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Cheap flights from New York, NY to Chicago from C$ 76

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 28/5. Fares are subject to change and may not be available on all flights or dates of travel.
NYC — CHI
5 Apr — 12 Apr1
1 adult

Cheapflights Tip: The best prices from New York to Chicago are usually found in September or January, booked 61 days in advance, depart on a Saturday or Monday 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 31 March 2025.

Round-trip from

C$ 197

One-way from

C$ 76

Popular in

December

Cheapest in

September

Average price

C$ 370

Good round-trip deal

C$ 219 or less

Good one-way deal

C$ 185 or less
Delta
  • Delta
  • 25/5-28/5
  • Nonstop
  • 5h 01m total
  • New York to Chicago
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Spirit Airlines
  • Spirit Airlines
  • 28/5
  • Nonstop
  • 2h 32m total
  • New York to Chicago
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Highest demand for flights based on searches. 3% potential increase in price (C$ 16 potential increase over avg. RT price).
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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 March 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 31 March 2025.

Sun 25/56:59 p.m.LGA - ORD
Nonstop2h 47mDelta
Wed 28/59:25 a.m.ORD - LGA
Nonstop2h 14mDelta
Deal found 31/3C$ 197
Thu 24/43:25 p.m.LGA - ORD
Nonstop2h 41mUnited Airlines
Fri 25/43:00 p.m.ORD - LGA
Nonstop2h 15mUnited Airlines
Deal found 31/3C$ 214
Tue 29/41:05 p.m.EWR - ORD
Nonstop2h 42mUnited Airlines
Tue 6/511:55 a.m.ORD - EWR
Nonstop2h 17mUnited Airlines
Deal found 31/3C$ 241
Wed 14/56:00 a.m.LGA - ORD
1 stop10h 00mSouthwest
Wed 14/54:00 p.m.ORD - LGA
1 stop5h 30mSouthwest
Deal found 31/3C$ 270
Wed 4/65:59 a.m.EWR - ORD
1 stop4h 52mDelta
Sat 7/65:57 p.m.ORD - EWR
1 stop6h 10mDelta
Deal found 31/3C$ 283
Tue 8/410:51 a.m.EWR - ORD
Nonstop2h 49mAmerican Airlines
Wed 9/46:43 p.m.ORD - EWR
Nonstop2h 24mAmerican Airlines
Deal found 31/3C$ 429
Mon 7/45:17 p.m.LGA - ORD
1 stop5h 04mAmerican Airlines
Wed 9/47:19 a.m.ORD - LGA
Nonstop2h 12mAmerican Airlines
Deal found 31/3C$ 444
Fri 29/811:41 a.m.EWR - ORD
1 stop8h 31mSun Country Air
Mon 1/98:10 p.m.ORD - EWR
1 stop13h 36mSun Country Air
Deal found 30/3C$ 510
Wed 30/43:29 p.m.EWR - ORD
2 stops15h 36mAlaska Airlines
Fri 2/56:58 p.m.ORD - EWR
1 stop18h 31mAlaska Airlines
Deal found 31/3C$ 554

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 31 March 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

Sun 25/5

6:59 p.m.-8:46 p.m.

Nonstop2h 47m

Chicago O'Hare Intl

Wed 28/5

9:25 a.m.-12:39 p.m.

Nonstop2h 14m

C$ 197

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Thu 24/4

3:25 p.m.-5:06 p.m.

Nonstop2h 41m

Chicago O'Hare Intl

Fri 25/4

3:00 p.m.-6:15 p.m.

Nonstop2h 15m

C$ 214

NewarkChicago

EWR - ORD

EWRORD

Newark

Tue 29/4

1:05 p.m.-2:47 p.m.

Nonstop2h 42m

Chicago O'Hare Intl

Tue 6/5

11:55 a.m.-3:12 p.m.

Nonstop2h 17m

C$ 241

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Wed 14/5

6:00 a.m.-3:00 p.m.

1 stop10h 00m

Chicago O'Hare Intl

Wed 14/5

4:00 p.m.-10:30 p.m.

1 stop5h 30m

C$ 270

NewarkChicago

EWR - ORD

EWRORD

Newark

Wed 4/6

5:59 a.m.-9:51 a.m.

1 stop4h 52m

Chicago O'Hare Intl

Sat 7/6

5:57 p.m.-1:07 a.m.

1 stop6h 10m

C$ 283

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Mon 21/4

7:00 a.m.-8:34 a.m.

Nonstop2h 34m

Chicago O'Hare Intl

Thu 24/4

12:07 p.m.-6:19 p.m.

1 stop5h 12m

C$ 392

NewarkChicago

EWR - ORD

EWRORD

Newark

Fri 29/8

11:41 a.m.-7:12 p.m.

1 stop8h 31m

Chicago O'Hare Intl

Mon 1/9

8:10 p.m.-10:46 a.m.

1 stop13h 36m

C$ 510

NewarkChicago

EWR - ORD

EWRORD

Newark

Wed 30/4

3:29 p.m.-6:05 a.m.

2 stops15h 36m

Chicago O'Hare Intl

Fri 2/5

6:58 p.m.-2:29 p.m.

1 stop18h 31m

C$ 554

NewarkChicago

EWR - ORD

EWRORD

Newark

Wed 28/5

5:55 a.m.-7:27 a.m.

Nonstop2h 32m

C$ 76

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Sun 20/4

6:05 a.m.-7:42 a.m.

Nonstop2h 37m

C$ 99

Flights are sorted by cheapest round-trip flights first.

Deals found on 31/3

Showing 1-10 of 21 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 28 March 2025.

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.

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 31 March 2025.

It’s typically best to fly out from New York to Chicago in the evening. Doing so could potentially save you 63% 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 31 March 2025.

The most flights from NYC to CHI are scheduled on a Monday (184 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (48 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 31 March 2025.
Get a feel of what it's like to fly with Alaska Airlines, Southwest 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.
Alaska Airlines
8.0
Very good
9,818 reviews
Check prices

Comfort

7.9

Boarding

8.2

Entertainment

7.1

Crew

8.5

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Alaska Airlines
8.0
Very good
9,818 reviews
Alaska Airlines
8.0
Very good
9,818 reviews
Check prices

Comfort

7.9

Boarding

8.2

Entertainment

7.1

Crew

8.5

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Southwest
8.0
Very good
4,275 reviews
Alaska Airlines
8.0
Very good
9,818 reviews
Check prices

Comfort

7.9

Boarding

8.2

Entertainment

7.1

Crew

8.5

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Delta
8.0
Very good
7,899 reviews
Alaska Airlines
8.0
Very good
9,818 reviews
Check prices

Comfort

7.9

Boarding

8.2

Entertainment

7.1

Crew

8.5

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
United Airlines
7.4
Good
8,614 reviews
Alaska Airlines
8.0
Very good
9,818 reviews
Check prices

Comfort

7.9

Boarding

8.2

Entertainment

7.1

Crew

8.5

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
JetBlue
7.3
Good
2,924 reviews
Alaska Airlines
8.0
Very good
9,818 reviews
Check prices

Comfort

7.9

Boarding

8.2

Entertainment

7.1

Crew

8.5

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

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$ 197, Delta will fly you from New York to Chicago and back. In addition to Delta, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from United Airlines and Southwest - these airlines can fly you to your destination from C$ 234 and C$ 333, respectively. Delta is priced at 39% 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$ 76. Users have also found prices from C$ 99 and C$ 108 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: Air Europa (95%), GOL (87%), Kenya Airways (85%).

  • 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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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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