Flights from New York (EWR) to Chicago (MDW)

The Gateway City may just be your jumping off point for getting to the Windy City! Southwest® flies nonstop from Newark Liberty International Airport to Chicago Midway International Airport. Whether you’re a Newark native or you’re departing from New York City proper, flying to Chicago (Midway) with Southwest Airlines® is straightforward, no-nonsense, and simple. When flying for business or pleasure, our Low Fare Calendar will reveal our cheapest fares within a range of dates—see what you might save. Looking for more? Check out Southwest Vacations® to see package deals with flights, hotels, rental cars, and more.

Explore New York (Newark) to Chicago (Midway) flights and book yours today!


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Check out New York (Newark) to Chicago (Midway) flights and book yours now!

Flight Details

Average Flight Time: 2 hours 20 minutes

Departing from: Newark Liberty International Airport (EWR)

Arriving at: Chicago Midway International Airport (MDW)


Route Information


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Explore Chicago

No matter whether you’re traveling to Chicago from Newark or New York City when you fly in from Newark Liberty International Airport, deplaning at Midway is the beginning of an adventure—you’re just a 30-minute CTA train ride from the center of the Second City. World-class shopping, dining, and sightseeing await, but so too do hidden gems and diamonds in the rough amongst the city’s 77 community areas. What are you waiting for? Hop on a train, a bus, a rented bike, or call a car—the city is calling.

If you’re hungry for a taste of Chicago (and you’re not in town for the annual summertime festival Taste of Chicago), you have lots of local fare from which to choose. Hot dogs, Italian beefs, and pizzas (deep dish, stuffed, or thin) are just the beginning. Find Michelin-starred dishes from celebrity chefs at world-famous restaurants amongst great, cheap street food options. There’s something for every palate in Chicago. There’s also something that no palate enjoys: Those in search of a nightcap should consider finding a neighborhood corner bar and asking for a beverage called the Chicago Handshake (think “grapefruit”).

Whether you’re a fan of indoor activities or outdoor exploits, Chicago’s got something for everyone—and every time of year. Temperate months invite you to the northern suburbs to enjoy the Chicago Botanic Gardens, the Western suburbs for Brookfield Zoo, and the Lincoln Park neighborhood for the Lincoln Park Zoo. When there’s a chill in the air, consider taking in a show—there are stadium concerts, back-room open mics, improv troupes, and more.

Travel Tips


Infant Policy

One child over 14 days and under two (2) years of age, not occupying a seat, may be carried free of charge when traveling with an adult (12 years of age or older). Learn more.


Pet Policy

Customers flying with a pet are subject to a pet fare. To learn more about traveling with your furry friend, explore the Southwest Pet Policy.


Unaccompanied Minor

Minors under the age of 18 are not permitted to fly unaccompanied on international flights or any itinerary that includes an international flight. Learn more.


Bags Fly Free1

Start packing! Every ticketed Customer’s first two checked bags are free. Learn more.


The Southwest Travel Experience

Making a memorable trip from New York (Newark) to Chicago (Midway) is about more than scoring a great deal on your flight. That’s why, from booking to boarding, Southwest Crew Members work hard to ensure the Customer Experience is the best it can be. Learn more about the Southwest Experience while you book your New York (Newark) to Chicago (Midway) flight.

When you plan a trip with Southwest to one of our dozens of destinations, you know your booking will be straightforward. Low fares. No hidden Fees. That’s our Transfarency® promise. And, as always, bags fly free1. Enroll in our Click 'N Save® emails to stay up to date on our latest and greatest deals. Looking for tours, activities, and more hidden gems? Check out Southwest Airlines® Experiences and earn Rapid Rewards® when you book.

1First and second checked bags. Weight and size limits apply.

2Fare difference may apply.