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Cheap flights from New York, NY to Chicago from C$ 131

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 21/7. Fares are subject to change and may not be available on all flights or dates of travel.
NYC — CHI
15 Jul — 22 Jul1
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 64 days in advance, depart on a Tuesday or Thursday and return on a Thursday

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 15 June 2026.

Fri 20/117:00 p.m.
LGA
-
ORD
Nonstop2h 39m
Delta
Mon 23/118:20 p.m.
ORD
-
LGA
Nonstop2h 20m
Delta
Deal found 10/6C$ 259
Wed 15/78:45 p.m.
LGA
-
ORD
Nonstop2h 51m
Delta
Wed 22/78:10 p.m.
ORD
-
LGA
Nonstop2h 34m
Delta
Deal found 15/6C$ 262
Thu 6/87:30 a.m.
LGA
-
ORD
Nonstop2h 36m
Delta
Wed 12/87:05 a.m.
ORD
-
LGA
Nonstop2h 14m
Delta
Deal found 10/6C$ 263
Mon 24/86:10 a.m.
LGA
-
ORD
Nonstop2h 49m
American Airlines
Thu 27/86:00 a.m.
ORD
-
LGA
Nonstop2h 13m
American Airlines
Deal found 10/6C$ 264
Wed 23/911:20 a.m.
LGA
-
ORD
Nonstop2h 44m
United Airlines
Sun 27/97:00 a.m.
ORD
-
LGA
Nonstop2h 17m
United Airlines
Deal found 14/6C$ 268
Tue 4/86:45 p.m.
LGA
-
ORD
Nonstop3h 04m
Delta
Thu 6/87:05 a.m.
ORD
-
LGA
Nonstop2h 14m
Delta
Deal found 14/6C$ 273
Tue 7/77:28 p.m.
LGA
-
ORD
1 stop5h 03m
United Airlines
Sat 11/74:00 p.m.
ORD
-
LGA
Nonstop2h 22m
United Airlines
Deal found 14/6C$ 275
Sun 26/76:59 a.m.
LGA
-
ORD
Nonstop2h 32m
Delta
Wed 12/87:05 a.m.
ORD
-
LGA
Nonstop2h 14m
Delta
Deal found 11/6C$ 277
Fri 14/89:45 p.m.
EWR
-
ORD
Nonstop2h 37m
United Airlines
Mon 17/85:00 a.m.
ORD
-
EWR
Nonstop2h 14m
United Airlines
Deal found 11/6C$ 278
Thu 17/97:20 a.m.
LGA
-
ORD
Nonstop2h 40m
United Airlines
Sat 19/912:55 p.m.
ORD
-
LGA
1 stop4h 50m
United Airlines
Deal found 10/6C$ 278
Thu 27/89:15 a.m.
EWR
-
ORD
Nonstop2h 43m
United Airlines
Mon 31/89:35 p.m.
ORD
-
EWR
Nonstop2h 22m
United Airlines
Deal found 11/6C$ 280
Thu 6/89:25 p.m.
LGA
-
ORD
Nonstop2h 33m
United Airlines
Sun 9/86:00 a.m.
ORD
-
LGA
Nonstop2h 11m
United Airlines
Deal found 10/6C$ 280

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 15 June 2026.

Round-trip from

C$ 259

One-way from

C$ 131

Popular in

June

Cheapest in

January

Average price

C$ 457

Good round-trip deal

C$ 812 or less

Good one-way deal

C$ 292 or less
Delta
  • Delta
  • 20/11-23/11
  • Nonstop
  • 4h 59m total
  • New York to Chicago
Search Deals
United Airlines
  • United Airlines
  • 7/7
  • Nonstop
  • 2h 52m total
  • New York to Chicago
Search Deals
Highest demand for flights based on searches. 16% potential increase in price (C$ 95 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (C$ 16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 2026
Search Deals
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).
Search Deals

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 15 June 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 - ORD

LGAORD

New York LaGuardia

Sat 18/7

7:21 a.m.-9:00 a.m.

Nonstop2h 39m

Chicago O'Hare Intl

Sat 18/7

2:00 p.m.-5:22 p.m.

Nonstop2h 22m

C$ 262
Quickest round-trip

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Wed 15/7

6:00 a.m.-7:32 a.m.

Nonstop2h 32m

Chicago O'Hare Intl

Tue 21/7

9:30 a.m.-12:46 p.m.

Nonstop2h 16m

C$ 262

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Wed 8/7

8:05 a.m.-9:44 a.m.

Nonstop2h 39m

Chicago O'Hare Intl

Sat 11/7

7:45 p.m.-11:15 p.m.

Nonstop2h 30m

C$ 262

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Tue 4/8

6:45 p.m.-8:49 p.m.

Nonstop3h 04m

Chicago O'Hare Intl

Wed 5/8

11:30 a.m.-3:00 p.m.

Nonstop2h 30m

C$ 262

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Tue 7/7

8:25 p.m.-10:12 p.m.

Nonstop2h 47m

Chicago O'Hare Intl

Sat 11/7

6:00 p.m.-9:25 p.m.

Nonstop2h 25m

C$ 262

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Wed 23/9

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

Nonstop2h 40m

Chicago O'Hare Intl

Mon 28/9

6:29 p.m.-9:54 p.m.

Nonstop2h 25m

C$ 268

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Thu 17/9

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

Nonstop2h 40m

Chicago O'Hare Intl

Thu 17/9

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

Nonstop2h 25m

C$ 275

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Sat 5/9

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

Nonstop2h 45m

Chicago O'Hare Intl

Tue 8/9

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

Nonstop2h 17m

C$ 281

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Wed 22/7

9:10 a.m.-10:56 a.m.

Nonstop2h 46m

Chicago O'Hare Intl

Thu 23/7

1:00 p.m.-4:22 p.m.

Nonstop2h 22m

C$ 294

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Tue 7/7

9:25 p.m.-10:58 p.m.

Nonstop2h 33m

Chicago O'Hare Intl

Thu 16/7

1:00 p.m.-4:22 p.m.

Nonstop2h 22m

C$ 296

Flights are sorted by cheapest round-trip flights first.

Deals found on 14/6

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$ 278). Flying from New York to Chicago in June is currently the most expensive (average of C$ 446). 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 15 June 2026.

It’s typically best to fly out from New York to Chicago in the morning. Doing so could potentially save you 41% on the flight price compared to flying in the evening, 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 15 June 2026.

The most flights from NYC to CHI are scheduled on a Friday (201 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (158 on average).

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

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 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 in the evening 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 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 61 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$ 259, Delta can have you in Chicago from New York in 2h 36m. 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: Atlas Air (100%), WestJet (86%), TAP AIR PORTUGAL (84%).

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

    While on average a flight from New York to Chicago is generally C$ 336, our data shows the cheapest flight currently is C$ 304. When looking at the most popular route, (New York LaGuardia - Chicago O'Hare Intl), you can expect to pay C$ 436 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$ 278). Flying from New York to Chicago in June is currently the most expensive (average of C$ 446). 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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