Cheap Flight Tickets from New York (JFK) to Chicago (MDW), Starting at $168

Good to Know: Cheapest and Fastest JFK - MDW Flights

Useful information for finding best airline tickets from John F Kennedy International to Chicago Midway International on your next trip.

Cheapest Round Trip Flight

$417

DL Delta Airlines • 1 stop • 9h 15m

Dec 18 – Jan 05

The cheapest round trip flight from New York to Chicago (JFK-MDW-JFK) is currently $417

🔍 Search Flights

Cheapest One way Flight

$168

DL Delta Airlines • 1 stop • 10h 59m

Sep 05

The cheapest one way flight from New York to Chicago (JFK-MDW) is currently $168

🔍 Search Flights

Fastest Flight

8h 49m

The fastest nonstop flight from New York to Chicago (JFK-MDW) takes 8h 49m

Top Airlines Flying from New York to Chicago

Delta Airline, DL

Delta Airlines

Southwest Airlines-WN

Southwest Airlines

United Airlines, UA

United Airlines

American Airlines, AA

American Airlines

Aeromexico Airline (AM)

Aeromexico

Latest Flight Deals from New York (JFK) to Chicago (MDW)

Compare and book low fare round-trip air tickets from New York to Chicago. Ideal for travelers with confirmed return itineraries.

Dec 18 - Jan 05, Economy
DL
New York → Chicago
9h 15m
11:55 AM - 4:50 PM • 1 stop
DL
New York → Chicago
3h 45m
1:30 PM - 4:55 PM • nonstop
$417
Delta Airlines
Dec 18 - Jan 05, Economy
DL
New York → Chicago
9h 19m
7:00 AM - 11:59 AM • 1 stop
DL
New York → Chicago
3h 40m
6:00 AM - 9:20 AM • nonstop
$417
Delta Airlines
Dec 18 - Jan 05, Economy
DL
New York → Chicago
10h 51m
7:10 AM - 1:01 PM • 1 stop
DL
New York → Chicago
3h 40m
6:00 AM - 9:20 AM • nonstop
$417
Delta Airlines
Dec 18 - Jan 05, Economy
DL
New York → Chicago
9h 8m
11:29 AM - 4:17 PM • 1 stop
DL
New York → Chicago
3h 44m
10:40 AM - 2:04 PM • nonstop
$417
Delta Airlines
Dec 18 - Jan 05, Economy
DL
New York → Chicago
8h 49m
6:00 AM - 10:29 AM • 1 stop
DL
New York → Chicago
3h 45m
1:30 PM - 4:55 PM • nonstop
$417
Delta Airlines
Dec 18 - Jan 05, Economy
DL
New York → Chicago
10h 5m
12:56 PM - 6:01 PM • 1 stop
DL
New York → Chicago
3h 45m
1:30 PM - 4:55 PM • nonstop
$417
Delta Airlines

Fly from New York to Chicago with the Best Airfare Deals on FareLeaders

Looking for a cheap last-minute deal or the best round-trip flight from New York to Chicago? Find the biggest savings on one-way and round-trip tickets right here.

FAQs on New York to Chicago Flights

What are the airports in New York?
JFK,LGA,EWR
What’s the most popular airline flying from JFK to MDW?
The most popular airline flying from New York to Chicago are
Can I fly from JFK to MDW non-stop?
NO
Which airlines fly nonstop between New York and Chicago?
The non-stop flights between New York and Chicago are .
What’s the earliest departure time from JFK to MDW Airport?
The earliest flight leaves JFK at 6:00 am and lands in MDW - Chicago Midway International
What are the airports in Chicago?
ORD,MDW
Can I make changes to my New York to Chicago flight tickets or cancel them on FareLeaders.com?
No. We are an airfare comparison site. All the tickets are booked by the travel agent offering the flight deal and any changes or cancellations to be made are directly done directly by them or the airlines.
Can I cancel my flight tickets from JFK to MDW?
Read the fare rules of the New York to Chicago air tickets booked. Some airlines allow you to cancel the tickets within a stipulated time period with a cancellation fee.
Which airline alliances offer flights from New York and Chicago?
operate flights between New York and Chicago
How long does a flight from New York to Chicago take?
It takes approximately 2 hour to fly non-stop from JFK to MDW, which is 731.63 miles by air.
Which airlines provide the cheapest flights from New York (JFK) to Chicago (MDW) ?
In the past couple of days, the cheapest tickets to MDW from JFK were found on DL : USD 168
Do I need a passport to fly between JFK and MDW?
No
What’s the latest departure time from JFK to MDW ?
The last flight leaves JFK at 5:40 pm

New York (JFK) to Chicago (MDW): Airport Information

Origin Airport John F Kennedy International , New York, US
Destination Airport Chicago Midway International , Chicago, US
Distance 732 miles

More Flight Options for New York (JFK) and Chicago (MDW)

Why Fareleaders for JFK to MDW Plane Tickets

Lowest Prices
Lowest Prices
Uncover the best deals on New York to Chicago flights by comparing fares from hundreds of airlines and agencies.
New Deals
New Deals Everyday
Get the best prices on JFK to MDW flights—we update our fares daily so you never miss a saving.
Best Travel Options
No Service Fees
Compare hundreds of New York to Chicago flights and secure the best deals—we never add any service fees.
Get Fare Drop Alert
Be the first to know when fares drop for the New York (JFK) to Chicago (MDW)
Terms and Conditions*