$111 Find Cheap Flights from New York to Chicago Midway Airport - Compare and Save

Among airlines operating New York to Chicago Midway Airport flights:

• Southwest: offers free seat selection

Extra legroom and free seat selection availability depends on fare class and route.

Only Southwest operates flights between New York and Chicago Midway Airport.

Flights from New York to Chicago Midway Airport may depart from several airports in New York area, including Newark (EWR), New York John F Kennedy Intl (JFK) and New York LaGuardia (LGA). Flights usually arrive at Chicago Midway (MDW).

Here are some options for this route, based on selected ticket types and cabin classes:

• Southwest: a cabin bag and a checked bag in Economy Class
• JetBlue: a cabin bag in Economy Class class
• Alaska Airlines: a cabin bag in Economy Class class

Bag allowance can vary by ticket type, cabin class, route and airline, so travelers should check the fare details before booking.

Two cabin classes are available on flights from New York to Chicago Midway Airport:

• Economy Class
• First Class

On this route, layover flights are cheaper than nonstop options on average. Layover fares average $243 round-trip via Atlanta Hartsfield-Jackson (ATL), compared to $257 for nonstop.

There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $45–$90 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

One-stop flights from New York to Chicago Midway Airport most commonly connect through:

• Atlanta Hartsfield-Jackson (ATL) - 61% of one-stop connections
• Detroit Metropolitan Wayne County (DTW) - 35% of one-stop connections
• Lambert-St Louis (STL) - 4% of one-stop connections

Atlanta Hartsfield-Jackson (ATL) handles the largest share of one-stop connections on this route.

Yes. Being flexible with your travel dates can save you up to 23% on the New York to Chicago Midway Airport route. Tuesday is the cheapest departure day at $225 round-trip on average, while Monday is the most expensive at $292, a difference of $67. KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

A flight is considered delayed when it departs 15 minutes or more after its scheduled time. This is the standard used by the US Department of Transportation and most airline industry reporting. On the New York to Chicago Midway Airport route, 23% of flights were delayed in the past 3 months, with delays averaging 2 hours 15 minutes.

Morning is the busiest departure period on New York to Chicago Midway Airport flights, with 51% of flights leaving in that window. Afternoon departures account for 33%, evening flights for 16%, and night flights for 0%.

Some of the most popular sights in Chicago Midway Airport are Magnificent Mile, Grant Park and River North. These are among the most viewed places in Chicago Midway Airport on KAYAK.

These are the earliest and latest flight times available from New York to Chicago Midway Airport:

• Earliest: departs at 6:00 am and lands at 8:29 am
• Latest: departs at 10:00 pm and lands at 12:29 am.

The flight takes about 2h 29m.

Last-minute fares on this route - booked within 2 weeks of departure - run 28% above the route average of $253. Book 13 weeks before departure for the lowest fares.

A nonstop flight from New York to Chicago Midway Airport takes 2h 29m, covering 717 miles.

No, a passport is not required for this domestic route, but you will need a real ID-compliant driver's license, a state ID, or another TSA-accepted form of identification.

Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $222 to $1,603. That means the highest observed fare was about 7x higher than the lowest one.

One-way fares from New York to Chicago Midway Airport are currently lower than usual. Average one-way flight prices are about $134, which is 28% below the typical average for this route.

Morning flights have the fewest delays on this route. Delays tend to pile up throughout the day as one late flight pushes the next, so earlier departures are usually more reliable.

Flying via Detroit Metropolitan Wayne County (DTW) gives the shortest average 1-stop total travel time at 4h 12m, compared with 5h 39m via Lambert-St Louis (STL) and 7h 38m via Atlanta Hartsfield-Jackson (ATL).

Chicago Midway Airport is 1 hour behind New York (Central Time vs Eastern Time). Plan for the time shift when scheduling connections or first-day activities.

Chicago Midway Airport (MDW) hosts 5 major car rental companies, with daily rates starting from around $32 for economy cars. Top options include:
· Hertz
· Dollar
· Budget
· Alamo
· Rent-A-Wreck

Round-trip flights from New York to Chicago Midway Airport range from $171 to $367, with an average of $253 over the past 12 months. Anything below $171 counts as a good deal.

JetBlue is the only airline on the New York to Chicago Midway Airport route offering in-flight Wi-Fi. Pricing depends on fare class.