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Midway

$59+ 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 3/12. Fares are subject to change and may not be available on all flights or dates of travel.
JFK — MDW
Jan 22 — Jan 291
Wed 1/22
Wed 1/29
1 adult, Economy
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Cheap flight deals from New York to Midway

Discover tips and strategies to find the most affordable flight options for your journey from New York (USNY) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 17, 2025.

Round-trip from

$115
(Mytrip)

One-way from

$59
(Trip.com)
From New York to Chicago Midway
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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 January 17, 2025.

This Mytrip deal was found by Cheapflights users on 1/16. 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.
Thu 1/3011:04 amJFK - MDW
1 stop26h 05mFrontier
Mon 2/37:15 amMDW - JFK
1 stop25h 50mFrontier
Deal found 1/16$115
This Booking.com deal was found by Cheapflights users on 1/15. 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.
Thu 3/64:00 pmLGA - MDW
1 stop7h 06mFrontier
Mon 3/1012:49 pmMDW - LGA
1 stop20h 11mFrontier
Deal found 1/15$120
This Southwest deal was found by Cheapflights users on 1/16. 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 2/286:30 amLGA - MDW
Nonstop2h 30mSouthwest
Sun 3/25:50 amMDW - LGA
Nonstop2h 10mSouthwest
Deal found 1/16$147
This Delta deal was found by Cheapflights users on 1/16. 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.
Wed 2/1211:29 amEWR - MDW
1 stop5h 51mDelta
Tue 2/259:33 amMDW - EWR
1 stop6h 32mDelta
Deal found 1/16$163
This Frontier deal was found by Cheapflights users on 1/16. 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 2/1710:10 pmEWR - MDW
1 stop10h 22mFrontier
Wed 2/198:12 amMDW - EWR
1 stop11h 58mFrontier
Deal found 1/16$222
This eDestinos deal was found by Cheapflights users on 1/16. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/1510:00 pmLGA - MDW
1 stop14h 28mMultiple Airlines
Sat 2/224:48 pmMDW - LGA
1 stop22h 03mMultiple Airlines
Deal found 1/16$227
This Delta deal was found by Cheapflights users on 1/16. 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.
Thu 1/306:15 amROC - MDW
1 stop3h 39mDelta
Sun 2/26:28 pmMDW - ROC
1 stop3h 37mDelta
Deal found 1/16$229
This Delta deal was found by Cheapflights users on 1/15. 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.
Wed 2/126:15 amSYR - MDW
1 stop6h 44mDelta
Wed 2/1910:57 amMDW - SYR
1 stop6h 18mDelta
Deal found 1/15$239
This Booking.com deal was found by Cheapflights users on 1/16. 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 2/247:45 pmSYR - MDW
1 stop20h 27mFrontier
Thu 2/2712:43 pmMDW - SYR
1 stop18h 39mFrontier
Deal found 1/16$240
This FlightHub deal was found by Cheapflights users on 1/16. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/98:17 pmBUF - MDW
1 stop19h 45mFrontier
Sun 2/1612:43 pmMDW - BUF
1 stop20h 41mFrontier
Deal found 1/16$240
This Delta deal was found by Cheapflights users on 1/16. 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.
Thu 3/207:50 amJFK - MDW
1 stop7h 25mDelta
Tue 4/16:00 amMDW - JFK
1 stop27h 00mDelta
Deal found 1/16$289
This Southwest deal was found by Cheapflights users on 1/16. 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 2/226:15 amBUF - MDW
Nonstop1h 55mSouthwest
Mon 2/247:05 pmMDW - BUF
Nonstop1h 30mSouthwest
Deal found 1/16$295

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 January 17, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Sat 2/8

3:00 pm-10:02 am

1 stop20h 02m

Chicago Midway

Mon 2/10

7:15 am-10:05 am

1 stop25h 50m

$115

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Tue 1/28

6:30 am-8:00 am

Nonstop2h 30m

Chicago Midway

Tue 1/28

8:05 pm-11:10 pm

Nonstop2h 05m

$117

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Fri 2/28

10:00 pm-11:28 am

1 stop14h 28m

Chicago Midway

Tue 3/4

8:30 am-10:00 pm

1 stop12h 30m

$120

NewarkChicago

EWR - MDW

EWRMDW

Newark

Wed 2/12

10:29 am-4:20 pm

1 stop6h 51m

Chicago Midway

Wed 2/19

6:00 am-12:15 pm

1 stop5h 15m

$163

NewarkChicago

EWR - MDW

EWRMDW

Newark

Mon 2/17

10:10 pm-7:32 am

1 stop10h 22m

Chicago Midway

Wed 2/19

8:12 am-9:10 pm

1 stop11h 58m

$222

RochesterChicago

ROC - MDW

ROCMDW

Rochester Greater Rochester Intl

Thu 1/30

6:15 am-8:54 am

1 stop3h 39m

Chicago Midway

Sun 2/2

6:28 pm-11:05 pm

1 stop3h 37m

$229

SyracuseChicago

SYR - MDW

SYRMDW

Syracuse Hancock Intl

Wed 2/12

6:15 am-11:59 am

1 stop6h 44m

Chicago Midway

Wed 2/19

10:57 am-6:15 pm

1 stop6h 18m

$239

SyracuseChicago

SYR - MDW

SYRMDW

Syracuse Hancock Intl

Mon 2/24

7:45 pm-3:12 pm

1 stop20h 27m

Chicago Midway

Thu 2/27

12:43 pm-8:22 am

1 stop18h 39m

$240

BuffaloChicago

BUF - MDW

BUFMDW

Buffalo

Sun 2/9

8:17 pm-3:02 pm

1 stop19h 45m

Chicago Midway

Sun 2/16

12:43 pm-10:24 am

1 stop20h 41m

$240

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Tue 1/28

6:00 am-10:12 am

1 stop5h 12m

Chicago Midway

Thu 1/30

12:44 pm-9:58 pm

1 stop8h 14m

$290

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/15

Showing 1-10 of 44 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.

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 January 17, 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 January 17, 2025.
Read reviews from past customers who have flown Southwest, Frontier and Delta 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
4,659 reviews

Boarding

8.2

Food

7.2

Overall

8.1

Comfort

8.1

Crew

8.7

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,659 reviews
Southwest
8.1
Very good
4,659 reviews

Boarding

8.2

Food

7.2

Overall

8.1

Comfort

8.1

Crew

8.7

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,511 reviews
Southwest
8.1
Very good
4,659 reviews

Boarding

8.2

Food

7.2

Overall

8.1

Comfort

8.1

Crew

8.7

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Allegiant Air
7.4
Good
801 reviews
Southwest
8.1
Very good
4,659 reviews

Boarding

8.2

Food

7.2

Overall

8.1

Comfort

8.1

Crew

8.7

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Spirit Airlines
6.3
Okay
8,098 reviews
Southwest
8.1
Very good
4,659 reviews

Boarding

8.2

Food

7.2

Overall

8.1

Comfort

8.1

Crew

8.7

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Frontier
6.1
Okay
3,435 reviews
Southwest
8.1
Very good
4,659 reviews

Boarding

8.2

Food

7.2

Overall

8.1

Comfort

8.1

Crew

8.7

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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 $59. 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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Dulles Intl to Midway flights
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Philadelphia to Midway flights
LaGuardia to Midway flights
George Bush Intcntl to O'Hare Intl flights
Reagan-National to Midway flights
Cleveland to O'Hare Intl flights
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San Francisco to Midway flights
Orlando to Midway flights
Tampa to O'Hare Intl flights
San Jose to O'Hare Intl flights
Hartford to O'Hare Intl flights
Portland to O'Hare Intl flights
Seattle 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 January 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$115Average$145FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$147Average$293FlexibilityNo cancel feeOn-time63%
DeltaCheapest$176Average$414FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$243Average$328FlexibilityNo cancel feeOn-time62%
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