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$89+ 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 7/15. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — NYC
Jun 18 — Jun 251
Thu 6/18
Thu 6/25
1 adult, Economy
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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 May 19, 2026.

This Southwest deal was found by Cheapflights users on 5/18. 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 7/27:45 pm
MDW
-
LGA
Nonstop2h 10m
Southwest
Thu 7/96:00 am
LGA
-
MDW
Nonstop2h 20m
Southwest
Deal found 5/18$177
This Southwest deal was found by Cheapflights users on 5/18. 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 7/25:15 am
MDW
-
LGA
Nonstop2h 00m
Southwest
Sun 7/56:00 am
LGA
-
MDW
Nonstop2h 20m
Southwest
Deal found 5/18$182
This Southwest deal was found by Cheapflights users on 5/16. 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 6/35:15 am
MDW
-
LGA
Nonstop2h 00m
Southwest
Sat 6/66:00 am
LGA
-
MDW
Nonstop2h 20m
Southwest
Deal found 5/16$186
This Southwest deal was found by Cheapflights users on 5/16. 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.
Fri 5/295:40 pm
MDW
-
LGA
1 stop4h 45m
Southwest
Sat 5/303:35 pm
LGA
-
MDW
Nonstop2h 40m
Southwest
Deal found 5/16$189
This Southwest deal was found by Cheapflights users on 5/17. 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.
Fri 7/35:15 pm
MDW
-
LGA
Nonstop2h 05m
Southwest
Sun 7/56:00 am
LGA
-
MDW
Nonstop2h 20m
Southwest
Deal found 5/17$192
This Southwest deal was found by Cheapflights users on 5/15. 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 6/172:35 pm
MDW
-
LGA
1 stop7h 45m
Southwest
Sat 6/206:00 am
LGA
-
MDW
Nonstop2h 20m
Southwest
Deal found 5/15$193
This Southwest deal was found by Cheapflights users on 5/16. 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 6/24:40 pm
MDW
-
LGA
1 stop5h 20m
Southwest
Sat 6/66:00 am
LGA
-
MDW
Nonstop2h 20m
Southwest
Deal found 5/16$195
This Southwest deal was found by Cheapflights users on 5/16. 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 5/305:30 am
MDW
-
LGA
Nonstop2h 00m
Southwest
Sat 6/66:00 am
LGA
-
MDW
Nonstop2h 20m
Southwest
Deal found 5/16$196
This Southwest deal was found by Cheapflights users on 5/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/135:00 am
MDW
-
LGA
Nonstop2h 00m
Southwest
Mon 6/156:00 am
LGA
-
MDW
Nonstop2h 20m
Southwest
Deal found 5/14$197
This Delta deal was found by Cheapflights users on 5/18. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/136:05 am
MDW
-
EWR
1 stop7h 09m
Delta
Tue 8/183:20 pm
EWR
-
MDW
1 stop8h 16m
Delta
Deal found 5/18$197
This Delta deal was found by Cheapflights users on 5/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/39:54 am
MDW
-
EWR
1 stop7h 03m
Delta
Tue 7/76:15 am
EWR
-
MDW
1 stop7h 54m
Delta
Deal found 5/19$202
This Delta deal was found by Cheapflights users on 5/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/61:27 pm
MDW
-
EWR
1 stop4h 58m
Delta
Wed 9/98:30 am
EWR
-
MDW
1 stop7h 57m
Delta
Deal found 5/17$207

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 May 19, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$177
(Southwest)

One-way from

$89
(Southwest)

Popular in

April

Cheapest in

October

Average price

$322

Good round-trip deal

$144 or less

Good one-way deal

$70 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. 25% potential increase in price ($85 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
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 May 19, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to New York that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Fri 7/31

7:45 pm-10:55 pm

Nonstop2h 10m

New York LaGuardia

Tue 8/4

7:25 am-8:45 am

Nonstop2h 20m

$187

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Wed 6/10

5:50 pm-8:55 pm

Nonstop2h 05m

New York LaGuardia

Mon 6/15

6:00 am-7:20 am

Nonstop2h 20m

$197
Quickest round-trip

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Sat 8/15

6:00 am-9:00 am

Nonstop2h 00m

New York LaGuardia

Tue 8/18

6:00 am-7:15 am

Nonstop2h 15m

$207

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Fri 6/19

7:45 pm-10:55 pm

Nonstop2h 10m

New York LaGuardia

Sat 6/20

6:00 am-7:20 am

Nonstop2h 20m

$207

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Fri 5/29

5:15 am-8:15 am

Nonstop2h 00m

New York LaGuardia

Wed 6/10

1:35 pm-3:00 pm

Nonstop2h 25m

$212

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Fri 6/19

7:45 pm-10:55 pm

Nonstop2h 10m

New York LaGuardia

Tue 6/23

6:00 am-7:20 am

Nonstop2h 20m

$217

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Fri 5/29

10:15 am-4:50 pm

1 stop5h 35m

New York LaGuardia

Tue 6/2

8:55 am-2:55 pm

1 stop7h 00m

$217

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Sat 6/13

6:40 pm-9:45 pm

Nonstop2h 05m

New York LaGuardia

Sun 6/14

6:00 am-7:20 am

Nonstop2h 20m

$217

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Fri 6/12

7:45 pm-10:55 pm

Nonstop2h 10m

New York LaGuardia

Sun 6/14

6:00 am-7:20 am

Nonstop2h 20m

$217

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Tue 6/2

7:25 pm-10:30 pm

Nonstop2h 05m

New York LaGuardia

Wed 6/10

6:00 am-7:20 am

Nonstop2h 20m

$222

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/16

Showing 1-10 of 60 resultsSorted by cheapest first
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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 May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
OvagoPrice Accuracy3 starsTrust Score*3 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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-New York flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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

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 $29). Flying from Chicago Midway Airport to New York in June is currently the most expensive (average of $169). 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 May 19, 2026.

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 34% on airfare.

How much does it cost to fly round-trip from Chicago Midway Airport to New York?

How often are flights from Chicago to New York delayed?

About 23% of weekly flights between Chicago and New York have experienced delays in the past year, with the average delay time being 126 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 Sunday 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 22% of flights being delayed.

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

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 52 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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 May 16, 2026.

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

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
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on MDW

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 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 May 19, 2026.
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
4,284 reviews

Comfort

8.0

Overall

7.9

Entertainment

7.5

Food

7.0

Crew

8.6

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
7.9
Good
4,284 reviews
Southwest
7.9
Good
4,284 reviews

Comfort

8.0

Overall

7.9

Entertainment

7.5

Food

7.0

Crew

8.6

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Frontier
5.7
Fair
2,945 reviews
Southwest
7.9
Good
4,284 reviews

Comfort

8.0

Overall

7.9

Entertainment

7.5

Food

7.0

Crew

8.6

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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 and Delta fly from Chicago Midway Airport to New York in about 2h 10m. The time it takes to get you to your destination can typically vary by up to 5h 53m. 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 ($56), Southwest ($169), and Delta ($176) offers the cheapest pricing from Chicago Midway Airport to New York. Frontier is currently priced 78% 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. Delta flights start at $68 while deals on Southwest 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 - Newark. You may also consider Chicago Midway - New York LaGuardia or Chicago Midway - New York John F Kennedy Intl.

  • 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 $29). Flying from Chicago Midway Airport to New York in June is currently the most expensive (average of $169). 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?

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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 May 19, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$56Average$162FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$169Average$357FlexibilityNo cancel feeOn-time63%
DeltaCheapest$176Average$326FlexibilityNo cancel feeOn-timeN/A

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