Midway

$60+ 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 2/8. Fares are subject to change and may not be available on all flights or dates of travel.
JFK — MDW
Dec 27 — Jan 31
We work with more than 300 partners to bring you better travel deals

Find cheap flights from New York to Midway with Cheapflights

1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”
2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.
3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 December 22, 2024.

Round-trip from

$128
(Booking.com)

One-way from

$60
(Mytrip)
From New York to Chicago Midway
One-way flight from New York to Chicago Midway

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 December 22, 2024.

This Frontier deal was found by Cheapflights users on 12/19. 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.
Mon 12/3012:20 pmLGA - MDW
1 stop11h 54mFrontier
Thu 1/97:30 amMDW - LGA
1 stop8h 30mFrontier
Deal found 12/19$198
This Southwest deal was found by Cheapflights users on 12/20. 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.
Fri 12/279:10 amLGA - MDW
Nonstop2h 30mSouthwest
Mon 1/65:50 pmMDW - LGA
Nonstop2h 10mSouthwest
Deal found 12/20$274
This Delta deal was found by Cheapflights users on 12/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/3112:00 pmJFK - MDW
1 stop6h 11mDelta
Fri 1/35:04 pmMDW - JFK
1 stop5h 45mDelta
Deal found 12/21$300
This Delta deal was found by Cheapflights users on 12/20. 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 12/316:00 amEWR - MDW
1 stop3h 50mDelta
Fri 1/36:25 pmMDW - EWR
1 stop3h 51mDelta
Deal found 12/20$328
This Delta deal was found by Cheapflights users on 12/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/315:45 amALB - MDW
1 stop4h 05mDelta
Sat 1/49:30 amMDW - ALB
1 stop6h 05mDelta
Deal found 12/21$390
This Gotogate deal was found by Cheapflights users on 12/21. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/2310:36 amSYR - MDW
1 stop8h 18mFrontier
Mon 1/66:49 pmMDW - SYR
1 stop15h 32mFrontier
Deal found 12/21$398
This FlightHub deal was found by Cheapflights users on 12/19. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/2311:57 amBUF - MDW
1 stop6h 57mFrontier
Thu 1/25:52 pmMDW - BUF
1 stop13h 56mFrontier
Deal found 12/19$403
This Southwest deal was found by Cheapflights users on 12/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/235:35 pmROC - MDW
1 stop6h 30mSouthwest
Wed 1/17:20 amMDW - ROC
1 stop7h 20mSouthwest
Deal found 12/21$408
This Southwest deal was found by Cheapflights users on 12/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/317:35 amALB - MDW
Nonstop2h 15mSouthwest
Sat 1/49:55 pmMDW - ALB
Nonstop1h 50mSouthwest
Deal found 12/21$427
This Delta deal was found by Cheapflights users on 12/20. 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 12/286:10 amBUF - MDW
1 stop3h 40mDelta
Wed 1/15:51 pmMDW - BUF
1 stop4h 12mDelta
Deal found 12/20$434
This Delta deal was found by Cheapflights users on 12/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/286:15 amROC - MDW
1 stop3h 35mDelta
Sat 1/46:25 pmMDW - ROC
1 stop3h 32mDelta
Deal found 12/21$438
This Southwest deal was found by Cheapflights users on 12/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/246:50 pmBUF - MDW
Nonstop1h 45mSouthwest
Tue 12/3112:35 pmMDW - BUF
Nonstop1h 25mSouthwest
Deal found 12/19$475

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 December 22, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Mon 1/6

10:00 am-12:29 pm

1 stop27h 29m

Chicago Midway

Sun 1/12

8:45 am-10:03 am

1 stop24h 18m

$128

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Sat 3/1

4:00 pm-10:04 pm

1 stop7h 04m

Chicago Midway

Wed 3/5

8:12 am-3:00 pm

1 stop5h 48m

$128

NewarkChicago

EWR - MDW

EWRMDW

Newark

Tue 2/18

10:10 pm-7:07 am

1 stop9h 57m

Chicago Midway

Wed 2/19

8:12 am-9:10 pm

1 stop11h 58m

$142

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Fri 1/17

9:30 pm-11:00 pm

Nonstop2h 30m

Chicago Midway

Mon 1/20

6:00 am-9:10 am

Nonstop2h 10m

$147

NewarkChicago

EWR - MDW

EWRMDW

Newark

Tue 1/21

1:00 pm-6:14 pm

1 stop6h 14m

Chicago Midway

Sat 1/25

9:34 am-5:05 pm

1 stop6h 31m

$158

RochesterChicago

ROC - MDW

ROCMDW

Rochester Greater Rochester Intl

Fri 2/7

1:10 pm-6:11 pm

1 stop6h 01m

Chicago Midway

Sun 2/9

3:41 pm-11:59 pm

1 stop7h 18m

$238

BuffaloChicago

BUF - MDW

BUFMDW

Buffalo

Tue 1/21

6:45 am-7:30 am

Nonstop1h 45m

Chicago Midway

Wed 1/22

6:25 pm-8:55 pm

Nonstop1h 30m

$238

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Sat 1/4

6:29 am-11:08 am

1 stop5h 39m

Chicago Midway

Sat 1/11

5:05 pm-11:14 pm

1 stop5h 09m

$294

SyracuseChicago

SYR - MDW

SYRMDW

Syracuse Hancock Intl

Mon 1/13

12:55 pm-6:14 pm

1 stop6h 19m

Chicago Midway

Sat 1/18

5:05 pm-11:20 pm

1 stop5h 15m

$298

AlbanyChicago

ALB - MDW

ALBMDW

Albany Intl

Mon 1/20

7:05 am-8:35 am

Nonstop2h 30m

Chicago Midway

Mon 1/27

1:45 pm-4:35 pm

Nonstop1h 50m

$300

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/21

Showing 1-10 of 40 results
1
2
3
4

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 December 22, 2024.

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 December 22, 2024.
Read reviews from past customers who have flown Frontier, Southwest 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.
8.1
Very good
4,804 reviews

Comfort

8.1

Overall

8.1

Crew

8.7

Food

7.2

Entertainment

7.7

Boarding

8.2

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.

8.1
Very good
4,804 reviews
8.1
Very good
4,804 reviews

Comfort

8.1

Overall

8.1

Crew

8.7

Food

7.2

Entertainment

7.7

Boarding

8.2

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.

8.0
Very good
8,597 reviews
8.1
Very good
4,804 reviews

Comfort

8.1

Overall

8.1

Crew

8.7

Food

7.2

Entertainment

7.7

Boarding

8.2

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.

7.4
Good
823 reviews
8.1
Very good
4,804 reviews

Comfort

8.1

Overall

8.1

Crew

8.7

Food

7.2

Entertainment

7.7

Boarding

8.2

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.

6.3
Okay
8,111 reviews
8.1
Very good
4,804 reviews

Comfort

8.1

Overall

8.1

Crew

8.7

Food

7.2

Entertainment

7.7

Boarding

8.2

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.

6.1
Okay
3,472 reviews
8.1
Very good
4,804 reviews

Comfort

8.1

Overall

8.1

Crew

8.7

Food

7.2

Entertainment

7.7

Boarding

8.2

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 $60. Southwest flights start at $74 while deals on Delta start at $83 one-way.

  • What are the most popular routes 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for New York to Midway

See prices for flight routes from nearby airports that may be better suited for you.

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 December 22, 2024.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$115Average$145FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$148Average$300FlexibilityNo cancel feeOn-time63%
DeltaCheapest$167Average$376FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$243Average$328FlexibilityNo cancel feeOn-time62%
100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.