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Cheap flights from New York, NY to Chicago from C$ 152

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 25/8. Fares are subject to change and may not be available on all flights or dates of travel.
NYC — CHI
7 Sep — 14 Sep1
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 Wednesday

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 8 August 2026.

Tue 25/88:30 p.m. -
Nonstop2h 54m
Wed 2/98:12 p.m. -
Nonstop2h 32m
Deal found 3/8C$ 303
Sat 29/86:10 a.m. -
Nonstop2h 40m
Wed 2/96:29 p.m. -
Nonstop2h 25m
Deal found 7/8C$ 317
Sat 29/87:30 a.m. -
Nonstop2h 44m
Mon 31/87:05 a.m. -
Nonstop2h 14m
Deal found 3/8C$ 319
Tue 8/97:30 a.m. -
Nonstop2h 43m
Wed 30/99:00 a.m. -
Nonstop2h 26m
Deal found 6/8C$ 324
Wed 2/94:25 p.m. -
Nonstop2h 44m
Wed 9/99:59 a.m. -
Nonstop2h 23m
Deal found 5/8C$ 324
Sat 5/911:15 a.m. -
Nonstop2h 44m
Sun 13/96:00 a.m. -
Nonstop2h 13m
Deal found 7/8C$ 331
Sat 26/911:35 a.m. -
1 stop7h 48m
Sun 27/911:15 a.m. -
1 stop12h 46m
Deal found 6/8C$ 333
Sat 29/82:30 p.m. -
Nonstop2h 45m
Sun 30/87:05 a.m. -
Nonstop2h 14m
Deal found 7/8C$ 333
Tue 29/99:45 p.m. -
Nonstop2h 36m
Mon 5/109:35 p.m. -
Nonstop2h 22m
Deal found 6/8C$ 338
Wed 9/92:50 p.m. -
Nonstop2h 40m
Thu 17/96:00 a.m. -
Nonstop2h 15m
Deal found 6/8C$ 338
Sat 26/95:23 a.m. -
Nonstop2h 50m
Sun 27/96:44 a.m. -
Nonstop2h 20m
Deal found 6/8C$ 340
Mon 31/87:30 a.m. -
Nonstop2h 36m
Wed 2/910:30 a.m. -
Nonstop2h 18m
Deal found 8/8C$ 340

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 8 August 2026.

Round-trip from

C$ 303

One-way from

C$ 152

Popular in

June

Cheapest in

January

Average price

C$ 407

Good one-way deal

C$ 250 or less
United Airlines
  • United Airlines
  • 1/9-1/9
  • Nonstop
  • 5h 02m total
  • New York to Chicago
Search Deals
American Airlines
  • American Airlines
  • 5/9
  • Nonstop
  • 2h 46m total
  • New York to Chicago
Search Deals
Highest demand for flights based on searches. 17% potential increase in price (C$ 106 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (C$ 14 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 2026
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 8 August 2026.
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

LGA New York LaGuardia - ORD Chicago O'Hare Intl

LGAORD

New York LaGuardia

Thu 27/8

7:29 p.m.-9:13 p.m.

Nonstop2h 44m

Chicago O'Hare Intl

Fri 28/8

12:00 p.m.-3:17 p.m.

Nonstop2h 17m

C$ 331

New YorkChicago

LGA New York LaGuardia - ORD Chicago O'Hare Intl

LGAORD

New York LaGuardia

Sat 29/8

2:30 p.m.-4:15 p.m.

Nonstop2h 45m

Chicago O'Hare Intl

Mon 31/8

6:00 a.m.-9:09 a.m.

Nonstop2h 09m

C$ 331

New YorkChicago

LGA New York LaGuardia - ORD Chicago O'Hare Intl

LGAORD

New York LaGuardia

Sat 29/8

2:55 p.m.-6:37 p.m.

1 stop4h 42m

Chicago O'Hare Intl

Sat 5/9

7:45 p.m.-11:10 p.m.

Nonstop2h 25m

C$ 331

New YorkChicago

LGA New York LaGuardia - ORD Chicago O'Hare Intl

LGAORD

New York LaGuardia

Fri 18/9

7:29 p.m.-9:13 p.m.

Nonstop2h 44m

Chicago O'Hare Intl

Mon 21/9

7:00 a.m.-10:17 a.m.

Nonstop2h 17m

C$ 331

New YorkChicago

LGA New York LaGuardia - ORD Chicago O'Hare Intl

LGAORD

New York LaGuardia

Sun 20/9

7:20 a.m.-9:00 a.m.

Nonstop2h 40m

Chicago O'Hare Intl

Mon 21/9

7:00 a.m.-10:15 a.m.

Nonstop2h 15m

C$ 345

New YorkChicago

LGA New York LaGuardia - ORD Chicago O'Hare Intl

LGAORD

New York LaGuardia

Fri 13/11

7:37 p.m.-11:39 p.m.

1 stop5h 02m

Chicago O'Hare Intl

Mon 16/11

7:00 a.m.-10:09 a.m.

Nonstop2h 09m

C$ 345

New YorkChicago

LGA New York LaGuardia - ORD Chicago O'Hare Intl

LGAORD

New York LaGuardia

Wed 30/9

6:00 a.m.-7:39 a.m.

Nonstop2h 39m

Chicago O'Hare Intl

Wed 30/9

2:00 p.m.-5:25 p.m.

Nonstop2h 25m

C$ 345

New YorkChicago

LGA New York LaGuardia - ORD Chicago O'Hare Intl

LGAORD

New York LaGuardia

Sat 26/9

6:00 a.m.-1:45 p.m.

1 stop8h 45m

Chicago O'Hare Intl

Sun 27/9

3:00 p.m.-11:09 p.m.

1 stop7h 09m

C$ 354

New YorkChicago

LGA New York LaGuardia - ORD Chicago O'Hare Intl

LGAORD

New York LaGuardia

Fri 2/10

4:15 p.m.-11:08 p.m.

1 stop7h 53m

Chicago O'Hare Intl

Mon 5/10

3:00 p.m.-11:09 p.m.

1 stop7h 09m

C$ 354
Quickest round-trip

New YorkChicago

LGA New York LaGuardia - ORD Chicago O'Hare Intl

LGAORD

New York LaGuardia

Tue 25/8

11:25 a.m.-1:00 p.m.

Nonstop2h 35m

Chicago O'Hare Intl

Fri 28/8

6:00 a.m.-9:09 a.m.

Nonstop2h 09m

C$ 359

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/8

Showing 1-10 of 46 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
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

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$ 264). Flying from New York to Chicago in July is currently the most expensive (average of C$ 482). 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 8 August 2026.

It’s typically best to fly out from New York to Chicago in the evening. Doing so could potentially save you 51% on the flight price compared to flying at noon, which is usually more expensive.

Weekly flight availability from New York to Chicago

Explore weekly flight availability from New York to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated 8 August 2026.

The most flights from NYC to CHI are scheduled on a Thursday (199 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (81 on average).

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

Airfare is below average for this route at the moment.
New York to Chicago flights typically cost between C$ 310 and C$ 533 in September.
The cheapest round-trip price found within the last 5 days was C$ 303 on United Airlines (1 Sep-1 Sep).

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 155 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 in the evening 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 14% of flights being delayed.

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

Booking 30 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

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$ 331, Delta can have you in Chicago from New York in 2h 44m. Airlines will cover a distance of 1176 km. Most flights are nonstop.

  • 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: Malaysia Airlines (87%), American Airlines (86%), Alaska Airlines (85%).

  • 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$ 264). Flying from New York to Chicago in July is currently the most expensive (average of C$ 482). 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

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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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