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$71+ Cheap flights from Midway (MDW) to New York, NY (NYC)

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 9/23. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — NYC
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago Midway to New York are usually found in August or September, booked 72 days in advance, depart on a Tuesday or Thursday and return on a Wednesday

Cheap flight deals from Midway to New York

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to New York (NYC). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated September 11, 2025.

Round-trip from

$119
(Southwest)

One-way from

$71
(Kiwi.com)

Popular in

December

Cheapest in

August

Average price

$207

Good round-trip deal

$84 or less

Good one-way deal

$58 or less
From Chicago Midway to New York (NYC)
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One-way flight from Chicago Midway to New York (NYC)
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Highest demand for flights based on searches. 10% potential increase in price ($27 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($10 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 (NYC).
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Price to beat on a one-way flight from Chicago Midway to New York (NYC).
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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 11, 2025.

This Southwest deal was found by Cheapflights users on 9/11. 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 11/194:45 pmLGA - MDW
Nonstop2h 30mSouthwest
Deal found 9/11$119
This Southwest deal was found by Cheapflights users on 9/10. 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 9/10$128
This Southwest deal was found by Cheapflights users on 9/11. 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 9/305:40 pmMDW - LGA
1 stop4h 20mSouthwest
Wed 10/13:35 pmLGA - MDW
Nonstop2h 30mSouthwest
Deal found 9/11$129
This Southwest deal was found by Cheapflights users on 9/10. 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 10/710:55 amMDW - LGA
Nonstop2h 00mSouthwest
Tue 10/146:05 amLGA - MDW
Nonstop2h 25mSouthwest
Deal found 9/10$132
This Southwest deal was found by Cheapflights users on 9/9. 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
Mon 11/109:55 pmLGA - MDW
Nonstop2h 25mSouthwest
Deal found 9/9$133
This Southwest deal was found by Cheapflights users on 9/11. 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 10/228:25 amMDW - LGA
Nonstop2h 05mSouthwest
Sat 10/256:45 amLGA - MDW
1 stop7h 15mSouthwest
Deal found 9/11$136
This Southwest deal was found by Cheapflights users on 9/11. 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 10/17:05 pmMDW - LGA
Nonstop2h 10mSouthwest
Thu 10/26:25 amLGA - MDW
Nonstop2h 20mSouthwest
Deal found 9/11$137
This Southwest deal was found by Cheapflights users on 9/11. 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 11/155:40 pmMDW - LGA
Nonstop2h 05mSouthwest
Mon 11/179:55 pmLGA - MDW
Nonstop2h 25mSouthwest
Deal found 9/11$140
This Gotogate deal was found by Cheapflights users on 9/11. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/302:32 pmMDW - JFK
1 stop9h 36mFrontier
Wed 10/19:00 amJFK - MDW
1 stop7h 58mFrontier
Deal found 9/11$145
This Gotogate deal was found by Cheapflights users on 9/10. 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 Gotogate 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
Mon 11/310:00 amJFK - MDW
1 stop9h 39mFrontier
Deal found 9/10$147
This Booking.com deal was found by Cheapflights users on 9/10. 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 10/24:56 pmMDW - JFK
1 stop7h 12mFrontier
Sat 10/41:01 pmJFK - MDW
1 stop11h 40mFrontier
Deal found 9/10$148
This Mytrip deal was found by Cheapflights users on 9/11. 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 11/81:37 pmMDW - JFK
1 stop9h 56mFrontier
Sun 11/94:00 pmJFK - MDW
1 stop9h 30mFrontier
Deal found 9/11$155

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 11, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to New York that are best for you.

Fly from

Midway

Fly to

New York

Route

Depart

Return

Price

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Wed 11/5

8:25 am-11:30 am

Nonstop2h 05m

New York LaGuardia

Sat 11/8

2:15 pm-3:45 pm

Nonstop2h 30m

$128

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Tue 12/9

7:15 pm-10:20 pm

Nonstop2h 05m

New York LaGuardia

Thu 12/11

6:00 am-7:30 am

Nonstop2h 30m

$138

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Tue 11/18

11:15 am-5:05 pm

1 stop4h 50m

New York LaGuardia

Wed 11/19

6:15 am-11:25 am

1 stop6h 10m

$139

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Wed 11/5

7:15 pm-10:20 pm

Nonstop2h 05m

New York LaGuardia

Sun 11/9

7:15 am-8:45 am

Nonstop2h 30m

$139

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Wed 10/22

3:00 pm-9:55 pm

1 stop5h 55m

New York LaGuardia

Sat 10/25

6:45 am-1:00 pm

1 stop7h 15m

$147

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Wed 10/1

8:35 am-2:55 pm

1 stop5h 20m

New York LaGuardia

Sat 10/4

10:40 am-4:30 pm

1 stop6h 50m

$147

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Tue 10/21

2:25 pm-5:25 pm

Nonstop2h 00m

New York LaGuardia

Sat 10/25

6:45 am-1:00 pm

1 stop7h 15m

$149

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Sun 11/16

6:10 am-9:15 am

Nonstop2h 05m

New York LaGuardia

Mon 11/17

9:55 pm-11:20 pm

Nonstop2h 25m

$153

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Wed 10/8

5:55 pm-11:10 pm

1 stop4h 15m

New York LaGuardia

Wed 10/15

6:05 am-7:30 am

Nonstop2h 25m

$159

ChicagoNew York

MDW - JFK

MDWJFK

Chicago Midway

Fri 10/17

5:28 pm-10:24 am

1 stop15h 56m

New York John F Kennedy Intl

Sun 10/19

6:00 am-9:33 am

1 stop28h 33m

$166

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

Showing 1-10 of 60 results
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The best insider tips for Chicago Midway Airport to New York flights

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
Cheapflights partnered with top experts to bring you the best recommendations for your Chicago Midway Airport to New York trip
Airports
MDW

Use the airport’s mobile system to order food directly to your gate, saving time and ensuring you don't miss boarding.

Read more about MDWby Ramsey Qubein
LGA

For a quick ride to Manhattan, take a taxi from LGA. It's often cheaper than rideshares and readily available.

Read more about LGAby Brandon Schultz
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on MDW

Ramsey Qubein

Ramsey Qubein

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more
Brandon Schultz

Brandon Schultz

Expert on LGA

Brandon Schultz

Brandon Schultz

Brandon Schultz is an award-winning food and travel writer based in New York City. His work has appeared in Forbes, AAA, Thrillist, Travel + Leisure, and The Daily Meal, among many others, and he is the author of 6 books, including 3 cookbooks.

Read more

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

How far ahead should I book a flight from Chicago Midway Airport to New York?

Use this chart to determine the optimal time to book a round-trip flight from Midway to New York. Price data was last updated on August 29, 2025.

The price you pay for your flight from Chicago Midway Airport to New York may vary depending on when you book. For the best chance of a lower fare, look to book 70 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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

Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to New York (average of $236). Flying from Chicago Midway Airport to New York in June is currently the most expensive (average of $314). 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 NYC?

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 11, 2025.

One of the essential ways to save on airfare from Chicago Midway Airport to New York is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the evening could potentially save you up to 11% on airfare.

What is the cheapest day to fly from Chicago Midway Airport to 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 December 16, 2024.

Travelers seeking maximum savings on their Chicago Midway Airport to New York flight should consider departing on Tuesday evenings when fares are most often at their lowest. Sunday afternoons 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 September 11, 2025.
Get a feel of what it's like to fly with Southwest, Delta, and United Airlines from Chicago Midway Airport to New York by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Boarding

8.1

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

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
4,248 reviews
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Boarding

8.1

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

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
7,960 reviews
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Boarding

8.1

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

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
United Airlines
7.4
Good
8,937 reviews
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Boarding

8.1

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

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
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Boarding

8.1

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

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
8,023 reviews
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Boarding

8.1

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

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 New York?

    Airlines like Southwest, Frontier, and Delta fly from Chicago Midway Airport to New York in about 2h 05m. The time it takes to get you to your destination can typically vary by up to 13h 51m. The distance from Chicago Midway Airport to 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 flying from Chicago Midway Airport to New York round-trip?

    According to our current data, Spirit Airlines ($63), Delta ($162), and Southwest ($162) offers the cheapest pricing from Chicago Midway Airport to New York. Spirit Airlines is currently priced 74% below the average price you’ll pay for this route.

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

    To fly one-way, consider booking your trip with Southwest, which is currently one of the cheapest options available, starting at $74. Frontier flights start at $78 while deals on Delta start at $89 one-way.

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

    The most popular route from Chicago Midway Airport to New York is Chicago Midway - New York LaGuardia. You may also consider Chicago Midway - New York John F Kennedy Intl or Chicago Midway - Newark.

  • 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 New York?

    Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to New York (average of $236). Flying from Chicago Midway Airport to New York in June is currently the most expensive (average of $314). 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 New York?

Book flights to New York if you plan to visit one of these locations
Queens
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Elizabeth
Mahwah
Secaucus
Yonkers
Ronkonkoma
East Rutherford
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Staten Island
Stamford
New Brunswick
Absecon
Carle Place
East Brunswick
Hoboken
Westbury
Avenel
Paterson
Fort Lee

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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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$63Average$125FlexibilityNo cancel feeOn-time65%
DeltaCheapest$162Average$391FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$162Average$291FlexibilityNo cancel feeOn-time63%

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