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Midway

$52+ 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 3/17. Fares are subject to change and may not be available on all flights or dates of travel.
JFK — MDW
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
1 adult, Economy
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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 February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$98
(Cheapflightsfares)

One-way from

$52
(Mytrip)

Popular in

December

Cheapest in

September

Average price

$207

Good round-trip deal

$206 or less

Good one-way deal

$169 or less
Provider with most accurate pricing for New York (NYC)-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for New York (NYC)-Chicago (CHI) flights.
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From New York to Chicago Midway
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One-way flight from New York to Chicago Midway
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Highest demand for flights based on searches. 3% potential increase in price ($8 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($5 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 New York to Chicago Midway.
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Price to beat on a one-way flight from New York to Chicago Midway.
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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 February 20, 2025.

This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/2511:01 amJFK - MDW
1 stop5h 52mFrontier
Tue 4/14:40 pmMDW - JFK
1 stop7h 03mFrontier
Deal found 2/19$98
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 3/14:00 pmLGA - MDW
1 stop7h 04mFrontier
Tue 3/117:50 amMDW - LGA
1 stop12h 09mFrontier
Deal found 2/19$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.
Mon 4/710:00 pmEWR - MDW
1 stop12h 11mFrontier
Tue 4/82:45 pmMDW - EWR
1 stop5h 15mFrontier
Deal found 2/20$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.
Thu 5/19:45 pmLGA - MDW
Nonstop2h 15mSouthwest
Thu 5/86:10 amMDW - LGA
Nonstop2h 00mSouthwest
Deal found 2/20$147
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 4/229:33 amEWR - MDW
1 stop4h 02mDelta
Tue 4/295:59 pmMDW - EWR
1 stop4h 00mDelta
Deal found 2/20$167
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 4/79:52 amROC - MDW
1 stop3h 43mDelta
Mon 4/145:59 pmMDW - ROC
1 stop3h 58mDelta
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 3/257:15 amJFK - MDW
1 stop11h 47mDelta
Thu 3/279:25 amMDW - JFK
1 stop8h 15mDelta
Deal found 2/20$233
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.
Sat 4/266:05 amLGA - MDW
1 stop7h 30mDelta
Mon 4/283:02 pmMDW - LGA
1 stop7h 37mDelta
Deal found 2/20$233
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/49:22 amSYR - MDW
1 stop6h 50mFrontier
Thu 3/612:45 pmMDW - SYR
1 stop18h 37mFrontier
Deal found 2/20$238
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 5/175:20 pmROC - MDW
1 stop4h 05mSouthwest
Tue 5/205:55 amMDW - ROC
1 stop6h 10mSouthwest
Deal found 2/20$253
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 3/202:30 pmALB - MDW
2 stops6h 20mSouthwest
Thu 3/277:15 amMDW - ALB
1 stop5h 25mSouthwest
Deal found 2/20$272
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 3/67:55 amBUF - MDW
Nonstop1h 50mSouthwest
Mon 3/109:30 pmMDW - BUF
Nonstop1h 25mSouthwest
Deal found 2/20$277

Find flights from New York to Midway within your budget

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 February 20, 2025.

Fly from

New York

Fly to

Midway

Route

Depart

Return

Price

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Tue 3/25

11:01 am-3:53 pm

1 stop5h 52m

Chicago Midway

Tue 4/1

4:40 pm-12:43 am

1 stop7h 03m

$98

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Sat 3/1

4:00 pm-10:04 pm

1 stop7h 04m

Chicago Midway

Sat 3/8

12:45 pm-10:00 pm

1 stop8h 15m

$100

NewarkChicago

EWR - MDW

EWRMDW

Newark

Mon 4/7

10:00 pm-9:11 am

1 stop12h 11m

Chicago Midway

Tue 4/8

2:45 pm-9:00 pm

1 stop5h 15m

$104

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Thu 5/1

6:30 am-7:50 am

Nonstop2h 20m

Chicago Midway

Mon 5/5

7:50 pm-11:00 pm

Nonstop2h 10m

$147

NewarkChicago

EWR - MDW

EWRMDW

Newark

Tue 4/22

9:33 am-12:35 pm

1 stop4h 02m

Chicago Midway

Tue 4/29

5:59 pm-10:59 pm

1 stop4h 00m

$167

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Tue 3/25

7:15 am-6:02 pm

1 stop11h 47m

Chicago Midway

Wed 3/26

2:55 pm-9:00 am

1 stop17h 05m

$223

RochesterChicago

ROC - MDW

ROCMDW

Rochester Greater Rochester Intl

Wed 3/26

9:52 am-12:36 pm

1 stop3h 44m

Chicago Midway

Sat 3/29

1:12 pm-5:11 pm

1 stop2h 59m

$223

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Sat 4/26

6:05 am-12:35 pm

1 stop7h 30m

Chicago Midway

Mon 4/28

3:02 pm-11:39 pm

1 stop7h 37m

$233

SyracuseChicago

SYR - MDW

SYRMDW

Syracuse Hancock Intl

Tue 3/4

9:22 am-3:12 pm

1 stop6h 50m

Chicago Midway

Thu 3/6

12:45 pm-8:22 am

1 stop18h 37m

$238

RochesterChicago

ROC - MDW

ROCMDW

Rochester Greater Rochester Intl

Sat 5/17

5:20 pm-8:25 pm

1 stop4h 05m

Chicago Midway

Tue 5/20

5:55 am-1:05 pm

1 stop6h 10m

$253

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

Showing 1-10 of 42 results
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2
3
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5

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.

Travel insights for flights from New York to Midway

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

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

Currently, April is the cheapest month in which you can book a flight from State of New York to Chicago Midway Airport (average of $160). Flying from State of New York to Chicago Midway Airport in November is currently the most expensive (average of $249). 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 February 20, 2025.

When flying from State of New York to Chicago Midway Airport, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Rainfall in Midway by month

Plan your trip to Midway by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

Temperature in Midway by month

Plan your trip to Midway by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago Midway Airport, 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 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated February 20, 2025.
Read reviews from past customers who have flown Southwest, Delta and Allegiant Air from New York to Chicago. 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

Entertainment

7.6

Crew

8.7

Food

7.1

Comfort

8.1

Boarding

8.2

Overall

8.1

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

Entertainment

7.6

Crew

8.7

Food

7.1

Comfort

8.1

Boarding

8.2

Overall

8.1

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

Entertainment

7.6

Crew

8.7

Food

7.1

Comfort

8.1

Boarding

8.2

Overall

8.1

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

Entertainment

7.6

Crew

8.7

Food

7.1

Comfort

8.1

Boarding

8.2

Overall

8.1

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

Entertainment

7.6

Crew

8.7

Food

7.1

Comfort

8.1

Boarding

8.2

Overall

8.1

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 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.

  • 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 $52. Southwest flights start at $74 while deals on Delta start at $84 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 New York LaGuardia - Chicago Midway, Newark - 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, April is the cheapest month in which you can book a flight from State of New York to Chicago Midway Airport (average of $160). Flying from State of New York to Chicago Midway Airport in November is currently the most expensive (average of $249). 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 New York State?

Book flights to New York State if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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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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Atlanta to Midway flights
Portland to O'Hare Intl flights
George Bush Intcntl to O'Hare Intl flights
Minneapolis to Midway flights
Philadelphia to Midway flights
Tampa to O'Hare Intl flights
Cleveland to O'Hare Intl flights
Hobby to O'Hare Intl flights
Oakland to O'Hare Intl flights
Denver to Midway flights
Hobby to Midway flights
Nashville to O'Hare Intl flights
Hartford 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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$105Average$145FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$147Average$305FlexibilityNo cancel feeOn-time63%
DeltaCheapest$156Average$421FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$243Average$328FlexibilityNo cancel feeOn-time62%
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