Cheap Flights from New York (JFK) to Chicago (MDW) from HK$1,164~

View HK$1,164 flight on Tue, 4 Nov 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$1,164 for one-way flights and HK$2,317 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Tue, 4 Nov - Fri, 7 Nov
JFK
New York
MDW
Chicago
HK$2,317 Return, found 21 hours ago
HK$2,317
Return
found 21 hours ago
Select Delta flight, departing Tue, 4 Nov from New York to Chicago, returning Fri, 7 Nov, priced at HK$2,317 found 21 hours ago
Delta
Tue, 4 Nov - Fri, 7 Nov
JFK
New York
MDW
Chicago
HK$2,349 Return, found 21 hours ago
HK$2,349
Return
found 21 hours ago
Select Delta flight, departing Tue, 4 Nov from New York to Chicago, returning Fri, 7 Nov, priced at HK$2,349 found 21 hours ago
Delta
Tue, 4 Nov - Fri, 7 Nov
JFK
New York
MDW
Chicago
HK$2,628 Return, found 21 hours ago
HK$2,628
Return
found 21 hours ago
Select Delta flight, departing Tue, 4 Nov from New York to Chicago, returning Fri, 7 Nov, priced at HK$2,628 found 21 hours ago
Delta
Tue, 4 Nov - Fri, 7 Nov
JFK
New York
MDW
Chicago
HK$2,854 Return, found 21 hours ago
HK$2,854
Return
found 21 hours ago
Select Delta flight, departing Tue, 4 Nov from New York to Chicago, returning Fri, 7 Nov, priced at HK$2,854 found 21 hours ago
Delta
Tue, 4 Nov - Fri, 7 Nov
JFK
New York
MDW
Chicago
HK$2,897 Return, found 21 hours ago
HK$2,897
Return
found 21 hours ago
Select Delta flight, departing Tue, 4 Nov from New York to Chicago, returning Fri, 7 Nov, priced at HK$2,897 found 21 hours ago
Delta
Tue, 4 Nov - Fri, 7 Nov
JFK
New York
MDW
Chicago
HK$3,015 Return, found 21 hours ago
HK$3,015
Return
found 21 hours ago
Select Delta flight, departing Tue, 4 Nov from New York to Chicago, returning Fri, 7 Nov, priced at HK$3,015 found 21 hours ago
Delta
Thu, 23 Oct - Tue, 28 Oct
JFK
New York
MDW
Chicago
HK$3,058 Return, found 1 day ago
HK$3,058
Return
found 1 day ago
Select Delta flight, departing Thu, 23 Oct from New York to Chicago, returning Tue, 28 Oct, priced at HK$3,058 found 1 day ago
Delta
Tue, 4 Nov - Fri, 7 Nov
JFK
New York
MDW
Chicago
HK$3,166 Return, found 21 hours ago
HK$3,166
Return
found 21 hours ago
Select Delta flight, departing Tue, 4 Nov from New York to Chicago, returning Fri, 7 Nov, priced at HK$3,166 found 21 hours ago
Delta
Tue, 4 Nov - Fri, 7 Nov
JFK
New York
MDW
Chicago
HK$3,327 Return, found 21 hours ago
HK$3,327
Return
found 21 hours ago
Select Delta flight, departing Tue, 4 Nov from New York to Chicago, returning Fri, 7 Nov, priced at HK$3,327 found 21 hours ago
Delta
Tue, 4 Nov - Fri, 7 Nov
JFK
New York
MDW
Chicago
HK$3,359 Return, found 21 hours ago
HK$3,359
Return
found 21 hours ago
Select Delta flight, departing Tue, 4 Nov from New York to Chicago, returning Fri, 7 Nov, priced at HK$3,359 found 21 hours ago

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

April is typically the cheapest month to fly

From HK$925 - HK$4,110 per traveller.

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$2,317. 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.

Travel information

Travel information

Origin airport
John F. Kennedy Intl.
Destination airport
Midway Intl.
Airlines serving
Delta
Return price
HK$2,317
Distance
1166 km

Book with confidence

Book with confidence

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$1,164 now!

 

Flights from New York to Chicago

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