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Midway

$62+ 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 4/26. Fares are subject to change and may not be available on all flights or dates of travel.
JFK — MDW
Feb 26 — Mar 51
Thu 2/26
Thu 3/5
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 January 27, 2026.

This Frontier deal was found by Cheapflights users on 1/25. 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 5/1411:30 am
EWR
-
MDW
Nonstop2h 30m
Frontier
Tue 5/197:30 am
MDW
-
EWR
Nonstop2h 08m
Frontier
Deal found 1/25$97
This Gotogate deal was found by Cheapflights users on 1/26. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/410:30 pm
EWR
-
MDW
1 stop16h 56m
Frontier
Tue 3/107:30 am
MDW
-
EWR
Nonstop2h 00m
Frontier
Deal found 1/26$98
This Frontier deal was found by Cheapflights users on 1/26. 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 4/2311:30 am
EWR
-
MDW
Nonstop2h 30m
Frontier
Fri 4/247:30 am
MDW
-
EWR
Nonstop2h 08m
Frontier
Deal found 1/26$99
This Frontier deal was found by Cheapflights users on 1/26. 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 4/2111:30 am
EWR
-
MDW
Nonstop2h 30m
Frontier
Tue 4/287:30 am
MDW
-
EWR
Nonstop2h 08m
Frontier
Deal found 1/26$100
This Frontier deal was found by Cheapflights users on 1/25. 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 4/2211:30 am
EWR
-
MDW
Nonstop2h 30m
Frontier
Fri 4/247:30 am
MDW
-
EWR
Nonstop2h 08m
Frontier
Deal found 1/25$101
This Frontier deal was found by Cheapflights users on 1/24. 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 4/1911:30 am
EWR
-
MDW
Nonstop2h 30m
Frontier
Wed 4/227:30 am
MDW
-
EWR
Nonstop2h 08m
Frontier
Deal found 1/24$102
This Frontier deal was found by Cheapflights users on 1/24. 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.
Mon 4/2011:30 am
EWR
-
MDW
Nonstop2h 30m
Frontier
Thu 4/237:30 am
MDW
-
EWR
Nonstop2h 08m
Frontier
Deal found 1/24$103
This Frontier deal was found by Cheapflights users on 1/24. 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.
Mon 4/2011:30 am
EWR
-
MDW
Nonstop2h 30m
Frontier
Tue 4/287:30 am
MDW
-
EWR
Nonstop2h 08m
Frontier
Deal found 1/24$104
This Trip.com deal was found by Cheapflights users on 1/25. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/1711:30 am
EWR
-
MDW
Nonstop2h 32m
Frontier
Thu 3/197:30 am
MDW
-
EWR
Nonstop2h 00m
Frontier
Deal found 1/25$105
This Frontier deal was found by Cheapflights users on 1/26. 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 4/2311:30 am
EWR
-
MDW
Nonstop2h 30m
Frontier
Sat 4/252:20 pm
MDW
-
EWR
1 stop6h 09m
Frontier
Deal found 1/26$108
This Frontier deal was found by Cheapflights users on 1/25. 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 4/1811:30 am
EWR
-
MDW
Nonstop2h 30m
Frontier
Tue 4/212:20 pm
MDW
-
EWR
1 stop9h 56m
Frontier
Deal found 1/25$110
This Southwest deal was found by Cheapflights users on 1/25. 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 2/209:05 am
LGA
-
MDW
Nonstop2h 40m
Southwest
Mon 2/238:40 am
MDW
-
LGA
Nonstop2h 10m
Southwest
Deal found 1/25$117

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 January 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$90
(Frontier)

One-way from

$62
(Frontier)

Popular in

August

Cheapest in

January

Average price

$187

Good round-trip deal

$222 or less

Good one-way deal

$135 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. 9% potential increase in price ($24 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 January 2026
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.
Search Deals

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 January 27, 2026.
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

Mon 2/23

6:00 am-7:40 am

Nonstop2h 40m

Chicago Midway

Mon 3/2

8:40 am-11:50 am

Nonstop2h 10m

$117

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Tue 3/10

6:50 am-8:20 am

Nonstop2h 30m

Chicago Midway

Thu 3/12

5:20 am-8:20 am

Nonstop2h 00m

$137

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Tue 3/24

9:00 am-10:35 am

Nonstop2h 35m

Chicago Midway

Wed 3/25

5:10 am-8:10 am

Nonstop2h 00m

$137

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Fri 2/27

9:05 am-10:45 am

Nonstop2h 40m

Chicago Midway

Sun 3/1

8:20 am-11:30 am

Nonstop2h 10m

$137

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Fri 3/6

6:40 pm-8:20 pm

Nonstop2h 40m

Chicago Midway

Mon 3/9

6:40 pm-9:45 pm

Nonstop2h 05m

$147

BuffaloChicago

BUF - MDW

BUFMDW

Buffalo

Mon 2/23

1:48 pm-7:47 pm

1 stop6h 59m

Chicago Midway

Thu 2/26

6:25 am-12:54 pm

1 stop5h 29m

$148

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Mon 2/23

9:00 am-10:40 am

Nonstop2h 40m

Chicago Midway

Wed 2/25

5:55 pm-9:00 pm

Nonstop2h 05m

$148

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Thu 2/19

9:00 am-10:40 am

Nonstop2h 40m

Chicago Midway

Mon 2/23

6:05 am-9:10 am

Nonstop2h 05m

$159

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Tue 2/24

7:20 am-4:35 pm

2 stops10h 15m

Chicago Midway

Tue 3/3

8:30 am-11:40 am

Nonstop2h 10m

$162

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Fri 2/20

9:05 am-10:45 am

Nonstop2h 40m

Chicago Midway

Mon 2/23

8:00 pm-11:00 pm

Nonstop2h 00m

$163

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/25

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, December is the cheapest month in which you can book a flight from State of New York to Chicago Midway Airport (average of $48). 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 January 27, 2026.

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 16% 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 January 24, 2026.

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.

How much does it cost to fly round-trip from State of New York to Chicago Midway Airport?

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, Frontier, 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 4h 19m. 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 Newark - Chicago Midway or New York LaGuardia - 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, December is the cheapest month in which you can book a flight from State of New York to Chicago Midway Airport (average of $48). 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.
Dallas/Fort Worth to O'Hare Intl flights
John F Kennedy Intl to O'Hare Intl flights
Los Angeles to O'Hare Intl flights
Newark to O'Hare Intl flights
LaGuardia to O'Hare Intl flights
San Francisco to O'Hare Intl flights
Reagan-National to O'Hare Intl flights
Dulles Intl to O'Hare Intl flights
Baltimore to O'Hare Intl flights
Atlanta to O'Hare Intl flights
Sky Harbor Intl to O'Hare Intl flights
Seattle to O'Hare Intl flights
Denver to O'Hare Intl flights
John F Kennedy Intl to Midway flights
Boston to O'Hare Intl flights
Philadelphia to O'Hare Intl flights
Dallas/Fort Worth to Midway flights
Newark to Midway flights
Los Angeles to Midway flights
Austin to O'Hare Intl flights
Raleigh to O'Hare Intl flights
Charlotte to O'Hare Intl flights
Ontario to O'Hare Intl flights
Santa Ana to O'Hare Intl flights
Fort Lauderdale to O'Hare Intl flights
Atlanta to Midway flights
San Francisco to Midway flights
Hobby to Midway flights
Dulles Intl to Midway flights
Miami to O'Hare Intl flights
LaGuardia to Midway flights
Minneapolis to O'Hare Intl flights
Baltimore to Midway flights
Hartford to O'Hare Intl flights
Hobby to O'Hare Intl flights
George Bush Intcntl to O'Hare Intl flights
Philadelphia to Midway flights
Reagan-National to Midway flights
Love Field to O'Hare Intl flights
Cleveland to O'Hare Intl flights
Tampa to O'Hare Intl flights
Orlando to O'Hare Intl flights
Minneapolis to Midway flights
San Diego to O'Hare Intl flights
Columbus to O'Hare Intl flights
Sacramento to O'Hare Intl flights
San Jose to O'Hare Intl flights
Kansas City to O'Hare Intl flights
Boston to Midway flights
San Antonio 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 January 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$58Average$208FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$118Average$306FlexibilityNo cancel feeOn-time69%
DeltaCheapest$122Average$345FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$158Average$341FlexibilityNo cancel feeOn-time63%

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