Question 1

What is the cheapest month to fly to Chicago?

Accepted Answer

The cheapest month to fly to Chicago from New York is in January. Flight prices, which tend to average around €157, are often lower during this time because this is during the off-season. 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 €162.

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 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 4

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 5

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

Accepted Answer

1,036 flights are operational weekly from New York to Chicago as of December 2025. The most popular departure day for this route is Wed, with 17% of flights per week taking off on this day.

Question 6

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 7

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 8

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 9

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 35m and 2h 46m, respectively.

Question 10

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

Accepted Answer

On average, the least expensive day to fly to Chicago from New York is on a Saturday. momondo users have found tickets for Saturday departures for as low as €137. However, this price may fluctuate depending on the airline, the season, and holidays. Be sure to avoid booking your departure on a Tuesday as prices are generally higher than usual. According to our data, the average ticket price to Chicago on Tuesday is €528.

Question 11

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 €106. Flying to Chicago in the evening is an ideal time because this is during off-peak travel hours. If you have a flexible travel schedule, then try to avoid flying at midday when prices are €312 on average. Flights to Chicago from New York at midday are generally more expensive because this time of day is more convenient for travellers’ schedules.

Question 12

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

Accepted Answer

You could potentially save up to 9% on your flight if you consider stops on a New York to Chicago flight.

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 €212 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 €159 on momondo.

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

Accepted Answer

There is only 1 cabin class 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 16

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

Accepted Answer

148 flights are operational daily from New York to Chicago as of December 2025. The most popular departure time for this route is 16:00, with 41% of flights per day taking off in the afternoon.

Question 17

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

Accepted Answer

We’ve found that taking a flight from New York to Chicago with {10} is more time-efficient when based simply on travel duration. A train from New York to Chicago or a bus from New York to Chicago can take you longer than a 2h 30m flight.

Question 18

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

Accepted Answer

A flight from New York to Chicago is currently going to be the least expensive option currently available. You can also find deals for a train from New York to Chicago starting at €170, or consider a bus from New York to Chicago starting at €199. Both of these alternative options are worth considering when looking to reach your destination.

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 were last updated today.

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 stopovers. 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 travel and health documents required for your trip to Chicago can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s licence, and a passport valid for six-months after you plan to arrive at Chicago. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

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

Cheap flights from New York to Chicago from €47

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 5/1. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Big names, great deals

Big names, great deals

Filter for what you want

Filter for what you want

Trusted and free

Trusted and free

Price Alerts

Price Alerts

Find the cheapest flights from New York to Chicago

Cheap return flights

Cheap one-way flights

Cheap last-minute flights

Cheap direct flights

Frontier flights from New York to Chicago

Our best Frontier deals on New York to Chicago flight tickets

Spirit Airlines flights from New York to Chicago

Our best Spirit Airlines deals on New York to Chicago flight tickets

momondo Fare Finder

Use the filters below to find and compare flights from New York to Chicago that are best for you.

See travel insights to Chicago from

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?

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 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 is only 1 cabin class 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 9% 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 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, 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 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 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?

148 flights are operational daily from New York to Chicago as of December 2025. The most popular departure time for this route is 16:00, with 41% of flights per day taking off in the afternoon.

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

1,036 flights are operational weekly from New York to Chicago as of December 2025. The most popular departure day for this route is Wed, with 17% 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 35m and 2h 46m, respectively.

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

Fastest flight time

Direct flights

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 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?

An easier way to manage your Chicago trip

We make it super easy to schedule, organise and travel with friends or family. Trips is free – and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 25.6 km from Chicago