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Midway

$69+ 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 5/27. Fares are subject to change and may not be available on all flights or dates of travel.
NYC — MDW
Mar 31 — Apr 71
Mon 3/31
Mon 4/7
1 adult, Economy
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1. Tell us where you want to go
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Cheapflights Tip: The best prices from New York to Chicago Midway are usually found in January or October, booked 82 days in advance, depart on a Wednesday 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 March 26, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$149
(Southwest)

One-way from

$69
(Southwest)

Popular in

July

Cheapest in

January

Average price

$305

Good round-trip deal

$213 or less

Good one-way deal

$138 or less
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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Highest demand for flights based on searches. 15% potential increase in price ($52 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in March 2025
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Price to beat on a round-trip flight from New York (NYC) to Chicago Midway.
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Price to beat on a one-way flight from New York (NYC) 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 March 26, 2025.

This Southwest deal was found by Cheapflights users on 3/25. 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 5/19:10 amLGA - MDW
Nonstop2h 30mSouthwest
Mon 5/56:10 amMDW - LGA
Nonstop2h 00mSouthwest
Deal found 3/25$149
This Delta deal was found by Cheapflights users on 3/25. 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 5/712:47 pmEWR - MDW
1 stop5h 58mDelta
Sat 5/109:20 amMDW - EWR
1 stop7h 10mDelta
Deal found 3/25$179
This Mytrip deal was found by Cheapflights users on 3/25. 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.
Fri 6/69:55 amEWR - MDW
1 stop5h 08mAllegiant Air
Mon 6/98:36 pmMDW - EWR
1 stop11h 29mAllegiant Air
Deal found 3/25$218
This Frontier deal was found by Cheapflights users on 3/25. 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 3/25$238
This Frontier deal was found by Cheapflights users on 3/25. 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 4/91:00 pmJFK - MDW
1 stop9h 33mFrontier
Sat 4/1212:58 pmMDW - JFK
1 stop10h 45mFrontier
Deal found 3/25$238
This CheapOair deal was found by Cheapflights users on 3/25. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/710:55 pmLGA - MDW
1 stop22h 58mFrontier
Sat 6/147:40 amMDW - LGA
1 stop12h 19mFrontier
Deal found 3/25$242
This Mytrip deal was found by Cheapflights users on 3/25. 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 5/299:55 pmEWR - MDW
2 stops21h 15mMultiple Airlines
Mon 6/28:04 pmMDW - EWR
1 stop12h 01mMultiple Airlines
Deal found 3/25$276
This Delta deal was found by Cheapflights users on 3/26. 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 4/227:15 amJFK - MDW
1 stop6h 20mDelta
Tue 4/296:04 amMDW - JFK
1 stop5h 26mDelta
Deal found 3/26$297
This Mytrip deal was found by Cheapflights users on 3/25. 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 6/1211:11 amSWF - MDW
2 stops27h 52mAllegiant Air
Sun 6/1511:45 amMDW - SWF
1 stop21h 46mAllegiant Air
Deal found 3/25$342
This eDestinos deal was found by Cheapflights users on 3/25. 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 4/411:29 amJFK - MDW
1 stop28h 31mMultiple Airlines
Fri 4/181:05 pmMDW - JFK
2 stops20h 18mMultiple Airlines
Deal found 3/25$486

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 March 26, 2025.
Use the filters below to find and compare flights from New York 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

Thu 5/1

9:10 am-10:40 am

Nonstop2h 30m

Chicago Midway

Mon 5/5

6:10 am-9:10 am

Nonstop2h 00m

$149

NewarkChicago

EWR - MDW

EWRMDW

Newark

Wed 5/7

12:47 pm-5:45 pm

1 stop5h 58m

Chicago Midway

Sat 5/10

9:20 am-5:30 pm

1 stop7h 10m

$179

NewarkChicago

EWR - MDW

EWRMDW

Newark

Fri 6/6

9:55 am-2:03 pm

1 stop5h 08m

Chicago Midway

Mon 6/9

8:36 pm-9:05 am

1 stop11h 29m

$218

NewarkChicago

EWR - MDW

EWRMDW

Newark

Mon 4/7

10:00 pm-9:11 am

1 stop12h 11m

Chicago Midway

Wed 4/9

2:26 pm-9:00 pm

1 stop5h 34m

$238

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Wed 4/9

1:00 pm-9:33 pm

1 stop9h 33m

Chicago Midway

Sat 4/12

12:58 pm-12:43 am

1 stop10h 45m

$238

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Sat 6/7

10:55 pm-8:53 pm

1 stop22h 58m

Chicago Midway

Sat 6/14

7:40 am-8:59 pm

1 stop12h 19m

$242

NewarkChicago

EWR - MDW

EWRMDW

Newark

Thu 5/29

9:55 pm-6:10 pm

2 stops21h 15m

Chicago Midway

Mon 6/2

8:04 pm-9:05 am

1 stop12h 01m

$276

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Tue 4/22

7:15 am-12:35 pm

1 stop6h 20m

Chicago Midway

Tue 4/29

6:04 am-12:30 pm

1 stop5h 26m

$297

New WindsorChicago

SWF - MDW

SWFMDW

New Windsor Stewart

Thu 6/12

11:11 am-2:03 pm

2 stops27h 52m

Chicago Midway

Sun 6/15

11:45 am-10:31 am

1 stop21h 46m

$342

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Fri 4/18

11:30 am-3:00 pm

1 stop28h 30m

Chicago Midway

Sun 4/20

8:50 pm-10:23 am

2 stops36h 33m

$487

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/25

Showing 1-10 of 22 results
1
2
3

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 March.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy1 starTrust Score*2 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.

Cheapflights Insights

Everything you need to know about your flight from New York to Chicago Midway Airport

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 March 21, 2025.

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 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 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 March 26, 2025.

It’s optimal to fly from New York to Chicago Midway Airport in the evening. By choosing this option you can save up to 33% on the cost of your flight, compared to a flight in the afternoon.

What is the cheapest day to fly from New York to Chicago Midway Airport?

Use this chart to determine the cheapest time to fly round-trip from New York to Midway. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their New York to Chicago Midway Airport flight should consider departing on Friday evenings when fares are most often at their lowest. Saturday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from New York to Chicago Midway Airport

Explore weekly flight availability from New York to Midway. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated March 26, 2025.

The most flights from NYC to MDW are scheduled on a Monday (7 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (1 on average).

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 March 26, 2025.
Get a feel of what it's like to fly with Southwest, Delta and Allegiant Air 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
4,273 reviews

Entertainment

7.6

Crew

8.6

Overall

8.1

Boarding

8.2

Comfort

8.1

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.1
Very good
4,273 reviews
Southwest
8.1
Very good
4,273 reviews

Entertainment

7.6

Crew

8.6

Overall

8.1

Boarding

8.2

Comfort

8.1

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Delta
8.0
Very good
7,891 reviews
Southwest
8.1
Very good
4,273 reviews

Entertainment

7.6

Crew

8.6

Overall

8.1

Boarding

8.2

Comfort

8.1

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Allegiant Air
7.3
Good
730 reviews
Southwest
8.1
Very good
4,273 reviews

Entertainment

7.6

Crew

8.6

Overall

8.1

Boarding

8.2

Comfort

8.1

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Frontier
6.0
Okay
3,272 reviews
Southwest
8.1
Very good
4,273 reviews

Entertainment

7.6

Crew

8.6

Overall

8.1

Boarding

8.2

Comfort

8.1

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

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 $149. Other airlines that can offer you cheap pricing are Delta, from $179, and Allegiant Air, from $218. Southwest is priced at 48% 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 Southwest. According to our data, you can fly for as low as $69. Users have also found prices from $79 and $113 on Delta and Frontier, 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 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?

Book flights to New York if you plan to visit one of these locations
Merrillville
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Hammond
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Porter
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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 March 26, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$88Average$145FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$148Average$249FlexibilityNo cancel feeOn-time63%
DeltaCheapest$203Average$423FlexibilityNo cancel feeOn-timeN/A
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