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$73+ Cheap flights from Midway (MDW) to New York State

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 7/2. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — JFK
May 24 — May 311
Sat 5/24
Sat 5/31
1 adult, Economy
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Cheap flight deals from Midway to New York

Keep the following information in mind while searching for Midway to New York flight deals. Data was last updated May 19, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$141
(Southwest)

One-way from

$73
(Southwest)

Popular in

December

Cheapest in

September

Average price

$201

Good round-trip deal

$210 or less

Good one-way deal

$80 or less
Provider with most accurate pricing for Chicago (CHI)-New York (NYC) flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-New York (NYC) flights.
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From Chicago Midway to New York
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One-way flight from Chicago Midway to New York
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Highest demand for flights based on searches. 7% potential increase in price ($16 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in May 2025
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Price to beat on a round-trip flight from Chicago Midway to New York.
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Price to beat on a one-way flight from Chicago Midway to New York.
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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 May 19, 2025.

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.
Tue 7/17:20 pmMDW - LGA
Nonstop2h 10mSouthwest
Sat 7/57:45 amLGA - MDW
1 stop9h 50mSouthwest
Deal found 5/18$141
This Flightnetwork 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/172:55 pmMDW - EWR
1 stop8h 49mFrontier
Sat 7/1911:01 amEWR - MDW
1 stop12h 34mFrontier
Deal found 5/18$155
This Flightnetwork 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/177:40 amMDW - LGA
1 stop12h 19mFrontier
Sat 7/1911:30 amLGA - MDW
1 stop12h 05mFrontier
Deal found 5/18$162
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.
Wed 7/24:26 pmMDW - EWR
1 stop7h 32mDelta
Wed 7/96:00 amEWR - MDW
1 stop6h 58mDelta
Deal found 5/18$168
This Flightnetwork 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/173:58 pmMDW - JFK
1 stop17h 17mFrontier
Sat 7/196:59 amJFK - MDW
1 stop14h 23mFrontier
Deal found 5/18$176
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/28:04 pmMDW - EWR
1 stop12h 01mAllegiant Air
Fri 6/69:55 amEWR - MDW
1 stop5h 08mAllegiant Air
Deal found 5/17$207
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/26:15 amMDW - BUF
1 stop8h 29mFrontier
Thu 10/29:45 pmBUF - MDW
1 stop10h 54mFrontier
Deal found 5/18$213
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 6/1910:00 pmMDW - BUF
Nonstop1h 25mSouthwest
Tue 6/246:00 amBUF - MDW
Nonstop1h 40mSouthwest
Deal found 5/18$217
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.
Tue 6/109:24 amMDW - JFK
1 stop13h 16mDelta
Tue 8/127:45 pmJFK - MDW
1 stop13h 50mDelta
Deal found 5/17$217
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.
Sat 9/276:00 amMDW - BUF
1 stop7h 30mDelta
Fri 10/33:50 pmBUF - MDW
1 stop3h 46mDelta
Deal found 5/18$237
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/1410:31 amMDW - EWR
1 stop21h 34mMultiple Airlines
Thu 7/179:10 amEWR - MDW
2 stops24h 12mMultiple Airlines
Deal found 5/18$243
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.
Mon 6/26:25 pmMDW - SYR
1 stop3h 38mDelta
Sat 6/78:30 amSYR - MDW
1 stop5h 45mDelta
Deal found 5/18$249

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

Fly from

Midway

Fly to

New York

Route

Depart

Return

Price

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Tue 7/1

7:20 pm-10:30 pm

Nonstop2h 10m

New York LaGuardia

Sat 7/5

7:45 am-4:35 pm

1 stop9h 50m

$141

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Thu 7/17

2:55 pm-12:44 am

1 stop8h 49m

Newark

Sat 7/19

11:01 am-10:35 pm

1 stop12h 34m

$155

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Thu 7/17

7:40 am-8:59 pm

1 stop12h 19m

New York LaGuardia

Sat 7/19

11:30 am-10:35 pm

1 stop12h 05m

$162

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Wed 7/2

4:26 pm-12:58 am

1 stop7h 32m

Newark

Wed 7/9

6:00 am-11:58 am

1 stop6h 58m

$168

ChicagoNew York

MDW - JFK

MDWJFK

Chicago Midway

Thu 7/17

3:58 pm-10:15 am

1 stop17h 17m

New York John F Kennedy Intl

Sat 7/19

6:59 am-8:22 pm

1 stop14h 23m

$176

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Mon 6/2

8:04 pm-9:05 am

1 stop12h 01m

Newark

Fri 6/6

9:55 am-2:03 pm

1 stop5h 08m

$207

ChicagoBuffalo

MDW - BUF

MDWBUF

Chicago Midway

Thu 10/2

6:15 am-3:44 pm

1 stop8h 29m

Buffalo

Thu 10/2

9:45 pm-7:39 am

1 stop10h 54m

$213

ChicagoBuffalo

MDW - BUF

MDWBUF

Chicago Midway

Thu 6/19

10:00 pm-12:25 am

Nonstop1h 25m

Buffalo

Tue 6/24

6:00 am-6:40 am

Nonstop1h 40m

$217

ChicagoNew York

MDW - JFK

MDWJFK

Chicago Midway

Tue 6/10

9:24 am-11:40 pm

1 stop13h 16m

New York John F Kennedy Intl

Tue 8/12

7:45 pm-8:35 am

1 stop13h 50m

$217

ChicagoBuffalo

MDW - BUF

MDWBUF

Chicago Midway

Sat 9/27

5:59 pm-11:03 pm

1 stop4h 04m

Buffalo

Wed 10/1

6:00 am-9:51 am

1 stop4h 51m

$237

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/18

Showing 1-10 of 49 results
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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 State

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

Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to State of New York (average of $236). Flying from Chicago Midway Airport to State of New York in July is currently the most expensive (average of $336). 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 NY?

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, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago Midway Airport to State of New York as you normally would.

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 State of 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 State of 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 State of 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 May 19, 2025.
Get a feel of what it's like to fly with Southwest, Delta and Allegiant Air from Chicago to New York by reading reviews from past customers. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,291 reviews

Entertainment

7.6

Crew

8.6

Overall

8.0

Boarding

8.2

Food

7.1

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Southwest
8.0
Very good
4,291 reviews
Southwest
8.0
Very good
4,291 reviews

Entertainment

7.6

Crew

8.6

Overall

8.0

Boarding

8.2

Food

7.1

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Delta
8.0
Very good
7,950 reviews
Southwest
8.0
Very good
4,291 reviews

Entertainment

7.6

Crew

8.6

Overall

8.0

Boarding

8.2

Food

7.1

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Allegiant Air
7.3
Good
732 reviews
Southwest
8.0
Very good
4,291 reviews

Entertainment

7.6

Crew

8.6

Overall

8.0

Boarding

8.2

Food

7.1

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Frontier
6.0
Okay
3,284 reviews
Southwest
8.0
Very good
4,291 reviews

Entertainment

7.6

Crew

8.6

Overall

8.0

Boarding

8.2

Food

7.1

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

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 to fly from Chicago Midway Airport to State of New York one-way?

    The cheapest airline one-way is Southwest, with whom users have recently found tickets for as low as $73. However, be on the lookout for offers from Delta and Frontier, as they are both options that can get you from Chicago Midway Airport to State of New York for a low price.

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

    While some choose either Chicago Midway - New York John F Kennedy Intl or Chicago Midway - New York LaGuardia, Chicago Midway - Newark is the most popular route from Chicago Midway Airport to State of New York.

  • 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 State of New York?

    Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to State of New York (average of $236). Flying from Chicago Midway Airport to State of New York in July is currently the most expensive (average of $336). 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

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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 May 19, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$63Average$115FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$149Average$329FlexibilityNo cancel feeOn-time63%
DeltaCheapest$162Average$436FlexibilityNo cancel feeOn-timeN/A

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