Cheap Flights from New York (JFK) to Chicago (MDW) from HK$1,166~

View HK$1,166 flight on Sat, 18 Oct 2025Opens in a new window

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

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

Prices were available within the past 7 days and start at HK$1,166 for one-way flights and HK$2,697 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Wed, 1 Oct - Thu, 16 Oct
JFK
New York
MDW
Chicago
HK$2,697 Return, found 5 days ago
HK$2,697
Return
found 5 days ago
Select Delta flight, departing Wed, 1 Oct from New York to Chicago, returning Thu, 16 Oct, priced at HK$2,697 found 5 days ago
Delta
Wed, 1 Oct - Thu, 16 Oct
JFK
New York
MDW
Chicago
HK$2,794 Return, found 5 days ago
HK$2,794
Return
found 5 days ago
Select Delta flight, departing Wed, 1 Oct from New York to Chicago, returning Thu, 16 Oct, priced at HK$2,794 found 5 days ago
Delta
Wed, 1 Oct - Thu, 16 Oct
JFK
New York
MDW
Chicago
HK$2,837 Return, found 5 days ago
HK$2,837
Return
found 5 days ago
Select Delta flight, departing Wed, 1 Oct from New York to Chicago, returning Thu, 16 Oct, priced at HK$2,837 found 5 days ago
Delta
Wed, 1 Oct - Thu, 16 Oct
JFK
New York
MDW
Chicago
HK$2,933 Return, found 5 days ago
HK$2,933
Return
found 5 days ago
Select Delta flight, departing Wed, 1 Oct from New York to Chicago, returning Thu, 16 Oct, priced at HK$2,933 found 5 days ago
Delta
Wed, 1 Oct - Thu, 16 Oct
JFK
New York
MDW
Chicago
HK$2,944 Return, found 5 days ago
HK$2,944
Return
found 5 days ago
Select Delta flight, departing Wed, 1 Oct from New York to Chicago, returning Thu, 16 Oct, priced at HK$2,944 found 5 days ago
Delta
Wed, 1 Oct - Thu, 16 Oct
JFK
New York
MDW
Chicago
HK$3,041 Return, found 5 days ago
HK$3,041
Return
found 5 days ago
Select Delta flight, departing Wed, 1 Oct from New York to Chicago, returning Thu, 16 Oct, priced at HK$3,041 found 5 days ago
Delta
Wed, 6 Aug - Thu, 7 Aug
JFK
New York
MDW
Chicago
HK$3,062 Return, found 5 days ago
HK$3,062
Return
found 5 days ago
Select Delta flight, departing Wed, 6 Aug from New York to Chicago, returning Thu, 7 Aug, priced at HK$3,062 found 5 days ago
Delta
Wed, 1 Oct - Thu, 16 Oct
JFK
New York
MDW
Chicago
HK$3,105 Return, found 5 days ago
HK$3,105
Return
found 5 days ago
Select Delta flight, departing Wed, 1 Oct from New York to Chicago, returning Thu, 16 Oct, priced at HK$3,105 found 5 days ago
Delta
Wed, 1 Oct - Thu, 16 Oct
JFK
New York
MDW
Chicago
HK$3,245 Return, found 5 days ago
HK$3,245
Return
found 5 days ago
Select Delta flight, departing Wed, 1 Oct from New York to Chicago, returning Thu, 16 Oct, priced at HK$3,245 found 5 days ago
Delta
Wed, 1 Oct - Thu, 16 Oct
JFK
New York
MDW
Chicago
HK$3,353 Return, found 5 days ago
HK$3,353
Return
found 5 days ago
Select Delta flight, departing Wed, 1 Oct from New York to Chicago, returning Thu, 16 Oct, priced at HK$3,353 found 5 days ago

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

April is typically the cheapest month to fly

From HK$932 - HK$4,003 per traveller.

Graph displaying average flight prices per month

New York to Chicago route information
Origin airport
John F. Kennedy Intl.
Destination airport
Midway Intl.
Return price
HK$2,697
Distance
1166 km

Flights from New York to Chicago

Book cheap flights from New York (JFK) to Chicago (MDW) on Expedia.com.hk. Find the best flight deals to destinations around the world for your next leisure or business travel on Expedia.com.hk.

Search for flights from New York (JFK) to Chicago (MDW) to find great flight deals suitable to your travel date and time. Expedia.com.hk flight booking search engine is simple to use and looking for cheap flights is as easy as a click of a mouse or on your mobile devices.

Be assured that you’re seeing the best price guaranteed! Our friendly customer service representatives are here to serve you 24 hours day to provide assistance and answer any questions that you may have about booking your New York (JFK) to Chicago (MDW) trip. Call us at 3077-4857 (direct number - 24 hours day for English).

Save more when combine your Chicago flight with a hotel for a package deal! Discover additional savings by booking in advance. Now you can find activities in Chicago and things to do in Chicago for your perfect vacation with Expedia Thing to Do.

If you would like to book flights to Chicago more flexibly, many prefer to purchase one-way tickets with options to take different airlines. A one way ticket to Chicago is HK$1,166 now!

 

Frequently asked questions

How much is a flight from JFK Airport to MDW?
Within the past 7 days on Expedia, for flights departing within the next year, the lowest price advertised for a round-trip journey from JFK to Midway Airport was HK$2,697. Cheap fares don't stick around for long, so make sure you book yours today. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from JFK to Midway Intl. Airport (MDW)?
Most flights can be conveniently canceled online, but whether or not you incur a fee differs between airlines. If you do have to cancel your trip, follow the instructions in the Customer Service Portal.
How do I find cheap flights from JFK to Midway Airport that have flexible change policies?
Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you're searching for JFK to MDW flights, you'll see a "no change fees" filter for you to select.
How far is the flight from John F. Kennedy Intl. Airport (JFK) to MDW?
It's just 1,150 kilometers between JFK and Chicago Airport. Chances are you'll spend more time traveling to and from the airport than actually flying!
Which airlines fly direct from JFK to Chicago Airport?
If you want to travel straight from JFK Airport to Midway Intl. Airport (MDW), you'll need to book a flight with at least one stop. Unfortunately, there are no airlines that fly directly on this route.
Are John F. Kennedy Intl. Airport (JFK) to Midway Intl. Airport (MDW) flight tickets cheaper when they're purchased at the last minute?
Late planners can occasionally score a bargain, with some of the cheapest fares from JFK Airport to Midway Airport appearing a few weeks before the departure date. If you'd rather plan ahead of time, Expedia compares and updates all the best flight deals frequently — as early as 12 months in advance in some cases. It does depend on the carrier though, as not all airlines advertise prices so far in advance.

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