Question 1

What are the cheapest airlines flying from New York to Chicago round-trip?

Accepted Answer

According to our current data, Spirit Airlines ($63), Frontier ($107), and JetBlue ($146) offers the cheapest pricing from New York to Chicago. Spirit Airlines is priced at 72% lower than the current average price of a flight leaving 3 months from now.

Question 2

What are the cheapest airlines to fly from New York to Chicago one-way?

Accepted Answer

To fly one-way, consider booking your trip with Spirit Airlines, which is currently one of the cheapest options available, starting at $37. Frontier flights start at $49 while deals on JetBlue start at $74 one-way.

Question 3

How far ahead should I book a flight from New York to Chicago?

Accepted Answer

To ensure you get the cheapest price possible for a flight from New York to Chicago, you should look to book at least 30 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

Question 4

What is the cheapest month to book a flight from New York to Chicago?

Accepted Answer

Currently, September is the cheapest month in which you can book a flight from New York to Chicago (average of $232). Flying from New York to Chicago in June is currently the most expensive (average of $308). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

Question 5

What is the cheapest day to fly from New York to Chicago?

Accepted Answer

Travelers seeking maximum savings on their New York to Chicago flight should consider departing on Saturday evenings when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Question 6

Weekly flight availability from New York to Chicago

Accepted Answer

The most flights from NYC to CHI are scheduled on a Monday (180 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (104 on average).

Question 7

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Accepted Answer

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Question 8

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Accepted Answer

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Question 9

What are the most popular routes from New York to Chicago?

Accepted Answer

The most popular route from New York to Chicago is New York John F Kennedy Intl - Chicago O'Hare Intl. You may also consider New York LaGuardia - Chicago O'Hare Intl or Newark - Chicago O'Hare Intl.

Question 10

What are the cheapest flights from New York to Chicago?

Accepted Answer

On average you can expect to pay $452 for a flight from New York to Chicago. The cheapest flight overall is $73 while the most popular route, (New York John F Kennedy Intl - Chicago O'Hare Intl) is currently priced at $128.

Question 11

What are the most reliable airlines from New York to Chicago?

Accepted Answer

No one likes to see their flight delayed. When booking a flight from New York to Chicago consider choosing Malaysia Airlines (96%), China Airlines (95%) or SkyWest Airlines (95%) as they are the most reliable in getting you off to your destination on time.

Question 12

What are the most popular airlines that fly from New York to Chicago?

Accepted Answer

The most popular airlines flying from New York to Chicago are American Airlines, JetBlue and Delta. Something to consider prior to booking your flight.

Question 13

What is the cheapest day to fly round-trip from New York to Chicago?

Accepted Answer

Users have found that leaving on a Monday can be a cost-effective option. It’s possible to save up to 33% on your flight compared to booking on days when demand is much higher.

Question 14

How far in advance should I book a flight from New York to Chicago?

Accepted Answer

When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 31 days in advance, which can save you up to 92% on flights from New York to Chicago compared to booking the week you need them. Waiting 31 days out may not be for everyone, so we have options available for flights within the next two weeks, with the lowest price starting at $211. For sooner than that we have options available in the next 3 days from $362.

Question 15

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

Accepted Answer

Due to multiple factors, expect to potentially pay more when booking in December. For low rates, September can be a great choice for travel to Chicago. Flights to Chicago from New York in September are about $228 on average during September, but can be found for as low as $74.

Question 16

What is the cheapest time of day to fly from NYC to CHI?

Accepted Answer

It’s typically best to fly out from New York to Chicago in the evening. Doing so could potentially save you 20% on the flight price compared to flying at noon, which is usually more expensive.

Question 17

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Accepted Answer

Most accurate provider: When it comes to deals on New York-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on New York-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from New York-Chicago flight searches over the past month and is updated monthly.

Question 18

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Accepted Answer

Most trusted provider: When it comes to deals on New York-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for New York-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Question 19

Can I find deals for flights from New York to Chicago that include hotel bookings?

Accepted Answer

Yes. In addition to deals on New York to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

Question 20

How can I find direct flights from New York to Chicago?

Accepted Answer

After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from New York to Chicago.

Question 21

Can I find deals for business class flights from New York to Chicago?

Accepted Answer

Yes. Cheapflights offers flight deals from New York to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

Question 22

What are the most eco-friendly airlines from New York to Chicago?

Accepted Answer

When you are traveling to Chicago from New York and you are looking for the most eco-friendly airlines to make the trip, some choices include American Airlines, Delta Air Lines, JetBlue Airlines, and United Airlines. Since 2013 American Airlines has retired and replaced over 600 aircraft with newer generation technologies that on average offer 10 to 15% improvements in their fuel efficiency. JetBlue offers a program to its passengers to allow them to offset the carbon footprint of their flight for about the price of a cup of coffee. Delta Air Lines has set a goal of replacing 10% of its jet fuel with sustainable aviation fuel by the end of 2030.

Question 23

How can I fly more sustainably from New York to Chicago?

Accepted Answer

In an effort to utilize sustainable travel methods, travelers have plenty of things they can do on trips to Chicago from New York. Start out at home by packing as little as possible to reduce the weight needed to carry you to your destination to save fuel. When booking your flight look for routes that employ newer advanced aircraft that are more fuel-efficient. As you are considering your ground transportation choices to get you to the airports in New York, think about one of the many light rail services offered by the Metropolitan Transit Authority of New York as this is one of the most fuel-efficient ways to get to the airport. Do the same thing when you arrive in Chicago by taking either the CTA Blue Line or the CTA Orange Line depending on which airport you arrive at in Chicago. During your time in Chicago do your best to shop locally so that the products that you consume during your stay have traveled the shortest distance to get to you, thus reducing their carbon footprint on the environment.

Question 24

How long is the flight from New York City to Chicago?

Accepted Answer

The flight from New York City to Chicago, just over 700 miles, will take you slightly less than two hours. Add to that the time spent getting to and from your gate, which may vary depending on the airport you choose.

Question 25

Which airlines operate flights from New York City to Chicago?

Accepted Answer

With two airports to choose from in Chicago and three in the area of New York City, you have a wide variety of airlines to choose from when booking your flight. Check out flights from American, Delta, jetBlue, Spirit, United and Southwest to find the right combination of time and price.

Question 26

How frequent are flights between New York City and Chicago?

Accepted Answer

With almost 100 flights running from New York's three airports to Chicago each day, you should be able to find a flight that meets your schedule. Flights begin at 6 a.m. each day, with the last flight departing shortly before midnight.

Question 27

Which airports serve New York City to Chicago?

Accepted Answer

You can reach Chicago departing from any of New York's three major airports - JFK International, LaGuardia, and Newark Liberty International Airport. Most Chicago-bound flights head to O'Hare, the second-busiest airport in the country, though a few land at Midway.

Question 28

Which direct flight route between New York City and Chicago is cheapest?

Accepted Answer

You'll typically find cheaper flights when departing from LaGuardia than from JFK, though prices do fluctuate seasonally and even daily. Landing at O'Hare in Chicago is typically a cheaper choice than looking for a flight to Midway.

Whether you're traveling for business or vacation, Chicago is a friendly, welcoming town that combines high-end urban style with Midwestern hospitality. Take a cruise down the Chicago River to marvel at the architecture of this city's startling skyscrapers, or head to the suburbs to explore some of Frank Lloyd Wright's greatest designs. The Art Institute of Chicago is home to some of the greatest Impressionist paintings in the world, and the Magnificent Mile along Michigan Avenue satisfies even the most demanding shopper. Finish a day in Chicago with uproarious laughter at one of the many improv performances around town.

Your visit to Chicago can combine business and fun seamlessly. Just remember to bundle up against the wind that sweeps off Lake Michigan during all seasons. To find a cheap flight to Chicago from NYC at the perfect time of day, use our smart search engine.

Question 29

How busy are the airports in New York and Chicago?

Accepted Answer

Because New York and Chicago are two very large cities in the United States there are several airport options in each city that allow you to make the trip between these cities. Some of the choices when you are leaving from the New York City area include John F. Kennedy International Airport (JFK), Newark International Airport (EWR), and New York La Guardia Airport (LGA) and the choice of which airport to use often comes down to which one is most convenient for you depending on your departure point within the New York City area. In terms of airports that are available to you in Chicago, they include both Chicago O' Hare International Airport (ORD) and Chicago Midway (MDW) both of which offer excellent public transportation options to get from the airport to downtown Chicago after your flight to Chicago from New York.

Question 30

Which airlines offer direct flights from New York to Chicago?

Accepted Answer

If the airport you will be using in New York City is New York La Guardia Airport, some of your direct flight options include those aboard United Airlines and American Airlines that both offer nonstop service to the Chicago O' Hare International Airport. If instead, you will be departing from John F. Kennedy International Airport there are nonstop flights available aboard American Airlines, Delta Airlines, and JetBlue to Chicago O' Hare International Airport. When departing from Newark International Airport you can fly directly to Chicago O' Hare International Airport from John F. Kennedy International Airport aboard both United Airlines and American Airlines.

Question 31

What are some of the layover options between New York to Chicago?

Accepted Answer

There are also one-stop flights that offer a better value than some of these nonstop flights. Spirit Airlines offers one-stop service that departs from both Newark International Airport (EWR) and New York La Guardia Airport that has a layover at Orlando (MCO) that will add about five hours to your travel time. You can also travel on a one-stop flight that has a layover in Orlando or Frontier Airlines and this trip will add about four hours to your travel time. If you would like to travel to Chicago Midway, you can do so from both Newark International Airport and John F. Kennedy International Airport aboard Delta Airlines with a layover at Detroit Metropolitan Wayne County (DTW).

Question 32

When I am flying from New York to Chicago will I require a visa or a passport?

Accepted Answer

Since the cities of both Chicago and New York lie within the United States citizens of the United States do not need a passport or visa to travel to these two cities. Something important to remember on this flight route is that in the very near future airlines will require a REAL ID to make this trip.

Most accurate provider	FlightHub 3 stars
Most trusted provider	FlightHub 3 stars
Popular in	December
Cheapest in	September
Round-trip from	$63 (Cheapflightsfares)
One-way from	$37 (Cheapflightsfares)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/5. Fares are subject to change and may not be available on all flights or dates of travel.

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The best prices from New York to Chicago are usually found in September or January, booked 30 days in advance, depart on a Tuesday or Wednesday and return on a Tuesday

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Cheapest flights from New York to Chicago
Explore the most affordable flight options available from New York to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 19, 2024.

Explore the most affordable flight options available from New York to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 19, 2024.

Best flights from New York to Chicago
Discover carefully curated flight deals from New York to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated November 19, 2024.

Discover carefully curated flight deals from New York to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated November 19, 2024.

Last-minute flights from New York to Chicago
Discover last-minute flight deals from New York to Chicago. Data last updated November 19, 2024 and is based on user searches.

Discover last-minute flight deals from New York to Chicago. Data last updated November 19, 2024 and is based on user searches.

One-way flights from New York to Chicago
Search for one-way flight options from New York to Chicago. Find affordable one-way fares based on user searches. Data last updated November 19, 2024.

Search for one-way flight options from New York to Chicago. Find affordable one-way fares based on user searches. Data last updated November 19, 2024.

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$37+ Cheap flights from New York (NYC) to Chicago (CHI)