Highest demand for flights based on searches. 6% potential increase in price ($15 potential increase over avg. RT price).
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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 January 2026
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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 January 6, 2026.

This Orbitz deal was found by Cheapflights users on 1/5. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/107:30 amMDW - EWR
Nonstop2h 00mFrontier
Thu 3/1211:30 amEWR - MDW
Nonstop2h 32mFrontier
Deal found 1/5$107
This Frontier deal was found by Cheapflights users on 1/6. 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.
Tue 3/177:30 amMDW - EWR
Nonstop2h 00mFrontier
Thu 3/1911:30 amEWR - MDW
Nonstop2h 32mFrontier
Deal found 1/6$109
This Southwest deal was found by Cheapflights users on 1/5. 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 2/56:05 pmMDW - LGA
Nonstop2h 05mSouthwest
Sat 2/74:50 pmLGA - MDW
Nonstop2h 40mSouthwest
Deal found 1/5$111
This Kiwi.com deal was found by Cheapflights users on 1/6. 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.
Thu 1/156:30 pmMDW - EWR
Nonstop2h 00mFrontier
Tue 1/206:00 amEWR - MDW
1 stop7h 05mFrontier
Deal found 1/6$112
This Kiwi.com deal was found by Cheapflights users on 1/6. 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.
Thu 1/156:30 pmMDW - EWR
Nonstop2h 00mMultiple Airlines
Thu 1/225:25 amEWR - MDW
1 stop7h 20mMultiple Airlines
Deal found 1/6$113
This Frontier deal was found by Cheapflights users on 1/6. 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.
Tue 1/136:30 pmMDW - EWR
Nonstop2h 00mFrontier
Wed 1/216:10 amEWR - MDW
1 stop6h 55mFrontier
Deal found 1/6$114
This CheapOair deal was found by Cheapflights users on 1/5. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/156:30 pmMDW - EWR
Nonstop2h 00mFrontier
Wed 1/216:10 amEWR - MDW
1 stop6h 55mFrontier
Deal found 1/5$115
This Southwest deal was found by Cheapflights users on 1/6. 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 2/56:05 pmMDW - LGA
Nonstop2h 05mSouthwest
Thu 2/126:15 amLGA - MDW
Nonstop2h 35mSouthwest
Deal found 1/6$120
This Trip.com deal was found by Cheapflights users on 1/5. 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.
Tue 1/136:30 pmMDW - EWR
Nonstop2h 00mFrontier
Tue 1/206:00 amEWR - MDW
1 stop7h 05mFrontier
Deal found 1/5$120
This Super.com deal was found by Cheapflights users on 1/5. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/271:20 pmMDW - LGA
1 stop7h 09mFrontier
Wed 1/286:25 amLGA - MDW
1 stop6h 40mFrontier
Deal found 1/5$123
This Super.com deal was found by Cheapflights users on 1/5. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/31:20 pmMDW - EWR
1 stop7h 15mFrontier
Wed 2/46:10 amEWR - MDW
1 stop6h 55mFrontier
Deal found 1/5$123
This Southwest deal was found by Cheapflights users on 1/5. 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.
Sat 1/245:35 pmMDW - LGA
Nonstop2h 05mSouthwest
Sat 1/3111:55 amLGA - MDW
Nonstop2h 35mSouthwest
Deal found 1/5$124

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 January 6, 2026.
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

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Wed 1/28

1:20 pm-9:35 pm

1 stop7h 15m

Newark

Wed 2/4

6:10 am-12:05 pm

1 stop6h 55m

$128

ChicagoNew York

MDW - JFK

MDWJFK

Chicago Midway

Wed 1/28

1:20 pm-12:43 am

1 stop10h 23m

New York John F Kennedy Intl

Wed 2/4

6:10 am-12:05 pm

1 stop6h 55m

$128

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Thu 2/5

6:05 pm-9:10 pm

Nonstop2h 05m

New York LaGuardia

Mon 2/9

6:30 pm-8:15 pm

Nonstop2h 45m

$139

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Wed 2/11

7:15 pm-10:20 pm

Nonstop2h 05m

New York LaGuardia

Wed 2/18

6:00 am-7:40 am

Nonstop2h 40m

$139

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Tue 1/27

7:15 pm-10:20 pm

Nonstop2h 05m

New York LaGuardia

Wed 1/28

6:00 am-7:40 am

Nonstop2h 40m

$147

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Mon 2/2

6:05 am-9:10 am

Nonstop2h 05m

New York LaGuardia

Wed 2/4

6:00 am-7:40 am

Nonstop2h 40m

$148

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Fri 1/30

9:45 am-5:54 pm

1 stop7h 09m

Newark

Sun 2/1

10:30 pm-11:45 am

1 stop14h 15m

$150

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Fri 2/20

6:00 am-11:29 pm

1 stop16h 29m

Newark

Tue 2/24

10:31 pm-7:07 pm

1 stop21h 36m

$154

ChicagoNew York

MDW - JFK

MDWJFK

Chicago Midway

Fri 2/20

6:00 am-1:08 am

1 stop18h 08m

New York John F Kennedy Intl

Tue 2/24

1:00 pm-7:07 pm

1 stop7h 07m

$154

ChicagoNew York

MDW - JFK

MDWJFK

Chicago Midway

Sat 1/31

4:30 pm-12:51 am

1 stop7h 21m

New York John F Kennedy Intl

Mon 2/2

12:25 pm-5:29 pm

1 stop6h 04m

$157

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/6

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 $44). 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 January 6, 2026.

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 28% 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 January 3, 2026.

Travelers seeking maximum savings on their Chicago Midway Airport to State of New York flight should consider departing on Tuesday afternoons 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 January 6, 2026.
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
4,247 reviews

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.1

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,247 reviews
Southwest
8.0
Very good
4,247 reviews

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.1

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Delta
7.9
Good
8,017 reviews
Southwest
8.0
Very good
4,247 reviews

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.1

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Spirit Airlines
6.3
Okay
8,276 reviews
Southwest
8.0
Very good
4,247 reviews

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.1

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Frontier
5.7
Fair
3,064 reviews
Southwest
8.0
Very good
4,247 reviews

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.1

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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 Frontier, Southwest, 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 5h 16m. 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 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, October is the cheapest month in which you can book a flight from Chicago Midway Airport to State of New York (average of $44). 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.

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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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 January 6, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$59Average$162FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$157Average$367FlexibilityNo cancel feeOn-time63%
DeltaCheapest$294Average$466FlexibilityNo cancel feeOn-timeN/A

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