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Midway

$67+ 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 11/17. Fares are subject to change and may not be available on all flights or dates of travel.
JFK — MDW
Nov 22 — Nov 291
Sat 11/22
Sat 11/29
1 adult, Economy
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Find 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 October 23, 2025.

This Southwest deal was found by Cheapflights users on 10/23. 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 11/139:00 amLGA - MDW
Nonstop2h 25mSouthwest
Sat 11/155:40 pmMDW - LGA
Nonstop2h 05mSouthwest
Deal found 10/23$117
This Southwest deal was found by Cheapflights users on 10/23. 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 12/127:15 amLGA - MDW
Nonstop2h 30mSouthwest
Wed 12/178:25 amMDW - LGA
Nonstop2h 05mSouthwest
Deal found 10/23$122
This Southwest deal was found by Cheapflights users on 10/23. 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 12/49:10 amLGA - MDW
Nonstop2h 30mSouthwest
Mon 12/85:15 pmMDW - LGA
1 stop5h 05mSouthwest
Deal found 10/23$124
This Southwest deal was found by Cheapflights users on 10/22. 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 12/106:00 amLGA - MDW
Nonstop2h 30mSouthwest
Wed 12/178:25 amMDW - LGA
Nonstop2h 05mSouthwest
Deal found 10/22$126
This Southwest deal was found by Cheapflights users on 10/22. 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 11/119:55 pmLGA - MDW
Nonstop2h 25mSouthwest
Thu 11/136:10 amMDW - LGA
Nonstop2h 05mSouthwest
Deal found 10/22$127
This Kiwi.com deal was found by Cheapflights users on 10/21. 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.
Sat 11/1510:00 amJFK - MDW
1 stop12h 35mFrontier
Tue 11/181:56 pmMDW - JFK
1 stop9h 37mFrontier
Deal found 10/21$130
This Kiwi.com deal was found by Cheapflights users on 10/21. 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.
Thu 12/41:00 pmJFK - MDW
1 stop6h 04mFrontier
Mon 12/88:42 pmMDW - JFK
1 stop11h 19mFrontier
Deal found 10/21$133
This Southwest deal was found by Cheapflights users on 10/23. 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 11/137:15 amLGA - MDW
Nonstop2h 30mSouthwest
Fri 11/146:15 pmMDW - LGA
Nonstop2h 10mSouthwest
Deal found 10/23$133
This Booking.com deal was found by Cheapflights users on 10/22. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/275:54 amEWR - MDW
1 stop12h 03mFrontier
Tue 11/46:26 pmMDW - EWR
Nonstop2h 04mFrontier
Deal found 10/22$137
This Southwest deal was found by Cheapflights users on 10/22. 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 11/137:15 amLGA - MDW
Nonstop2h 30mSouthwest
Mon 11/176:00 amMDW - LGA
Nonstop2h 00mSouthwest
Deal found 10/22$137
This Frontier deal was found by Cheapflights users on 10/21. 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 10/2511:26 amEWR - MDW
1 stop12h 21mFrontier
Tue 10/285:56 pmMDW - EWR
Nonstop2h 04mFrontier
Deal found 10/21$138
This Southwest deal was found by Cheapflights users on 10/23. 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 12/56:00 amLGA - MDW
Nonstop2h 30mSouthwest
Mon 12/85:15 pmMDW - LGA
1 stop5h 05mSouthwest
Deal found 10/23$138

Cheap 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 October 23, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$117
(Southwest)

One-way from

$67
(Kiwi.com)

Popular in

August

Cheapest in

January

Average price

$241

Good round-trip deal

$261 or less

Good one-way deal

$156 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. 7% potential increase in price ($19 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 October 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 October 23, 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

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Thu 11/13

9:00 am-10:25 am

Nonstop2h 25m

Chicago Midway

Mon 11/17

6:00 am-9:00 am

Nonstop2h 00m

$117

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Fri 12/12

7:15 am-8:45 am

Nonstop2h 30m

Chicago Midway

Wed 12/17

8:25 am-11:30 am

Nonstop2h 05m

$122

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Mon 11/10

9:55 pm-11:20 pm

Nonstop2h 25m

Chicago Midway

Mon 11/17

7:15 pm-10:20 pm

Nonstop2h 05m

$127

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Wed 1/21

6:00 pm-7:35 pm

Nonstop2h 35m

Chicago Midway

Mon 1/26

10:30 am-1:30 pm

Nonstop2h 00m

$133

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Fri 12/5

6:00 am-7:30 am

Nonstop2h 30m

Chicago Midway

Mon 12/8

2:10 pm-9:55 pm

1 stop6h 45m

$149

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Sat 1/17

8:00 am-9:30 am

Nonstop2h 30m

Chicago Midway

Sun 1/18

8:10 am-2:55 pm

1 stop5h 45m

$151

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Sat 12/6

2:15 pm-3:45 pm

Nonstop2h 30m

Chicago Midway

Mon 12/8

6:00 am-9:00 am

Nonstop2h 00m

$154

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Sat 11/8

2:15 pm-3:45 pm

Nonstop2h 30m

Chicago Midway

Mon 11/10

8:25 pm-11:25 pm

Nonstop2h 00m

$157

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Sat 11/8

6:00 am-4:30 pm

2 stops11h 30m

Chicago Midway

Tue 11/11

7:15 pm-10:20 pm

Nonstop2h 05m

$162

NewarkChicago

EWR - MDW

EWRMDW

Newark

Wed 12/3

9:37 am-12:34 pm

1 stop3h 57m

Chicago Midway

Wed 12/3

5:29 pm-12:59 am

1 stop6h 30m

$177

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/21

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, November is the cheapest month in which you can book a flight from State of New York to Chicago Midway Airport (average of $54). 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 October 23, 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 30% 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 October 19, 2025.

Travelers seeking maximum savings on their State of New York to Chicago Midway Airport flight should consider departing on Tuesday afternoons when fares are most often at their lowest. Monday evenings 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?

    Southwest, Delta, and Frontier can get you from State of New York to Chicago Midway Airport in just under 2h 25m. Your travel time can differ by up to 8h 17m. 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 $68. Southwest flights start at $68 while deals on Delta start at $79 one-way.

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

    While some choose either New York LaGuardia - Chicago Midway or Newark - Chicago Midway, New York John F Kennedy Intl - 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, November is the cheapest month in which you can book a flight from State of New York to Chicago Midway Airport (average of $54). 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
Merrillville
Lansing
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.
John F Kennedy Intl to O'Hare Intl flights
Dallas/Fort Worth to O'Hare Intl flights
LaGuardia to O'Hare Intl flights
Newark to O'Hare Intl flights
Los Angeles to O'Hare Intl flights
San Francisco to O'Hare Intl flights
Reagan-National to O'Hare Intl flights
Baltimore to O'Hare Intl flights
Dallas/Fort Worth to Midway flights
Dulles Intl to O'Hare Intl flights
Philadelphia to O'Hare Intl flights
Atlanta to O'Hare Intl flights
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John F Kennedy Intl to Midway flights
Denver to O'Hare Intl flights
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Atlanta to Midway flights
Ontario to O'Hare Intl flights
LaGuardia to Midway flights
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Sky Harbor Intl to O'Hare Intl flights
Philadelphia to Midway flights
Newark to Midway flights
Minneapolis to O'Hare Intl flights
Dulles Intl to Midway flights
George Bush Intcntl to O'Hare Intl flights
Minneapolis to Midway flights
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Santa Ana to O'Hare Intl flights
Hobby to O'Hare Intl flights
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Denver to Midway flights
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Reagan-National to Midway flights
San Francisco to Midway flights
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Portland to O'Hare Intl flights
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Hartford to O'Hare Intl flights
Orlando to Midway flights
Cleveland to O'Hare Intl flights
San Jose to O'Hare Intl flights
Miami to O'Hare Intl flights
Detroit to O'Hare Intl 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 October 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$91Average$225FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$92Average$161FlexibilityNo cancel feeOn-time65%
DeltaCheapest$134Average$373FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$156Average$361FlexibilityNo cancel feeOn-time63%

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