Question 1

Which airline has the best punctuality record on New York to Chicago flights?

Accepted Answer

According to our data, United Airlines have had the fewest delays on this route over the last 12 months, with about 12% of their flights experiencing any sort of delay.

Question 2

What is the cheapest airline that flies from New York to Chicago?

Accepted Answer

Spirit Airlines, United Airlines, and Delta are the most popular carriers operating from New York to Chicago

Question 3

Can stopping save me money on New York to Chicago flights?

Accepted Answer

You could potentially save up to 14% on your flight if you consider stops on a New York to Chicago flight.

Question 4

What is the cheapest month to fly to Chicago?

Accepted Answer

In general, January is the cheapest month to fly from New York to Chicago. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around ₹ 16,375. The month of February is another great option to travel to Chicago, with average flight prices from New York averaging around ₹ 17,099.

Question 5

What is the cheapest day to depart on your flight to Chicago?

Accepted Answer

According to our data, Saturday is the cheapest day to fly to Chicago from New York. The lowest ticket price found for a Saturday departure recently was ₹ 17,006. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. The most expensive day to fly to Chicago is Tuesday, with ticket prices averaging around ₹ 56,091.

Question 6

How long does it take to fly to Chicago?

Accepted Answer

If you’re flying from a popular airport in New York, such as Newark or New York, and flying into Chicago, then you can expect flight times to average 2h 37m and 2h 48m, respectively.

Question 7

How many flights depart from New York to Chicago on average per day?

Accepted Answer

47 flights are operational daily from New York to Chicago as of December 2025. The most popular departure time for this route is 15:00, with 40% of flights per day taking off at midday.

Question 8

How often are flights from New York to Chicago delayed?

Accepted Answer

Historically, on average around 16% of flights between New York and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 159 minutes.

Question 9

How many flights depart from New York to Chicago on average per week?

Accepted Answer

334 flights are operational weekly from New York to Chicago as of December 2025. The most popular departure day for this route is Wed, with 39% of flights per week taking off on this day.

Question 10

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

Accepted Answer

You are more likely to see cheaper flights to Chicago from New York when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around ₹ 21,781 when searching weeks before you fly. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from New York for as low as ₹ 15,742 on momondo.

Question 11

What cabin class options are available on New York to Chicago flights?

Accepted Answer

There are 4 cabin classes available to choose from on New York to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Question 12

What is the most punctual flight time for New York to Chicago flights?

Accepted Answer

Generally, flights departing in the morning tend to experience fewer delays. Flights departing at night have, in the past, seen delays more frequently in comparison.

Question 13

What is the cheapest time of day to depart on your flight to Chicago?

Accepted Answer

In the evening is the cheapest time of day to fly from New York to Chicago when you can find flight prices for as low as ₹ 21,141. Flying to Chicago in the evening is an ideal time because this is during off-peak travel hours. Flights to Chicago are more costly in the afternoon, with an average ticket price of ₹ 27,861. Departure times in the afternoon fall within the peak daily travel times, which is why tickets can be more expensive.

Question 14

What day of the week experiences the fewest flight delays on this route?

Accepted Answer

Saturday is statistically the day of the week that experiences the fewest delays on this flight route. Thursday has historically seen more delays on average compared to the rest of the week.

Question 15

What is the cheapest New York to Chicago flight route?

Accepted Answer

Fly from New York LaGuardia to Chicago O'Hare Intl for the best New York - Chicago flight prices

Question 16

How have New York to Chicago flight prices changed over time?

Accepted Answer

As of December 2025, prices for New York to Chicago flights are approximately 15% cheaper when compared to flights at the same time last year.

Question 17

Is flying the fastest way to get from New York to Chicago?

Accepted Answer

To save time, the fastest way to travel is by flight from New York to Chicago on Spirit Airlines. Expect the length of time you’ll spend onboard Spirit Airlines to be about 2h 38m compared to taking a train from New York to Chicago or a bus from New York to Chicago which have been found to be slower alternatives.

Question 18

Is flying the cheapest way to get from New York to Chicago?

Accepted Answer

A flight from New York to Chicago from ₹ 8,233 can save you up to 57% on the cost of your trip compared to booking a train from New York to Chicago or a bus from New York to Chicago.

Question 19

When did momondo last update prices for flights from New York to Chicago?

Accepted Answer

Prices for flights from New York to Chicago are updated daily.

Question 20

How many operators does momondo search for flights from New York to Chicago?

Accepted Answer

There is 1 operator available for flights from New York to Chicago as of December 2025.

Question 21

How old do you have to be to fly from New York to Chicago?

Accepted Answer

The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from New York to Chicago.

Question 22

What documentation or ID do you need to fly to Chicago?

Accepted Answer

The necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

Best price found	₹ 7,644
Fastest flight time	2h 37m
Direct flights	Every day
Airports in Chicago	3 airports

Cheap flights from New York to Chicago from ₹ 4,976

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from New York to Chicago departing on 19/1. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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How to get the cheapest flight ticket from New York to Chicago

What is the cheapest month to fly to Chicago?

What is the cheapest day to depart on your flight to Chicago?

What is the cheapest time of day to depart on your flight to Chicago?

What is the cheapest New York to Chicago flight route?

Fly from New York LaGuardia to Chicago O'Hare Intl for the best New York - Chicago flight prices

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

What cabin class options are available on New York to Chicago flights?

There are 4 cabin classes available to choose from on New York to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on New York to Chicago flights?

You could potentially save up to 14% on your flight if you consider stops on a New York to Chicago flight.

How have New York to Chicago flight prices changed over time?

As of December 2025, prices for New York to Chicago flights are approximately 15% cheaper when compared to flights at the same time last year.

What is the cheapest airline that flies from New York to Chicago?

Spirit Airlines, United Airlines, and Delta are the most popular carriers operating from New York to Chicago

How often are flights from New York to Chicago delayed?

Historically, on average around 16% of flights between New York and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 159 minutes.

What is the most punctual flight time for New York to Chicago flights?

Generally, flights departing in the morning tend to experience fewer delays. Flights departing at night have, in the past, seen delays more frequently in comparison.

What day of the week experiences the fewest flight delays on this route?

Saturday is statistically the day of the week that experiences the fewest delays on this flight route. Thursday has historically seen more delays on average compared to the rest of the week.

Which airline has the best punctuality record on New York to Chicago flights?

According to our data, United Airlines have had the fewest delays on this route over the last 12 months, with about 12% of their flights experiencing any sort of delay.

How many flights depart from New York to Chicago on average per day?

47 flights are operational daily from New York to Chicago as of December 2025. The most popular departure time for this route is 15:00, with 40% of flights per day taking off at midday.

How many flights depart from New York to Chicago on average per week?

334 flights are operational weekly from New York to Chicago as of December 2025. The most popular departure day for this route is Wed, with 39% of flights per week taking off on this day.

How long does it take to fly to Chicago?

If you’re flying from a popular airport in New York, such as Newark or New York, and flying into Chicago, then you can expect flight times to average 2h 37m and 2h 48m, respectively.

When to book flights from New York to Chicago

Cheap New York to Chicago (NYC to CHI) flight deals and tips

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How old do you have to be to fly from New York to Chicago?

What documentation or ID do you need to fly to Chicago?

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