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$100+ 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 9/23. Fares are subject to change and may not be available on all flights or dates of travel.
JFK — CHI
Aug 28 — Sep 41
Fri 8/28
Fri 9/4
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 July 29, 2026.

This American Airlines deal was found by Cheapflights users on 7/26. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/29:24 am
LGA
-
ORD
Nonstop2h 48m
American Airlines
Wed 9/23:05 pm
ORD
-
LGA
Nonstop2h 18m
American Airlines
Deal found 7/26$202
This Delta deal was found by Cheapflights users on 7/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/197:33 am
JFK
-
ORD
Nonstop2h 54m
Delta
Tue 8/256:00 pm
ORD
-
JFK
Nonstop2h 37m
Delta
Deal found 7/28$207
This Delta deal was found by Cheapflights users on 7/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/257:30 am
LGA
-
ORD
Nonstop2h 36m
Delta
Tue 9/15:40 pm
ORD
-
LGA
Nonstop2h 27m
Delta
Deal found 7/29$207
This Southwest deal was found by Cheapflights users on 7/28. 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 8/2510:55 am
LGA
-
MDW
Nonstop2h 20m
Southwest
Tue 9/17:05 pm
MDW
-
LGA
Nonstop2h 05m
Southwest
Deal found 7/28$207
This American Airlines deal was found by Cheapflights users on 7/26. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/28:27 am
JFK
-
ORD
Nonstop3h 03m
American Airlines
Wed 9/24:30 pm
ORD
-
JFK
Nonstop2h 31m
American Airlines
Deal found 7/26$208
This American Airlines deal was found by Cheapflights users on 7/27. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/18:29 pm
LGA
-
ORD
Nonstop3h 01m
American Airlines
Sat 9/58:25 pm
ORD
-
LGA
Nonstop2h 20m
American Airlines
Deal found 7/27$208
This Super.com deal was found by Cheapflights users on 7/24. 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 8/193:40 pm
JFK
-
ORD
Nonstop2h 55m
JetBlue
Sat 8/226:00 am
ORD
-
JFK
Nonstop2h 17m
JetBlue
Deal found 7/24$209
This Super.com deal was found by Cheapflights users on 7/26. 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 8/228:00 pm
JFK
-
ORD
Nonstop2h 58m
JetBlue
Tue 8/256:30 pm
ORD
-
JFK
Nonstop2h 36m
JetBlue
Deal found 7/26$210
This Super.com deal was found by Cheapflights users on 7/26. 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 8/297:00 am
JFK
-
ORD
Nonstop2h 46m
JetBlue
Tue 9/86:00 am
ORD
-
JFK
Nonstop2h 17m
JetBlue
Deal found 7/26$213
This flygcity.se deal was found by Cheapflights users on 7/28. 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 flygcity.se is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/86:55 am
JFK
-
ORD
Nonstop2h 47m
JetBlue
Fri 9/119:38 am
ORD
-
JFK
1 stop6h 51m
JetBlue
Deal found 7/28$214
This Cheapflightsfares deal was found by Cheapflights users on 7/26. 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 9/58:00 pm
JFK
-
ORD
Nonstop2h 58m
JetBlue
Tue 9/89:35 am
ORD
-
JFK
Nonstop2h 19m
JetBlue
Deal found 7/26$215
This JetBlue deal was found by Cheapflights users on 7/28. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/188:00 pm
JFK
-
ORD
Nonstop2h 58m
JetBlue
Wed 8/269:40 am
ORD
-
JFK
Nonstop2h 19m
JetBlue
Deal found 7/28$217

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 July 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$202
(American Airlines)

One-way from

$100
(Frontier)

Popular in

June

Cheapest in

January

Average price

$310

Good round-trip deal

$219 or less

Good one-way deal

$156 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. 17% potential increase in price ($53 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
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 July 29, 2026.
Use the filters below to find and compare flights from New York State to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Wed 8/19

10:30 am-12:17 pm

Nonstop2h 47m

Chicago O'Hare Intl

Wed 8/19

6:00 pm-9:37 pm

Nonstop2h 37m

$207

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Wed 8/19

7:30 am-9:06 am

Nonstop2h 36m

Chicago O'Hare Intl

Tue 8/25

6:00 am-9:09 am

Nonstop2h 09m

$207

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Sat 8/22

5:55 pm-7:57 pm

Nonstop3h 02m

Chicago O'Hare Intl

Tue 9/1

6:00 am-9:09 am

Nonstop2h 09m

$207

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Wed 9/2

12:05 pm-4:50 pm

1 stop5h 45m

Chicago Midway

Wed 9/2

7:05 pm-10:10 pm

Nonstop2h 05m

$217

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Thu 8/27

6:00 am-7:15 am

Nonstop2h 15m

Chicago Midway

Wed 9/2

7:05 pm-10:10 pm

Nonstop2h 05m

$218

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Thu 8/27

7:33 am-9:27 am

Nonstop2h 54m

Chicago O'Hare Intl

Wed 9/2

10:07 am-1:30 pm

Nonstop2h 23m

$218

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Fri 8/21

5:00 pm-7:12 pm

Nonstop3h 12m

Chicago O'Hare Intl

Sat 8/22

7:05 am-10:19 am

Nonstop2h 14m

$222

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Sat 8/15

7:35 pm-9:52 pm

Nonstop3h 17m

Chicago O'Hare Intl

Thu 8/20

6:00 am-9:24 am

Nonstop2h 24m

$223

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Sat 8/22

8:20 am-2:05 pm

1 stop6h 45m

Chicago Midway

Tue 9/1

4:40 pm-11:15 pm

1 stop5h 35m

$227

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Wed 9/2

5:45 pm-9:50 pm

1 stop5h 05m

Chicago Midway

Tue 9/8

7:15 am-3:50 pm

1 stop7h 35m

$227

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/27

Showing 1-10 of 60 resultsSorted by cheapest first
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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, January is the cheapest month in which you can book a flight from State of New York to Chicago (average of $201). Flying from State of New York to Chicago in June is currently the most expensive (average of $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 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 July 29, 2026.

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 24% versus a flight at noon.

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 July 29, 2026.

The most flights from USNY to CHI are scheduled on a Monday (54 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (27 on average).

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

Airfare is below average for this route at the moment.
State of New York to Chicago flights typically cost between $219 and $404 in August.
The cheapest round-trip price found within the last 5 days was $207 on Delta (Aug 19-Aug 25).

How far ahead should I book a flight from State of New York to Chicago?

The best time to book flights from State of New York to Chicago is 30 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

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 July 25, 2026.

Travelers seeking maximum savings on their State of New York to Chicago flight should consider departing on Wednesday evenings when fares are most often at their lowest. Thursday 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 47m. Delta provides one of the quickest options available for as low as $207. State of New York and Chicago are separated by a distance of 738 mi. This flight may include one or multiple stops.

  • 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. JetBlue flights start at $74 while deals on Delta start at $74 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, Newark - Chicago O'Hare Intl or New York LaGuardia - 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 Malaysia Airlines (89%), TAP AIR PORTUGAL (86%) and American Airlines (83%).

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

    Looking at all options, your cheapest flight can be booked for $93. While the most popular route (New York John F Kennedy Intl - Chicago O'Hare Intl) can be booked for $206 on average, our data indicates $394 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, January is the cheapest month in which you can book a flight from State of New York to Chicago (average of $201). Flying from State of New York to Chicago in June is currently the most expensive (average of $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

Traveling to a place near Chicago?

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

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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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LaGuardia to St. Louis flights
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Newark to St. Louis flights
Reagan-National to Midway flights
Salt Lake City to O'Hare Intl flights
Baltimore to Midway flights
Minneapolis to Midway flights
George Bush Intcntl to Midway flights

Top 6 airlines flying from New York to Chicago

Discover the top 6 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 July 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$39Average$179FlexibilityNo cancel feeOn-time62%
DeltaCheapest$74Average$368FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$122Average$252FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$145Average$365FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$148Average$359FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$164Average$389FlexibilityNo cancel feeOn-time63%

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