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When’s a good time to book a flight from New York City to Chicago?

What’s the cheapest day of the week to fly from New York City to Chicago?‡

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What is the cheapest month to fly from New York City to Chicago?‡

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‡This information is based on historical data from the last 365 days.

Finding Affordable Flights from New York City to Chicago
  • Plan Ahead - One of the keys to securing cheap flights from New York City to Chicago is to plan your trip well in advance. Airlines often offer lower prices for those who book tickets months ahead. Keep an eye on special promotions and sales events, which can yield significant savings.
  • Flexibility is Key - Being flexible with your travel dates can also lead to substantial cost savings. Consider flying during off-peak seasons or on weekdays when prices tend to be lower.
  • Set Price Alerts - To keep tabs on flight prices, consider setting up fare alerts. These alerts will notify you when fares from New York City to Chicago drop, giving you the opportunity to grab cheap deals.
  • Consider Nearby Airports - If Chicago has multiple airports, check the prices at each one. Sometimes, flying into a nearby airport and then taking a short train or bus ride to your destination can be a much cheaper option.
  • Bundle and Save - Booking your flight and accommodation together as a package can often result in significant savings. CheapOair offers these bundled deals, so make sure to explore this option.

When is the Cheapest Time to Book Flights from New York City to Chicago?

‡

Got flexible travel dates? Use our flight data from the past year to discover ideal times to fly from New York City to Chicago. Find out which months and days typically offer lower fares and score our best savings.

CheapOair provides the predicted prices for one-way trips or round-trips with a duration of 7 days for domestic and 14 days for international trips based on historical data and available flight information. Graphs are estimates only. Prices are subject to change and can't be guaranteed until ticketed.
Estimated price for
Round-trip

‡Graphs are estimates only. Based on historical data and available flight information. Prices are subject to change and cannot be guaranteed until ticketed.

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New York City to Chicago Flight Route Information

Travel Distance:738 Miles
Airlines Flying This Route: American Airlines, United Airlines, Spirit Airlines
Weekly Flights:6
Avg. Flight Duration:05.27 Hours

Insights About Flying from New York City to Chicago

Q. Which is the high season to travel from New York City to Chicago?

A. The month of July is considered the high season for flying from NYC to CHI. Traveling during the high season can affect ticket prices and availability, making this data crucial for trip planning.

Q. How many direct flights are available from NYC to CHI?

A. There are a total of 1099 direct flights from New York City to Chicago. For travelers seeking convenience and shorter travel times, this data is important when choosing flight options.

Q. Which is the low season to travel from New York City to Chicago?

A. March is considered the low season for traveling from New York City to Chicago, Illinois. Travelers looking for cost-effective options and fewer crowds may consider traveling during this period.

Q. How many daily flights are there between New York City to Chicago?

A. There are as many as 36 daily flights available for travelers between NYC to CHI. This data offers flexibility in choosing departure times that best suit your schedule.

Q. At what time does the last flight depart to Chicago?

A. The last flight to Chicago typically departs between 10:00PM - 11:00PM. Travelers who prefer late-night departures will find this information valuable for planning their journey.

Q. What percentage of travelers spent an average of 3 days in Chicago, Illinois?

A. Approximately 43.77% of travelers spent an average of 3 days exploring Chicago. This information can assist in planning the duration of your stay in Chicago

Q. What percentage of NYC to CHI flyers traveled with kids under 14?

A. About 4% of passengers on flights from New York City to Chicago were accompanied by children under the age of 14. This information is useful if you're planning a family trip and want to know how common it is to travel with young children on this route.

Q. What percentage of New York City to Chicago travelers were over 60 years old?

A. A notable 11% of travelers were aged 60 or older. This statistic provides insights for senior travelers or those seeking a mature travel demographic.

Q. What percentage of NYC to CHI travelers were millennials?

A. Millennials make up a significant portion of travelers on this route, accounting for 44% of all passengers. If you're a millennial looking to connect with like-minded travelers, this statistic might interest you.

Q. What percentage of New York City to Chicago travelers were female?

A. Almost half of the passengers, approximately 46% were female. Knowing the gender distribution can be useful for solo female travelers or those interested in gender-related travel insights.

Q. What percent of New York City to Chicago travellers booked first or business class?

A. 2% of travelers booked first or business class on this route.

Q. At what time the earliest flight departs from New York City?

A. The earliest flight departs at 7:00AM - 8:00AM.

Q. On which days one can have the most flight options in Chicago?

A. Monday offer the most flight options in Chicago.

§ All flight facts are based on last 3 months' data except the highest and lowest booking months that are based on last 3 months' data.

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.

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