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Cheap flights from New York, NY to Chicago from C$ 203

NYC — CHI
12 Dec — 19 Dec1
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 Tuesday or Saturday 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

Tue 1/126:30 a.m. -
1 stop30h 14m
Fri 4/127:08 p.m. -
1 stop12h 22m
Deal found 10/11C$ 410
Tue 1/126:05 a.m. -
1 stop8h 46m
Fri 4/125:24 p.m. -
1 stop27h 05m
Deal found 10/11C$ 441
Tue 1/127:10 a.m. -
Nonstop2h 52m
Wed 2/128:50 a.m. -
Nonstop2h 15m
Deal found 8/11C$ 452
Tue 8/1210:55 a.m. -
Nonstop2h 55m
Wed 9/1210:15 a.m. -
Nonstop2h 25m
Deal found 9/11C$ 454
Wed 2/1211:15 a.m. -
Nonstop2h 47m
Tue 8/126:17 a.m. -
Nonstop2h 07m
Deal found 8/11C$ 454
Tue 8/127:10 a.m. -
Nonstop2h 52m
Tue 15/128:25 p.m. -
Nonstop2h 19m
Deal found 9/11C$ 454
Tue 1/125:35 p.m. -
Nonstop2h 40m
Wed 2/125:00 a.m. -
Nonstop2h 05m
Deal found 9/11C$ 454
Sat 5/123:25 p.m. -
Nonstop2h 58m
Sun 6/1210:15 a.m. -
Nonstop2h 25m
Deal found 9/11C$ 462
Mon 7/127:05 p.m. -
Nonstop2h 40m
Wed 9/126:10 p.m. -
Nonstop2h 21m
Deal found 9/11C$ 462
Sat 5/125:35 p.m. -
Nonstop2h 50m
Sun 6/1210:05 a.m. -
Nonstop2h 15m
Deal found 8/11C$ 464
Sat 5/127:45 p.m. -
Nonstop2h 48m
Sun 6/125:29 p.m. -
Nonstop2h 23m
Deal found 9/11C$ 467
Sat 5/122:00 p.m. -
Nonstop2h 30m
Sun 6/122:20 p.m. -
Nonstop2h 00m
Deal found 7/11C$ 467

Find flight deals from New York to Chicago

Round-trip from

C$ 410

One-way from

C$ 203

Popular in

October

Cheapest in

January

Average price

C$ 425

Good round-trip deal

C$ 268 or less

Good one-way deal

C$ 243 or less
Frontier
  • Frontier
  • 1/12-4/12
  • 2 total stops
  • 42h 36m total
  • New York to Chicago
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Frontier
  • Frontier
  • 17/11-31/12
  • 1 total stop
  • 7h 55m total
  • New York to Chicago
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Highest demand for flights based on searches. 12% potential increase in price (C$ 82 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease (C$ 13 potential savings vs. average RT price).
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Average for round-trip flights in November 2026
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Price to beat on a round-trip flight from New York (NYC) to Chicago (CHI).
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Price to beat on a one-way flight from New York (NYC) to Chicago (CHI).
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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

New YorkChicago

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

JFKORD

New York John F Kennedy Intl

Tue 8/12

3:25 p.m.-5:23 p.m.

Nonstop2h 58m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 228

NewarkChicago

EWR Newark - ORD Chicago O'Hare Intl

EWRORD

Newark

Wed 27/1

12:25 p.m.-2:15 p.m.

Nonstop2h 50m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 228

New YorkChicago

LGA New York LaGuardia - ORD Chicago O'Hare Intl

LGAORD

New York LaGuardia

Tue 8/12

3:15 p.m.-5:04 p.m.

Nonstop2h 49m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 228

New YorkChicago

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

JFKORD

New York John F Kennedy Intl

Wed 9/12

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$ 235

NewarkChicago

EWR Newark - ORD Chicago O'Hare Intl

EWRORD

Newark

Wed 2/12

9:00 a.m.-10:46 a.m.

Nonstop2h 46m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 235

New YorkChicago

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

JFKORD

New York John F Kennedy Intl

Sat 12/12

3:25 p.m.-5:23 p.m.

Nonstop2h 58m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 235

New YorkChicago

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

JFKORD

New York John F Kennedy Intl

Wed 9/12

10:55 a.m.-12:50 p.m.

Nonstop2h 55m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 235

New YorkChicago

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

JFKORD

New York John F Kennedy Intl

Tue 5/1

7:56 a.m.-10:00 a.m.

Nonstop3h 04m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 235

New YorkChicago

LGA New York LaGuardia - ORD Chicago O'Hare Intl

LGAORD

New York LaGuardia

Tue 5/1

7:10 a.m.-9:03 a.m.

Nonstop2h 53m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 235

New YorkChicago

LGA New York LaGuardia - MDW Chicago Midway

LGAMDW

New York LaGuardia

Fri 25/12

3:15 p.m.-5:00 p.m.

Nonstop2h 45m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 240

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/11

Showing 1-10 of 60 resultsSorted by cheapest first
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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$ 279). Flying from New York to Chicago in October is currently the most expensive (average of C$ 538). 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 55% 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 Tuesday (198 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (78 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$ 306 and C$ 565 in December.
The cheapest round-trip price found within the last 5 days was C$ 410 on Frontier (1 Dec-4 Dec).

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 88 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$ 467, Delta can have you in Chicago from New York in 2h 47m. Airlines will cover a distance of 1152 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: Air Europa (100%), WestJet (88%), China Airlines (86%).

  • What are the cheapest flights from New York to Chicago?

    While on average a flight from New York to Chicago is generally C$ 843, our data shows the cheapest flight currently is C$ 170. When looking at the most popular route, (New York LaGuardia - Chicago O'Hare Intl), you can expect to pay C$ 474 for that flight.

  • 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$ 279). Flying from New York to Chicago in October is currently the most expensive (average of C$ 538). 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

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Alternative routes for New York to Chicago

Buffalo to O'Hare Intl flights
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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.

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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.

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