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Cheap flights from New York, NY to Chicago from C$ 108

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 19/8. Fares are subject to change and may not be available on all flights or dates of travel.
NYC — CHI
3 Aug — 10 Aug1
1 adult

Cheapflights Tip: The best prices from New York to Chicago are usually found in September or January, booked 35 days in advance, depart on a Saturday or Monday 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 29 July 2025.

Round-trip from

C$ 209

One-way from

C$ 108

Popular in

June

Cheapest in

September

Average price

C$ 366

Good one-way deal

C$ 232 or less
Delta
  • Delta
  • 31/8-3/9
  • Nonstop
  • 5h 05m total
  • New York to Chicago
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Delta
  • Delta
  • 19/8
  • Nonstop
  • 2h 57m total
  • New York to Chicago
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Highest demand for flights based on searches. 12% potential increase in price (C$ 60 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 July 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 29 July 2025.

Sun 31/88:30 p.m.LGA - ORD
Nonstop2h 50mDelta
Wed 3/97:10 a.m.ORD - LGA
Nonstop2h 15mDelta
Deal found 29/7C$ 209
Tue 26/85:55 a.m.LGA - ORD
1 stop11h 15mSpirit Airlines
Tue 2/98:12 p.m.ORD - LGA
1 stop12h 48mSpirit Airlines
Deal found 27/7C$ 211
Fri 19/99:44 p.m.EWR - ORD
Nonstop2h 41mUnited Airlines
Mon 22/97:10 a.m.ORD - EWR
Nonstop2h 18mUnited Airlines
Deal found 29/7C$ 229
Sun 31/86:00 a.m.EWR - ORD
1 stop5h 03mDelta
Wed 3/97:15 a.m.ORD - EWR
1 stop3h 48mDelta
Deal found 29/7C$ 236
Wed 20/86:00 a.m.LGA - ORD
1 stop4h 36mUnited Airlines
Tue 26/812:00 p.m.ORD - LGA
Nonstop2h 13mUnited Airlines
Deal found 27/7C$ 236
Sat 18/1011:00 a.m.EWR - ORD
1 stop11h 58mSpirit Airlines
Tue 21/106:30 a.m.ORD - EWR
1 stop9h 10mSpirit Airlines
Deal found 27/7C$ 239
Thu 4/99:40 a.m.LGA - ORD
1 stop7h 45mSouthwest
Fri 5/92:55 p.m.ORD - LGA
1 stop6h 55mSouthwest
Deal found 28/7C$ 258
Thu 11/1211:50 a.m.EWR - ORD
1 stop24h 01mSun Country Air
Thu 18/128:08 p.m.ORD - EWR
1 stop11h 53mSun Country Air
Deal found 26/7C$ 342

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 29 July 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 31/8

8:30 p.m.-10:20 p.m.

Nonstop2h 50m

Chicago O'Hare Intl

Wed 3/9

7:10 a.m.-10:25 a.m.

Nonstop2h 15m

C$ 209

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Tue 26/8

5:55 a.m.-4:10 p.m.

1 stop11h 15m

Chicago O'Hare Intl

Tue 2/9

8:12 p.m.-10:00 a.m.

1 stop12h 48m

C$ 211

NewarkChicago

EWR - ORD

EWRORD

Newark

Fri 19/9

9:44 p.m.-11:25 p.m.

Nonstop2h 41m

Chicago O'Hare Intl

Sun 21/9

6:00 a.m.-9:15 a.m.

Nonstop2h 15m

C$ 229

NewarkChicago

EWR - ORD

EWRORD

Newark

Sun 31/8

6:00 a.m.-10:03 a.m.

1 stop5h 03m

Chicago O'Hare Intl

Wed 3/9

7:15 a.m.-12:03 p.m.

1 stop3h 48m

C$ 236

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Wed 20/8

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

1 stop4h 36m

Chicago O'Hare Intl

Tue 26/8

12:00 p.m.-3:13 p.m.

Nonstop2h 13m

C$ 236

NewarkChicago

EWR - ORD

EWRORD

Newark

Sat 18/10

11:00 a.m.-9:58 p.m.

1 stop11h 58m

Chicago O'Hare Intl

Tue 21/10

6:30 a.m.-4:40 p.m.

1 stop9h 10m

C$ 239

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Thu 4/9

2:10 p.m.-9:30 p.m.

1 stop8h 20m

Chicago O'Hare Intl

Sun 7/9

7:30 a.m.-5:35 p.m.

1 stop9h 05m

C$ 258

NewarkChicago

EWR - ORD

EWRORD

Newark

Thu 11/12

11:50 a.m.-10:51 a.m.

1 stop24h 01m

Chicago O'Hare Intl

Thu 18/12

8:08 p.m.-9:01 a.m.

1 stop11h 53m

C$ 342

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Tue 19/8

4:05 p.m.-6:02 p.m.

Nonstop2h 57m

C$ 108

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Sat 16/8

10:59 a.m.-7:07 p.m.

1 stop9h 08m

C$ 111

Flights are sorted by cheapest round-trip flights first.

Deals found on 29/7

Showing 1-10 of 17 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 25 July 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$ 352). 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 29 July 2025.

It’s typically best to fly out from New York to Chicago in the evening. Doing so could potentially save you 48% 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 29 July 2025.

The most flights from NYC to CHI are scheduled on a Tuesday (190 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (47 on average).

How much does it cost to fly round-trip from New York to Chicago?

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 29 July 2025.
Read through reviews of airlines operating flights from New York to Chicago, such as Southwest,Delta, andUnited Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,238 reviews
Check prices

Comfort

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,238 reviews
Southwest
8.0
Very good
4,238 reviews
Check prices

Comfort

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,977 reviews
Southwest
8.0
Very good
4,238 reviews
Check prices

Comfort

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
United Airlines
7.4
Good
8,899 reviews
Southwest
8.0
Very good
4,238 reviews
Check prices

Comfort

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Sun Country Air
6.9
Okay
333 reviews
Southwest
8.0
Very good
4,238 reviews
Check prices

Comfort

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Spirit Airlines
6.3
Okay
8,040 reviews
Southwest
8.0
Very good
4,238 reviews
Check prices

Comfort

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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$ 209, 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 Spirit Airlines and United Airlines - these airlines can fly you to your destination from C$ 211 and C$ 229, respectively. Delta is priced at 34% 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 Delta. According to our data, you can fly for as low as C$ 108. Users have also found prices from C$ 111 and C$ 115 on Spirit Airlines 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: Cathay Pacific (100%), China Airlines (83%), LATAM Airlines (76%).

  • 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$ 352). 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.

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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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