What is the cheapest day to fly from New York John F Kennedy Intl Airport to Chicago Midway Airport?

Travelers seeking maximum savings on their New York John F Kennedy Intl Airport to Chicago Midway Airport flight should consider departing on Tuesday mornings when fares are most often at their lowest. Sunday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

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.

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).

What is the cheapest day to fly round-trip from New York John F Kennedy Intl Airport to Chicago Midway Airport?

Saturday flights are found to be more expensive to fly from New York John F Kennedy Intl Airport to Chicago Midway Airport. This shouldn’t discourage you from searching, as you can still find great deals by being flexible with your options. Use our search form to find deals on tickets to Chicago Midway Airport.

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

Due to multiple factors, expect to potentially pay more when booking in June. For low rates, September can be a great choice for travel to Chicago Midway Airport. Flights to Chicago Midway Airport from New York John F Kennedy Intl Airport in September are about $232 on average during September, but can be found for as low as $75.

What is the cheapest time of day to fly from JFK to MDW?

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.

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.

$109+ Flights from New York John F Kennedy Intl Airport, NY to Chicago Midway Airport

Q: How far in advance should I book a flight from New York John F Kennedy Intl Airport to Chicago Midway Airport?

To save on the cost of your flight from New York John F Kennedy Intl Airport to Chicago Midway Airport, book at least 36 days before your planned departure. Booking around this time can save you about 93% on the cost of this flight compared to booking a flight leaving this week. We have found prices from $234 if you need a flight within two weeks. For flights within the next 72 hours, you can find tickets from as low as $367.

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Cheap flight deals from John F Kennedy Intl to Midway

Round-trip from	$218 (Frontier)
One-way from	$109 (Frontier)
Popular in	December
Cheapest in	May
Average price	$511

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. 22% potential increase in price ($112 potential increase over avg. RT price).

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Cheapest flight prices on average. 11% potential price decrease ($39 potential savings vs. average RT price).

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Average for round-trip flights in August 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 August 1, 2025.

Sat 11/16:15 amJFK - MDW

1 stop17h 54mFrontier

Wed 11/58:00 amMDW - JFK

1 stop15h 40mFrontier

Deal found 7/29

$206

Tue 8/197:45 pmJFK - MDW

1 stop23h 52mDelta

Tue 8/261:08 pmMDW - JFK

1 stop9h 30mDelta

Deal found 7/30

$262

Best flights from John F Kennedy Intl to Midway
Discover carefully curated flight deals from John F Kennedy Intl to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 1, 2025.

Wed 8/276:00 amJFK - MDW

1 stop9h 01mFrontier

Wed 9/33:03 pmMDW - JFK

1 stop9h 10mFrontier

Deal found 7/30

$218

Tue 8/197:45 pmJFK - MDW

1 stop23h 52mDelta

Tue 8/261:08 pmMDW - JFK

1 stop9h 30mDelta

Deal found 7/30

$262

Last-minute flights from John F Kennedy Intl to Midway
Discover last-minute flight deals from John F Kennedy Intl to Midway. Data last updated August 1, 2025 and is based on user searches.

Wed 8/67:30 amJFK - MDW

1 stop6h 36mDelta

Tue 8/126:17 pmMDW - JFK

1 stop4h 21mDelta

Deal found 8/1

$380

Thu 8/79:00 amJFK - MDW

1 stop5h 47mFrontier

Tue 8/1211:39 amMDW - JFK

1 stop12h 03mFrontier

Deal found 7/31

$228

Sat 8/239:35 pmJFK - MDW

1 stop12h 00mDelta

Tue 8/261:08 pmMDW - JFK

1 stop9h 30mDelta

Deal found 7/30

$257

Wed 8/276:00 amJFK - MDW

1 stop9h 01mFrontier

Wed 9/33:03 pmMDW - JFK

1 stop9h 10mFrontier

Deal found 7/30

$218

One-way flights from John F Kennedy Intl to Midway
Search for one-way flight options from John F Kennedy Intl to Midway. Find affordable one-way fares based on user searches. Data last updated August 1, 2025.

Wed 8/279:00 amJFK - MDW

1 stop6h 01mFrontier

Deal found 7/31

$109

Tue 8/197:22 amJFK - MDW

1 stop6h 06mDelta

Deal found 7/31

$179

Cheapflights Fare Finder

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

Fly to

Route

Depart

Return

Price

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Wed 8/27

6:00 am-2:01 pm

1 stop9h 01m

Chicago Midway

Wed 9/3

3:03 pm-1:13 am

1 stop9h 10m

$218

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Tue 8/19

7:45 pm-6:37 pm

1 stop23h 52m

Chicago Midway

Tue 8/26

1:08 pm-11:38 pm

1 stop9h 30m

$262

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Wed 8/27

9:00 am-2:01 pm

1 stop6h 01m

$109

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Tue 8/19

7:22 am-12:28 pm

1 stop6h 06m

$179

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/31

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.

Reviews of airlines servicing Midway

Read reviews from past customers who have flown Delta and Frontier from New York John F Kennedy Intl Airport to Chicago Midway Airport. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.

Delta

8.0

Very good

7,981 reviews

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

7,981 reviews

Delta

8.0

Very good

7,981 reviews

Reviews

1 / 20

10.0

Excellent

Kymberlee,Oct 2024

JFK - ATL

Frontier

5.9

Fair

3,239 reviews

Delta

8.0

Very good

7,981 reviews

Reviews

1 / 20

10.0

Excellent

Kymberlee,Oct 2024

JFK - ATL

Related info for your journey

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 $218. Another option worth looking into is Delta, starting at $262 round trip. Frontier is currently priced 43% 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.

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Top airline flying from John F Kennedy Intl to Midway

Airline	Cheapest	Average	Flexibility	On-time
Delta	Cheapest$294	Average$417	FlexibilityNo cancel fee	On-timeN/A

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$109+ 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 8/27. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from John F Kennedy Intl to Midway with Cheapflights

1. Tell us where you want to go

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Cheap flight deals from John F Kennedy Intl to Midway

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Find flight deals from John F Kennedy Intl to Midway

Cheapest flights from John F Kennedy Intl to MidwayExplore 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 August 1, 2025.

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 August 1, 2025.

Cheapflights Fare Finder

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.

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.

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?

Reviews of airlines servicing Midway

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?

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

How can I 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?

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

Traveling to a place near Chicago Midway Airport?

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Alternative routes for John F Kennedy Intl to Midway

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Top airline flying from John F Kennedy Intl to Midway

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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 August 1, 2025.