Find Cheap Flights from New York City (NYC) to Chicago (CHI)

Ready for your next trip? See local COVID-19 requirements here.

Book Cheap Flights from New York City to Chicago

A trip to the Windy City offers something for every type of traveler. Whether you prefer to meander around museums or search for the best deep-dish in the city, a cheap ticket from New York City to Chicago unlocks endless possibilities. From history to sports, Chicago has a rich culture that surprises and captivates. And with CheapOair's tools for finding cheap flights from LGA to ORD, you may even have some leftover funds for the trip itself.

Why Purchase Cheap Flights From New York City To Chicago? 5 Attractions To Experience

Visit Millennium Park.

Your trip to Chicago would not be complete without a trip to Millennium Park. Here you will find “The Bean,” Chicago’s iconic reflective sculpture that has appeared in countless films and TV shows. Often, you can also catch a concert or festival while you are there.

Learn at the Field Museum.

History buffs can revel at Chicago’s famous natural history museum. Here you will find dinosaur bones, models of animals, and information about our planet’s past. This is a great destination for families and people of all ages.

Cheer on the Cubs at Wrigley Field.

This stadium is home to Chicago’s own Cubs, so grab some team gear and cheer like a local. As one of the most famous baseball fields in the U.S., Wrigley will be a blast for sports fans and sightseers alike.

Wander through Shedd Aquarium.

This must-see attraction sits on the banks of Lake Michigan, offering a glimpse of over 30,000 aquatic creatures. You are welcome to walk around and watch the animals, or you can opt for more interactive animal experiences.

Sightsee at Navy Pier.

History is alive in Chicago at Navy Pier. While strolling down the pier, you will see the large ferris wheel, beautiful carousel, and other attractions. Shop and eat at the shops along the pier or simply walk and enjoy the stunning views.

Have some laughs with Second City

Chicago is well known for having one of the most vibrant theater scenes in the country, and many comedy legends got their start at the city's famous Second City improv theater. Visit one of the many local comedy clubs and you might just see the next big late-night comedy star.

Looking for cheap flight tickets and deals to LGA (New York) to ORD (Chicago)? Whether you're going for business, pleasure, or to visit one of the area's many colleges and universities, CheapOair has you covered. Browse our discount ticket database, book your cheap flight, and get ready to experience this iconic Midwestern city.