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$56+ 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 1/12. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — JFK
Jan 9 — Jan 161
Fri 1/9
Fri 1/16
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 December 10, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/147:44 amMDW - EWR
Nonstop2h 01mFrontier
Thu 12/1811:30 amEWR - MDW
Nonstop2h 31mFrontier
Deal found 12/8$103
This Frontier deal was found by Cheapflights users on 12/7. 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 12/187:44 amMDW - EWR
Nonstop2h 01mFrontier
Thu 12/2511:30 amEWR - MDW
Nonstop2h 31mFrontier
Deal found 12/7$104
This Super.com deal was found by Cheapflights users on 12/8. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/167:44 amMDW - EWR
Nonstop2h 01mFrontier
Thu 12/2511:30 amEWR - MDW
Nonstop2h 31mFrontier
Deal found 12/8$107
This Kiwi.com deal was found by Cheapflights users on 12/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/147:44 amMDW - EWR
Nonstop2h 01mMultiple Airlines
Tue 1/62:49 pmEWR - MDW
1 stop24h 17mMultiple Airlines
Deal found 12/7$119
This Frontier deal was found by Cheapflights users on 12/8. 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.
Sun 12/147:44 amMDW - EWR
Nonstop2h 01mFrontier
Tue 12/1610:30 pmEWR - MDW
1 stop11h 16mFrontier
Deal found 12/8$120
This Super.com deal was found by Cheapflights users on 12/7. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/257:44 amMDW - EWR
Nonstop2h 01mFrontier
Tue 12/3011:30 amEWR - MDW
Nonstop2h 31mFrontier
Deal found 12/7$123
This Super.com deal was found by Cheapflights users on 12/9. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/167:44 amMDW - EWR
Nonstop2h 01mFrontier
Thu 12/1811:30 amEWR - MDW
Nonstop2h 31mFrontier
Deal found 12/9$128
This Kiwi.com deal was found by Cheapflights users on 12/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/158:42 pmMDW - EWR
1 stop27h 28mFrontier
Thu 12/1811:30 amEWR - MDW
Nonstop2h 31mFrontier
Deal found 12/8$144
This Frontier deal was found by Cheapflights users on 12/8. 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 12/162:49 pmMDW - LGA
1 stop7h 16mFrontier
Sat 1/1012:30 pmLGA - MDW
1 stop10h 57mFrontier
Deal found 12/8$162
This Frontier deal was found by Cheapflights users on 12/7. 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 12/172:49 pmMDW - LGA
1 stop7h 16mFrontier
Tue 1/612:30 pmLGA - MDW
1 stop10h 47mFrontier
Deal found 12/7$163
This Super.com deal was found by Cheapflights users on 12/9. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/313:32 pmMDW - JFK
1 stop7h 56mFrontier
Wed 1/76:00 amJFK - MDW
1 stop9h 06mFrontier
Deal found 12/9$163
This Southwest deal was found by Cheapflights users on 12/7. 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 12/177:15 pmMDW - LGA
Nonstop2h 05mSouthwest
Tue 1/62:30 pmLGA - MDW
Nonstop2h 40mSouthwest
Deal found 12/7$174

Find 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 December 10, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$106
(Kiwi.com)

One-way from

$56
(Kiwi.com)

Popular in

June

Cheapest in

January

Average price

$232

Good round-trip deal

$183 or less

Good one-way deal

$196 or less
Provider with most accurate pricing for Chicago (CHI)-New York (NYC) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-New York (NYC) flights.
Search Deals
From Chicago Midway to New York
Search Deals
One-way flight from Chicago Midway to New York
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($13 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from Chicago Midway to New York.
Search Deals
Price to beat on a one-way flight from Chicago Midway to New York.
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 December 10, 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

Sat 2/7

5:35 pm-8:40 pm

Nonstop2h 05m

New York LaGuardia

Mon 2/9

6:30 pm-8:05 pm

Nonstop2h 35m

$139

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Wed 1/7

5:55 pm-9:00 pm

Nonstop2h 05m

New York LaGuardia

Fri 1/9

6:00 am-7:40 am

Nonstop2h 40m

$149

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Thu 1/15

6:05 am-9:10 am

Nonstop2h 05m

New York LaGuardia

Sun 1/18

6:00 am-7:40 am

Nonstop2h 40m

$159

ChicagoNew York

MDW - JFK

MDWJFK

Chicago Midway

Mon 1/19

10:07 am-3:27 pm

1 stop28h 20m

New York John F Kennedy Intl

Thu 1/22

1:00 pm-10:19 pm

1 stop10h 19m

$164

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Fri 1/30

7:15 pm-10:20 pm

Nonstop2h 05m

New York LaGuardia

Wed 2/4

6:30 am-1:30 pm

1 stop8h 00m

$173

ChicagoBuffalo

MDW - BUF

MDWBUF

Chicago Midway

Fri 1/23

6:20 am-12:44 pm

1 stop5h 24m

Buffalo

Sun 1/25

1:39 pm-10:19 pm

1 stop9h 40m

$180

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Sat 1/10

6:45 am-2:57 pm

1 stop7h 12m

Newark

Mon 1/12

1:00 pm-5:34 pm

1 stop5h 34m

$183

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Wed 1/7

11:21 am-5:29 pm

1 stop5h 08m

Newark

Sat 1/10

6:00 am-10:32 am

1 stop5h 32m

$183

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Sat 1/17

11:21 am-5:29 pm

1 stop5h 08m

Newark

Sun 1/18

9:39 am-12:48 pm

1 stop4h 09m

$183

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Sat 1/17

5:31 pm-11:55 pm

1 stop5h 24m

Newark

Tue 1/20

9:47 am-12:51 pm

1 stop4h 04m

$183

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/10

Showing 1-10 of 60 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, October is the cheapest month in which you can book a flight from Chicago Midway Airport to State of New York (average of $44). Flying from Chicago Midway Airport to State of New York in August is currently the most expensive (average of $227). 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 December 10, 2025.

One of the essential ways to save on airfare from Chicago Midway Airport to State of 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 32% on airfare.

What is the cheapest day to fly from Chicago Midway Airport to State of 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 6, 2025.

Travelers seeking maximum savings on their Chicago Midway Airport to State of New York flight should consider departing on Tuesday mornings when fares are most often at their lowest. Sunday at noon 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 December 10, 2025.
See what other customers who have flown with Southwest, Delta, and Frontier from Chicago Midway Airport to New York State have to say. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
7.9
Good
4,252 reviews

Crew

8.6

Entertainment

7.5

Boarding

8.1

Overall

7.9

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
7.9
Good
4,252 reviews
Southwest
7.9
Good
4,252 reviews

Crew

8.6

Entertainment

7.5

Boarding

8.1

Overall

7.9

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Delta
7.9
Good
8,007 reviews
Southwest
7.9
Good
4,252 reviews

Crew

8.6

Entertainment

7.5

Boarding

8.1

Overall

7.9

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Frontier
5.8
Fair
3,085 reviews
Southwest
7.9
Good
4,252 reviews

Crew

8.6

Entertainment

7.5

Boarding

8.1

Overall

7.9

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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 State of New York?

    Airlines like Southwest, Frontier, and Delta fly from Chicago Midway Airport to State of New York in about 2h 05m. The time it takes to get you to your destination can typically vary by up to 26h 15m. The distance between Chicago Midway Airport and State of 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 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 $47. 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 - Newark, Chicago Midway - New York John F Kennedy Intl 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, October is the cheapest month in which you can book a flight from Chicago Midway Airport to State of New York (average of $44). Flying from Chicago Midway Airport to State of New York in August is currently the most expensive (average of $227). 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 December 10, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$59Average$162FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$157Average$345FlexibilityNo cancel feeOn-time63%
DeltaCheapest$294Average$466FlexibilityNo cancel feeOn-timeN/A

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