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Cheap flights from New York, NY to Chicago from C$ 97

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 7/10. Fares are subject to change and may not be available on all flights or dates of travel.
NYC — CHI
11 Oct — 18 Oct1
1 adult
1 adult, Economy

Cheapflights Tip: The best prices from New York to Chicago are usually found in January or September, booked 35 days in advance, depart on a Saturday or Thursday and return on a Sunday

Cheap 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 11 September 2025.

Round-trip from

C$ 184

One-way from

C$ 97

Popular in

August

Cheapest in

January

Average price

C$ 256

Good round-trip deal

C$ 242 or less

Good one-way deal

C$ 400 or less
United Airlines
  • United Airlines
  • 30/9-1/10
  • Nonstop
  • 4h 53m total
  • New York to Chicago
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Southwest
  • Southwest
  • 18/11
  • 1 total stop
  • 7h 10m total
  • New York to Chicago
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Highest demand for flights based on searches. 4% potential increase in price (C$ 20 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease (C$ 9 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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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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Find flight deals from New York to Chicago

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 11 September 2025.

Mon 15/99:59 a.m.LGA - ORD
1 stop12h 59mSpirit Airlines
Wed 15/106:58 p.m.ORD - LGA
1 stop13h 02mSpirit Airlines
Deal found 10/9C$ 179
Tue 30/96:30 p.m.LGA - ORD
Nonstop2h 37mUnited Airlines
Wed 1/108:00 a.m.ORD - LGA
Nonstop2h 16mUnited Airlines
Deal found 11/9C$ 184
Wed 8/102:06 p.m.LGA - ORD
Nonstop2h 52mAmerican Airlines
Wed 15/107:00 a.m.ORD - LGA
Nonstop2h 08mAmerican Airlines
Deal found 10/9C$ 186
Wed 8/105:55 a.m.LGA - ORD
1 stop16h 38mSpirit Airlines
Wed 15/106:58 p.m.ORD - LGA
1 stop13h 02mSpirit Airlines
Deal found 10/9C$ 190
Tue 28/107:44 a.m.LGA - ORD
1 stop11h 54mSpirit Airlines
Thu 30/1011:08 a.m.ORD - LGA
Nonstop1h 55mSpirit Airlines
Deal found 10/9C$ 191
Tue 21/107:20 a.m.LGA - ORD
1 stop9h 00mSouthwest
Wed 22/1012:40 p.m.ORD - LGA
1 stop9h 40mSouthwest
Deal found 11/9C$ 193
Wed 8/104:28 p.m.LGA - ORD
Nonstop2h 37mUnited Airlines
Fri 17/106:30 p.m.ORD - LGA
Nonstop2h 24mUnited Airlines
Deal found 11/9C$ 195
Tue 30/98:25 a.m.LGA - ORD
Nonstop2h 37mUnited Airlines
Sun 5/106:00 a.m.ORD - LGA
Nonstop2h 16mUnited Airlines
Deal found 11/9C$ 200
Sat 4/106:25 a.m.LGA - ORD
Nonstop2h 37mUnited Airlines
Fri 10/106:00 p.m.ORD - LGA
Nonstop2h 17mUnited Airlines
Deal found 10/9C$ 202
Mon 29/96:25 a.m.LGA - ORD
Nonstop2h 37mUnited Airlines
Wed 1/108:00 p.m.ORD - LGA
Nonstop2h 24mUnited Airlines
Deal found 10/9C$ 204
Sat 25/102:55 p.m.LGA - ORD
Nonstop2h 39mDelta
Mon 27/106:00 a.m.ORD - LGA
Nonstop2h 07mDelta
Deal found 10/9C$ 205
Sat 18/106:59 a.m.EWR - ORD
Nonstop2h 38mUnited Airlines
Sun 19/106:00 a.m.ORD - EWR
Nonstop2h 15mUnited Airlines
Deal found 11/9C$ 236

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 11 September 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

Mon 26/1

5:45 a.m.-7:13 a.m.

Nonstop2h 28m

Chicago O'Hare Intl

Fri 30/1

7:05 p.m.-10:14 p.m.

Nonstop2h 09m

C$ 202

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Fri 24/10

8:45 p.m.-10:26 p.m.

Nonstop2h 41m

Chicago O'Hare Intl

Wed 29/10

6:00 a.m.-9:07 a.m.

Nonstop2h 07m

C$ 205

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Wed 10/12

6:00 a.m.-9:36 a.m.

1 stop4h 36m

Chicago O'Hare Intl

Wed 17/12

12:00 p.m.-3:11 p.m.

Nonstop2h 11m

C$ 209

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Fri 30/1

4:00 p.m.-5:51 p.m.

Nonstop2h 51m

Chicago O'Hare Intl

Mon 2/2

6:00 a.m.-9:23 a.m.

Nonstop2h 23m

C$ 211

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Wed 7/1

2:30 p.m.-4:17 p.m.

Nonstop2h 47m

Chicago O'Hare Intl

Thu 8/1

7:00 a.m.-10:22 a.m.

Nonstop2h 22m

C$ 218

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Tue 28/10

5:40 p.m.-7:25 p.m.

Nonstop2h 45m

Chicago O'Hare Intl

Tue 4/11

7:00 a.m.-10:11 a.m.

Nonstop2h 11m

C$ 218

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Fri 24/10

2:20 p.m.-3:57 p.m.

Nonstop2h 37m

Chicago O'Hare Intl

Sun 26/10

5:00 p.m.-8:07 p.m.

Nonstop2h 07m

C$ 220

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Sun 5/10

8:30 p.m.-10:07 p.m.

Nonstop2h 37m

Chicago O'Hare Intl

Tue 7/10

2:00 p.m.-5:17 p.m.

Nonstop2h 17m

C$ 224

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Tue 25/11

6:15 a.m.-7:55 a.m.

Nonstop2h 40m

Chicago O'Hare Intl

Tue 2/12

6:00 a.m.-9:17 a.m.

Nonstop2h 17m

C$ 224

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Fri 3/10

11:20 a.m.-12:57 p.m.

Nonstop2h 37m

Chicago O'Hare Intl

Fri 3/10

5:00 p.m.-8:17 p.m.

Nonstop2h 17m

C$ 229

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/9

Showing 1-10 of 43 results
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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 29 August 2025.

Booking 35 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, January is the cheapest month in which you can book a flight from New York to Chicago (average of C$ 261). Flying from New York to Chicago in March is currently the most expensive (average of C$ 349). 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 11 September 2025.

It’s typically best to fly out from New York to Chicago in the afternoon. Doing so could potentially save you 33% 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 11 September 2025.

The most flights from NYC to CHI are scheduled on a Thursday (185 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (81 on average).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated 11 September 2025.
Read through reviews of airlines operating flights from New York to Chicago, such as Spirit Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Spirit Airlines
6.3
Okay
8,023 reviews
Check prices

Crew

7.0

Overall

6.3

Entertainment

5.0

Comfort

5.9

Food

5.1

Boarding

6.6

Reviews

1 / 20
8.0
Excellent

Rebecca,Sep 2025

DTW - LAX

At least one free drink and snack. Plugs for charging on long flights and wider seats.
Spirit Airlines
6.3
Okay
8,023 reviews
Spirit Airlines
6.3
Okay
8,023 reviews
Check prices

Crew

7.0

Overall

6.3

Entertainment

5.0

Comfort

5.9

Food

5.1

Boarding

6.6

Reviews

1 / 20
8.0
Excellent

Rebecca,Sep 2025

DTW - LAX

At least one free drink and snack. Plugs for charging on long flights and wider seats.

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$ 202, Spirit Airlines can have you in Chicago from New York in 2h 28m. 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 cheapest airlines to fly from New York to Chicago one-way?

    For one-way options, check prices for Southwest. According to our data, you can fly for as low as C$ 97. Users have also found prices from C$ 108 and C$ 123 on United Airlines and Delta, respectively.

  • 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: LATAM Airlines (93%), China Airlines (92%), Republic Airways (80%).

  • 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$ 261). Flying from New York to Chicago in March is currently the most expensive (average of C$ 349). 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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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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