What is the cheapest airline to fly 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 $146. Frontier is currently priced 59% below the average price you’ll pay for this route.

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 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 December. 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 $229 on average during September, but can be found for as low as $74.

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.

$77+ Flights from New York John F Kennedy Intl Airport, NY to Chicago Midway Airport

Q: 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.

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 90% on the cost of this flight compared to booking a flight leaving this week. We have found prices from $228 if you need a flight within two weeks. For flights within the next 72 hours, you can find tickets from as low as $375.

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Cheap flight deals from John F Kennedy Intl to Midway

Round-trip from	$146 (Priceline)
One-way from	$77 (Priceline)
Popular in	December
Cheapest in	May
Average price	$302

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. 27% potential increase in price ($136 potential increase over avg. RT price).

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Cheapest flight prices on average. 12% potential price decrease ($42 potential savings vs. average RT price).

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Average for round-trip flights in July 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 July 3, 2025.

Fri 10/249:00 amJFK - MDW

1 stop10h 18mFrontier

Sun 10/2610:03 pmMDW - JFK

1 stop11h 22mFrontier

Deal found 7/2

$146

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 July 3, 2025.

Fri 9/59:00 amJFK - MDW

1 stop7h 58mFrontier

Mon 9/85:04 pmMDW - JFK

1 stop6h 38mFrontier

Deal found 7/2

$146

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 July 3, 2025 and is based on user searches.

Thu 7/106:20 amJFK - MDW

1 stop8h 27mFrontier

Thu 7/102:55 pmMDW - JFK

1 stop8h 47mFrontier

Deal found 7/1

$205

Sat 7/127:22 amJFK - MDW

1 stop6h 07mDelta

Tue 7/221:09 pmMDW - JFK

1 stop4h 33mDelta

Deal found 6/30

$300

Sat 8/239:00 amJFK - MDW

1 stop15h 08mFrontier

Mon 8/256:15 amMDW - JFK

1 stop24h 14mFrontier

Deal found 7/3

$155

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 July 3, 2025.

Mon 8/46:59 amJFK - MDW

1 stop9h 07mFrontier

Deal found 7/3

$77

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

Fri 10/24

9:00 am-6:18 pm

1 stop10h 18m

Chicago Midway

Sun 10/26

10:03 pm-10:25 am

1 stop11h 22m

$146

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Mon 8/4

6:59 am-3:06 pm

1 stop9h 07m

$77

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/3

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?

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.

How much does it cost to fly round-trip from New York John F Kennedy Intl Airport to Chicago Midway Airport?

Reviews of airlines servicing Midway

Read reviews from past customers who have flown 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.

Frontier

5.9

Fair

3,286 reviews

Reviews

1 / 20

8.0

Excellent

Anonymous,Jun 2025

TTN - TPA

TTN is a small airport for Frontier. Drop off is easy as is parking. The location is remote so there is zero traffic. The place could use a renovation but for the price you pay it is not necessary. Good-Staff is very friendly. Flight left on time. Bad- run down, deplaning/boarding on the tarmac. I got wet on the stairs outside of the plane while waiting to board.

Frontier

5.9

Fair

3,286 reviews

Frontier

5.9

Fair

3,286 reviews

Reviews

1 / 20

8.0

Excellent

Anonymous,Jun 2025

TTN - TPA

Related info for your journey

What is the cheapest airline to fly 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 $146. Frontier is currently priced 59% 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$474	FlexibilityNo cancel fee	On-timeN/A

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$77+ 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 8/4. 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

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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 July 3, 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 July 3, 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?

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 July 3, 2025.

How much does it cost to fly round-trip from New York John F Kennedy Intl Airport to Chicago Midway Airport?

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 July 3, 2025.

Read reviews from past customers who have flown 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.

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 is the cheapest airline to fly 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 New York John F Kennedy Intl 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 July 3, 2025.