HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
New York

$69+ 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 5/24. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — NYC
Apr 20 — Apr 271
Sun 4/20
Sun 4/27
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

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

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheapflights Tip: The best prices from Chicago Midway to New York are usually found in September or February, booked 29 days in advance, depart on a Wednesday or Tuesday 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 April 15, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$137
(Southwest)

One-way from

$69
(Southwest)

Popular in

July

Cheapest in

September

Average price

$233

Good round-trip deal

$189 or less

Good one-way deal

$103 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. 14% potential increase in price ($45 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 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

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 April 15, 2025.

This Southwest deal was found by Cheapflights users on 4/14. 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 5/246:15 pmMDW - LGA
Nonstop2h 10mSouthwest
Tue 5/276:10 amLGA - MDW
Nonstop2h 20mSouthwest
Deal found 4/14$137
This Delta deal was found by Cheapflights users on 4/13. 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.
Sat 5/175:25 pmMDW - EWR
1 stop4h 04mDelta
Sun 5/256:05 amEWR - MDW
1 stop8h 10mDelta
Deal found 4/13$168
This Cheapflightsfares deal was found by Cheapflights users on 4/14. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/139:34 amMDW - LGA
1 stop5h 55mFrontier
Wed 5/146:30 amLGA - MDW
1 stop5h 56mFrontier
Deal found 4/14$176
This Frontier deal was found by Cheapflights users on 4/14. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/139:34 amMDW - EWR
1 stop10h 32mFrontier
Sat 5/2411:00 amEWR - MDW
1 stop12h 02mFrontier
Deal found 4/14$178
This Frontier deal was found by Cheapflights users on 4/14. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/304:28 pmMDW - JFK
1 stop7h 05mFrontier
Wed 5/76:00 amJFK - MDW
1 stop6h 26mFrontier
Deal found 4/14$178
This Mytrip deal was found by Cheapflights users on 4/15. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/308:04 pmMDW - EWR
1 stop14h 01mAllegiant Air
Fri 6/69:55 amEWR - MDW
1 stop5h 08mAllegiant Air
Deal found 4/15$215
This eDestinos deal was found by Cheapflights users on 4/15. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/308:04 pmMDW - EWR
1 stop14h 01mMultiple Airlines
Fri 6/65:59 amEWR - MDW
1 stop27h 48mMultiple Airlines
Deal found 4/15$263
This Delta deal was found by Cheapflights users on 4/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/131:08 pmMDW - JFK
1 stop9h 06mDelta
Mon 8/257:25 pmJFK - MDW
1 stop14h 15mDelta
Deal found 4/14$268
This Mytrip deal was found by Cheapflights users on 4/13. 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.
Thu 5/2911:03 amMDW - SWF
1 stop24h 22mAllegiant Air
Thu 6/511:11 amSWF - MDW
2 stops27h 52mAllegiant Air
Deal found 4/13$333

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 April 15, 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

Sat 5/24

6:15 pm-9:25 pm

Nonstop2h 10m

New York LaGuardia

Tue 5/27

6:10 am-7:30 am

Nonstop2h 20m

$137

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Sat 5/17

5:25 pm-10:29 pm

1 stop4h 04m

Newark

Sun 5/25

6:05 am-1:15 pm

1 stop8h 10m

$168

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Tue 5/13

9:34 am-4:29 pm

1 stop5h 55m

New York LaGuardia

Wed 5/14

6:30 am-11:26 am

1 stop5h 56m

$176

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Tue 5/13

9:34 am-9:06 pm

1 stop10h 32m

Newark

Sat 5/24

11:00 am-10:02 pm

1 stop12h 02m

$178

ChicagoNew York

MDW - JFK

MDWJFK

Chicago Midway

Wed 4/30

4:28 pm-12:33 am

1 stop7h 05m

New York John F Kennedy Intl

Wed 5/7

6:00 am-11:26 am

1 stop6h 26m

$178

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Fri 5/30

8:04 pm-11:05 am

1 stop14h 01m

Newark

Fri 6/6

9:55 am-2:03 pm

1 stop5h 08m

$215

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Fri 5/30

8:04 pm-11:05 am

1 stop14h 01m

Newark

Fri 6/6

5:59 am-8:47 am

1 stop27h 48m

$263

ChicagoNew York

MDW - JFK

MDWJFK

Chicago Midway

Tue 5/13

1:08 pm-11:14 pm

1 stop9h 06m

New York John F Kennedy Intl

Mon 8/25

7:25 pm-8:40 am

1 stop14h 15m

$268

ChicagoNew Windsor

MDW - SWF

MDWSWF

Chicago Midway

Thu 5/29

11:03 am-12:25 pm

1 stop24h 22m

New Windsor Stewart

Thu 6/5

11:11 am-2:03 pm

2 stops27h 52m

$333

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Sat 5/24

6:15 pm-9:25 pm

Nonstop2h 10m

$69

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/14

Showing 1-10 of 21 results
1
2
3

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 April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*2 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
MytripPrice Accuracy3 starsTrust Score*3 stars
GotogatePrice Accuracy3 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 Mytrip to be most consistent on Cheapflights vs. Mytrip Users can find the same prices on Chicago Midway Airport-New York flight deals on Cheapflights vs. Mytrip >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 Mytrip the most. Mytrip 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 April 11, 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 29 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 $351). 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 April 15, 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 in the afternoon tend to be the most expensive. A flight in the evening could potentially save you up to 12% 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.

Rainfall in New York by month

Plan your trip to New York by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in New York ranges from 2.8 - 4.5 inches per month. July is typically the wettest month, when rainfall can reach 4.5 in. February is typically the driest time to visit New York when rainfall is around 2.8 in.

Temperature in New York by month

Plan your trip to New York by taking into account the average temperature totals by month.

If weather is an important factor for your trip to New York, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 77.0 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 33.8 F).

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 April 15, 2025.
To help decide which airline to fly from Chicago to New York, see what other customers have to say about Southwest, Delta and Allegiant Air. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,279 reviews

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.0
Very good
4,279 reviews
Southwest
8.0
Very good
4,279 reviews

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Delta
8.0
Very good
7,918 reviews
Southwest
8.0
Very good
4,279 reviews

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Allegiant Air
7.3
Good
734 reviews
Southwest
8.0
Very good
4,279 reviews

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Frontier
6.0
Okay
3,281 reviews
Southwest
8.0
Very good
4,279 reviews

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

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.

  • What are the cheapest airlines flying from Chicago Midway Airport to New York round-trip?

    According to our current data, Southwest ($137), Delta ($168), and Frontier ($176) offers the cheapest pricing from Chicago Midway Airport to New York. Southwest is currently priced 48% 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 $69. Delta flights start at $79 while deals on Frontier start at $87 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 John F Kennedy Intl or Chicago Midway - New York LaGuardia.

  • 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 $351). 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 Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Queens
Bronx
Woodbridge
Elizabeth
Staten Island
Ronkonkoma
Yonkers
Secaucus
Parsippany
East Rutherford
Absecon
Carteret
Carle Place
Stamford
East Brunswick
Fairfield
North Bergen
Tannersville
Saddle Brook
Paterson

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Midway to New York

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to LaGuardia flights
O'Hare Intl to John F Kennedy Intl flights
O'Hare Intl to Newark flights
Midway to Newark flights
Midway to John F Kennedy Intl flights
Midway to LaGuardia flights
O'Hare Intl to Syracuse flights
O'Hare Intl to Buffalo flights
O'Hare Intl to Albany flights
O'Hare Intl to White Plains flights
O'Hare Intl to Rochester flights
Midway to Buffalo flights
Midway to Rochester flights
Midway to Syracuse flights
Midway to Albany flights
Midway to White Plains flights
O'Hare Intl to Islip flights
O'Hare Intl to Stewart flights
O'Hare Intl to Ithaca flights
Midway to Ithaca flights
O'Hare Intl to Binghamton flights
Midway to Binghamton flights
O'Hare Intl to Rutland flights
O'Hare Intl to Elmira flights
O'Hare Intl to Niagara Falls flights
O'Hare Intl to Plattsburgh flights
Midway to Stewart flights
O'Hare Intl to Watertown flights
O'Hare Intl to Saranac Lake flights

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 April 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$63Average$131FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$149Average$271FlexibilityNo cancel feeOn-time63%
DeltaCheapest$162Average$443FlexibilityNo cancel feeOn-timeN/A

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.