Question 1

How long does a flight from New York to Chicago take?

Accepted Answer

The duration of a direct flight to Chicago from New York is typically 2h 30m. The journey crosses a distance of 1,841 km. Visit our flight page for the latest deals!>/a>

Question 2

How many flights are there between New York and Chicago per day?

Accepted Answer

Each day, there are between 44 and 68 nonstop flights that take off from New York and land in Chicago, with an average flight time of 2h 50m. The most common departure time is 7:00 a.m. and most flights take off in the morning, while the most flights land at Chicago O'Hare Intl Airport. Each week, there are 435 flights. The most frequent day of departure is Friday, when 16% of all weekly flights depart. The fewest flights depart on a Saturday. Visit our flight page for the latest deals!>/a>

Question 3

How many flights are there between New York and Chicago per day?

Accepted Answer

Each day, there are between 44 and 68 nonstop flights that take off from New York and land in Chicago, with an average flight time of 2h 50m. The most common departure time is 7:00 a.m. and most flights take off in the morning, while the most flights land at Chicago O'Hare Intl Airport. Each week, there are 435 flights. The most frequent day of departure is Friday, when 16% of all weekly flights depart. The fewest flights depart on a Saturday. Visit our flight page for the latest deals!>/a>

Question 4

What is the cheapest flight from New York to Chicago?

Accepted Answer

In the last 3 days, the lowest price for a flight from New York to Chicago was C$ 81 for a one-way ticket and C$ 131 for a round-trip. <a href='/flight-routes/New-York-NYC/Chicago-CHI'>Visit our flight page for the latest deals!>/a>

Question 5

Which airlines fly most frequently between New York and Chicago?

Accepted Answer

New York and Chicago are connected by different airlines. The airlines that fly that route the most regularly are United Airlines (178 flights per week), American Airlines (112 flights per week), and Delta (77 flights per week). Visit our flight page for the latest deals!>/a>

Question 6

Which airlines fly most frequently between New York and Chicago?

Accepted Answer

New York and Chicago are connected by different airlines. The airlines that fly that route the most regularly are United Airlines (178 flights per week), American Airlines (112 flights per week), and Delta (77 flights per week). Visit our flight page for the latest deals!>/a>

Question 7

What’s the earliest departure time from New York to Chicago?

Accepted Answer

Early birds can take the earliest flight from New York at 6:00 am and will be landing in Chicago at 7:50 am.

Question 8

What’s the latest departure time from New York to Chicago?

Accepted Answer

If you prefer to fly at night, the latest flight from New York to Chicago jets off at 11:05 pm and lands at 12:40 am.

Question 9

Which airlines offer Wi-Fi service onboard planes from New York to Chicago?

Accepted Answer

American Airlines, Delta, and JetBlue offer inflight Wi-Fi service on the New York to Chicago flight route.

Question 10

Which aircraft models fly most regularly from New York to Chicago?

Accepted Answer

The Boeing 737-800 is the aircraft model that flies most regularly on the New York to Chicago flight route.

Question 11

On which days can I fly direct from New York to Chicago?

Accepted Answer

There are direct flights from New York to Chicago on a daily basis.

Question 12

When looking for flights from New York to Chicago which Chicago airport should I choose?

Accepted Answer

Chicago Midway is closer to downtown Chicago, and since it is a smaller airport it can be less busy and easier to navigate; however, because of the airport size difference, Chicago O'Hare International tends to have more flights and is served by more carriers.

Question 13

What is the cost of an Uber from Chicago O'Hare International to downtown Chicago?

Accepted Answer

Rides start at $38 but can, of course, be higher depending on the time of day and traffic conditions.

Question 14

What is the best way for someone to pick me up at Chicago O'Hare International?

Accepted Answer

Chicago O'Hare International utilizes a cell phone lot for those wishing to pick up arriving passengers. The lot has a flight information display to let those waiting know when you have arrived. The airport does not allow stopping in front of the terminal except for immediate pickup of passengers, so the cell phone lot is an excellent option for those waiting for arriving passengers.

Question 15

What is the fastest way to get to New York LaGuardia airport?

Accepted Answer

One very convenient and unique way to get to New York LaGuardia is via the New York City Ferry. You can take the ferry from New York to the last stop at Astoria and then get a taxi or Uber to the airport. The ferry offers alcoholic and non-alcoholic drinks as well as a variety of snacks on board, making it a comfortable journey overall.

Question 16

What is the cheapest month to fly from New York to Chicago?

Accepted Answer

The cheapest month for flights from New York to Chicago is January, where tickets cost C$ 256 (return) on average. On the other hand, the most expensive months are August and June, where the average cost of round-trip tickets is C$ 382 and C$ 379 respectively.

Question 17

What is the cheapest month to fly from New York to Chicago?

Accepted Answer

The cheapest month for flights from New York to Chicago is January, where tickets cost C$ 256 (return) on average. On the other hand, the most expensive months are August and June, where the average cost of round-trip tickets is C$ 382 and C$ 379 respectively.

Question 18

How does KAYAK find such low prices on flights from New York to Chicago?

Accepted Answer

KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from New York to Chicago. <a href='/flight-routes/New-York-NYC/Chicago-CHI'>Visit our flight page for the latest deals!>/a>

Question 19

How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from New York to Chicago?

Accepted Answer

KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from New York is likely to change within 7 days, so travelers know whether to wait or book now. <a href='/flight-routes/New-York-NYC/Chicago-CHI'>Visit our flight page for the latest deals!>/a>

Question 20

What is the Hacker Fare option on flights from New York to Chicago?

Accepted Answer

Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to New York with another airline. <a href='/flight-routes/New-York-NYC/Chicago-CHI'>Visit our flight page for the latest deals!>/a>

Question 21

What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from New York to Chicago?

Accepted Answer

Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from New York up to 3 days before/after your preferred dates. You can then pick the flights that suit you best. <a href='/flight-routes/New-York-NYC/Chicago-CHI'>Visit our flight page for the latest deals!>/a>

Question 22

How often are flights from New York to Chicago delayed?

Accepted Answer

Weekly flights between New York and Chicago historically see delays in approximately 18% of cases, with the average delay over the past year being 159 minutes.

Question 23

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

Accepted Answer

Based on our data, United Airlines have experienced the fewest delays on this route in the past 12 months, with only about 14% of their flights encountering any delays.

Question 24

What day of the week experiences the fewest flight delays on this route?

Accepted Answer

Statistically, Saturday is the day of the week with the fewest delays on this flight route, while Sunday has typically experienced more delays than other days.

Question 25

What is the most punctual flight time for New York to Chicago flights?

Accepted Answer

Typically, flights leaving in the morning tend to face fewer delays, whereas flights at night have historically encountered delays more often.

Question 26

Which cabin class options are there for flights between New York and Chicago?

Accepted Answer

There are 3 cabin class options for the route. These are Business, Economy and Prem Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

Question 27

Which cabin class options are there for flights between New York and Chicago?

Accepted Answer

There are 3 cabin class options for the route. These are Business, Economy and Prem Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

Question 28

Which airlines provide the cheapest flights from New York to Chicago?

Accepted Answer

In the past 3 days, the cheapest round-trip tickets from New York to Chicago were found on Spirit Airlines (C$ 131) and United Airlines (C$ 160).

Question 29

Which airlines provide the cheapest flights from New York to Chicago?

Accepted Answer

In the past 3 days, the cheapest round-trip tickets from New York to Chicago were found on Spirit Airlines (C$ 131) and United Airlines (C$ 160).

Question 30

What is the cheapest New York to Chicago flight route?

Accepted Answer

The absolute cheapest return flight from New York to Chicago costs C$ 241 on the route between Newark Airport (EWR) and Chicago O'Hare Intl Airport (ORD). However, over the past month, flights between New York John F Kennedy Intl Airport (JFK) and Chicago O'Hare Intl Airport (ORD) were, on average, 20% cheaper than other New York-Chicago routes. The most popular route is between Newark Airport (EWR) and Chicago O'Hare Intl Airport (ORD).

Question 31

What is the cheapest New York to Chicago flight route?

Accepted Answer

The absolute cheapest return flight from New York to Chicago costs C$ 241 on the route between Newark Airport (EWR) and Chicago O'Hare Intl Airport (ORD). However, over the past month, flights between New York John F Kennedy Intl Airport (JFK) and Chicago O'Hare Intl Airport (ORD) were, on average, 20% cheaper than other New York-Chicago routes. The most popular route is between Newark Airport (EWR) and Chicago O'Hare Intl Airport (ORD).

Question 32

How far in advance should I book a flight from New York to Chicago?

Accepted Answer

To get a below average price on the flight from New York to Chicago, you should book around 3 weeks before departure, which saves you about 42% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 18 weeks before departure.

Question 33

How far in advance should I book a flight from New York to Chicago?

Accepted Answer

To get a below average price on the flight from New York to Chicago, you should book around 3 weeks before departure, which saves you about 42% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 18 weeks before departure.

Question 34

Can I save money by flying with a layover from New York to Chicago?

Accepted Answer

No, with an average price for the route of C$ 321, prices are generally cheapest when you fly direct.

Question 35

Can I save money by flying with a layover from New York to Chicago?

Accepted Answer

No, with an average price for the route of C$ 321, prices are generally cheapest when you fly direct.

Low season	January
High season	May

NYC - CHI

C$ 81 Find Cheap Flights from New York to Chicago

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago

Everything you should know

Cheap Flights from New York to Chicago (NYC-CHI)

Recent round-trip flight deals from New York to Chicago

Recent one-way flight deals from New York to Chicago

Recent last minute flight deals from New York to Chicago

Recent direct flight deals from New York to Chicago

KAYAK's insights & trends for New York to Chicago flights

Get data-powered insights and trends into flights from New York to Chicago to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest New York to Chicago flight route?

What is the cheapest month to fly from New York to Chicago?

The cheapest month for flights from New York to Chicago is January, where tickets cost C$ 256 (return) on average. On the other hand, the most expensive months are August and June, where the average cost of round-trip tickets is C$ 382 and C$ 379 respectively.

Can I save money by flying with a layover from New York to Chicago?

No, with an average price for the route of C$ 321, prices are generally cheapest when you fly direct.

How far in advance should I book a flight from New York to Chicago?

To get a below average price on the flight from New York to Chicago, you should book around 3 weeks before departure, which saves you about 42% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 18 weeks before departure.

Which airlines provide the cheapest flights from New York to Chicago?

In the past 3 days, the cheapest round-trip tickets from New York to Chicago were found on Spirit Airlines (C$ 131) and United Airlines (C$ 160).

Which airlines fly most frequently between New York and Chicago?

New York and Chicago are connected by different airlines. The airlines that fly that route the most regularly are United Airlines (178 flights per week), American Airlines (112 flights per week), and Delta (77 flights per week).

How often are flights from New York to Chicago delayed?

Weekly flights between New York and Chicago historically see delays in approximately 18% of cases, with the average delay over the past year being 159 minutes.

What is the most punctual flight time for New York to Chicago flights?

Typically, flights leaving in the morning tend to face fewer delays, whereas flights at night have historically encountered delays more often.

What day of the week experiences the fewest flight delays on this route?

Statistically, Saturday is the day of the week with the fewest delays on this flight route, while Sunday has typically experienced more delays than other days.

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

Based on our data, United Airlines have experienced the fewest delays on this route in the past 12 months, with only about 14% of their flights encountering any delays.

Which cabin class options are there for flights between New York and Chicago?

There are 3 cabin class options for the route. These are Business, Economy and Prem Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

How many flights are there between New York and Chicago per day?

How long does a flight from New York to Chicago take?

The duration of a direct flight to Chicago from New York is typically 2h 30m. The journey crosses a distance of 1,841 km.

What’s the earliest departure time from New York to Chicago?

Early birds can take the earliest flight from New York at 6:00 am and will be landing in Chicago at 7:50 am.

What’s the latest departure time from New York to Chicago?

If you prefer to fly at night, the latest flight from New York to Chicago jets off at 11:05 pm and lands at 12:40 am.

Expert advice for your flight from New York to Chicago

Good to know

When to book flights from New York to Chicago

Flights from New York to Chicago: the best tips from KAYAK users' own experiences

FAQs for booking flights from New York to Chicago

When looking for flights from New York to Chicago which Chicago airport should I choose?

Chicago Midway is closer to downtown Chicago, and since it is a smaller airport it can be less busy and easier to navigate; however, because of the airport size difference, Chicago O'Hare International tends to have more flights and is served by more carriers.

What is the cost of an Uber from Chicago O'Hare International to downtown Chicago?

Rides start at $38 but can, of course, be higher depending on the time of day and traffic conditions.

What is the best way for someone to pick me up at Chicago O'Hare International?

What is the fastest way to get to New York LaGuardia airport?

What is the cheapest flight from New York to Chicago?

In the last 3 days, the lowest price for a flight from New York to Chicago was C$ 81 for a one-way ticket and C$ 131 for a round-trip.

Which airlines offer Wi-Fi service onboard planes from New York to Chicago?

American Airlines, Delta, and JetBlue offer inflight Wi-Fi service on the New York to Chicago flight route.

Which aircraft models fly most regularly from New York to Chicago?

The Boeing 737-800 is the aircraft model that flies most regularly on the New York to Chicago flight route.

On which days can I fly direct from New York to Chicago?

There are direct flights from New York to Chicago on a daily basis.

How does KAYAK find such low prices on flights from New York to Chicago?

KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from New York to Chicago.

How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from New York to Chicago?

KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from New York is likely to change within 7 days, so travelers know whether to wait or book now.

What is the Hacker Fare option on flights from New York to Chicago?

Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to New York with another airline.

What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from New York to Chicago?

Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from New York up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from New York to Chicago

Prefer to fly direct from New York to Chicago?

Reviews of the top airline flying from New York to Chicago

Everything you need to know for your flight from New York to Chicago

Cabin class types available on flights from New York to Chicago

Complete your trip to Chicago with a hotel stay or car rental

Find direct flights to and from New York and Chicago

Flights to other popular destinations

Flights from domestic origins to Chicago