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Midway

$74+ Cheap flights from New York, NY (NYC) 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 1/7. Fares are subject to change and may not be available on all flights or dates of travel.
NYC — MDW
Dec 23 — Dec 301
Mon 12/23
Mon 12/30
1 adult, Economy
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The best prices from New York to Chicago Midway are usually found in January or June, booked 83 days in advance, depart on a Tuesday or Friday and return on a Wednesday

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 (NYC) 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 18, 2024.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$124
(CheapOair)

One-way from

$74
(Cheapflightsfares)

Popular in

May

Cheapest in

January

Average price

$399
Provider with most accurate pricing for New York (NYC)-Chicago Midway flight deals.
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Provider most trusted by Cheapflights users for New York (NYC)-Chicago Midway flights.
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From New York (NYC) to Chicago Midway
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One-way flight from New York (NYC) to Chicago Midway
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High demand for flights, 11% potential price rise
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Best time to find cheap flights, 7% potential price drop
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Average for round-trip flights in December 2024
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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 December 18, 2024.

This Southwest deal was found by Cheapflights users on 12/17. 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 12/312:30 pmLGA - MDW
Nonstop2h 30mSouthwest
Wed 1/88:05 pmMDW - LGA
Nonstop2h 05mSouthwest
Deal found 12/17$194
This Frontier deal was found by Cheapflights users on 12/17. 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 12/17$208
This eDestinos deal was found by Cheapflights users on 12/18. 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.
Tue 12/3110:00 pmEWR - MDW
1 stop24h 17mMultiple Airlines
Thu 1/27:17 amMDW - EWR
2 stops36h 43mMultiple Airlines
Deal found 12/18$264
This Delta deal was found by Cheapflights users on 12/17. 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.
Sun 12/296:00 amEWR - MDW
1 stop3h 50mDelta
Mon 1/66:28 pmMDW - EWR
1 stop3h 41mDelta
Deal found 12/17$288
This eDestinos deal was found by Cheapflights users on 12/17. 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.
Mon 12/308:55 amLGA - MDW
1 stop15h 19mMultiple Airlines
Thu 1/27:17 amMDW - LGA
2 stops23h 43mMultiple Airlines
Deal found 12/17$397
This Trip.com deal was found by Cheapflights users on 12/17. 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.
Thu 12/2611:00 amJFK - MDW
1 stop6h 57mFrontier
Sat 1/44:08 pmMDW - JFK
1 stop15h 55mFrontier
Deal found 12/17$419
This Delta deal was found by Cheapflights users on 12/17. 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 12/17$489

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 18, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Wed 1/29

11:00 am-7:06 pm

1 stop9h 06m

Chicago Midway

Fri 1/31

3:37 pm-1:59 pm

1 stop21h 22m

$124

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Sat 1/18

5:00 pm-10:02 am

1 stop18h 02m

Chicago Midway

Sun 1/26

10:58 am-9:45 am

1 stop21h 47m

$126

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

$145

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Fri 1/17

6:00 am-7:35 am

Nonstop2h 35m

Chicago Midway

Tue 1/21

6:00 am-9:10 am

Nonstop2h 10m

$148

NewarkChicago

EWR - MDW

EWRMDW

Newark

Tue 1/21

7:00 am-11:59 am

1 stop5h 59m

Chicago Midway

Wed 1/22

6:00 am-12:15 pm

1 stop5h 15m

$158

NewarkChicago

EWR - MDW

EWRMDW

Newark

Fri 1/24

10:00 pm-11:29 pm

1 stop26h 29m

Chicago Midway

Sun 1/26

7:25 am-9:01 am

1 stop24h 36m

$215

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Wed 1/8

7:05 am-1:08 pm

1 stop7h 03m

Chicago Midway

Wed 1/8

6:28 pm-11:14 pm

1 stop3h 46m

$296

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Tue 1/7

11:00 am-4:14 pm

1 stop6h 14m

$74

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Mon 3/17

9:45 pm-11:15 pm

Nonstop2h 30m

$74

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Wed 1/15

5:59 pm-3:13 pm

1 stop22h 14m

$75

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/17

Showing 1-10 of 18 results
1
2

Compare providers for flights from New York to Midway

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from New York to Midway in December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on New York-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on New York-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from New York-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on New York-Chicago Midway Airport flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for New York-Chicago Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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.

How far ahead should I book a flight from New York to Chicago Midway Airport?

Use this chart to determine the optimal time to book a round-trip flight from New York to Midway. Price data was last updated on December 13, 2024.

The price you pay for your flight from New York to Chicago Midway Airport may vary depending on when you book. For the best chance of a lower fare, look to book 81 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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

Currently, April is the cheapest month in which you can book a flight from New York to Chicago Midway Airport (average of $160). Flying from New York to Chicago Midway Airport in October is currently the most expensive (average of $232). 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 NYC 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 18, 2024.

It’s optimal to fly from New York to Chicago Midway Airport in the evening. By choosing this option you can save up to 23% on the cost of your flight, compared to a flight in the morning.

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 18, 2024.
Get a feel of what it's like to fly with Delta, Southwest and Frontier from New York to Chicago by reading reviews from past customers. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,848 reviews

Overall

8.1

Boarding

8.2

Crew

8.7

Food

7.2

Comfort

8.1

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
4,848 reviews
Southwest
8.1
Very good
4,848 reviews

Overall

8.1

Boarding

8.2

Crew

8.7

Food

7.2

Comfort

8.1

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
8,604 reviews
Southwest
8.1
Very good
4,848 reviews

Overall

8.1

Boarding

8.2

Crew

8.7

Food

7.2

Comfort

8.1

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
829 reviews
Southwest
8.1
Very good
4,848 reviews

Overall

8.1

Boarding

8.2

Crew

8.7

Food

7.2

Comfort

8.1

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
8,119 reviews
Southwest
8.1
Very good
4,848 reviews

Overall

8.1

Boarding

8.2

Crew

8.7

Food

7.2

Comfort

8.1

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
3,479 reviews
Southwest
8.1
Very good
4,848 reviews

Overall

8.1

Boarding

8.2

Crew

8.7

Food

7.2

Comfort

8.1

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 flying from New York to Chicago Midway Airport round-trip?

    Cheapflights users have booked flights from New York to Chicago Midway Airport round-trip from $124. Other airlines that can offer you cheap pricing are Southwest, from $148, and Delta, from $158. Frontier is priced at 58% lower than the current average price of a flight leaving 3 months from now.

  • What are the cheapest airlines to fly from New York to Chicago Midway Airport one-way?

    For one-way options, check prices for Frontier. According to our data, you can fly for as low as $74. Users have also found prices from $74 and $83 on Southwest and Delta, respectively.

  • What are the most popular routes from 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 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 New York to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from New York to Chicago Midway Airport (average of $160). Flying from New York to Chicago Midway Airport in October is currently the most expensive (average of $232). 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.

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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.
John F Kennedy Intl to O'Hare Intl flights
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LaGuardia to O'Hare Intl flights
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Newark to Rockford flights
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Stewart to Rockford flights
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Elmira to Midway flights
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Binghamton to Midway flights
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Stewart to Midway flights

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 December 18, 2024.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$115Average$145FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$147Average$256FlexibilityNo cancel feeOn-time63%
DeltaCheapest$167Average$347FlexibilityNo cancel feeOn-timeN/A
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