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$58+ 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 3/22. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — NYC
Jan 11 — Jan 181
Sun 1/11
Sun 1/18
1 adult, Economy
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Find cheap flights from Midway to New York with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

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Cheapflights Tip: The best prices from Chicago Midway to New York are usually found in October or January, booked 66 days in advance, depart on a Thursday or Tuesday and return on a Tuesday

Cheap 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 December 12, 2025.

This Frontier deal was found by Cheapflights users on 12/10. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/237:44 amMDW - EWR
Nonstop2h 01mFrontier
Thu 12/2511:30 amEWR - MDW
Nonstop2h 31mFrontier
Deal found 12/10$115
This Kiwi.com deal was found by Cheapflights users on 12/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/237:44 amMDW - EWR
Nonstop2h 01mFrontier
Thu 1/111:30 amEWR - MDW
Nonstop2h 31mFrontier
Deal found 12/11$122
This CheapOair deal was found by Cheapflights users on 12/9. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/167:44 amMDW - EWR
Nonstop2h 01mFrontier
Thu 12/1811:30 amEWR - MDW
Nonstop2h 31mFrontier
Deal found 12/9$130
This Frontier deal was found by Cheapflights users on 12/11. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/217:44 amMDW - EWR
Nonstop2h 01mFrontier
Thu 1/111:30 amEWR - MDW
Nonstop2h 31mFrontier
Deal found 12/11$138
This Super.com deal was found by Cheapflights users on 12/11. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/257:44 amMDW - EWR
Nonstop2h 01mFrontier
Tue 12/3011:30 amEWR - MDW
Nonstop2h 31mFrontier
Deal found 12/11$143
This Trip.com deal was found by Cheapflights users on 12/11. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/237:44 amMDW - EWR
Nonstop2h 01mFrontier
Wed 1/216:10 amEWR - MDW
1 stop6h 55mFrontier
Deal found 12/11$146
This CheapOair deal was found by Cheapflights users on 12/10. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/187:44 amMDW - EWR
Nonstop2h 01mFrontier
Thu 12/2511:30 amEWR - MDW
Nonstop2h 31mFrontier
Deal found 12/10$147
This Frontier deal was found by Cheapflights users on 12/9. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/172:49 pmMDW - EWR
1 stop9h 21mFrontier
Thu 12/2511:30 amEWR - MDW
Nonstop2h 31mFrontier
Deal found 12/9$152
This Super.com deal was found by Cheapflights users on 12/10. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/147:44 amMDW - EWR
Nonstop2h 01mFrontier
Tue 12/1611:30 amEWR - MDW
Nonstop2h 31mFrontier
Deal found 12/10$155
This Kiwi.com deal was found by Cheapflights users on 12/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/187:44 amMDW - EWR
Nonstop2h 01mFrontier
Thu 1/15:50 amEWR - MDW
1 stop12h 48mFrontier
Deal found 12/11$156
This Super.com deal was found by Cheapflights users on 12/9. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/313:32 pmMDW - JFK
1 stop7h 56mFrontier
Wed 1/76:00 amJFK - MDW
1 stop9h 06mFrontier
Deal found 12/9$163
This Trip.com deal was found by Cheapflights users on 12/10. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/2410:21 amMDW - LGA
1 stop9h 39mFrontier
Thu 1/16:20 amLGA - MDW
1 stop12h 18mFrontier
Deal found 12/10$202

Find 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 December 12, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$106
(Kiwi.com)

One-way from

$58
(Kiwi.com)

Popular in

December

Cheapest in

October

Average price

$285

Good round-trip deal

$62 or less

Good one-way deal

$69 or less
Provider with most accurate pricing for Chicago Midway-New York (NYC) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago Midway-New York (NYC) flights.
Search Deals
From Chicago Midway to New York (NYC)
Search Deals
One-way flight from Chicago Midway to New York (NYC)
Search Deals
Highest demand for flights based on searches. 0% potential increase in price ($1 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from Chicago Midway to New York (NYC).
Search Deals
Price to beat on a one-way flight from Chicago Midway to New York (NYC).
Search Deals

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 December 12, 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

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Fri 1/23

5:01 pm-1:08 am

1 stop7h 07m

Newark

Sun 1/25

6:00 am-11:45 am

1 stop6h 45m

$128

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Mon 2/2

6:05 am-9:10 am

Nonstop2h 05m

New York LaGuardia

Thu 2/5

6:30 pm-8:05 pm

Nonstop2h 35m

$139

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Sat 2/7

5:35 pm-8:40 pm

Nonstop2h 05m

New York LaGuardia

Mon 2/9

6:30 pm-8:05 pm

Nonstop2h 35m

$139

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Fri 1/30

7:15 pm-10:20 pm

Nonstop2h 05m

New York LaGuardia

Wed 2/4

9:45 pm-11:15 pm

Nonstop2h 30m

$148

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Wed 1/7

5:55 pm-9:00 pm

Nonstop2h 05m

New York LaGuardia

Fri 1/9

6:00 am-7:40 am

Nonstop2h 40m

$149

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Thu 1/15

6:05 am-9:10 am

Nonstop2h 05m

New York LaGuardia

Sun 1/18

9:15 am-10:55 am

Nonstop2h 40m

$159

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Sun 2/8

2:30 pm-5:30 pm

Nonstop2h 00m

New York LaGuardia

Wed 2/11

6:00 pm-7:35 pm

Nonstop2h 35m

$159

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Fri 1/23

5:55 pm-9:00 pm

Nonstop2h 05m

New York LaGuardia

Mon 1/26

5:55 pm-7:30 pm

Nonstop2h 35m

$169

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Sat 1/10

6:45 am-2:57 pm

1 stop7h 12m

Newark

Wed 1/14

9:39 am-12:48 pm

1 stop4h 09m

$183

ChicagoNew York

MDW - JFK

MDWJFK

Chicago Midway

Sat 4/11

12:33 pm-12:45 am

1 stop11h 12m

New York John F Kennedy Intl

Mon 4/13

1:00 pm-11:42 pm

1 stop11h 42m

$183

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/10

Showing 1-10 of 57 results
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Compare providers for flights from Midway to New York

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Midway to New York in December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
OvagoPrice Accuracy2 starsTrust Score*2 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago Midway Airport-New York flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago Midway Airport-New York flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-New York flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago Midway Airport-New York flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago Midway Airport-New York flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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 December 5, 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 49 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, October is the cheapest month in which you can book a flight from Chicago Midway Airport to New York (average of $44). Flying from Chicago Midway Airport to 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 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 December 12, 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 afternoon could potentially save you up to 35% 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 6, 2025.

Travelers seeking maximum savings on their Chicago Midway Airport to 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.

How often are flights from Chicago to New York delayed?

About 20% of weekly flights between Chicago and New York have experienced delays in the past year, with the average delay time being 125 minutes.

What is the most punctual flight time for Chicago to New York flights?

Historically, flights departing at night are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Saturday tends to have the lowest number of delays on this route, whereas Thursday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on Chicago to New York flights?

Over the last year, Southwest have had the lowest number of delays on this route, with just 19% of flights being delayed.

The best insider tips for Chicago Midway Airport to New York flights

AI-powered summary based on content written by travel experts. AI can make mistakes.
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

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 December 12, 2025.
Get a feel of what it's like to fly with Southwest and Frontier 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
7.9
Good
4,252 reviews

Crew

8.6

Food

7.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Overall

7.9

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
7.9
Good
4,252 reviews
Southwest
7.9
Good
4,252 reviews

Crew

8.6

Food

7.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Overall

7.9

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
5.8
Fair
3,084 reviews
Southwest
7.9
Good
4,252 reviews

Crew

8.6

Food

7.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Overall

7.9

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 New York?

    Airlines like Frontier, Southwest, 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 5h 07m. 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, Frontier ($59), Southwest ($157), and Delta ($294) offers the cheapest pricing from Chicago Midway Airport to New York. Frontier is currently priced 73% 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 Frontier, which is currently one of the cheapest options available, starting at $39. Southwest flights start at $84 while deals on Delta start at $88 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 John F Kennedy Intl. You may also consider Chicago Midway - New York LaGuardia 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, October is the cheapest month in which you can book a flight from Chicago Midway Airport to New York (average of $44). Flying from Chicago Midway Airport to 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

Traveling to a place near New York?

Book flights to New York if you plan to visit one of these locations
Queens
Bronx
East Rutherford
Mahwah
Yonkers
Elizabeth
Secaucus
North Bergen
Ronkonkoma
Stamford
Staten Island
Edgewater
Carteret
Seaside Heights
Absecon
Carle Place
Parsippany
New Brunswick
Mount Laurel
Carlstadt

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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 December 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$59Average$162FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$157Average$302FlexibilityNo cancel feeOn-time63%
DeltaCheapest$294Average$466FlexibilityNo cancel feeOn-timeN/A

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