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Cheap flights from New York, NY to Chicago from C$ 104

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 22/3. Fares are subject to change and may not be available on all flights or dates of travel.
NYC — CHI
27 Feb — 6 Mar1
1 adult

The best prices from New York to Chicago are usually found in September or January, booked 84 days in advance, depart on a Monday or Wednesday and return on a Friday

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 22 February 2025.

Round-trip from

C$ 131

One-way from

C$ 104

Popular in

December

Cheapest in

September

Average price

C$ 294

Good one-way deal

C$ 295 or less
Spirit Airlines
  • Spirit Airlines
  • 16/5-18/5
  • Nonstop
  • 4h 55m total
  • New York to Chicago
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Spirit Airlines
  • Spirit Airlines
  • 22/3
  • 1 total stop
  • 14h 13m total
  • New York to Chicago
Search Deals
Highest demand for flights based on searches. 3% potential increase in price (C$ 14 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (C$ 11 potential savings vs. average RT price).
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Average for round-trip flights in February 2025
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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 22 February 2025.

Fri 16/59:33 p.m.EWR - ORD
Nonstop2h 37mSpirit Airlines
Sun 18/55:10 p.m.ORD - EWR
Nonstop2h 18mSpirit Airlines
Deal found 21/2C$ 131
Sun 13/46:00 a.m.LGA - ORD
Nonstop2h 40mDelta
Tue 15/48:45 a.m.ORD - LGA
Nonstop2h 12mDelta
Deal found 22/2C$ 209
Sat 17/57:00 a.m.EWR - ORD
Nonstop2h 40mUnited Airlines
Sat 24/56:00 a.m.ORD - EWR
Nonstop2h 13mUnited Airlines
Deal found 21/2C$ 210
Fri 16/510:00 p.m.EWR - ORD
1 stop12h 06mMultiple Airlines
Sun 18/56:00 a.m.ORD - EWR
1 stop5h 18mMultiple Airlines
Deal found 21/2C$ 212
Thu 3/41:15 p.m.LGA - ORD
Nonstop2h 40mUnited Airlines
Mon 7/49:00 a.m.ORD - LGA
Nonstop2h 13mUnited Airlines
Deal found 21/2C$ 212
Sat 26/45:55 a.m.EWR - ORD
1 stop4h 29mDelta
Tue 29/45:05 p.m.ORD - EWR
1 stop4h 54mDelta
Deal found 21/2C$ 237
Wed 2/46:05 a.m.LGA - ORD
1 stop8h 55mSouthwest
Tue 15/47:00 a.m.ORD - LGA
1 stop10h 05mSouthwest
Deal found 22/2C$ 240
Mon 24/27:55 p.m.LGA - ORD
Nonstop2h 38mSpirit Airlines
Thu 27/25:44 p.m.ORD - LGA
Nonstop1h 45mSpirit Airlines
Deal found 21/2C$ 356
Wed 2/49:30 a.m.EWR - ORD
1 stop5h 54mAmerican Airlines
Fri 4/41:14 p.m.ORD - EWR
Nonstop2h 15mAmerican Airlines
Deal found 21/2C$ 416
Mon 24/210:00 p.m.LGA - ORD
1 stop12h 51mMultiple Airlines
Thu 27/25:44 p.m.ORD - LGA
Nonstop1h 45mMultiple Airlines
Deal found 21/2C$ 416
Wed 30/711:41 a.m.EWR - ORD
1 stop8h 30mSun Country Air
Sun 3/88:10 p.m.ORD - EWR
1 stop13h 32mSun Country Air
Deal found 22/2C$ 433
Mon 3/39:20 a.m.LGA - ORD
Nonstop2h 39mAmerican Airlines
Wed 5/312:25 p.m.ORD - LGA
1 stop5h 00mAmerican Airlines
Deal found 22/2C$ 439

Find flights from New York to Chicago within your budget

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 22 February 2025.

Fly from

New York

Fly to

Chicago

Route

Depart

Return

Price

NewarkChicago

EWR - ORD

EWRORD

Newark

Fri 16/5

9:33 p.m.-11:10 p.m.

Nonstop2h 37m

Chicago O'Hare Intl

Sun 18/5

5:10 p.m.-8:28 p.m.

Nonstop2h 18m

C$ 131

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Sun 13/4

6:00 a.m.-7:40 a.m.

Nonstop2h 40m

Chicago O'Hare Intl

Tue 15/4

8:45 a.m.-11:57 a.m.

Nonstop2h 12m

C$ 209

NewarkChicago

EWR - ORD

EWRORD

Newark

Sat 17/5

7:00 a.m.-8:40 a.m.

Nonstop2h 40m

Chicago O'Hare Intl

Sat 24/5

6:00 a.m.-9:13 a.m.

Nonstop2h 13m

C$ 210

NewarkChicago

EWR - ORD

EWRORD

Newark

Fri 16/5

10:00 p.m.-9:06 a.m.

1 stop12h 06m

Chicago O'Hare Intl

Sun 18/5

6:00 a.m.-12:18 p.m.

1 stop5h 18m

C$ 212

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Thu 3/4

1:15 p.m.-2:55 p.m.

Nonstop2h 40m

Chicago O'Hare Intl

Mon 7/4

9:00 a.m.-12:13 p.m.

Nonstop2h 13m

C$ 212

NewarkChicago

EWR - ORD

EWRORD

Newark

Sat 26/4

5:55 a.m.-9:24 a.m.

1 stop4h 29m

Chicago O'Hare Intl

Tue 29/4

5:05 p.m.-10:59 p.m.

1 stop4h 54m

C$ 237

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Wed 2/4

6:05 a.m.-2:00 p.m.

1 stop8h 55m

Chicago O'Hare Intl

Tue 15/4

7:00 a.m.-6:05 p.m.

1 stop10h 05m

C$ 240

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Thu 6/3

6:30 a.m.-12:15 p.m.

1 stop6h 45m

Chicago O'Hare Intl

Mon 10/3

1:15 p.m.-9:15 p.m.

1 stop7h 00m

C$ 415

NewarkChicago

EWR - ORD

EWRORD

Newark

Wed 2/4

9:30 a.m.-2:24 p.m.

1 stop5h 54m

Chicago O'Hare Intl

Fri 4/4

1:14 p.m.-4:29 p.m.

Nonstop2h 15m

C$ 416

NewarkChicago

EWR - ORD

EWRORD

Newark

Wed 30/7

11:41 a.m.-7:11 p.m.

1 stop8h 30m

Chicago O'Hare Intl

Sun 3/8

8:10 p.m.-10:42 a.m.

1 stop13h 32m

C$ 433

Flights are sorted by cheapest round-trip flights first.

Deals found on 20/2

Showing 1-10 of 24 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.

Travel insights for flights from New York to Chicago

Get recent, data-driven insights about flights from New York to Chicago including ideal travel times, pricing trends, and more.

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 14 February 2025.

Booking 84 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$ 355). 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 22 February 2025.

It’s typically best to fly out from New York to Chicago in the evening. Doing so could potentially save you 33% on the flight price compared to flying in the afternoon, 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 22 February 2025.

The most flights from NYC to CHI are scheduled on a Thursday (173 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (121 on average).

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 43.0 - 125.0 mm per month. August is typically the wettest month, when rainfall can reach 125.0 mm. January is typically the driest time to visit Chicago when rainfall is around 43.0 mm.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 23.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around -5.0 C).

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 22 February 2025.
Get a feel of what it's like to fly with Southwest, Alaska Airlines and Delta from New York to Chicago by reading reviews from past customers. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,395 reviews
Check prices

Entertainment

7.6

Crew

8.7

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,395 reviews
Southwest
8.1
Very good
4,395 reviews
Check prices

Entertainment

7.6

Crew

8.7

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Alaska Airlines
8.0
Very good
9,700 reviews
Southwest
8.1
Very good
4,395 reviews
Check prices

Entertainment

7.6

Crew

8.7

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,203 reviews
Southwest
8.1
Very good
4,395 reviews
Check prices

Entertainment

7.6

Crew

8.7

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

JetBlue
7.4
Good
3,068 reviews
Southwest
8.1
Very good
4,395 reviews
Check prices

Entertainment

7.6

Crew

8.7

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

United Airlines
7.4
Good
8,754 reviews
Southwest
8.1
Very good
4,395 reviews
Check prices

Entertainment

7.6

Crew

8.7

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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.

  • What are the cheapest airlines flying from New York to Chicago round-trip?

    Currently priced at C$ 131, Spirit Airlines will fly you from New York to Chicago and back. In addition to Spirit Airlines, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from Delta and United Airlines - these airlines can fly you to your destination from C$ 209 and C$ 210, respectively. Spirit Airlines is priced at 59% lower than the current average price of a flight leaving 3 months from now.

  • What are the cheapest airlines to fly from New York to Chicago one-way?

    For one-way options, check prices for Spirit Airlines. According to our data, you can fly for as low as C$ 104. Users have also found prices from C$ 105 and C$ 106 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: Royal Air Maroc (100%), Royal Jordanian (100%), Air Europa (93%).

  • 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$ 355). 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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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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