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Cheap flights from New York, NY to Chicago from C$ 101

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 15/4. Fares are subject to change and may not be available on all flights or dates of travel.
NYC — CHI
26 Jan — 2 Feb1
1 adult

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

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 21 January 2025.

Round-trip from

C$ 187

One-way from

C$ 101

Popular in

December

Cheapest in

September

Average price

C$ 279
Spirit Airlines
  • Spirit Airlines
  • 9/2-16/2
  • 1 total stop
  • 13h 57m total
  • New York to Chicago
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Spirit Airlines
  • Spirit Airlines
  • 15/4
  • Nonstop
  • 2h 42m total
  • New York to Chicago
Search Deals
High demand for flights, 4% potential price rise
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Best time to find cheap flights, 2% potential price drop
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Average for round-trip flights in January 2025
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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 21 January 2025.

Sun 9/210:59 a.m.LGA - ORD
Nonstop2h 40mSpirit Airlines
Sun 16/27:13 p.m.ORD - LGA
1 stop11h 17mSpirit Airlines
Deal found 19/1C$ 187
Tue 18/26:00 p.m.LGA - ORD
Nonstop2h 55mDelta
Thu 20/27:30 a.m.ORD - LGA
Nonstop2h 21mDelta
Deal found 19/1C$ 209
Sat 15/29:29 p.m.EWR - ORD
Nonstop2h 40mUnited Airlines
Tue 18/212:55 p.m.ORD - EWR
Nonstop2h 15mUnited Airlines
Deal found 20/1C$ 212
Fri 21/38:15 p.m.LGA - ORD
Nonstop2h 48mUnited Airlines
Wed 22/101:00 p.m.ORD - LGA
Nonstop2h 05mUnited Airlines
Deal found 20/1C$ 219
Tue 18/25:50 p.m.EWR - ORD
1 stop4h 03mDelta
Tue 25/211:15 a.m.ORD - EWR
1 stop7h 20mDelta
Deal found 19/1C$ 229
Sun 9/26:41 p.m.EWR - ORD
2 stops20h 42mSpirit Airlines
Sun 16/25:15 a.m.ORD - EWR
Nonstop2h 09mSpirit Airlines
Deal found 19/1C$ 284
Wed 12/210:55 a.m.LGA - ORD
1 stop8h 00mJetBlue
Tue 18/212:45 p.m.ORD - LGA
1 stop5h 14mJetBlue
Deal found 20/1C$ 286
Fri 4/47:30 a.m.LGA - ORD
1 stop8h 30mSouthwest
Sat 5/412:15 p.m.ORD - LGA
1 stop9h 35mSouthwest
Deal found 20/1C$ 297
Tue 11/21:41 p.m.EWR - ORD
1 stop5h 15mAmerican Airlines
Fri 14/26:45 p.m.ORD - EWR
Nonstop2h 12mAmerican Airlines
Deal found 20/1C$ 393
Fri 11/711:41 a.m.EWR - ORD
1 stop8h 30mSun Country Air
Sun 13/78:10 p.m.ORD - EWR
1 stop13h 32mSun Country Air
Deal found 20/1C$ 439
Tue 18/25:37 p.m.EWR - ORD
1 stop25h 23mAlaska Airlines
Tue 25/24:05 p.m.ORD - EWR
2 stops25h 24mAlaska Airlines
Deal found 19/1C$ 596

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 21 January 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Sun 9/2

10:59 a.m.-12:39 p.m.

Nonstop2h 40m

Chicago O'Hare Intl

Sun 16/2

7:13 p.m.-7:30 a.m.

1 stop11h 17m

C$ 187

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Tue 18/2

6:00 p.m.-7:55 p.m.

Nonstop2h 55m

Chicago O'Hare Intl

Thu 20/2

7:30 a.m.-10:51 a.m.

Nonstop2h 21m

C$ 209

NewarkChicago

EWR - ORD

EWRORD

Newark

Sat 15/2

9:29 p.m.-11:09 p.m.

Nonstop2h 40m

Chicago O'Hare Intl

Tue 18/2

12:55 p.m.-4:10 p.m.

Nonstop2h 15m

C$ 212

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Fri 21/3

8:15 p.m.-10:03 p.m.

Nonstop2h 48m

Chicago O'Hare Intl

Wed 22/10

1:00 p.m.-4:05 p.m.

Nonstop2h 05m

C$ 219

NewarkChicago

EWR - ORD

EWRORD

Newark

Tue 18/2

5:50 p.m.-8:53 p.m.

1 stop4h 03m

Chicago O'Hare Intl

Tue 25/2

11:15 a.m.-7:35 p.m.

1 stop7h 20m

C$ 229

NewarkChicago

EWR - ORD

EWRORD

Newark

Sun 9/2

6:41 p.m.-2:23 p.m.

2 stops20h 42m

Chicago O'Hare Intl

Sun 16/2

5:15 a.m.-8:24 a.m.

Nonstop2h 09m

C$ 284

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Wed 12/2

10:55 a.m.-5:55 p.m.

1 stop8h 00m

Chicago O'Hare Intl

Tue 18/2

12:45 p.m.-6:59 p.m.

1 stop5h 14m

C$ 286

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Fri 4/4

7:30 a.m.-3:00 p.m.

1 stop8h 30m

Chicago O'Hare Intl

Sat 5/4

12:15 p.m.-10:50 p.m.

1 stop9h 35m

C$ 297

NewarkChicago

EWR - ORD

EWRORD

Newark

Tue 11/2

1:41 p.m.-5:56 p.m.

1 stop5h 15m

Chicago O'Hare Intl

Fri 14/2

6:45 p.m.-9:57 p.m.

Nonstop2h 12m

C$ 393

NewarkChicago

EWR - ORD

EWRORD

Newark

Fri 4/7

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

1 stop8h 30m

Chicago O'Hare Intl

Mon 7/7

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

1 stop13h 32m

C$ 425

Flights are sorted by cheapest round-trip flights first.

Deals found on 20/1

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 17 January 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 21 January 2025.

It’s typically best to fly out from New York to Chicago in the morning. Doing so could potentially save you 13% 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 21 January 2025.

The most flights from NYC to CHI are scheduled on a Monday (175 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (103 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 21 January 2025.
Get a feel of what it's like to fly with Delta, United Airlines and JetBlue 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
4,659 reviews
Check prices

Crew

8.7

Food

7.2

Overall

8.1

Comfort

8.1

Entertainment

7.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,659 reviews
Southwest
8.1
Very good
4,659 reviews
Check prices

Crew

8.7

Food

7.2

Overall

8.1

Comfort

8.1

Entertainment

7.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Alaska Airlines
8.0
Very good
9,696 reviews
Southwest
8.1
Very good
4,659 reviews
Check prices

Crew

8.7

Food

7.2

Overall

8.1

Comfort

8.1

Entertainment

7.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,521 reviews
Southwest
8.1
Very good
4,659 reviews
Check prices

Crew

8.7

Food

7.2

Overall

8.1

Comfort

8.1

Entertainment

7.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

JetBlue
7.4
Good
3,201 reviews
Southwest
8.1
Very good
4,659 reviews
Check prices

Crew

8.7

Food

7.2

Overall

8.1

Comfort

8.1

Entertainment

7.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

United Airlines
7.4
Good
8,982 reviews
Southwest
8.1
Very good
4,659 reviews
Check prices

Crew

8.7

Food

7.2

Overall

8.1

Comfort

8.1

Entertainment

7.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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$ 187, 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$ 212, respectively. Spirit Airlines is priced at 42% 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$ 101. Users have also found prices from C$ 107 and C$ 107 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%), Etihad Airways (100%), Royal Jordanian (100%).

  • 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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Alternative routes for New York to Chicago

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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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