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$51+ 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 3/3. Fares are subject to change and may not be available on all flights or dates of travel.
JFK — CHI
Jan 15 — Jan 221
Thu 1/15
Thu 1/22
1 adult, Economy
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Cheap 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 December 16, 2025.

This Super.com deal was found by Cheapflights users on 12/15. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/318:37 pmLGA - ORD
Nonstop2h 30mSpirit Airlines
Tue 1/64:38 pmORD - LGA
Nonstop2h 04mSpirit Airlines
Deal found 12/15$84
This Cheapflightsfares deal was found by Cheapflights users on 12/14. 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 12/318:37 pmLGA - ORD
Nonstop2h 30mSpirit Airlines
Mon 1/54:38 pmORD - LGA
Nonstop2h 04mSpirit Airlines
Deal found 12/14$102
This Kiwi.com deal was found by Cheapflights users on 12/15. 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 12/316:55 amEWR - ORD
Nonstop2h 36mSpirit Airlines
Mon 1/59:34 amORD - EWR
Nonstop2h 16mSpirit Airlines
Deal found 12/15$111
This Kiwi.com deal was found by Cheapflights users on 12/15. 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.
Thu 12/256:55 amEWR - ORD
Nonstop2h 36mSpirit Airlines
Mon 1/59:34 amORD - EWR
Nonstop2h 16mSpirit Airlines
Deal found 12/15$116
This Super.com deal was found by Cheapflights users on 12/13. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/276:55 amEWR - ORD
Nonstop2h 36mSpirit Airlines
Sat 1/104:38 pmORD - EWR
Nonstop2h 08mSpirit Airlines
Deal found 12/13$120
This Priceline deal was found by Cheapflights users on 12/14. 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.
Sun 12/286:55 amEWR - ORD
Nonstop2h 36mSpirit Airlines
Thu 1/84:38 pmORD - EWR
Nonstop2h 08mSpirit Airlines
Deal found 12/14$121
This Super.com deal was found by Cheapflights users on 12/16. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/3111:00 amJFK - ORD
Nonstop2h 57mFrontier
Mon 1/56:40 amORD - JFK
Nonstop2h 24mFrontier
Deal found 12/16$122
This Kiwi.com deal was found by Cheapflights users on 12/15. 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 12/316:55 amEWR - ORD
Nonstop2h 36mSpirit Airlines
Thu 1/88:43 pmORD - EWR
1 stop13h 59mSpirit Airlines
Deal found 12/15$123
This Cheapflightsfares deal was found by Cheapflights users on 12/14. 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 12/316:55 amEWR - ORD
Nonstop2h 36mSpirit Airlines
Sat 1/39:34 amORD - EWR
Nonstop2h 16mSpirit Airlines
Deal found 12/14$124
This CheapOair deal was found by Cheapflights users on 12/15. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/236:00 amLGA - ORD
1 stop13h 39mSpirit Airlines
Sun 1/115:53 pmORD - LGA
Nonstop2h 06mSpirit Airlines
Deal found 12/15$130
This Cheapflightsfares deal was found by Cheapflights users on 12/15. 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 12/316:55 amEWR - ORD
Nonstop2h 36mSpirit Airlines
Sun 1/49:34 amORD - EWR
Nonstop2h 16mSpirit Airlines
Deal found 12/15$134
This Kiwi.com deal was found by Cheapflights users on 12/15. 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.
Thu 12/258:37 pmLGA - ORD
Nonstop2h 30mSpirit Airlines
Tue 1/64:38 pmORD - LGA
Nonstop2h 04mSpirit Airlines
Deal found 12/15$134

Find 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 December 16, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$83
(Frontier)

One-way from

$51
(CheapOair)

Popular in

August

Cheapest in

January

Average price

$272

Good round-trip deal

$137 or less

Good one-way deal

$93 or less
Provider with most accurate pricing for New York (NYC)-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for New York (NYC)-Chicago (CHI) flights.
Search Deals
From New York to Chicago (CHI)
Search Deals
One-way flight from New York to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($22 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from New York to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from New York to Chicago (CHI).
Search Deals

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 December 16, 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

NewarkChicago

EWR - ORD

EWRORD

Newark

Sun 1/18

9:05 pm-10:42 pm

Nonstop2h 37m

Chicago O'Hare Intl

Tue 1/20

10:48 am-11:27 pm

1 stop11h 39m

$107

NewarkChicago

EWR - ORD

EWRORD

Newark

Tue 1/20

1:00 pm-11:46 pm

1 stop11h 46m

Chicago O'Hare Intl

Thu 1/22

8:43 pm-11:42 am

1 stop13h 59m

$119

NewarkChicago

EWR - ORD

EWRORD

Newark

Wed 5/13

9:05 pm-10:43 pm

Nonstop2h 38m

Chicago O'Hare Intl

Sun 5/17

4:47 pm-7:55 pm

Nonstop2h 08m

$120

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Mon 3/2

6:00 am-6:52 pm

1 stop13h 52m

Chicago O'Hare Intl

Wed 3/4

12:44 pm-10:38 pm

1 stop8h 54m

$124

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Thu 2/19

9:55 am-7:45 pm

1 stop10h 50m

Chicago O'Hare Intl

Fri 2/20

5:58 pm-8:59 pm

Nonstop2h 01m

$127

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Fri 5/8

8:48 pm-9:12 am

1 stop13h 24m

Chicago O'Hare Intl

Mon 5/11

9:04 am-12:04 pm

Nonstop2h 00m

$137

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Sat 1/17

7:00 pm-8:53 pm

Nonstop2h 53m

Chicago O'Hare Intl

Thu 1/22

7:01 am-10:30 am

Nonstop2h 29m

$139

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Thu 1/15

6:00 am-7:40 am

Nonstop2h 40m

Chicago Midway

Sun 1/18

7:15 pm-10:20 pm

Nonstop2h 05m

$139

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Sun 1/18

7:50 am-9:49 am

Nonstop2h 59m

Chicago O'Hare Intl

Tue 1/20

1:57 pm-5:30 pm

Nonstop2h 33m

$139

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Mon 1/19

7:50 am-9:49 am

Nonstop2h 59m

Chicago O'Hare Intl

Wed 1/21

6:25 pm-9:59 pm

Nonstop2h 34m

$139

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/15

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, May is the cheapest month in which you can book a flight from State of New York to Chicago (average of $55). Flying from State of New York to Chicago in August is currently the most expensive (average of $106). 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 December 16, 2025.

When flying from State of New York to Chicago, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 31% versus a flight at noon.

What is the cheapest day to fly from State of New York to Chicago?

Use this chart to determine the cheapest time to fly round-trip from New York to Chicago. Price data was last updated on December 13, 2025.

Travelers seeking maximum savings on their State of New York to Chicago flight should consider departing on Tuesday mornings when fares are most often at their lowest. Friday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

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 37m. Spirit Airlines provides one of the quickest options available for as low as $107. State of New York and Chicago are separated by a distance of 716 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 Frontier, which is currently one of the cheapest options available, starting at $29. Spirit Airlines flights start at $32 while deals on JetBlue start at $69 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 China Airlines (85%), LATAM Airlines (81%) and Delta (76%).

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

    Looking at all options, your cheapest flight can be booked for $45. While the most popular route (New York John F Kennedy Intl - Chicago O'Hare Intl) can be booked for $62 on average, our data indicates $557 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, May is the cheapest month in which you can book a flight from State of New York to Chicago (average of $55). Flying from State of New York to Chicago in August is currently the most expensive (average of $106). 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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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 December 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$55Average$202FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$67Average$186FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$87Average$229FlexibilityNo cancel feeOn-time62%
DeltaCheapest$101Average$374FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$118Average$329FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$147Average$337FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$153Average$452FlexibilityNo cancel feeOn-time63%

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