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

The number of flights available between New York and Chicago is 599 per week as of July 2025. The most frequent departure day is Wed, with 22% of weekly flights leaving on this day.

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

The number of flights available between New York and Chicago is 85 per day as of July 2025. The most frequent departure time is 7:00a.m., with 45% of daily flights leaving at noon.

How long does it take to fly to Chicago?

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 38m 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 39m. Keep in mind that layovers or delays could extend your travel time.

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

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 23m. 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.

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

Expect a flight to be one of the cheapest options available to you for travel. Currently, a flight has deals available from C$ 110. While they may not be the most cost-effective options currently available a train from New York to Chicago or a bus from New York to Chicago can also be options worth looking into if other factors outside of cost are a higher priority.

When did momondo last update prices for flights from New York to Chicago?

Prices for flights from New York to Chicago are refreshed on a daily basis.

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

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.

What documentation or ID do you need to fly to Chicago?

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.

C$ 55 Cheap Flights from New York to Chicago in 2025

1 adult

Save money when you book flights with momondo

Big names, great deals

Search 100s of travel sites to compare prices.

Filter for what you want

Free Wi-Fi? Early arrival? Instantly customize your results

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Not ready to book? to track prices.

Search flight deals

Find the cheapest flights from New York to Chicago

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

3:12 p.m. - 4:50 p.m.LGA-ORD

2h 38mdirect

11:13 a.m. - 2:18 p.m.ORD-LGA

2h 05mdirect

C$ 110Spirit Airlines

Find Deal

Sat, 18 Oct - Tue, 21 Oct

3:13 p.m. - 4:51 p.m.LGA-ORD

2h 38mdirect

11:13 a.m. - 2:18 p.m.ORD-LGA

2h 05mdirect

C$ 141Spirit Airlines

Find Deal

Thu, 30 Oct - Sun, 2 Nov

3:13 p.m. - 4:51 p.m.LGA-ORD

2h 38mdirect

11:13 a.m. - 2:18 p.m.ORD-LGA

2h 05mdirect

C$ 177Spirit Airlines

Find Deal

Thu, 25 Sep - Sun, 28 Sep

8:30 p.m. - 10:20 p.m.LGA-ORD

2h 50mdirect

9:25 a.m. - 12:40 p.m.ORD-LGA

2h 15mdirect

C$ 189Delta

Find Deal

Tue, 2 Sep - Wed, 3 Sep

5:55 a.m. - 4:12 p.m.LGA-ORD

11h 17m1 stop

5:05 a.m. - 3:59 p.m.ORD-LGA

9h 54m1 stop

C$ 195Spirit Airlines

Find Deal

Thu, 25 Sep - Sun, 28 Sep

8:30 p.m. - 10:20 p.m.LGA-ORD

2h 50mdirect

10:30 a.m. - 1:44 p.m.ORD-LGA

2h 14mdirect

C$ 196Delta

Find Deal

Tue, 2 Sep - Wed, 10 Sep

7:00 a.m. - 8:38 a.m.EWR-ORD

2h 38mdirect

1:12 p.m. - 4:30 p.m.ORD-EWR

2h 18mdirect

C$ 196United Airlines

Find Deal

Wed, 3 Sep - Wed, 3 Sep

6:00 a.m. - 7:38 a.m.EWR-ORD

2h 38mdirect

6:00 a.m. - 9:15 a.m.ORD-EWR

2h 15mdirect

C$ 203United Airlines

Find Deal

Sat, 13 Sep - Tue, 16 Sep

7:20 a.m. - 2:15 p.m.LGA-ORD

7h 55m1 stop

7:00 a.m. - 3:40 p.m.ORD-LGA

7h 40m1 stop

C$ 261Southwest

Find Deal

Sun, 31 Aug - Wed, 3 Sep

11:25 a.m. - 10:00 p.m.LGA-ORD

11h 35m2 stops

7:30 a.m. - 5:25 p.m.ORD-LGA

8h 55m1 stop

C$ 268Southwest

Find Deal

Sat, 6 Sep - Mon, 8 Sep

Spirit Airlines flights from New York to Chicago

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

Spirit Airlines

18 Oct

LGA3:12 p.m.New York LaGuardia

2h 38m

ORD4:50 p.m.Chicago O'Hare Intl

21 Oct

ORD11:13 a.m.Chicago O'Hare Intl

2h 05m

LGA2:18 p.m.New York LaGuardia

C$ 110

Find similar

Spirit Airlines

30 Oct

LGA3:13 p.m.New York LaGuardia

2h 38m

ORD4:51 p.m.Chicago O'Hare Intl

2 Nov

ORD11:13 a.m.Chicago O'Hare Intl

2h 05m

LGA2:18 p.m.New York LaGuardia

C$ 141

Find similar

Spirit Airlines

25 Sep

LGA3:13 p.m.New York LaGuardia

2h 38m

ORD4:51 p.m.Chicago O'Hare Intl

28 Sep

ORD11:13 a.m.Chicago O'Hare Intl

2h 05m

LGA2:18 p.m.New York LaGuardia

C$ 177

Find similar

Southwest flights from New York to Chicago

Our best Southwest deals on New York to Chicago flight tickets

Southwest

31 Aug

LGA7:20 a.m.New York LaGuardia

7h 55m

1 stop

ORD2:15 p.m.Chicago O'Hare Intl

3 Sep

ORD7:00 a.m.Chicago O'Hare Intl

7h 40m

1 stop

LGA3:40 p.m.New York LaGuardia

C$ 261

Find similar

Southwest

6 Sep

LGA11:25 a.m.New York LaGuardia

11h 35m

2 stops

ORD10:00 p.m.Chicago O'Hare Intl

8 Sep

ORD7:30 a.m.Chicago O'Hare Intl

8h 55m

1 stop

LGA5:25 p.m.New York LaGuardia

C$ 268

Find similar

Southwest

6 Sep

LGA8:15 a.m.New York LaGuardia

14h 45m

2 stops

ORD10:00 p.m.Chicago O'Hare Intl

8 Sep

ORD2:55 p.m.Chicago O'Hare Intl

6h 55m

1 stop

LGA10:50 p.m.New York LaGuardia

C$ 274

Find similar

Fly from

Fly to

Route

Depart

Return

Price

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Sat 18/10

3:12 p.m.-4:50 p.m.

Nonstop2h 38m

Chicago O'Hare Intl

Tue 21/10

11:13 a.m.-2:18 p.m.

Nonstop2h 05m

C$ 110

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Thu 30/10

3:13 p.m.-4:51 p.m.

Nonstop2h 38m

Chicago O'Hare Intl

Sun 2/11

11:13 a.m.-2:18 p.m.

Nonstop2h 05m

C$ 141

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Thu 25/9

3:13 p.m.-4:51 p.m.

Nonstop2h 38m

Chicago O'Hare Intl

Sun 28/9

11:13 a.m.-2:18 p.m.

Nonstop2h 05m

C$ 177

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Tue 2/9

8:30 p.m.-10:20 p.m.

Nonstop2h 50m

Chicago O'Hare Intl

Wed 3/9

9:25 a.m.-12:40 p.m.

Nonstop2h 15m

C$ 189

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Thu 25/9

5:55 a.m.-4:12 p.m.

1 stop11h 17m

Chicago O'Hare Intl

Sun 28/9

5:05 a.m.-3:59 p.m.

1 stop9h 54m

C$ 194

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Tue 2/9

8:30 p.m.-10:20 p.m.

Nonstop2h 50m

Chicago O'Hare Intl

Wed 10/9

10:30 a.m.-1:44 p.m.

Nonstop2h 14m

C$ 196

NewarkChicago

EWR - ORD

EWRORD

Newark

Wed 3/9

7:00 a.m.-8:38 a.m.

Nonstop2h 38m

Chicago O'Hare Intl

Wed 3/9

1:12 p.m.-4:30 p.m.

Nonstop2h 18m

C$ 196

NewarkChicago

EWR - ORD

EWRORD

Newark

Sat 13/9

6:00 a.m.-7:38 a.m.

Nonstop2h 38m

Chicago O'Hare Intl

Tue 16/9

6:00 a.m.-9:15 a.m.

Nonstop2h 15m

C$ 203

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Sun 31/8

7:20 a.m.-2:15 p.m.

1 stop7h 55m

Chicago O'Hare Intl

Wed 3/9

7:00 a.m.-3:40 p.m.

1 stop7h 40m

C$ 261

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Sat 6/9

11:25 a.m.-10:00 p.m.

2 stops11h 35m

Chicago O'Hare Intl

Mon 8/9

7:30 a.m.-5:25 p.m.

1 stop8h 55m

C$ 268

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

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

Prices

Airlines

Other information

What is the cheapest month to fly to Chicago?

The month of January is another great option to travel to Chicago, with average flight prices from New York averaging around C$ 248.

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 Saturday when prices can be found for as low as C$ 311. 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 Sunday because tickets tend to average around C$ 584. These prices are subject to change though, so be sure to set up a Price Alert for flights to Chicago.

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

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 C$ 274. Flying to Chicago in the evening is an ideal time because this is during off-peak travel hours. At noon is when there is more demand to fly to Chicago, so prices are often more expensive at around C$ 519 per ticket.

What is the cheapest New York to Chicago flight route?

Fly from New York LaGuardia to Chicago Midway for the best New York - Chicago flight prices

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

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$ 338 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$ 262 on momondo.

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

There are 3 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.

When to book flights from New York to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from New York to Chicago according to our flight data. Find out which month and days have the cheapest flights.

Estimated round-trip price

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

Best price found	C$ 55
Fastest flight time	2h 23m
Direct flights	Every day
Airports in Chicago	1 airport

The best one-way flight to Chicago from New York in the past 72 hours is C$ 55. The best round-trip flight deal from New York to Chicago found on momondo in the last 72 hours is C$ 110.

The fastest flight from New York to Chicago takes 2h 23m

Direct flights go from New York to Chicago every day.

There is 1 airport near Chicago: Chicago O'Hare Intl (ORD)

Search flight deals

Is flying the fastest way to get from New York to Chicago?
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 23m. 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.
Is flying the cheapest way to get from New York to Chicago?
Expect a flight to be one of the cheapest options available to you for travel. Currently, a flight has deals available from C$ 110. While they may not be the most cost-effective options currently available a train from New York to Chicago or a bus from New York to Chicago can also be options worth looking into if other factors outside of cost are a higher priority.
How far is New York to Chicago by plane?
There are 1143.9 km between New York and Chicago. Typically, this will take 2h 23m by plane in normal conditions.
When did momondo last update prices for flights from New York to Chicago?
Prices for flights from New York to Chicago are refreshed on a daily basis.
How old do you have to be to fly from New York to Chicago?
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.
What documentation or ID do you need to fly to Chicago?
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.
What is the most popular plane model from New York to Chicago?
momondo data reveals that the most frequently booked plane model on the route from New York to Chicago is Boeing 737-800, representing 20.41% of all bookings. The subsequent popular models are Boeing 737 MAX 8 at 13.40%, Airbus A321neo at 10.50%, and Airbus A320 (sharklets) at 8.63%.
What is the most popular airline from New York to Chicago?
momondo data reveals that the most frequently booked airline on the route from New York to Chicago is Spirit Airlines, representing 100% of all bookings.

Hammond

Munster

Benton Harbor

Merrillville

Why use momondo?

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

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from New York to Chicago. momondo saves you time and could save you money on your trip.

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

Yes. momondo enables you to select and highlight flights to Chicago from New York with this policy.

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

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight 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?

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from New York and alert you when they change.

An easier way to manage your Chicago trip

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

Start using Trips

Find my bookings

Get notified when prices go down

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

1 adult

Mon 4/8

Mon 11/8

Email me momondo's favourite deals

By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to the United States

Cheap flights from New York to Chicago from C$ 55

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 13/9. 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 round-trip flights

Cheap one-way flights

Cheap last-minute flights

Cheap direct flights

Spirit Airlines flights from New York to Chicago

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

Southwest flights from New York to Chicago

Our best Southwest 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?

The month of January is another great option to travel to Chicago, with average flight prices from New York averaging around C$ 248.

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 New York LaGuardia 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 3 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?

Spirit Airlines, United Airlines, and Delta are the most popular carriers operating from New York 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 85 per day as of July 2025. The most frequent departure time is 7:00a.m., with 45% 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 599 per week as of July 2025. The most frequent departure day is Wed, with 22% 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

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

Best price found

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?

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

Travelling to a place near 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, organize 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