Question 1

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

Accepted Answer

In the afternoon is the cheapest time of day to fly from New York to Chicago when you can find flight prices for as low as C$ 373. Flying to Chicago in the afternoon is an ideal time because this is during off-peak travel hours. In the evening is when there is more demand to fly to Chicago, so prices are often more expensive at around C$ 576 per ticket.

Question 2

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

Accepted Answer

Spirit Airlines, Frontier, and Southwest are the most popular carriers operating from New York to Chicago

Question 3

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 24% cheaper when compared to flights at the same time last year.

Question 4

What is the cheapest New York to Chicago flight route?

Accepted Answer

Fly from Newark to Chicago Midway for the best New York - Chicago flight prices

Question 5

How often are flights from New York to Chicago delayed?

Accepted Answer

Historically, on average around 15% 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 6

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

Accepted Answer

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

Question 7

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 8

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 9

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

Accepted Answer

The number of flights available between New York and Chicago is 79 per day as of December 2025. The most frequent departure time is 4:00p.m., with 41% of daily flights leaving in the afternoon.

Question 10

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

Accepted Answer

The number of flights available between New York and Chicago is 557 per week as of December 2025. The most frequent departure day is Tue, with 24% of weekly flights leaving on this day.

Question 11

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

Accepted Answer

The cheapest day to depart on your flight to Chicago is on a Tuesday when prices can be found for as low as C$ 275. This is often the case because there is less demand to fly during this day of the week. If your travel schedule is flexible, try to avoid departing on a Friday because tickets tend to average around C$ 601. These prices are subject to change though, so be sure to set up a Price Alert for flights to Chicago.

Question 12

What is the cheapest month to fly to Chicago?

Accepted Answer

The month of February is another great option to travel to Chicago, with average flight prices from New York averaging around C$ 264.

Question 13

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 14

How long does it take to fly to Chicago?

Accepted Answer

Flight times from New York to Chicago vary, but if you’re flying out of New York and flying into Chicago O'Hare Intl Airport (one of the most popular routes), then the duration is 2h 35m on average. Another popular route from New York to Chicago is flying from Newark to Chicago O'Hare Intl Airport, which will take roughly 2h 47m. Keep in mind that layovers or delays could extend your travel time.

Question 15

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 C$ 345 when searching weeks out. 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 C$ 259 on momondo.

Question 16

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

Accepted Answer

No. A direct flight is the cheapest option for a flight between New York to Chicago.

Question 17

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

Accepted Answer

Based on just travel duration our users have found a flight from New York to Chicago to be the fastest option to their destination at just 2h 28m. If travel time is less of a concern you may want to look into booking some alternative forms of transportation like a train from New York to Chicago or a bus from New York to Chicago.

Question 18

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

Accepted Answer

Expect a flight to be one of the cheapest options available to you for travel. Currently, a flight has deals available from C$ 134. While they may not be the most cost-effective options currently available a train from New York to Chicago or a bus from New York to Chicago can also be options worth looking into if other factors outside of cost are a higher priority.

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 refreshed on a daily basis.

Question 20

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

Accepted Answer

Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from New York to Chicago.

Question 21

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	C$ 104
Fastest flight time	2h 35m
Direct flights	Every day
Airports in Chicago	1 airport

Cheap flights from New York to Chicago from C$ 77

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

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Chicago?

The month of February is another great option to travel to Chicago, with average flight prices from New York averaging around C$ 264.

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 Newark to Chicago Midway 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?

No. A direct flight is the cheapest option for a flight between New York to Chicago.

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

As of December 2025, prices for New York to Chicago flights are approximately 24% 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, Frontier, and Southwest 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 15% 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 has had the least 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?

The number of flights available between New York and Chicago is 79 per day as of December 2025. The most frequent departure time is 4:00p.m., with 41% of daily flights leaving in the afternoon.

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

The number of flights available between New York and Chicago is 557 per week as of December 2025. The most frequent departure day is Tue, with 24% of weekly flights leaving on this day.

How long does it take to fly to Chicago?

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

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

How far is New York to Chicago by plane?

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

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?

What is the most popular plane model from New York to Chicago?

Travelling to a place near Chicago?

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