Flights To New York From Chicago

Find cheap flights to New York from Chicago with CheapFlightCheck. Compare fares, save big, and book the best deals hassle-free!

Cheap Flights, Special Deals From Chicago to new york

Interactive map with cheap flight prices from Chicago

Flights To New York From Chicago

Taking a trip from the Windy City to the Big Apple? Flying between Chicago and New York is one of the busiest travel routes in the United States. These two amazing cities are connected by many flights every day, making it easy to plan your trip whenever you want to go.

Chicago Airports You Can Fly From

O'Hare International Airport (ORD)

O’Hare is one of the biggest and busiest airports in the world. Located about 17 miles northwest of downtown Chicago, this airport offers the most flights to New York City. Here’s what you should know:

  • Most major airlines fly from here to all New York airports
  • The airport has lots of shops and restaurants while you wait
  • You can take the Blue Line train from downtown Chicago to get here

Midway International Airport (MDW)

Midway is Chicago’s second airport, located just 8 miles from downtown. It’s smaller and often less crowded than O’Hare.

If you live on the south side of Chicago, this might be more convenient for you. Southwest Airlines has many flights from Midway to New York.

New York Airports You Can Fly To

John F. Kennedy Airport (JFK)

JFK is New York’s biggest international airport. It’s in Queens, about 15 miles from Manhattan. If you’re staying in Brooklyn or Queens, this might be the best choice. From JFK, you can take the AirTrain to the subway to get into the city.

LaGuardia Airport (LGA)

LaGuardia is the closest airport to Manhattan, just 8 miles from Times Square. Many domestic flights from Chicago land here. Taxis and ride-shares are popular ways to get from LaGuardia into the city.

Newark Liberty International Airport (EWR)

While technically in New Jersey, Newark is considered one of New York’s airports. It’s about 16 miles from Manhattan but has good train connections into the city. If you’re staying in west Manhattan or New Jersey, this might be your best option.

How Long Does the Flight Take?

A direct flight from Chicago to New York takes about 2 to 2.5 hours. That’s just enough time to watch a movie or read a few chapters of a book! The distance between the two cities is around 800 miles.

When to Book Your Ticket

Booking your flight 1-3 months before your trip usually gets you the best price. Prices tend to go up as the travel date gets closer.

Best Days to Fly

Flying on Tuesday, Wednesday, or Saturday often means cheaper tickets. Friday and Sunday flights are usually more expensive because these are popular travel days.

Best Seasons for Travel

Winter (except for holidays) usually has the cheapest flights between Chicago and New York. Summer and holidays like Thanksgiving and Christmas have the most expensive tickets.

Airlines That Fly This Route

Many airlines offer flights between Chicago and New York:

  • United Airlines
  • American Airlines
  • Delta Air Lines
  • JetBlue
  • Spirit Airlines
  • Southwest Airlines (from Midway)

Each airline has different prices, seating options, and services. Some offer free carry-on bags while others charge extra, so check what’s included in your ticket.

Tips for Your Flight

Getting to the Airport

Both Chicago airports can have heavy traffic, so plan to arrive:

  • 2 hours early for domestic flights
  • 3 hours early for international flights

What to Pack

New York weather can be different from Chicago’s, so check the forecast before you pack. In winter, New York gets cold and snowy just like Chicago. In summer, it can be hot and humid.

Fun Facts About Both Cities

Chicago and New York are both famous for:

  • Tall buildings and amazing skylines
  • Delicious food (Chicago has deep dish pizza, New York has thin crust)
  • Great museums and art galleries
  • Beautiful parks and waterfronts

When you fly between these cities, you’re traveling between two of America’s greatest urban centers!

Making the Most of Your Trip

A quick flight from Chicago puts all of New York City’s famous sights within reach:

  • The Statue of Liberty
  • Central Park
  • Times Square
  • Broadway shows
  • Empire State Building
  • Brooklyn Bridge

Whether you’re going for fun, work, or to visit family, flights between Chicago and New York connect you to endless possibilities in the city that never sleeps.

Use our search tool above to find the perfect flight for your Chicago to New York adventure!