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$67+ 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 8/14. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — NYC
Jul 8 — Jul 151
Tue 7/8
Tue 7/15
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago Midway to New York are usually found in September or February, booked 72 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 July 3, 2025.

Round-trip from

$121
(Priceline)

One-way from

$67
(Priceline)

Popular in

December

Cheapest in

September

Average price

$249

Good round-trip deal

$191 or less

Good one-way deal

$123 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. 8% potential increase in price ($24 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 3, 2025.

This Priceline deal was found by Cheapflights users on 7/1. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/255:04 pmMDW - JFK
1 stop6h 38mFrontier
Mon 9/299:00 amJFK - MDW
1 stop7h 58mFrontier
Deal found 7/1$121
This Priceline deal was found by Cheapflights users on 7/2. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/125:04 pmMDW - LGA
1 stop5h 27mFrontier
Mon 9/156:30 amLGA - MDW
1 stop10h 28mFrontier
Deal found 7/2$122
This Southwest deal was found by Cheapflights users on 7/1. 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 9/36:00 amMDW - LGA
Nonstop2h 00mSouthwest
Wed 9/39:35 pmLGA - MDW
Nonstop2h 20mSouthwest
Deal found 7/1$137
This Priceline deal was found by Cheapflights users on 7/1. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/45:04 pmMDW - EWR
1 stop6h 30mFrontier
Sun 9/711:15 amEWR - MDW
1 stop5h 43mFrontier
Deal found 7/1$145
This Delta deal was found by Cheapflights users on 7/3. 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.
Wed 9/36:00 amMDW - EWR
1 stop5h 11mDelta
Wed 9/106:15 amEWR - MDW
1 stop7h 48mDelta
Deal found 7/3$167
This Mytrip deal was found by Cheapflights users on 7/1. 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 8/11:11 pmMDW - SWF
2 stops20h 02mAllegiant Air
Thu 8/78:03 pmSWF - MDW
2 stops18h 53mAllegiant Air
Deal found 7/1$341
This Mytrip deal was found by Cheapflights users on 7/2. 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 7/252:54 pmMDW - SWF
2 stops18h 19mMultiple Airlines
Sun 7/277:52 pmSWF - MDW
2 stops19h 12mMultiple Airlines
Deal found 7/2$425

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 July 3, 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 - JFK

MDWJFK

Chicago Midway

Thu 9/25

5:04 pm-12:42 am

1 stop6h 38m

New York John F Kennedy Intl

Mon 9/29

9:00 am-3:58 pm

1 stop7h 58m

$121

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Fri 9/12

5:04 pm-11:31 pm

1 stop5h 27m

New York LaGuardia

Mon 9/15

6:30 am-3:58 pm

1 stop10h 28m

$122

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Wed 9/3

6:00 am-9:00 am

Nonstop2h 00m

New York LaGuardia

Wed 9/3

9:35 pm-10:55 pm

Nonstop2h 20m

$137

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Thu 9/4

5:04 pm-12:34 am

1 stop6h 30m

Newark

Sun 9/7

11:15 am-3:58 pm

1 stop5h 43m

$145

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Wed 9/3

6:00 am-12:11 pm

1 stop5h 11m

Newark

Wed 9/10

6:15 am-1:03 pm

1 stop7h 48m

$167

ChicagoNew Windsor

MDW - SWF

MDWSWF

Chicago Midway

Fri 8/1

1:11 pm-10:13 am

2 stops20h 02m

New Windsor Stewart

Thu 8/7

8:03 pm-1:56 pm

2 stops18h 53m

$341

ChicagoNew Windsor

MDW - SWF

MDWSWF

Chicago Midway

Fri 7/25

2:54 pm-10:13 am

2 stops18h 19m

New Windsor Stewart

Sun 7/27

7:52 pm-2:04 pm

2 stops19h 12m

$425

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Thu 8/14

2:55 pm-12:38 am

1 stop8h 43m

$67

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Thu 9/4

5:04 pm-11:31 pm

1 stop5h 27m

$78

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Wed 8/13

6:00 am-9:00 am

Nonstop2h 00m

$79

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/1

Showing 1-10 of 14 results
1
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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

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 June 27, 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 July is currently the most expensive (average of $319). 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 July 3, 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 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.

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 July 3, 2025.
Get a feel of what it's like to fly with Southwest, Delta, and Allegiant Air 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
4,266 reviews

Overall

8.0

Food

7.0

Comfort

8.0

Boarding

8.2

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,266 reviews
Southwest
8.0
Very good
4,266 reviews

Overall

8.0

Food

7.0

Comfort

8.0

Boarding

8.2

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,982 reviews
Southwest
8.0
Very good
4,266 reviews

Overall

8.0

Food

7.0

Comfort

8.0

Boarding

8.2

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Allegiant Air
7.3
Good
708 reviews
Southwest
8.0
Very good
4,266 reviews

Overall

8.0

Food

7.0

Comfort

8.0

Boarding

8.2

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Frontier
5.9
Fair
3,286 reviews
Southwest
8.0
Very good
4,266 reviews

Overall

8.0

Food

7.0

Comfort

8.0

Boarding

8.2

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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, Frontier ($121), Southwest ($137), and Delta ($167) offers the cheapest pricing from Chicago Midway Airport to New York. Frontier is currently priced 52% 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 $67. Southwest flights start at $79 while deals on Delta start at $84 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 July is currently the most expensive (average of $319). 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
Secaucus
Elizabeth
East Rutherford
Ronkonkoma
Yonkers
Parsippany
North Bergen
Staten Island
Stamford
Mahwah
Carle Place
New Brunswick
Westbury
Hoboken
East Brunswick
Paterson
Fort Lee
Princeton

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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.
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 Buffalo flights
O'Hare Intl to Syracuse flights
O'Hare Intl to Albany flights
O'Hare Intl to Stewart flights
O'Hare Intl to Rochester flights
Midway to Buffalo flights
O'Hare Intl to White Plains flights
Midway to Syracuse flights
Midway to Albany flights
O'Hare Intl to Ithaca flights
O'Hare Intl to Islip flights
Midway to Rochester flights
Midway to White Plains flights
O'Hare Intl to Rutland flights
O'Hare Intl to Binghamton flights
O'Hare Intl to Elmira flights
Midway to Stewart flights
Midway to Binghamton flights
O'Hare Intl to Niagara Falls flights
Midway to Ithaca flights
O'Hare Intl to Saranac Lake flights
O'Hare Intl to Watertown flights
O'Hare Intl to Plattsburgh 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 July 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$63Average$115FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$149Average$276FlexibilityNo cancel feeOn-time63%
DeltaCheapest$162Average$436FlexibilityNo cancel feeOn-timeN/A

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