Question 1

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

Accepted Answer

As of July 2025, there are 850 flights per week flying from New York to Chicago. The most common day of the week flights depart is Tue, with 22% of flights taking off on this day.

Question 2

Which airlines fly to Chicago?

Accepted Answer

American Airlines, Spirit Airlines and JetBlue are the top three most popular airlines that fly to Chicago from New York according to our data. American Airlines is the first choice among our users, with 40% of people opting to fly with this airline when travelling to Chicago. Keep in mind that there are 3 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

Question 3

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 £121. This is often the case because there is less demand to fly during this day of the week. The most expensive day to fly to Chicago is Thursday, with ticket prices averaging around £238.

Question 4

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

Accepted Answer

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

Question 5

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 6

How long does it take to fly to Chicago?

Accepted Answer

On average, it takes 2h 35m to fly from New York to Chicago if you fly out of New York (the most popular airport in New York) and into Chicago O'Hare Intl Airport (the most popular airport in Chicago). If you’re flying out of Newark and into Chicago O'Hare Intl Airport, then the flight time is around 2h 38m.

Question 7

What is the cheapest New York to Chicago flight route?

Accepted Answer

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

Question 8

What is the cheapest month to fly to Chicago?

Accepted Answer

The cheapest month to fly to Chicago from New York is in September. Flight prices, which tend to average around £133, are often lower during this time because this is during the off-season. If you aren’t able to travel during the month of September, then book flights to Chicago from New York during January instead. Flights to Chicago in January, while not as cheap as those in September, still average around £135.

Question 9

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

Accepted Answer

Flying to Chicago from New York in the morning is the least expensive time of day to depart. momondo users have found prices as low as £182 when looking at flights departing in the morning. Flights in the afternoon are often more expensive, with an average ticket price of £290.

Question 10

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 121 per day as of July 2025. The most frequent departure time is 07:00, with 45% of daily flights leaving at midday.

Question 11

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 12

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 £126 to £242.
The lowest price recently found on this route was £67.

Question 13

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 £183 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 £142 on momondo.

Question 14

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

Accepted Answer

As of July 2025, prices for New York to Chicago flights are approximately 21% cheaper when compared to flights at the same time last year.

Question 15

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 24m. 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 16

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

Accepted Answer

Planning to book a flight from New York to Chicago can be a safe bet when looking for a low-cost deal to your destination. Currently, a train and a bus are priced higher than the cost of a flight. You can search prices for a train from New York starting at £135 to Chicago or a bus from New York to Chicago starting at £117 if that is your preferred method of transportation.

Question 17

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 18

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

Accepted Answer

The number of operators available for flights from New York to Chicago is 3 as of July 2025.

Question 19

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 20

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	£29
Fastest flight time	2h 24m
Direct flights	Every day
Airports in Chicago	1 airport

Airline	Rating	Free Cancellation	Price
JetBlue	PriceFrom £51	Free Cancellation	Rating 7.2 2,913 reviews	Search JetBlue flights
Spirit Airlines	PriceFrom £85	Free Cancellation	Rating 6.3 8,044 reviews	Search Spirit Airlines flights
American Airlines	PriceFrom £95	Free Cancellation	Rating 7.2 10,000 reviews	Search American Airlines flights

Cheap flights from New York to Chicago from £29

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 3/12. 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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What is the typical price of a round-trip flight between New York and Chicago?

What is the cheapest month to fly to Chicago?

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

The cheapest day to depart on your flight to Chicago is on a Tuesday when prices can be found for as low as £121. This is often the case because there is less demand to fly during this day of the week. The most expensive day to fly to Chicago is Thursday, with ticket prices averaging around £238.

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

Flying to Chicago from New York in the morning is the least expensive time of day to depart. momondo users have found prices as low as £182 when looking at flights departing in the morning. Flights in the afternoon are often more expensive, with an average ticket price of £290.

What is the cheapest New York to Chicago flight route?

Fly from Newark 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?

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 July 2025, prices for New York to Chicago flights are approximately 21% cheaper when compared to flights at the same time last year.

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

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

Which airlines fly to Chicago?

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

The number of flights available between New York and Chicago is 121 per day as of July 2025. The most frequent departure time is 07:00, with 45% of daily flights leaving at midday.

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

As of July 2025, there are 850 flights per week flying from New York to Chicago. The most common day of the week flights depart is Tue, with 22% of flights taking off 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

Find info about flight duration, direct flights, and airports for your flight from New York to Chicago

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Airports in Chicago

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 many operators does momondo search 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?

What is the most popular airline from New York to Chicago?

Best airlines flying from New York to Chicago

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JetBlue Flights From New York to Chicago

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Why use momondo?

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Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago