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$98+ 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 8/19. Fares are subject to change and may not be available on all flights or dates of travel.
JFK — MDW
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
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 June 12, 2025.

Round-trip from

$184
(Booking.com)

One-way from

$98
(FlightHub)

Popular in

December

Cheapest in

May

Average price

$381
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. 26% potential increase in price ($133 potential increase over avg. RT price).
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Cheapest flight prices on average. 12% potential price decrease ($41 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 12, 2025.

This Mytrip deal was found by Cheapflights users on 6/10. 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.
Sat 9/201:01 pmJFK - MDW
1 stop11h 08mFrontier
Tue 9/238:00 amMDW - JFK
1 stop22h 28mFrontier
Deal found 6/10$182
This Delta deal was found by Cheapflights users on 6/12. 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 11/2410:00 amJFK - MDW
1 stop9h 36mDelta
Tue 12/29:30 amMDW - JFK
1 stop7h 42mDelta
Deal found 6/12$238

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 June 12, 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

Tue 9/9

1:01 pm-10:58 pm

1 stop10h 57m

Chicago Midway

Tue 9/16

8:00 am-12:40 am

1 stop15h 40m

$184

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Tue 8/19

12:29 pm-5:47 pm

1 stop6h 18m

Chicago Midway

Tue 8/26

9:30 am-8:12 pm

1 stop9h 42m

$260

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Tue 8/19

1:00 pm-2:01 pm

1 stop26h 01m

$98

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Wed 7/9

1:00 pm-6:40 pm

1 stop6h 40m

$146

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Thu 7/10

11:29 am-9:41 am

2 stops23h 12m

$280

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/9

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 June 12, 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 June 12, 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
7,946 reviews

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Overall

8.0

Food

7.3

Crew

8.5

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
7,946 reviews
Delta
8.0
Very good
7,946 reviews

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Overall

8.0

Food

7.3

Crew

8.5

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
3,295 reviews
Delta
8.0
Very good
7,946 reviews

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Overall

8.0

Food

7.3

Crew

8.5

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 $184. Another option worth looking into is Delta, starting at $253 round trip. Frontier is currently priced 49% 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
Lansing
Benton Harbor
Porter
Hammond
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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$294Average$474FlexibilityNo cancel feeOn-timeN/A

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