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$50+ 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 5/8. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — JFK
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
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 February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$100
(Frontier)

One-way from

$50
(Cheapflightsfares)

Popular in

December

Cheapest in

September

Average price

$185

Good round-trip deal

$185 or less

Good one-way deal

$88 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. 9% potential increase in price ($18 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in February 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 February 20, 2025.

This Frontier deal was found by Cheapflights users on 2/20. 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 4/234:28 pmMDW - LGA
1 stop5h 35mFrontier
Wed 5/76:30 amLGA - MDW
1 stop5h 56mFrontier
Deal found 2/20$100
This Frontier deal was found by Cheapflights users on 2/20. 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 4/14:40 pmMDW - JFK
1 stop7h 03mFrontier
Tue 4/89:00 amJFK - MDW
1 stop11h 45mFrontier
Deal found 2/20$100
This Frontier deal was found by Cheapflights users on 2/19. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/310:48 amMDW - EWR
1 stop9h 18mFrontier
Mon 5/510:00 pmEWR - MDW
1 stop11h 19mFrontier
Deal found 2/19$104
This Southwest deal was found by Cheapflights users on 2/20. 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 4/266:15 pmMDW - LGA
Nonstop2h 10mSouthwest
Tue 4/296:10 amLGA - MDW
Nonstop2h 20mSouthwest
Deal found 2/20$147
This Flightnetwork deal was found by Cheapflights users on 2/19. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/35:15 amMDW - BUF
1 stop8h 40mFrontier
Mon 4/75:45 amBUF - MDW
1 stop15h 01mFrontier
Deal found 2/19$152
This Delta deal was found by Cheapflights users on 2/20. 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 4/155:59 pmMDW - EWR
1 stop4h 00mDelta
Tue 4/2912:40 pmEWR - MDW
1 stop6h 40mDelta
Deal found 2/20$167
This Southwest deal was found by Cheapflights users on 2/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/162:40 pmMDW - ALB
1 stop6h 25mSouthwest
Mon 5/197:30 amALB - MDW
Nonstop2h 10mSouthwest
Deal found 2/19$207
This Delta deal was found by Cheapflights users on 2/20. 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 4/145:59 pmMDW - ROC
1 stop3h 58mDelta
Tue 4/221:00 pmROC - MDW
1 stop6h 20mDelta
Deal found 2/20$217
This Delta deal was found by Cheapflights users on 2/20. 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 3/252:55 pmMDW - JFK
1 stop7h 19mDelta
Wed 4/27:15 amJFK - MDW
1 stop11h 47mDelta
Deal found 2/20$223
This Southwest deal was found by Cheapflights users on 2/20. 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 3/69:30 pmMDW - BUF
Nonstop1h 25mSouthwest
Mon 3/107:55 amBUF - MDW
Nonstop1h 50mSouthwest
Deal found 2/20$277
This Mytrip deal was found by Cheapflights users on 2/19. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/62:53 pmMDW - EWR
1 stop18h 12mAllegiant Air
Sun 6/812:55 pmEWR - MDW
1 stop20h 27mAllegiant Air
Deal found 2/19$290
This Southwest deal was found by Cheapflights users on 2/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/510:05 amMDW - ROC
2 stops6h 15mSouthwest
Sun 3/96:15 pmROC - MDW
1 stop5h 55mSouthwest
Deal found 2/19$293

Find flights from Midway to New York within your budget

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 February 20, 2025.

Fly from

Midway

Fly to

New York

Route

Depart

Return

Price

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Wed 4/23

4:28 pm-11:03 pm

1 stop5h 35m

New York LaGuardia

Thu 5/8

6:30 am-1:34 pm

1 stop8h 04m

$100

ChicagoNew York

MDW - JFK

MDWJFK

Chicago Midway

Tue 4/1

4:40 pm-12:43 am

1 stop7h 03m

New York John F Kennedy Intl

Tue 4/8

9:00 am-7:45 pm

1 stop11h 45m

$100

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Sat 5/3

10:48 am-9:06 pm

1 stop9h 18m

Newark

Mon 5/5

10:00 pm-8:19 am

1 stop11h 19m

$104

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Sat 4/26

6:15 pm-9:25 pm

Nonstop2h 10m

New York LaGuardia

Tue 4/29

6:10 am-7:30 am

Nonstop2h 20m

$147

ChicagoBuffalo

MDW - BUF

MDWBUF

Chicago Midway

Thu 4/3

5:15 am-2:55 pm

1 stop8h 40m

Buffalo

Mon 4/7

5:45 am-7:46 pm

1 stop15h 01m

$152

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Tue 4/15

5:59 pm-10:59 pm

1 stop4h 00m

Newark

Tue 4/29

12:40 pm-6:20 pm

1 stop6h 40m

$167

ChicagoAlbany

MDW - ALB

MDWALB

Chicago Midway

Fri 5/16

2:40 pm-10:05 pm

1 stop6h 25m

Albany Intl

Mon 5/19

7:30 am-8:40 am

Nonstop2h 10m

$207

ChicagoRochester

MDW - ROC

MDWROC

Chicago Midway

Mon 4/14

5:59 pm-10:57 pm

1 stop3h 58m

Rochester Greater Rochester Intl

Tue 4/22

1:00 pm-6:20 pm

1 stop6h 20m

$217

ChicagoNew York

MDW - JFK

MDWJFK

Chicago Midway

Tue 3/25

2:55 pm-11:14 pm

1 stop7h 19m

New York John F Kennedy Intl

Wed 4/2

7:15 am-6:02 pm

1 stop11h 47m

$223

ChicagoBuffalo

MDW - BUF

MDWBUF

Chicago Midway

Thu 3/6

9:30 pm-11:55 pm

Nonstop1h 25m

Buffalo

Mon 3/10

7:55 am-8:45 am

Nonstop1h 50m

$277

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

Showing 1-10 of 41 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.

Travel insights for flights from Midway to New York

Get recent, data-driven insights about flights from Midway to New York including ideal travel times, pricing trends, and more.

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 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 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 February 20, 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 February 20, 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
8.1
Very good
4,411 reviews

Crew

8.7

Food

7.1

Comfort

8.1

Overall

8.1

Boarding

8.2

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Food

7.1

Comfort

8.1

Overall

8.1

Boarding

8.2

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,220 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Food

7.1

Comfort

8.1

Overall

8.1

Boarding

8.2

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Allegiant Air
7.3
Good
765 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Food

7.1

Comfort

8.1

Overall

8.1

Boarding

8.2

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Frontier
6.0
Okay
3,355 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Food

7.1

Comfort

8.1

Overall

8.1

Boarding

8.2

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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 Frontier, with whom users have recently found tickets for as low as $50. However, be on the lookout for offers from Southwest and Delta, 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 LaGuardia or Chicago Midway - New York John F Kennedy Intl, 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 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.

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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 4 airlines flying from Midway to New York

Discover the top 4 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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$54Average$144FlexibilityNo cancel feeOn-time65%
FrontierCheapest$95Average$198FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$148Average$331FlexibilityNo cancel feeOn-time63%
DeltaCheapest$162Average$443FlexibilityNo cancel feeOn-timeN/A
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