Find flights
Deals
When to book
FAQs

Cheap flights from New York, NY to Chicago from C$ 180

NYC — CHI
26 Oct — 2 Nov1
1 adult
1 adult, Economy, 0 bags
Cheapflights Tip: The best prices from New York to Chicago are usually found in January or February, booked 83 days in advance, depart on a Monday or Tuesday and return on a Tuesday

Cheap flight deals from New York to Chicago

Enter your travel dates to find the best prices.

Cheapest flights from New York to Chicago

Mon 9/116:30 a.m. -
1 stop12h 17m
Mon 16/116:16 a.m. -
1 stop8h 45m
Deal found 25/9C$ 348
Thu 15/105:55 a.m. -
1 stop26h 36m
Sun 18/106:58 p.m. -
1 stop29h 04m
Deal found 22/9C$ 376
Sat 31/106:40 a.m. -
1 stop6h 20m
Mon 2/111:00 p.m. -
1 stop5h 59m
Deal found 25/9C$ 379
Mon 9/116:40 a.m. -
1 stop6h 20m
Mon 16/111:00 p.m. -
1 stop5h 59m
Deal found 25/9C$ 380
Tue 10/116:40 a.m. -
1 stop6h 20m
Tue 17/111:00 p.m. -
1 stop5h 59m
Deal found 26/9C$ 382
Wed 11/116:40 a.m. -
1 stop6h 20m
Tue 17/111:00 p.m. -
1 stop7h 29m
Deal found 26/9C$ 383
Fri 23/101:00 p.m. -
1 stop7h 00m
Tue 27/101:00 p.m. -
1 stop7h 29m
Deal found 25/9C$ 386
Sat 17/101:00 p.m. -
1 stop7h 14m
Mon 19/106:10 a.m. -
Nonstop2h 20m
Deal found 25/9C$ 390
Sat 24/107:17 a.m. -
Nonstop2h 43m
Sat 31/109:48 p.m. -
Nonstop2h 10m
Deal found 24/9C$ 392
Sat 17/108:10 a.m. -
Nonstop2h 37m
Tue 20/106:00 a.m. -
Nonstop2h 15m
Deal found 25/9C$ 392
Sat 17/106:15 a.m. -
Nonstop2h 30m
Mon 19/105:10 a.m. -
Nonstop2h 05m
Deal found 25/9C$ 392
Sat 17/105:30 p.m. -
Nonstop2h 50m
Mon 19/107:20 p.m. -
Nonstop2h 29m
Deal found 26/9C$ 393

Find flight deals from New York to Chicago

Round-trip from

C$ 348

One-way from

C$ 180

Popular in

July

Cheapest in

January

Average price

C$ 436

Good one-way deal

C$ 125 or less
Frontier
  • Frontier
  • 9/11-16/11
  • 2 total stops
  • 21h 02m total
  • New York to Chicago
Search Deals
Frontier
  • Frontier
  • 1/10-31/12
  • 1 total stop
  • 12h 31m total
  • New York to Chicago
Search Deals
Highest demand for flights based on searches. 16% potential increase in price (C$ 103 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (C$ 13 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2026
Search Deals
Price to beat on a one-way flight from New York (NYC) to Chicago (CHI).
Search Deals

Cheapflights Fare Finder

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

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

NewarkChicago

EWR Newark - ORD Chicago O'Hare Intl

EWRORD

Newark

Sat 20/2

10:30 a.m.-12:15 p.m.

Nonstop2h 45m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 197

New YorkChicago

LGA New York LaGuardia - MDW Chicago Midway

LGAMDW

New York LaGuardia

Mon 9/11

8:30 a.m.-10:05 a.m.

Nonstop2h 35m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 197

NewarkChicago

EWR Newark - ORD Chicago O'Hare Intl

EWRORD

Newark

Thu 29/10

8:30 p.m.-10:18 p.m.

Nonstop2h 48m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 197

New YorkChicago

LGA New York LaGuardia - MDW Chicago Midway

LGAMDW

New York LaGuardia

Mon 23/11

8:30 a.m.-10:05 a.m.

Nonstop2h 35m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 197

New YorkChicago

LGA New York LaGuardia - MDW Chicago Midway

LGAMDW

New York LaGuardia

Thu 29/10

5:45 p.m.-7:15 p.m.

Nonstop2h 30m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 197

New YorkChicago

LGA New York LaGuardia - MDW Chicago Midway

LGAMDW

New York LaGuardia

Thu 19/11

6:35 p.m.-8:15 p.m.

Nonstop2h 40m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 197

New YorkChicago

JFK New York John F Kennedy Intl - ORD Chicago O'Hare Intl

JFKORD

New York John F Kennedy Intl

Mon 16/11

7:35 p.m.-9:42 p.m.

Nonstop3h 07m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 204

New YorkChicago

JFK New York John F Kennedy Intl - ORD Chicago O'Hare Intl

JFKORD

New York John F Kennedy Intl

Sun 8/11

6:40 a.m.-12:00 p.m.

1 stop6h 20m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 204

New YorkChicago

JFK New York John F Kennedy Intl - ORD Chicago O'Hare Intl

JFKORD

New York John F Kennedy Intl

Mon 8/2

3:40 p.m.-5:34 p.m.

Nonstop2h 54m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 204

New YorkChicago

JFK New York John F Kennedy Intl - ORD Chicago O'Hare Intl

JFKORD

New York John F Kennedy Intl

Tue 15/12

12:35 p.m.-4:42 p.m.

1 stop5h 07m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 204

Flights are sorted by cheapest round-trip flights first.

Deals found on 25/9

Showing 1-10 of 60 resultsSorted by cheapest first
1
2
3
...
6

Best time to book a flight from New York to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from New York with our price prediction graph.
Estimated round-trip price

Cheapflights Insights

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

What is the cheapest month to book a flight from New York to Chicago?

Currently, January is the cheapest month in which you can book a flight from New York to Chicago (average of C$ 270). Flying from New York to Chicago in July is currently the most expensive (average of C$ 488). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from NYC to CHI?

It’s typically best to fly out from New York to Chicago in the morning. Doing so could potentially save you 52% on the flight price compared to flying at noon, which is usually more expensive.

Weekly flight availability from New York to Chicago

The most flights from NYC to CHI are scheduled on a Friday (193 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (96 on average).

How much does it cost to fly round-trip from New York to Chicago?

Airfare is typical for this route at the moment.
New York to Chicago flights typically cost between C$ 274 and C$ 530 in November.
The cheapest round-trip price found within the last 5 days was C$ 348 on Frontier (9 Nov-16 Nov).

How often are flights from New York to Chicago delayed?

About 19% of weekly flights between New York and Chicago have experienced delays in the past year, with the average delay time being 150 minutes.

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

Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving at night tend to experience delays more often.

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

Tuesday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.

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

Over the past year, United Airlines has had the lowest number of delays on this route, with just 13% of flights being delayed.

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

Booking 82 days in advance of your planned departure date is, on average, the best time to get cheap flights from New York to Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

Related info for your journey

  • How long is the flight from New York to Chicago?

    For as low as C$ 392, JetBlue can have you in Chicago from New York in 2h 40m. Airlines will cover a distance of 1162 km. When browsing for deals, the options you’ll see will be for both direct flights and flights with stops.

  • What are the most reliable airlines from New York to Chicago?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from New York to Chicago on time: American Airlines (76%), Air Europa (75%), Malaysia Airlines (75%).

  • Can I find deals for flights from New York to Chicago that include hotel bookings?

    Yes. In addition to deals on New York to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from New York to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from New York to Chicago.

  • Can I find deals for business class flights from New York to Chicago?

    Yes. Cheapflights offers flight deals from New York to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from New York to Chicago?

    Currently, January is the cheapest month in which you can book a flight from New York to Chicago (average of C$ 270). Flying from New York to Chicago in July is currently the most expensive (average of C$ 488). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Alternative routes for New York to Chicago

Buffalo to O'Hare Intl flights
Buffalo to St. Louis flights

Fly with Cheapflights

How does Cheapflights help users find flights from New York to Chicago?

When you search for this flight from New York to Chicago, Cheapflights searches on 900+ travel sites to save you time finding great flight deals online. Additionally, we offer filter features so you can choose a preferred cabin class or airline, see different price ranges, and much more so you can book the flight for you.

Why should you use Cheapflights to find cheap flight tickets from New York to Chicago?

By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights to Chicago from New York.

Can Cheapflights find flights from New York to Chicago with no change fees?

Certainly. Search results for flights to Chicago from New York shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.

Can Cheapflights notify me if prices for flights from New York to Chicago become cheaper?

Yes, Cheapflights has a feature called Price Alert, which notifies users when flight prices change. Track prices for your flight to Chicago from New York today and book when prices fit your budget.

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.