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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 14/1. Fares are subject to change and may not be available on all flights or dates of travel.
NYC — CHI
23 Dec — 30 Dec1
1 adult

The best prices from New York to Chicago are usually found in September or January, booked 50 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 18 December 2024.

Round-trip from

C$ 183

One-way from

C$ 101

Popular in

December

Cheapest in

September

Average price

C$ 428
Frontier
  • Frontier
  • 9/1-10/1
  • 2 total stops
  • 34h 49m total
  • New York to Chicago
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Spirit Airlines
  • Spirit Airlines
  • 14/1
  • 1 total stop
  • 11h 14m total
  • New York to Chicago
Search Deals
High demand for flights, 6% potential price rise
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Best time to find cheap flights, 3% potential price drop
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Average for round-trip flights in December 2024
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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 18 December 2024.

Tue 31/128:10 p.m.EWR - ORD
Nonstop2h 42mUnited Airlines
Tue 7/16:00 a.m.ORD - EWR
Nonstop2h 11mUnited Airlines
Deal found 17/12C$ 331
Thu 26/128:00 a.m.LGA - ORD
Nonstop2h 44mDelta
Fri 10/16:00 a.m.ORD - LGA
Nonstop2h 25mDelta
Deal found 17/12C$ 370
Thu 26/127:29 p.m.LGA - ORD
1 stop4h 56mUnited Airlines
Wed 8/14:00 p.m.ORD - LGA
1 stop6h 30mUnited Airlines
Deal found 17/12C$ 390
Sat 28/126:00 a.m.EWR - ORD
1 stop4h 09mDelta
Wed 8/14:58 p.m.ORD - EWR
1 stop5h 11mDelta
Deal found 17/12C$ 430
Tue 31/127:20 a.m.LGA - ORD
2 stops11h 50mSouthwest
Sat 4/17:30 a.m.ORD - LGA
2 stops9h 25mSouthwest
Deal found 16/12C$ 493
Wed 18/127:07 a.m.EWR - ORD
Nonstop2h 54mAmerican Airlines
Wed 18/1212:25 p.m.ORD - EWR
1 stop5h 02mAmerican Airlines
Deal found 16/12C$ 696

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 18 December 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Thu 9/1

5:00 p.m.-9:54 a.m.

1 stop17h 54m

Chicago O'Hare Intl

Fri 10/1

10:01 p.m.-3:56 p.m.

1 stop16h 55m

C$ 183

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Tue 7/1

8:35 a.m.-10:07 a.m.

Nonstop2h 32m

Chicago O'Hare Intl

Sat 11/1

5:06 p.m.-8:10 p.m.

Nonstop2h 04m

C$ 186

NewarkChicago

EWR - ORD

EWRORD

Newark

Wed 8/1

5:35 p.m.-7:19 p.m.

Nonstop2h 44m

Chicago O'Hare Intl

Sun 12/1

5:50 a.m.-9:06 a.m.

Nonstop2h 16m

C$ 190

NewarkChicago

EWR - ORD

EWRORD

Newark

Wed 15/1

9:25 p.m.-10:57 p.m.

Nonstop2h 32m

Chicago O'Hare Intl

Wed 22/1

6:00 a.m.-9:11 a.m.

Nonstop2h 11m

C$ 204

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Fri 17/1

4:45 p.m.-6:41 p.m.

Nonstop2h 56m

Chicago O'Hare Intl

Wed 22/1

7:40 p.m.-11:00 p.m.

Nonstop2h 20m

C$ 210

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Fri 17/1

7:29 p.m.-11:15 p.m.

1 stop4h 46m

Chicago O'Hare Intl

Fri 24/1

6:00 a.m.-9:10 a.m.

Nonstop2h 10m

C$ 224

NewarkChicago

EWR - ORD

EWRORD

Newark

Tue 21/1

1:00 p.m.-6:25 p.m.

1 stop6h 25m

Chicago O'Hare Intl

Sat 25/1

9:46 a.m.-5:05 p.m.

1 stop6h 19m

C$ 226

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Tue 7/1

10:55 a.m.-5:59 p.m.

1 stop8h 04m

Chicago O'Hare Intl

Sat 11/1

7:00 a.m.-3:28 p.m.

1 stop7h 28m

C$ 283

NewarkChicago

EWR - ORD

EWRORD

Newark

Wed 22/1

7:00 a.m.-8:46 a.m.

Nonstop2h 46m

Chicago O'Hare Intl

Sat 25/1

6:20 p.m.-9:32 p.m.

Nonstop2h 12m

C$ 287

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Mon 20/1

9:35 p.m.-10:45 a.m.

1 stop14h 10m

Chicago O'Hare Intl

Sat 25/1

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

1 stop11h 30m

C$ 294

Flights are sorted by cheapest round-trip flights first.

Deals found on 17/12

Showing 1-10 of 20 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 13 December 2024.

Booking 50 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 May is currently the most expensive (average of C$ 342). 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 18 December 2024.

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 18 December 2024.

The most flights from NYC to CHI are scheduled on a Wednesday (181 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (6 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 18 December 2024.
Get a feel of what it's like to fly with Spirit Airlines, Delta and United Airlines 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
4,848 reviews
Check prices

Entertainment

7.7

Boarding

8.2

Crew

8.7

Comfort

8.1

Food

7.2

Overall

8.1

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
4,848 reviews
Southwest
8.1
Very good
4,848 reviews
Check prices

Entertainment

7.7

Boarding

8.2

Crew

8.7

Comfort

8.1

Food

7.2

Overall

8.1

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
9,552 reviews
Southwest
8.1
Very good
4,848 reviews
Check prices

Entertainment

7.7

Boarding

8.2

Crew

8.7

Comfort

8.1

Food

7.2

Overall

8.1

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
8,604 reviews
Southwest
8.1
Very good
4,848 reviews
Check prices

Entertainment

7.7

Boarding

8.2

Crew

8.7

Comfort

8.1

Food

7.2

Overall

8.1

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
3,279 reviews
Southwest
8.1
Very good
4,848 reviews
Check prices

Entertainment

7.7

Boarding

8.2

Crew

8.7

Comfort

8.1

Food

7.2

Overall

8.1

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
9,059 reviews
Southwest
8.1
Very good
4,848 reviews
Check prices

Entertainment

7.7

Boarding

8.2

Crew

8.7

Comfort

8.1

Food

7.2

Overall

8.1

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$ 183, Frontier will fly you from New York to Chicago and back. In addition to Frontier, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from Spirit Airlines and United Airlines - these airlines can fly you to your destination from C$ 186 and C$ 204, respectively. Frontier is priced at 43% 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$ 104 and C$ 106 on Delta and United Airlines, 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: China Airlines (97%), Republic Airways (96%), Kenya Airways (96%).

  • 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 May is currently the most expensive (average of C$ 342). 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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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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