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Cheap flights from New York, NY to Chicago from C$ 76

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 19/1. Fares are subject to change and may not be available on all flights or dates of travel.
NYC — CHI
17 Jan — 24 Jan1
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 81 days in advance, depart on a Tuesday or Thursday and return on a Sunday

Cheap flight deals from New York to Chicago

Enter your travel dates to find the best prices.

Cheapest flights from New York to Chicago
Explore the most affordable flight options available from New York to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 18 December 2025.

Thu 25/127:10 a.m.EWR - ORD
Nonstop2h 54mUnited Airlines
Thu 25/123:53 p.m.ORD - EWR
Nonstop2h 16mUnited Airlines
Deal found 17/12C$ 192
Wed 31/127:15 a.m.EWR - ORD
Nonstop2h 55mUnited Airlines
Thu 1/16:00 a.m.ORD - EWR
Nonstop2h 10mUnited Airlines
Deal found 16/12C$ 205
Thu 25/126:15 p.m.LGA - ORD
Nonstop2h 47mUnited Airlines
Wed 31/125:10 p.m.ORD - LGA
Nonstop2h 14mUnited Airlines
Deal found 17/12C$ 209
Wed 31/1211:15 a.m.LGA - ORD
Nonstop2h 48mUnited Airlines
Wed 31/126:00 p.m.ORD - LGA
Nonstop2h 14mUnited Airlines
Deal found 16/12C$ 222
Fri 26/128:37 p.m.LGA - ORD
Nonstop2h 30mSpirit Airlines
Wed 31/124:38 p.m.ORD - LGA
Nonstop2h 04mSpirit Airlines
Deal found 17/12C$ 227
Wed 24/129:58 p.m.EWR - ORD
Nonstop2h 37mUnited Airlines
Tue 20/13:35 p.m.ORD - EWR
Nonstop2h 16mUnited Airlines
Deal found 16/12C$ 242
Thu 25/1211:15 a.m.LGA - ORD
Nonstop2h 48mUnited Airlines
Thu 25/125:10 p.m.ORD - LGA
Nonstop2h 14mUnited Airlines
Deal found 17/12C$ 242
Thu 18/124:35 p.m.LGA - ORD
1 stop8h 55mSpirit Airlines
Mon 5/17:57 p.m.ORD - LGA
1 stop14h 03mSpirit Airlines
Deal found 17/12C$ 256
Wed 31/129:58 p.m.EWR - ORD
Nonstop2h 37mUnited Airlines
Fri 2/19:05 a.m.ORD - EWR
Nonstop2h 16mUnited Airlines
Deal found 16/12C$ 259
Wed 24/129:15 p.m.LGA - ORD
Nonstop2h 48mUnited Airlines
Sun 4/16:00 p.m.ORD - LGA
Nonstop2h 14mUnited Airlines
Deal found 16/12C$ 259
Wed 31/127:15 p.m.LGA - ORD
Nonstop2h 48mUnited Airlines
Sat 3/16:21 p.m.ORD - LGA
1 stop4h 22mUnited Airlines
Deal found 17/12C$ 273
Thu 25/127:15 p.m.LGA - ORD
Nonstop2h 48mUnited Airlines
Fri 2/17:00 a.m.ORD - LGA
Nonstop2h 08mUnited Airlines
Deal found 16/12C$ 274

Find flight deals from New York to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from New York (NYC) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated 18 December 2025.

Round-trip from

C$ 125

One-way from

C$ 76

Popular in

August

Cheapest in

January

Average price

C$ 375

Good round-trip deal

C$ 413 or less

Good one-way deal

C$ 103 or less
Spirit Airlines
  • Spirit Airlines
  • 12/5-17/5
  • Nonstop
  • 4h 42m total
  • New York to Chicago
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Spirit Airlines
  • Spirit Airlines
  • 19/1
  • Nonstop
  • 2h 37m total
  • New York to Chicago
Search Deals
Highest demand for flights based on searches. 8% potential increase in price (C$ 41 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease (C$ 9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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Price to beat on a round-trip flight from New York (NYC) to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from New York (NYC) to Chicago (CHI).
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Cheapflights Fare Finder

 
Customize your flight search to find flights from New York to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 629,999 searches. Data last updated 18 December 2025.
Use the filters below to find and compare flights from New York to Chicago that are best for you.

Fly from

New York

Fly to

Chicago

Route

Depart

Return

Price

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Sat 24/1

9:55 a.m.-7:41 p.m.

1 stop10h 46m

Chicago O'Hare Intl

Sun 25/1

5:53 p.m.-8:59 p.m.

Nonstop2h 06m

C$ 135

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Tue 13/1

12:59 p.m.-9:03 p.m.

1 stop9h 04m

Chicago O'Hare Intl

Tue 20/1

6:05 a.m.-5:58 p.m.

1 stop10h 53m

C$ 164

NewarkChicago

EWR - ORD

EWRORD

Newark

Mon 2/2

1:00 p.m.-7:38 p.m.

1 stop7h 38m

Chicago O'Hare Intl

Tue 3/2

7:20 a.m.-9:14 p.m.

1 stop12h 54m

C$ 171

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Thu 15/1

6:30 a.m.-5:52 p.m.

1 stop12h 22m

Chicago O'Hare Intl

Sun 18/1

12:44 p.m.-8:00 p.m.

1 stop6h 16m

C$ 171

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Tue 14/4

7:30 a.m.-9:10 a.m.

Nonstop2h 40m

Chicago O'Hare Intl

Thu 16/4

9:04 a.m.-12:04 p.m.

Nonstop2h 00m

C$ 176

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Sun 25/1

7:15 a.m.-9:11 a.m.

Nonstop2h 56m

Chicago O'Hare Intl

Thu 29/1

6:00 a.m.-9:08 a.m.

Nonstop2h 08m

C$ 192

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Thu 22/1

6:05 a.m.-7:58 a.m.

Nonstop2h 53m

Chicago O'Hare Intl

Sun 25/1

7:10 a.m.-10:41 a.m.

Nonstop2h 31m

C$ 192

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Sat 6/6

4:54 p.m.-11:41 p.m.

1 stop7h 47m

Chicago O'Hare Intl

Tue 9/6

9:04 a.m.-12:04 p.m.

Nonstop2h 00m

C$ 194

NewarkChicago

EWR - ORD

EWRORD

Newark

Tue 14/4

10:05 p.m.-11:33 p.m.

Nonstop2h 28m

Chicago O'Hare Intl

Thu 16/4

5:15 a.m.-3:08 p.m.

1 stop8h 53m

C$ 197

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Fri 8/5

8:48 p.m.-9:12 a.m.

1 stop13h 24m

Chicago O'Hare Intl

Sun 10/5

9:04 a.m.-12:04 p.m.

Nonstop2h 00m

C$ 198

Flights are sorted by cheapest round-trip flights first.

Deals found on 16/12

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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
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

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

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

Use this chart to determine the optimal time to book a round-trip flight from New York to Chicago. Price data was last updated on 12 December 2025.

Booking 81 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.

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

Currently, May is the cheapest month in which you can book a flight from New York to Chicago (average of C$ 76). Flying from New York to Chicago in July is currently the most expensive (average of C$ 174). 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?

Find hourly flight availability from New York to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 18 December 2025.

It’s typically best to fly out from New York to Chicago in the afternoon. Doing so could potentially save you 54% on the flight price compared to flying in the evening, which is usually more expensive.

How often are flights from New York to Chicago delayed?

About 16% of weekly flights between New York and Chicago have experienced delays in the past year, with the average delay time being 159 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?

Saturday tends to have the lowest number of delays on this route, whereas Thursday 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 12% of flights being delayed.

Related info for your journey

Find useful and relevant information for your journey from New York to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

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

    For as low as C$ 192, Spirit Airlines can have you in Chicago from New York in 2h 56m. Airlines will cover a distance of 1176 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: China Airlines (85%), LATAM Airlines (81%), Delta (76%).

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

    While on average a flight from New York to Chicago is generally C$ 238, our data shows the cheapest flight currently is C$ 103. When looking at the most popular route, (New York LaGuardia - Chicago O'Hare Intl), you can expect to pay C$ 247 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, May is the cheapest month in which you can book a flight from New York to Chicago (average of C$ 76). Flying from New York to Chicago in July is currently the most expensive (average of C$ 174). 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

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Fly with Cheapflights

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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.

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