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Midway

$51+ Cheap flights from New York State to Midway (MDW)

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 3/10. Fares are subject to change and may not be available on all flights or dates of travel.
JFK — MDW
ene. 9 — ene. 161
vie. 1/9
vie. 1/16
1 adult, Economy
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Cheap flight deals from New York to Midway

Cheapest flights from New York to Midway
Explore the most affordable flight options available from New York to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on diciembre 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.
mar. 12/1611:30 amEWR - MDW
Nonstop2h 31mFrontier
mié. 12/172:49 pmMDW - EWR
1 stop9h 21mFrontier
Deal found 12/8$113
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/911:30 amEWR - MDW
Nonstop2h 31mFrontier
mar. 12/167:44 amMDW - EWR
Nonstop2h 01mFrontier
Deal found 12/9$131
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.
jue. 12/2511:30 amEWR - MDW
Nonstop2h 31mFrontier
dom. 1/47:44 amMDW - EWR
Nonstop2h 01mFrontier
Deal found 12/8$134
This CheapOair deal was found by Cheapflights users on 12/10. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 12/2511:30 amEWR - MDW
Nonstop2h 31mFrontier
dom. 1/255:01 pmMDW - EWR
1 stop7h 07mFrontier
Deal found 12/10$136
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/911:30 amEWR - MDW
Nonstop2h 31mFrontier
dom. 12/147:44 amMDW - EWR
Nonstop2h 01mFrontier
Deal found 12/8$137
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/1611:30 amEWR - MDW
Nonstop2h 31mFrontier
jue. 1/17:44 amMDW - EWR
Nonstop2h 01mFrontier
Deal found 12/9$138
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.
jue. 12/1112:00 pmEWR - MDW
1 stop10h 53mMultiple Airlines
mar. 12/167:44 amMDW - EWR
Nonstop2h 01mMultiple Airlines
Deal found 12/8$141
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.
mar. 12/1611:30 amEWR - MDW
Nonstop2h 31mMultiple Airlines
jue. 12/186:12 amMDW - EWR
1 stop13h 53mMultiple Airlines
Deal found 12/8$142
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.
jue. 12/1112:00 pmEWR - MDW
1 stop10h 53mMultiple Airlines
dom. 12/147:44 amMDW - EWR
Nonstop2h 01mMultiple Airlines
Deal found 12/7$145
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.
jue. 12/1811:30 amEWR - MDW
Nonstop2h 31mFrontier
jue. 12/257:44 amMDW - EWR
Nonstop2h 01mFrontier
Deal found 12/8$147
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.
lun. 12/156:59 amJFK - MDW
1 stop15h 59mFrontier
mié. 12/172:49 pmMDW - JFK
1 stop9h 10mFrontier
Deal found 12/8$194
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/156:59 amJFK - MDW
1 stop15h 59mFrontier
jue. 1/225:01 pmMDW - JFK
1 stop7h 02mFrontier
Deal found 12/9$197

Find flight deals from New York to Midway

Keep the following information in mind while searching for New York to Midway flight deals. Data was last updated diciembre 10, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$108
(Frontier)

One-way from

$51
(CheapOair)

Popular in

August

Cheapest in

January

Average price

$267

Good round-trip deal

$292 or less

Good one-way deal

$171 or less
Provider with most accurate pricing for New York (NYC)-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for New York (NYC)-Chicago (CHI) flights.
Search Deals
From New York to Chicago Midway
Search Deals
One-way flight from New York to Chicago Midway
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($22 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 New York to Chicago Midway.
Search Deals
Price to beat on a one-way flight from New York to Chicago Midway.
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Cheapflights Fare Finder

 
Customize your flight search to find flights from New York to Midway 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 diciembre 10, 2025.
Use the filters below to find and compare flights from New York State to Chicago Midway Airport that are best for you.

Fly from

New York

Fly to

Midway

Route

Depart

Return

Price

BuffaloChicago

BUF - MDW

BUFMDW

Buffalo

vie. 1/23

1:39 pm-10:19 pm

1 stop9h 40m

Chicago Midway

lun. 1/26

6:20 am-12:44 pm

1 stop5h 24m

$128

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

mié. 1/21

6:00 am-7:40 am

Nonstop2h 40m

Chicago Midway

dom. 1/25

8:40 am-11:50 am

Nonstop2h 10m

$159

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

jue. 2/19

6:00 am-7:40 am

Nonstop2h 40m

Chicago Midway

lun. 2/23

8:00 pm-11:00 pm

Nonstop2h 00m

$159

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

jue. 1/15

9:00 am-10:40 am

Nonstop2h 40m

Chicago Midway

dom. 1/18

7:15 pm-10:20 pm

Nonstop2h 05m

$169

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

sáb. 1/10

7:00 am-1:30 pm

1 stop7h 30m

Chicago Midway

jue. 1/15

6:05 am-9:10 am

Nonstop2h 05m

$173

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

jue. 1/8

6:30 am-1:30 pm

1 stop8h 00m

Chicago Midway

jue. 1/15

6:05 am-9:10 am

Nonstop2h 05m

$178

NewarkChicago

EWR - MDW

EWRMDW

Newark

sáb. 2/7

5:36 pm-10:22 pm

1 stop5h 46m

Chicago Midway

sáb. 2/14

4:13 pm-11:53 pm

1 stop6h 40m

$179

NewarkChicago

EWR - MDW

EWRMDW

Newark

vie. 1/9

9:39 am-12:48 pm

1 stop4h 09m

Chicago Midway

sáb. 1/10

5:31 pm-11:55 pm

1 stop5h 24m

$183

NewarkChicago

EWR - MDW

EWRMDW

Newark

sáb. 1/10

9:39 am-12:48 pm

1 stop4h 09m

Chicago Midway

dom. 1/11

6:30 pm-11:13 pm

1 stop3h 43m

$183

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

vie. 1/16

6:00 am-7:40 am

Nonstop2h 40m

Chicago Midway

dom. 1/18

9:55 am-5:15 pm

1 stop6h 20m

$183

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/9

Showing 1-10 of 60 results
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Best time to book a flight from New York to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from New York 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 New York State to Chicago Midway Airport

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

Currently, May is the cheapest month in which you can book a flight from State of New York to Chicago Midway Airport (average of $55). Flying from State of New York to Chicago Midway Airport in August is currently the most expensive (average of $194). 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 NY to MDW?

Find hourly flight availability from New York to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated diciembre 10, 2025.

One of the essential ways to save on airfare from State of New York to Chicago Midway Airport 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 31% on airfare.

What is the cheapest day to fly from State of New York to Chicago Midway Airport?

Use this chart to determine the cheapest time to fly round-trip from New York to Midway. Price data was last updated on December 6, 2025.

Travelers seeking maximum savings on their State of New York to Chicago Midway Airport flight should consider departing on Wednesday evenings when fares are most often at their lowest. Monday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Related info for your journey

Find useful and relevant information for your journey from New York to Midway. 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 State of New York to Chicago Midway Airport?

    Frontier, Southwest, and Delta can get you from State of New York to Chicago Midway Airport in just under 2h 40m. Your travel time can differ by up to 7h. The distance from State of New York to Chicago Midway Airport 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 State of New York to Chicago Midway Airport one-way?

    To fly one-way, consider booking your trip with Frontier, which is currently one of the cheapest options available, starting at $35. Southwest flights start at $74 while deals on Delta start at $89 one-way.

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

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

  • Can I find deals for flights from New York to Midway that include hotel bookings?

    Yes. In addition to deals on New York to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from New York to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from New York to Midway.

  • Can I find deals for business class flights from New York to Midway?

    Yes. Cheapflights offers flight deals from New York to Midway 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 State of New York to Chicago Midway Airport?

    Currently, May is the cheapest month in which you can book a flight from State of New York to Chicago Midway Airport (average of $55). Flying from State of New York to Chicago Midway Airport in August is currently the most expensive (average of $194). 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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Alternative routes for New York to Midway

See prices for flight routes from nearby airports that may be better suited for you.
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San Diego to O'Hare Intl flights
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George Bush Intcntl to Midway flights
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George Bush Intcntl to O'Hare Intl flights
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Raleigh to Midway flights

Top 4 airlines flying from New York to Midway

Discover the top 4 airlines that operate flights from New York to Midway. 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 diciembre 10, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$59Average$209FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$118Average$306FlexibilityNo cancel feeOn-time69%
DeltaCheapest$134Average$396FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$151Average$342FlexibilityNo cancel feeOn-time63%

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