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$74+ Cheap flights from John F Kennedy Intl, NY (JFK) 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 4/1. Fares are subject to change and may not be available on all flights or dates of travel.
JFK — MDW
Mar 26 — Apr 21
Wed 3/26
Wed 4/2
1 adult, Economy
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Cheap flight deals from John F Kennedy Intl to Midway

Discover tips and strategies to find the most affordable flight options for your journey from John F Kennedy Intl (JFK) 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 21, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$240
(Frontier)

One-way from

$74
(Trip.com)

Popular in

December

Cheapest in

January

Average price

$355
Provider with most accurate pricing for New York John F Kennedy Intl-Chicago Midway flight deals.
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Provider most trusted by Cheapflights users for New York John F Kennedy Intl-Chicago Midway flights.
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From New York John F Kennedy Intl to Chicago Midway
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One-way flight from New York John F Kennedy Intl to Chicago Midway
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Highest demand for flights based on searches. 15% potential increase in price ($78 potential increase over avg. RT price).
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Cheapest flight prices on average. 8% potential price decrease ($34 potential savings vs. average RT price).
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Average for round-trip flights in March 2025
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Find flight deals from John F Kennedy Intl to Midway

Cheapest flights from John F Kennedy Intl to Midway
Explore the most affordable flight options available from John F Kennedy Intl to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 21, 2025.

This Frontier deal was found by Cheapflights users on 3/21. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/21:00 pmJFK - MDW
1 stop9h 33mFrontier
Wed 4/912:46 pmMDW - JFK
1 stop10h 57mFrontier
Deal found 3/21$240
This Delta deal was found by Cheapflights users on 3/20. 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.
Mon 5/58:40 amJFK - MDW
2 stops14h 42mDelta
Sat 5/179:20 amMDW - JFK
1 stop12h 54mDelta
Deal found 3/20$284
This eDestinos deal was found by Cheapflights users on 3/19. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/41:00 pmJFK - MDW
2 stops34h 01mMultiple Airlines
Fri 4/187:25 amMDW - JFK
2 stops25h 58mMultiple Airlines
Deal found 3/19$540

Cheapflights Fare Finder

Customize your flight search to find flights from John F Kennedy Intl 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 21, 2025.
Use the filters below to find and compare flights from New York John F Kennedy Intl Airport to Chicago Midway Airport that are best for you.

Fly from

John F Kennedy Intl

Fly to

Midway

Route

Depart

Return

Price

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Wed 4/2

1:00 pm-9:33 pm

1 stop9h 33m

Chicago Midway

Tue 4/8

4:40 pm-12:43 am

1 stop7h 03m

$240

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Mon 5/5

8:40 am-10:22 pm

2 stops14h 42m

Chicago Midway

Sat 5/17

9:20 am-11:14 pm

1 stop12h 54m

$284

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Fri 4/4

1:00 pm-10:01 pm

2 stops34h 01m

Chicago Midway

Fri 4/18

7:25 am-10:23 am

2 stops25h 58m

$540

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Tue 4/1

6:59 am-5:23 am

1 stop23h 24m

$74

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Wed 5/28

7:15 am-6:45 pm

1 stop12h 30m

$107

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Thu 7/31

11:29 am-9:41 am

2 stops23h 12m

$286

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/20

Compare providers for flights from John F Kennedy Intl 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 John F Kennedy Intl 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
PricelinePrice Accuracy1 starTrust 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 John F Kennedy Intl Airport-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 John F Kennedy Intl Airport-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from New York John F Kennedy Intl Airport-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on New York John F Kennedy Intl Airport-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 John F Kennedy Intl Airport-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 John F Kennedy Intl to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from John F Kennedy Intl 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 John F Kennedy Intl Airport to Chicago Midway Airport

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

Currently, April is the cheapest month in which you can book a flight from New York John F Kennedy Intl Airport to Chicago Midway Airport (average of $160). Flying from New York John F Kennedy Intl Airport 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 JFK to MDW?

Find hourly flight availability from John F Kennedy Intl 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 21, 2025.

It’s typically best to fly out from New York John F Kennedy Intl Airport to Chicago Midway Airport at noon. Doing so could potentially save you 38% on the flight price compared to flying in the morning, which is usually more expensive.

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 21, 2025.
Peruse reviews from past customers who have flown with Delta and Frontier from New York to Chicago to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,895 reviews

Comfort

8.0

Entertainment

7.9

Overall

8.0

Crew

8.5

Boarding

8.2

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kymberlee,Oct 2024

JFK - ATL

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.
Delta
8.0
Very good
7,895 reviews
Delta
8.0
Very good
7,895 reviews

Comfort

8.0

Entertainment

7.9

Overall

8.0

Crew

8.5

Boarding

8.2

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kymberlee,Oct 2024

JFK - ATL

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.
Frontier
6.0
Okay
3,272 reviews
Delta
8.0
Very good
7,895 reviews

Comfort

8.0

Entertainment

7.9

Overall

8.0

Crew

8.5

Boarding

8.2

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kymberlee,Oct 2024

JFK - ATL

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.

Related info for your journey

Find useful and relevant information for your journey from John F Kennedy Intl 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 John F Kennedy Intl Airport to Chicago Midway Airport round-trip?

    Flying on Frontier is currently your cheapest option to Chicago Midway Airport, with prices starting at $240. Another option worth looking into is Delta, starting at $283 round trip. Frontier is currently priced 45% below the average price you’ll pay for this route.

  • Can I find deals for flights from John F Kennedy Intl to Midway that include hotel bookings?

    Yes. In addition to deals on John F Kennedy Intl to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from John F Kennedy Intl to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from John F Kennedy Intl to Midway.

  • Can I find deals for business class flights from John F Kennedy Intl to Midway?

    Yes. Cheapflights offers flight deals from John F Kennedy Intl 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 John F Kennedy Intl Airport to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from New York John F Kennedy Intl Airport to Chicago Midway Airport (average of $160). Flying from New York John F Kennedy Intl Airport 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 John F Kennedy Intl Airport?

Book flights to New York John F Kennedy Intl Airport if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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Top airline flying from John F Kennedy Intl to Midway

Discover the top airline that operate flights from John F Kennedy Intl 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 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$294Average$477FlexibilityNo cancel feeOn-timeN/A
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