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Midway

$69+ 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 5/28. Fares are subject to change and may not be available on all flights or dates of travel.
JFK — MDW
May 6 — May 131
Tue 5/6
Tue 5/13
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 May 1, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$157
(Southwest)

One-way from

$69
(Southwest)

Popular in

December

Cheapest in

September

Average price

$249

Good round-trip deal

$242 or less

Good one-way deal

$126 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. 2% potential increase in price ($6 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 May 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 May 1, 2025.

This Southwest deal was found by Cheapflights users on 4/30. 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 5/309:45 pmLGA - MDW
Nonstop2h 15mSouthwest
Tue 7/17:20 pmMDW - LGA
Nonstop2h 10mSouthwest
Deal found 4/30$157
This Delta deal was found by Cheapflights users on 4/30. 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 6/43:55 pmEWR - MDW
1 stop6h 32mDelta
Tue 6/106:00 amMDW - EWR
1 stop5h 39mDelta
Deal found 4/30$179
This eDestinos deal was found by Cheapflights users on 4/29. 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.
Fri 6/65:59 amEWR - MDW
1 stop27h 48mFrontier
Wed 6/112:10 pmMDW - EWR
1 stop9h 36mFrontier
Deal found 4/29$194
This eDestinos deal was found by Cheapflights users on 4/29. 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 7/199:00 amJFK - MDW
1 stop14h 35mFrontier
Sun 7/206:20 amMDW - JFK
1 stop24h 08mFrontier
Deal found 4/29$194
This Frontier deal was found by Cheapflights users on 4/29. 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 5/76:30 amLGA - MDW
1 stop5h 56mFrontier
Sat 5/1010:48 amMDW - LGA
1 stop11h 15mFrontier
Deal found 4/29$198
This Mytrip deal was found by Cheapflights users on 4/29. 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.
Sun 7/279:55 amEWR - MDW
1 stop24h 46mAllegiant Air
Fri 8/110:31 amMDW - EWR
1 stop21h 34mAllegiant Air
Deal found 4/29$212
This Frontier deal was found by Cheapflights users on 4/30. 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 5/13:51 pmBUF - MDW
1 stop8h 48mFrontier
Sun 5/48:30 amMDW - BUF
1 stop5h 25mFrontier
Deal found 4/30$238
This Southwest deal was found by Cheapflights users on 4/29. 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.
Sun 5/257:25 amBUF - MDW
Nonstop1h 40mSouthwest
Tue 5/271:00 pmMDW - BUF
Nonstop1h 25mSouthwest
Deal found 4/29$249
This Delta deal was found by Cheapflights users on 4/30. 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 5/316:10 amSYR - MDW
1 stop3h 30mDelta
Tue 6/34:15 pmMDW - SYR
1 stop6h 44mDelta
Deal found 4/30$264
This Delta deal was found by Cheapflights users on 4/29. 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 7/166:00 amALB - MDW
1 stop3h 39mDelta
Wed 7/236:20 pmMDW - ALB
1 stop3h 43mDelta
Deal found 4/29$269
This Delta deal was found by Cheapflights users on 4/30. 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 5/216:00 amBUF - MDW
1 stop4h 40mDelta
Tue 7/810:26 amMDW - BUF
1 stop7h 14mDelta
Deal found 4/30$269
This Southwest deal was found by Cheapflights users on 4/30. 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 7/306:30 amALB - MDW
Nonstop2h 10mSouthwest
Fri 8/18:10 pmMDW - ALB
Nonstop1h 55mSouthwest
Deal found 4/30$272

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 May 1, 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

Fri 5/30

9:45 pm-11:00 pm

Nonstop2h 15m

Chicago Midway

Tue 7/1

7:20 pm-10:30 pm

Nonstop2h 10m

$157

NewarkChicago

EWR - MDW

EWRMDW

Newark

Wed 6/4

3:55 pm-9:27 pm

1 stop6h 32m

Chicago Midway

Tue 6/10

6:00 am-12:39 pm

1 stop5h 39m

$179

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Wed 5/7

6:30 am-11:26 am

1 stop5h 56m

Chicago Midway

Wed 5/7

2:12 pm-11:03 pm

1 stop7h 51m

$193

NewarkChicago

EWR - MDW

EWRMDW

Newark

Fri 6/6

5:59 am-8:47 am

1 stop27h 48m

Chicago Midway

Wed 6/11

2:10 pm-12:46 am

1 stop9h 36m

$194

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Sat 7/19

9:00 am-10:35 pm

1 stop14h 35m

Chicago Midway

Sun 7/20

6:20 am-7:28 am

1 stop24h 08m

$194

NewarkChicago

EWR - MDW

EWRMDW

Newark

Sun 7/27

9:55 am-9:41 am

1 stop24h 46m

Chicago Midway

Fri 8/1

10:31 am-9:05 am

1 stop21h 34m

$212

BuffaloChicago

BUF - MDW

BUFMDW

Buffalo

Fri 6/27

8:50 am-8:17 pm

1 stop12h 27m

Chicago Midway

Sun 6/29

9:12 pm-7:50 am

1 stop9h 38m

$242

BuffaloChicago

BUF - MDW

BUFMDW

Buffalo

Sun 5/25

7:25 am-8:05 am

Nonstop1h 40m

Chicago Midway

Tue 5/27

1:00 pm-3:25 pm

Nonstop1h 25m

$249

SyracuseChicago

SYR - MDW

SYRMDW

Syracuse Hancock Intl

Sat 5/31

6:10 am-8:40 am

1 stop3h 30m

Chicago Midway

Tue 6/3

4:15 pm-11:59 pm

1 stop6h 44m

$264

AlbanyChicago

ALB - MDW

ALBMDW

Albany Intl

Wed 7/16

6:00 am-8:39 am

1 stop3h 39m

Chicago Midway

Wed 7/23

6:20 pm-11:03 pm

1 stop3h 43m

$269

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

Showing 1-10 of 45 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, 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 May 1, 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 May 1, 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
8.0
Very good
4,294 reviews

Boarding

8.2

Overall

8.0

Entertainment

7.6

Crew

8.6

Comfort

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Southwest
8.0
Very good
4,294 reviews
Southwest
8.0
Very good
4,294 reviews

Boarding

8.2

Overall

8.0

Entertainment

7.6

Crew

8.6

Comfort

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Delta
8.0
Very good
7,934 reviews
Southwest
8.0
Very good
4,294 reviews

Boarding

8.2

Overall

8.0

Entertainment

7.6

Crew

8.6

Comfort

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Allegiant Air
7.3
Good
734 reviews
Southwest
8.0
Very good
4,294 reviews

Boarding

8.2

Overall

8.0

Entertainment

7.6

Crew

8.6

Comfort

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Frontier
6.0
Okay
3,287 reviews
Southwest
8.0
Very good
4,294 reviews

Boarding

8.2

Overall

8.0

Entertainment

7.6

Crew

8.6

Comfort

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

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 Southwest, which is currently one of the cheapest options available, starting at $69. Delta flights start at $89 while deals on Frontier start at $96 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, 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
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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Top 3 airlines flying from New York to Midway

Discover the top 3 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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$37Average$172FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$148Average$304FlexibilityNo cancel feeOn-time63%
DeltaCheapest$176Average$411FlexibilityNo cancel feeOn-timeN/A

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