$109 Cheap Flights from Chicago (MDW) to New York (JFK)

View $109 flight on Sun, Nov 9, 2025Opens in a new window

Popular airlines from Chicago Midway Airport (MDW) to John F. Kennedy Intl. Airport (JFK)

Cheap Flights from Chicago to New York (MDW-JFK)

Prices were available within the past 7 days and start at $109 for one-way flights and $217 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Tue, Oct 21 - Tue, Oct 28
MDW
Chicago
JFK
New York
$217 Roundtrip, found 1 day ago
$217
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Oct 21 from Chicago to New York, returning Tue, Oct 28, priced at $217 found 1 day ago
Delta
Mon, Sep 22 - Tue, Oct 7
MDW
Chicago
JFK
New York
$220 Roundtrip, found 5 days ago
$220
Roundtrip
found 5 days ago
Select Delta flight, departing Mon, Sep 22 from Chicago to New York, returning Tue, Oct 7, priced at $220 found 5 days ago
Delta
Mon, Jan 5 - Tue, Jan 20
MDW
Chicago
JFK
New York
$223 Roundtrip, found 16 hours ago
$223
Roundtrip
found 16 hours ago
Select Delta flight, departing Mon, Jan 5 from Chicago to New York, returning Tue, Jan 20, priced at $223 found 16 hours ago
Frontier Airlines
Tue, Sep 30 - Sat, Oct 4
MDW
Chicago
JFK
New York
$224 Roundtrip, found 17 hours ago
$224
Roundtrip
found 17 hours ago
Select Frontier Airlines flight, departing Tue, Sep 30 from Chicago to New York, returning Sat, Oct 4, priced at $224 found 17 hours ago
Delta
Wed, Oct 29 - Sat, Nov 15
MDW
Chicago
JFK
New York
$227 Roundtrip, found 5 days ago
$227
Roundtrip
found 5 days ago
Select Delta flight, departing Wed, Oct 29 from Chicago to New York, returning Sat, Nov 15, priced at $227 found 5 days ago
Delta
Mon, Oct 27 - Sat, Nov 15
MDW
Chicago
JFK
New York
$230 Roundtrip, found 5 days ago
$230
Roundtrip
found 5 days ago
Select Delta flight, departing Mon, Oct 27 from Chicago to New York, returning Sat, Nov 15, priced at $230 found 5 days ago
Delta
Fri, Aug 15 - Thu, Aug 21
MDW
Chicago
JFK
New York
$231 Roundtrip, found 3 days ago
$231
Roundtrip
found 3 days ago
Select Delta flight, departing Fri, Aug 15 from Chicago to New York, returning Thu, Aug 21, priced at $231 found 3 days ago
Delta
Wed, Sep 24 - Fri, Oct 3
MDW
Chicago
JFK
New York
$232 Roundtrip, found 5 hours ago
$232
Roundtrip
found 5 hours ago
Select Delta flight, departing Wed, Sep 24 from Chicago to New York, returning Fri, Oct 3, priced at $232 found 5 hours ago
Delta
Mon, Jan 5 - Sat, Jan 24
MDW
Chicago
JFK
New York
$233 Roundtrip, found 16 hours ago
$233
Roundtrip
found 16 hours ago
Select Delta flight, departing Mon, Jan 5 from Chicago to New York, returning Sat, Jan 24, priced at $233 found 16 hours ago
Frontier Airlines
Tue, Sep 30 - Sun, Oct 5
MDW
Chicago
JFK
New York
$234 Roundtrip, found 10 hours ago
$234
Roundtrip
found 10 hours ago
Select Frontier Airlines flight, departing Tue, Sep 30 from Chicago to New York, returning Sun, Oct 5, priced at $234 found 10 hours ago

Find the cheapest month to fly from Chicago (MDW) to New York (JFK)

April is typically the cheapest month to fly

From $113 - $504 per traveler.

Graph displaying average flight prices per month

Flights from Chicago (MDW) to New York (JFK)
Origin airport
Midway Intl.
Destination airport
John F. Kennedy Intl.
Airlines serving
Delta, Frontier Airlines
Roundtrip price
$217
Distance
728 mi

Chicago to New York Flights

The cheapest times to fly from Chicago to New York

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to New York are during the month of October. You can find some of the cheapest flights from Chicago to New York with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to New York

Sunday is one of the best days to book for cheap flights from Chicago to New York: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Chicago to New York

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to New York in 2025. You can also book with separate airlines for your outbound and return journeys, from $109 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to New York flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to New York airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to John F. Kennedy Intl. Airport (JFK) cost?
Discover the latest flight deals from MDW to JFK by entering your preferred travel dates and searching on Expedia. Easily compare prices by departure date if you have flexibility with your schedule and use handy filters to explore prices for your preferred journey. As a member of One Key™, our free loyalty program, you can use Price Tracking to watch fares and receive notifications if prices go up or down.
What is the cheapest month to fly from MDW to JFK?
The cheapest flights from MDW to JFK are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
Which airlines fly direct from Midway Intl. Airport (MDW) to John F. Kennedy Intl. Airport (JFK)?
Although Chicago, IL (MDW-Midway Intl.) doesn't offer any direct flights to John F. Kennedy Intl. Airport (JFK), other airports have nonstop options. Leaving from O'Hare Intl. Airport (ORD) will get you to New York without any layovers.
What is the cheapest airline that flies from MDW to JFK?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that'll take you from MDW to JFK. Sort your results by "Price (lowest to highest)" to snap up a great deal.
How many flights per day from Midway Intl. Airport (MDW) to John F. Kennedy Intl. Airport (JFK)?
There are no daily direct flights from Midway Intl. Airport (MDW) to John F. Kennedy Intl. Airport (JFK). But you can opt for flights with layovers. Filter your search results on Expedia to include one or more stops, and you'll be on your way before you know it.
What day of the week has the most flights from MDW to JFK?
You'll generally find Tuesday the quietest day for flights, while Fridays tend to be the busiest.* However this can change from season to season and during peak travel times or public holidays.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Midway Intl. Airport (MDW) to John F. Kennedy Intl. Airport (JFK)?
Select a flight from Midway Intl. Airport (MDW) to John F. Kennedy Intl. Airport (JFK) that leaves before 3 PM to reduce the risk of cancellations. Departures after this time have a 22% higher chance of being canceled, on average.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for New York from Midway Intl. Airport (MDW)?
Explore your flight options from Midway Intl. Airport (MDW) to LaGuardia Airport (LGA). This is the only New York airport you can jet into if you're taking a direct flight.
Is it cheaper to buy a plane ticket from Midway Intl. Airport (MDW) to John F. Kennedy Intl. Airport (JFK) last-minute?
Last-minute fares from MDW to JFK are generally more expensive. To lock in the best rates, start looking for flights ahead of time. That being said, if you can play around with your travel dates, you may find a cheap fare just before your departure.
Is it cheaper to book a MDW to JFK flight and hotel package?
Compared with arranging flights and hotels separately, booking a MDW to JFK flight and hotel package with Expedia could result in significant savings. Better yet, having everything in one easy place takes the hassle out of travel planning. Simply pick your flights and choose from our wide range of hotels, then customize your trip with other add-ons like tours, activities and car rentals.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to John F. Kennedy Intl. Airport (JFK)?
You can usually cancel or reschedule your MDW to JFK flight. However, if it's been more than 24 hours since booking, additional charges may apply. Check your airline's policies in your itinerary to see what changes are allowed and if any costs are involved. You'll also find further details on our Customer Service portal.

Explore a world of travel with Expedia

*Available to One Key members.