Question 1

What is the cheapest month to fly to Chicago?

Accepted Answer

If you don’t want to visit Chicago in January, then you should wait until February to fly from New York, when ticket prices are also cheap, with an average price of $281.

Question 2

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 3

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 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 day to depart on your flight to Chicago?

Accepted Answer

Our data shows that Tuesday is the least expensive day to fly to Chicago. Tickets to fly out on this day can be as low as $261. Flights from New York to Chicago on a Monday will generally be more expensive and average around $2,071. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

Question 6

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 7

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 8

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 41 per day as of January 2026. The most frequent departure time is 15:00, with 44% of daily flights leaving in the afternoon.

Question 9

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

Accepted Answer

Our data shows that the cheapest New York to Chicago flights are usually those with departure times in the evening. Our users have found flights to Chicago in the evening for as low as $215. Flights in the afternoon are often more expensive, with an average ticket price of $1,955.

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 $353 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 $250 on momondo.

Question 11

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

Accepted Answer

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

Question 14

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

Accepted Answer

As of January 2026, prices for New York to Chicago flights are approximately 24% cheaper when compared to flights at the same time last year.

Question 15

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 291 per week as of January 2026. The most frequent departure day is Mon, with 18% of weekly flights leaving on this day.

Question 16

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

Accepted Answer

The quickest way to travel this route is to take a flight from New York to Chicago, doing so can potentially save up to 16h 57m of travel time. While these options may take longer, booking a train from New York to Chicago or a bus from New York to Chicago may suit your needs if travel time is less of a factor in your decision making.

Question 17

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 $267 to Chicago or a bus from New York to Chicago starting at $266 if that is your preferred method of transportation.

Question 18

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 19

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

Accepted Answer

The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to 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 licence 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.

Fastest flight time	4h 29m
Direct flights	Every day
Airports in Chicago	3 airports

Cheap flights from New York to Chicago from $88

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 11/2. 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?

If you don’t want to visit Chicago in January, then you should wait until February to fly from New York, when ticket prices are also cheap, with an average price of $281.

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?

Our data shows that the cheapest New York to Chicago flights are usually those with departure times in the evening. Our users have found flights to Chicago in the evening for as low as $215. Flights in the afternoon are often more expensive, with an average ticket price of $1,955.

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 January 2026, 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?

United Airlines, Spirit 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?

The number of flights available between New York and Chicago is 41 per day as of January 2026. The most frequent departure time is 15:00, with 44% 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 291 per week as of January 2026. The most frequent departure day is Mon, with 18% of weekly flights leaving on this day.

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?

Why use momondo?

Why should I use momondo to find a flight deal from New York to Chicago?

Can I find flights from New York to Chicago with flexible booking policies on momondo?

How can momondo help me find flights from New York to Chicago?

I’m not ready to book a flight from New York to Chicago right now. Can momondo alert me if prices change?

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Airports listed have a maximum distance of 25.6 km from Chicago