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

Want to trade the hustle and bustle of the Windy City for that of the Big Apple? Southwest Airlines® has flights from Chicago Midway International Airport to LaGuardia Airport that will make visiting the city that never sleeps even more affordable. Find your flight to New York (LaGuardia) with Southwest® and book with confidence. If your upcoming excursion has flexible dates, search for flights with our Low Fare Calendar and discover the lowest fares we’ve got. Don't forget to explore Southwest Vacations® to find package deals on flights, hotels, rental cars, and more.

Check out Chicago (Midway) to New York (LaGuardia) flights and book your flight now!


Best Airline in the US and North America

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

Flight Details

Departing from: Chicago Midway International Airport (MDW)

Arriving at: LaGuardia Airport (LGA)


Route Information


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Flight after 6pm

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Explore New York

The city that never sleeps is full of amazing sights and sounds. Maybe you can squeeze a Broadway show into your itinerary, or spend time at the Metropolitan Museum of Art—the largest art museum in the United States. Consider exploring Ellis Island to learn about a very different type of travel experience! Climb the Statue of Liberty and admire the view. See the magnificent architecture of Gotham's skyscrapers for yourself, from the Empire State Building to the Flatiron or the Chrysler Building. These iconic sights can be accompanied by world-class restaurants and eateries or a simple slice of New York-style pizza—it's up to you!

New York City is one of the United States' great centers for culture and art. Whether you're interested in musicals, opera, ballet, or rock concerts, the Big Apple has it all. Award-winning shows are a constant feature of the New York arts scene. Get tickets for Shakespeare plays, the ballet, the hottest musicals, and more. From classical to modern, dramas to comedies, New York City has something for everyone.

Chicago to New York City flights allow you to experience more of the world—or at least more of the East Coast. Take full advantage of your time in New York by getting great deals on hotel rates and car rentals through Southwest. We can even help you plan your entire New York City vacation. Let us help you get the best deals on your New York City travel arrangements. Even if your final destination isn’t the Big Apple, this historic burg can be your gateway to the world. Let us help you get there.

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

At Southwest, we know that a memorable trip from Chicago (Midway) to New York (LaGuardia) is made of more than cheap flights. That’s why we offer services and perks, from booking to boarding, that make your travel experience as smooth as possible. Find out more about the Southwest Experience before you book your next flight.

It’s simple and fun to fly with Southwest, no matter which of our destinations you choose. And when you search for your next flight to New York (LaGuardia), you know you won’t be hassled by hidden fees—we offer low fares and, as always, bags fly free1. That’s our Transfarency® promise. Enroll in our Click 'N Save® emails and stay in the know about our latest flight deals. Looking for tours, activities, and more hidden gems? Check out Southwest Airlines® Experiences and earn Rapid Rewards® points when you book.

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

2Fare difference may apply.