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$59+ Cheap flights from New York State to Chicago (CHI)

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 1/10. Fares are subject to change and may not be available on all flights or dates of travel.
JFK — CHI
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheap flight deals from New York to Chicago

Keep the following information in mind while searching for New York to Chicago flight deals. Data was last updated September 11, 2025.

Round-trip from

$129
(Frontier)

One-way from

$59
(United Airlines)

Popular in

August

Cheapest in

January

Average price

$185

Good round-trip deal

$184 or less

Good one-way deal

$134 or less
From New York to Chicago (CHI)
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One-way flight from New York to Chicago (CHI)
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Highest demand for flights based on searches. 4% potential increase in price ($10 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from New York to Chicago (CHI).
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Price to beat on a one-way flight from New York 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 September 11, 2025.

This Frontier deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1111:00 amJFK - ORD
Nonstop2h 45mFrontier
Fri 11/146:40 amORD - JFK
Nonstop2h 23mFrontier
Deal found 9/9$129
This Cheapflightsfares deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/113:21 pmLGA - ORD
Nonstop2h 44mSpirit Airlines
Tue 10/146:58 pmORD - LGA
1 stop13h 02mSpirit Airlines
Deal found 9/9$129
This Southwest deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/306:15 pmLGA - MDW
1 stop5h 10mSouthwest
Wed 10/16:00 amMDW - LGA
Nonstop2h 00mSouthwest
Deal found 9/9$129
This Priceline deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/294:00 pmJFK - ORD
1 stop9h 12mFrontier
Sun 11/25:40 amORD - JFK
Nonstop2h 23mFrontier
Deal found 9/9$130
This Kiwi.com deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/297:59 pmLGA - ORD
1 stop14h 19mSpirit Airlines
Thu 10/911:13 amORD - LGA
Nonstop1h 55mSpirit Airlines
Deal found 9/10$130
This Frontier deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/2511:00 amJFK - ORD
Nonstop2h 45mFrontier
Sat 11/16:40 amORD - JFK
Nonstop2h 23mFrontier
Deal found 9/10$131
This Cheapflightsfares deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/243:29 pmLGA - ORD
Nonstop2h 44mSpirit Airlines
Tue 10/284:03 pmORD - LGA
Nonstop1h 57mSpirit Airlines
Deal found 9/10$131
This Cheapflightsfares deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2211:00 amJFK - ORD
Nonstop2h 45mFrontier
Sun 10/265:05 amORD - JFK
1 stop5h 54mFrontier
Deal found 9/11$132
This Mytrip deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/256:35 amLGA - ORD
1 stop6h 00mMultiple Airlines
Mon 10/2711:08 amORD - LGA
Nonstop1h 55mMultiple Airlines
Deal found 9/11$132
This Southwest deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/156:05 amLGA - MDW
Nonstop2h 25mSouthwest
Tue 10/212:25 pmMDW - LGA
Nonstop2h 00mSouthwest
Deal found 9/11$132
This Priceline deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/110:30 amJFK - ORD
Nonstop2h 40mJetBlue
Sat 10/48:34 amORD - JFK
Nonstop2h 30mJetBlue
Deal found 9/9$133
This Kiwi.com deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/243:13 pmLGA - ORD
Nonstop2h 38mSpirit Airlines
Sat 9/2711:12 amORD - LGA
Nonstop2h 05mSpirit Airlines
Deal found 9/11$133

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 2,558,603 searches. Data last updated September 11, 2025.
Use the filters below to find and compare flights from New York State to Chicago that are best for you.

Fly from

New York

Fly to

Chicago

Route

Depart

Return

Price

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Tue 10/21

10:30 am-12:22 pm

Nonstop2h 52m

Chicago O'Hare Intl

Sat 10/25

8:34 am-12:01 pm

Nonstop2h 27m

$133

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Wed 10/8

3:29 pm-5:13 pm

Nonstop2h 44m

Chicago O'Hare Intl

Wed 10/15

11:13 am-2:08 pm

Nonstop1h 55m

$133

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Wed 12/10

8:00 pm-9:48 pm

Nonstop2h 48m

Chicago O'Hare Intl

Tue 12/16

7:00 am-10:13 am

Nonstop2h 13m

$133

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Sat 11/1

8:15 am-9:40 am

Nonstop2h 25m

Chicago Midway

Wed 11/5

6:00 am-9:00 am

Nonstop2h 00m

$138

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Tue 9/30

6:15 pm-10:25 pm

1 stop5h 10m

Chicago Midway

Wed 10/1

8:35 am-2:55 pm

1 stop5h 20m

$139

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Tue 10/21

12:45 pm-7:25 pm

1 stop7h 40m

Chicago Midway

Wed 10/22

5:55 pm-11:10 pm

1 stop4h 15m

$139

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Fri 11/7

9:15 pm-10:57 pm

Nonstop2h 42m

Chicago O'Hare Intl

Tue 11/11

2:00 pm-5:07 pm

Nonstop2h 07m

$141

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Wed 10/29

9:15 pm-10:57 pm

Nonstop2h 42m

Chicago O'Hare Intl

Sun 11/2

5:00 am-8:07 am

Nonstop2h 07m

$141

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Fri 10/24

8:45 pm-10:26 pm

Nonstop2h 41m

Chicago O'Hare Intl

Wed 10/29

6:00 am-9:07 am

Nonstop2h 07m

$148

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Tue 9/23

10:30 am-12:10 pm

Nonstop2h 40m

Chicago O'Hare Intl

Tue 9/30

6:45 am-9:59 am

Nonstop2h 14m

$150

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

Showing 1-10 of 60 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 State to Chicago

What is the cheapest month to book a flight from State of New York to Chicago?

Currently, August is the cheapest month in which you can book a flight from State of New York to Chicago (average of $245). Flying from State of New York to Chicago in March is currently the most expensive (average of $321). 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 NY 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 September 11, 2025.

When flying from State of New York to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Weekly flight availability from State of 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 September 11, 2025.

The most flights from USNY to CHI are scheduled on a Thursday (49 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (26 on average).

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.

  • How long is the flight from State of New York to Chicago?

    A quick flight from State of New York to Chicago can take about 2h 25m. JetBlue provides one of the quickest options available for as low as $138. State of New York and Chicago are separated by a distance of 722 mi. All flights are typically nonstop.

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

    To fly one-way, consider booking your trip with United Airlines, which is currently one of the cheapest options available, starting at $59. Southwest flights start at $70 while deals on Spirit Airlines start at $73 one-way.

  • What are the most popular routes from State of New York to Chicago?

    Most travelers choose New York John F Kennedy Intl - Chicago O'Hare Intl, New York LaGuardia - Chicago O'Hare Intl or Newark - Chicago O'Hare Intl when deciding on the best route from State of New York to Chicago.

  • What are the most reliable airlines from State of New York to Chicago?

    The top 3 most reliable airlines when flying from State of New York to Chicago are LATAM Airlines (93%), China Airlines (92%) and Republic Airways (80%).

  • What are the cheapest flights from State of New York to Chicago?

    Looking at all options, your cheapest flight can be booked for $69. While the most popular route (New York John F Kennedy Intl - Chicago O'Hare Intl) can be booked for $82 on average, our data indicates $511 when flying from State of New York to Chicago.

  • 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 State of New York to Chicago?

    Currently, August is the cheapest month in which you can book a flight from State of New York to Chicago (average of $245). Flying from State of New York to Chicago in March is currently the most expensive (average of $321). 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

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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Alternative routes for New York to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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Top 7 airlines flying from New York to Chicago

Discover the top 7 airlines that operate flights from New York to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$58Average$244FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$67Average$202FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$84Average$230FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$96Average$360FlexibilityNo cancel feeOn-time69%
DeltaCheapest$101Average$360FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$147Average$333FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$154Average$377FlexibilityNo cancel feeOn-time63%

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