Question 1

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

Accepted Answer

Currently priced at ₹ 11,916, Southwest will fly you from New York to Chicago and back. In addition to Southwest, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from Spirit Airlines and United Airlines - these airlines can fly you to your destination from ₹ 12,002 and ₹ 12,173, respectively. Southwest is 39% cheaper than the average price of flights available within the next 90 days to this destination. Find deals

Question 2

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

Accepted Answer

For one-way options, check prices for United Airlines. According to our data, you can fly for as low as ₹ 5,915. Users have also found prices from ₹ 6,515 and ₹ 6,687 on Spirit Airlines and Delta, respectively. Find deals

Question 3

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

Accepted Answer

Booking 35 days in advance of your planned departure date is, on average, the best time to get cheap flights from New York to Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be. Find deals

Question 4

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

Accepted Answer

Currently, October is the cheapest month in which you can book a flight from New York to Chicago (average of ₹ 973). Flying from New York to Chicago in August is currently the most expensive (average of ₹ 1,331). 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. Find deals

Question 5

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 Saturday evenings when fares are most often at their lowest. Tuesday afternoons 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 (194 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (74 on average).

Question 7

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 8

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 9

What are the cheapest flights from New York to Chicago?

Accepted Answer

Looking at all options, your cheapest flight can be booked for ₹ 6,729. While the most popular route (Newark - Chicago O'Hare Intl) can be booked for ₹ 22,546 on average our data indicates ₹ 22,930 when flying from New York to Chicago.

Question 10

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

Accepted Answer

The top 3 most reliable airlines when flying from New York to Chicago are Cathay Pacific (100%), China Airlines (84%) and American Airlines (80%).

Question 11

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

Accepted Answer

Leaving on a Friday is a viable option for saving on travel. Heavily demanded days of the week can typically drive up the prices you see. Booking your travel for a less competitive day can save up to 190% on the overall cost on flights from New York to Chicago.

Question 12

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

Accepted Answer

Find a great deal and save up to 90% by booking at least 36 days prior to your desired departure date, rather than waiting until the week of travel. According to our data, there are a number of flights available from New York to Chicago within the next two weeks, with the cheapest ticket starting at ₹ 19,546.

Question 13

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

Accepted Answer

Our data shows that September tends to be the cheapest month to fly to Chicago from New York. Users have commonly found prices around ₹ 19,624 for the month, but tickets can be as low as ₹ 6,344. Due to multiple factors, prepare for potentially higher prices in December.

Question 14

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

Accepted Answer

It’s optimal to fly from New York to Chicago in the evening. By choosing this option you can save up to 47% on the cost of your flight, compared to a flight in the afternoon.

Question 15

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 16

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 17

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 18

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 19

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

Accepted Answer

It’s simple! Cheapflights, which is free to use for everyone, saves millions of users time and money every year by helping them find the cheapest and most suitable flights from New York to Chicago.

Question 20

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

Accepted Answer

Need flexible booking options for your flight to Chicago from New York? Don’t worry, Cheapflights have you covered. Use our search filter to only show flights with no change fees.

Question 21

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

Accepted Answer

Of course! You can now track prices for flights from New York to Chicago and get an alert from Cheapflights when they change. Have a valid email address ready and click the bell icon next to the flight deals above to set up your price alerts.

Round-trip from	₹ 11,916
One-way from	₹ 5,915
Popular in	December
Cheapest in	September
Average price	₹ 20,231
Good round-trip deal	₹ 21,139 or less
Good one-way deal	₹ 6,723 or less

Airline	Cheapest	Average	Flexibility	On-time
Spirit Airlines	Cheapest₹ 5,919	Average₹ 8,969	FlexibilityNo cancel fee	On-time65%	Search Spirit Airlines flights
American Airlines	Cheapest₹ 10,550	Average₹ 19,299	FlexibilityNo cancel fee	On-time71%	Search American Airlines flights

Cheap flights from New York to Chicago from ₹ 5,915

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 Thursday and return on a Thursday

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 9 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 9 July 2025.

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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 month to book a flight from New York to Chicago?

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 9 July 2025.

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

Use this chart to determine the cheapest time to fly return from New York to Chicago. Price data was last updated on 6 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 9 July 2025.

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated 9 July 2025.

Check out reviews from past customers who have flown with Southwest, Delta, andUnited Airlines from New York to Chicago to help guide your decision. You can also see how each airline stacks up 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?

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

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for New York to Chicago

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Top 2 airlines flying 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 9 July 2025.