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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 4/7. Fares are subject to change and may not be available on all flights or dates of travel.
JFK — CHI
May 2 — May 91
Sat 5/2
Sat 5/9
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 April 2, 2026.

This Cheapflightsfares deal was found by Cheapflights users on 3/28. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/182:38 pm
LGA
-
ORD
Nonstop2h 36m
Spirit Airlines
Sat 4/2510:33 am
ORD
-
LGA
Nonstop2h 10m
Spirit Airlines
Deal found 3/28$106
This Kiwi.com deal was found by Cheapflights users on 3/31. 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.
Tue 4/216:15 pm
LGA
-
ORD
Nonstop2h 42m
Spirit Airlines
Wed 4/222:09 pm
ORD
-
LGA
Nonstop2h 11m
Spirit Airlines
Deal found 3/31$108
This Cheapflightsfares deal was found by Cheapflights users on 3/28. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/1410:59 am
LGA
-
ORD
1 stop8h 32m
Spirit Airlines
Tue 4/212:09 pm
ORD
-
LGA
Nonstop2h 11m
Spirit Airlines
Deal found 3/28$111
This Cheapflightsfares deal was found by Cheapflights users on 3/31. 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.
Tue 4/216:15 pm
LGA
-
ORD
Nonstop2h 42m
Spirit Airlines
Fri 4/242:09 pm
ORD
-
LGA
Nonstop2h 11m
Spirit Airlines
Deal found 3/31$112
This Booking.com deal was found by Cheapflights users on 3/31. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/166:15 pm
LGA
-
ORD
Nonstop2h 42m
Spirit Airlines
Mon 4/202:09 pm
ORD
-
LGA
Nonstop2h 11m
Spirit Airlines
Deal found 3/31$113
This Kiwi.com deal was found by Cheapflights users on 3/31. 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 4/226:15 pm
LGA
-
ORD
Nonstop2h 42m
Spirit Airlines
Mon 4/272:09 pm
ORD
-
LGA
Nonstop2h 11m
Spirit Airlines
Deal found 3/31$114
This Cheapflightsfares deal was found by Cheapflights users on 3/30. 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 4/116:30 am
LGA
-
ORD
Nonstop2h 31m
Spirit Airlines
Tue 4/147:31 pm
ORD
-
LGA
Nonstop2h 05m
Spirit Airlines
Deal found 3/30$116
This Mytrip deal was found by Cheapflights users on 3/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/1810:08 am
EWR
-
ORD
Nonstop2h 34m
Multiple Airlines
Wed 4/226:08 pm
ORD
-
EWR
1 stop6h 08m
Multiple Airlines
Deal found 3/29$117
This Cheapflightsfares deal was found by Cheapflights users on 3/31. 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 4/156:15 pm
LGA
-
ORD
Nonstop2h 42m
Spirit Airlines
Sat 4/1810:33 am
ORD
-
LGA
Nonstop2h 10m
Spirit Airlines
Deal found 3/31$117
This Frontier deal was found by Cheapflights users on 3/31. 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 4/2111:30 am
EWR
-
MDW
Nonstop2h 30m
Frontier
Thu 4/232:15 pm
MDW
-
EWR
1 stop10h 01m
Frontier
Deal found 3/31$118
This Cheapflightsfares deal was found by Cheapflights users on 3/28. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/1010:54 pm
EWR
-
ORD
Nonstop2h 28m
Spirit Airlines
Fri 4/1712:47 pm
ORD
-
EWR
Nonstop2h 07m
Spirit Airlines
Deal found 3/28$118
This Cheapflightsfares deal was found by Cheapflights users on 3/31. 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.
Thu 4/236:15 pm
LGA
-
ORD
Nonstop2h 42m
Spirit Airlines
Mon 4/272:09 pm
ORD
-
LGA
Nonstop2h 11m
Spirit Airlines
Deal found 3/31$118

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 April 2, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$106
(Cheapflightsfares)

One-way from

$59
(Expedia)

Popular in

June

Cheapest in

January

Average price

$239

Good round-trip deal

$207 or less

Good one-way deal

$114 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. 11% potential increase in price ($31 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 April 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 April 2, 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

NewarkChicago

EWR - ORD

EWRORD

Newark

Thu 5/28

9:40 pm-11:30 pm

Nonstop2h 50m

Chicago O'Hare Intl

Sat 5/30

9:19 pm-12:42 am

Nonstop2h 23m

$177

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Thu 4/23

7:30 am-9:23 am

Nonstop2h 53m

Chicago O'Hare Intl

Mon 4/27

7:44 pm-10:59 pm

Nonstop2h 15m

$177

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Thu 4/23

6:00 am-7:25 am

Nonstop2h 25m

Chicago Midway

Mon 4/27

7:50 pm-10:55 pm

Nonstop2h 05m

$177

NewarkChicago

EWR - ORD

EWRORD

Newark

Sat 5/23

6:10 pm-8:05 pm

Nonstop2h 55m

Chicago O'Hare Intl

Sat 5/30

6:00 am-9:12 am

Nonstop2h 12m

$177
Quickest round-trip

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Fri 4/24

9:45 pm-11:10 pm

Nonstop2h 25m

Chicago Midway

Sun 4/26

5:20 am-8:20 am

Nonstop2h 00m

$177

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Thu 5/28

6:10 am-7:49 am

Nonstop2h 39m

Chicago O'Hare Intl

Sat 5/30

6:30 pm-9:59 pm

Nonstop2h 29m

$177

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Mon 4/27

6:00 am-7:25 am

Nonstop2h 25m

Chicago Midway

Mon 5/4

8:10 am-11:15 am

Nonstop2h 05m

$177

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Sat 5/23

7:25 pm-9:13 pm

Nonstop2h 48m

Chicago O'Hare Intl

Sat 5/30

4:00 pm-7:22 pm

Nonstop2h 22m

$177

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Fri 4/17

8:25 pm-10:15 pm

Nonstop2h 50m

Chicago O'Hare Intl

Mon 4/20

6:00 am-9:14 am

Nonstop2h 14m

$187

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Thu 5/7

7:30 am-9:11 am

Nonstop2h 41m

Chicago O'Hare Intl

Thu 5/14

6:00 am-9:12 am

Nonstop2h 12m

$187

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/29

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, December is the cheapest month in which you can book a flight from State of New York to Chicago (average of $48). 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 April 2, 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 15% 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 March 28, 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. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

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 April 2, 2026.

The most flights from USNY to CHI are scheduled on a Thursday (38 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (9 on average).

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

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. United Airlines provides one of the quickest options available for as low as $177. 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 Frontier, which is currently one of the cheapest options available, starting at $29. Spirit Airlines flights start at $42 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, 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 Etihad Airways (77%), Hawaiian Airlines (73%) and Qatar Airways (70%).

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

    Looking at all options, your cheapest flight can be booked for $78. While the most popular route (New York John F Kennedy Intl - Chicago O'Hare Intl) can be booked for $172 on average, our data indicates $821 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, December is the cheapest month in which you can book a flight from State of New York to Chicago (average of $48). 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.
John F Kennedy Intl to O'Hare Intl flights
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Atlanta to O'Hare Intl flights
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Miami to O'Hare Intl flights
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Minneapolis to Midway flights
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Newark to St. Louis flights
Boston to Midway flights
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Fort Lauderdale to O'Hare Intl flights

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 April 2, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$47Average$176FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$59Average$150FlexibilityNo cancel feeOn-time65%
DeltaCheapest$78Average$334FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$84Average$222FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$139Average$332FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$145Average$347FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$158Average$466FlexibilityNo cancel feeOn-time63%

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