Question 1

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

Accepted Answer

Cheapflights users have booked flights from New York to Chicago round-trip from $217. Other airlines that can offer you cheap pricing are Spirit Airlines, from $219, and Delta, from $240. You may be able to fly from New York to Chicago for 37% less than the average price by searching for these airlines. Find deals

Question 2

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

Accepted Answer

The cheapet airlines for a one-way flight from New York to Chicago are United Airlines ($106), Spirit Airlines ($116), and Delta ($119). Find deals

Question 3

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

Accepted Answer

The best time to book flights from New York to Chicago is 35 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight. Find deals

Question 4

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

Accepted Answer

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

Question 5

Weekly flight availability from New York to Chicago

Accepted Answer

The most flights from NYC to CHI are scheduled on a Thursday (188 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (72 on average).

Question 6

E

Accepted Answer

In terms of precipitation, rainfall in Chicago ranges from 43.0 - 125.0 inches per month. August is typically the wettest month, when rainfall can reach 125.0 mm. January is typically the driest time to visit Chicago when rainfall is around 43.0 mm.

Question 7

E

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 23.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around -5.0 C).

Question 8

What are the cheapest flights from New York to Chicago?

Accepted Answer

The cheapest flight price from New York to Chicago is $48. On average you can expect to pay $74. The most popular route, (Newark - Chicago O'Hare Intl), can usually be booked for $277.

Question 9

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

Accepted Answer

Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from New York to Chicago on time: Cathay Pacific (100%), China Airlines (84%), American Airlines (80%).

Question 10

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

Accepted Answer

Users have found that flying from New York to Chicago on a Thursday typically leans towards higher prices. However, this doesn’t mean you still can’t find a deal. Flexibility with other aspects of your flight can still land a great price for your trip.

Question 11

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 36 days in advance, which can save you up to 90% on flights from New York to Chicago compared to booking the week you need them. Waiting 36 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 $349. For sooner than that we have options available in the next 3 days from $574.

Question 12

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

Accepted Answer

Flights from New York to Chicago lean towards being more expensive in December. Prices are generally better when you fly from New York to Chicago in September, with the cheapest ticket starting at $113.

Question 13

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

Accepted Answer

When flying from New York to Chicago, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 86% versus a flight in the afternoon.

Question 14

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 holiday packages that include both flights and hotel.

Question 15

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 16

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 17

How does Cheapflights help users find flights from New York to Chicago?

Accepted Answer

Cheapflights makes it easy to find New York to Chicago flights by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.

Question 18

Why should you use Cheapflights to find cheap flight tickets from New York to Chicago?

Accepted Answer

Cheapflights helps you find that perfect flight to Chicago from New York by searching from hundreds of airlines and agencies you know and love. We are also free to use, in case you were wondering!

Question 19

Can Cheapflights find flights from New York to Chicago with no change fees?

Accepted Answer

Yes, we can. To see specific flights from New York to Chicago with no change fees, users can toggle flexible booking options after using the search form above to find flights.

Question 20

Can Cheapflights notify me if prices for flights from New York to Chicago become cheaper?

Accepted Answer

Yes, Cheapflights has a feature called Price Alert, which notifies users when flight prices change. Track prices for your flight to Chicago from New York today and book when prices fit your budget.

Round-trip from	$217
One-way from	$106
Popular in	December
Cheapest in	September
Average price	$361
Good one-way deal	$74 or less

Cheap flights from New York to Chicago from $106

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 13/8. Fares are subject to change and may not be available on all flights or dates of travel.

Cheapflights Tip: The best prices from New York to Chicago are usually found in September or January, booked 35 days in advance, depart on a Saturday or Tuesday and return on a Tuesday

Cheap flight deals from New York to Chicago

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Find flight deals from New York to Chicago

Cheapest flights from New York to ChicagoExplore 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 10 July 2025.

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 10 July 2025.

Cheapflights Fare Finder

Use the filters below to find and compare flights from New York to Chicago that are best for you.

Best time to book a flight from New York to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from New York with our price prediction graph.

Cheapflights Insights

Everything you need to know about your flight from New York to Chicago

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

Use this chart to determine the optimal time to book a return flight from New York to Chicago. Price data was last updated on 27 June 2025.

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

Find hourly flight availability from New York to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 10 July 2025.

Weekly flight availability from New York to Chicago

Explore weekly flight availability from New York to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated 10 July 2025.

Reviews of airlines servicing Chicago

Get a feel of what it's like to fly with Delta, United Airlines, andAmerican Airlines from New York to Chicago by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.

Related info for your journey

Find useful and relevant information for your journey from New York to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

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

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

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

What are the cheapest flights from New York to Chicago?

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

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

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

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How does Cheapflights help users find flights from New York to Chicago?

Why should you use Cheapflights to find cheap flight tickets from New York to Chicago?

Can Cheapflights find flights from New York to Chicago with no change fees?

Can Cheapflights notify me if prices for flights from New York to Chicago become cheaper?

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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 10 July 2025.