Question 1

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

Accepted Answer

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

Question 2

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 3

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 4

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 5

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$ 260.

Question 6

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 7

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$ 332 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$ 240 on momondo.

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 92 per day as of December 2025. The most frequent departure time is 3:00p.m., with 40% of daily flights leaving at noon.

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 644 per week as of December 2025. The most frequent departure day is Sun, with 19% of weekly flights leaving on this day.

Question 11

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 12

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 13

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 14

What is the typical price of a round-trip flight between New York and Chicago?

Accepted Answer

Prices are currently low for flights on this route.Typical prices usually range from C$ 223 to C$ 543.
The lowest price recently found on this route was C$ 125.

Question 15

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$ 368. 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$ 567 per ticket.

Question 16

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$ 271. 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$ 547. These prices are subject to change though, so be sure to set up a Price Alert for flights to Chicago.

Question 17

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 16% cheaper when compared to flights at the same time last year.

Question 18

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 37m. 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 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$ 103
Fastest flight time	2h 35m
Direct flights	Every day
Airports in Chicago	3 airports

Cheap flights from New York to Chicago from C$ 76

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 18/3. 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 typical price of a round-trip flight between New York and Chicago?

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$ 260.

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 16% 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 and United Airlines 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 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 92 per day as of December 2025. The most frequent departure time is 3:00p.m., with 40% of daily flights leaving at noon.

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

The number of flights available between New York and Chicago is 644 per week as of December 2025. The most frequent departure day is Sun, with 19% 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?

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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?

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Travelling to a place near Chicago?

Why use momondo?

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