HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$55+ 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 11/20. Fares are subject to change and may not be available on all flights or dates of travel.
JFK — CHI
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from New York to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 October 30, 2025.

This Frontier deal was found by Cheapflights users on 10/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/141:08 pmJFK - ORD
1 stop12h 51mFrontier
Mon 11/176:40 amORD - JFK
Nonstop2h 23mFrontier
Deal found 10/30$101
This Kiwi.com deal was found by Cheapflights users on 10/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/237:30 amLGA - ORD
Nonstop2h 31mSpirit Airlines
Tue 12/23:53 pmORD - LGA
Nonstop2h 07mSpirit Airlines
Deal found 10/30$101
This Booking.com deal was found by Cheapflights users on 10/30. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/176:20 amJFK - ORD
1 stop11h 36mFrontier
Tue 11/186:40 amORD - JFK
Nonstop2h 23mFrontier
Deal found 10/30$102
This Priceline deal was found by Cheapflights users on 10/29. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/1412:59 pmLGA - ORD
Nonstop2h 32mSpirit Airlines
Tue 11/1810:52 amORD - LGA
1 stop7h 08mSpirit Airlines
Deal found 10/29$102
This Priceline deal was found by Cheapflights users on 10/28. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1311:00 amJFK - ORD
Nonstop2h 45mFrontier
Sat 11/156:40 amORD - JFK
Nonstop2h 23mFrontier
Deal found 10/28$103
This Cheapflightsfares deal was found by Cheapflights users on 10/30. 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 11/88:59 amLGA - ORD
Nonstop2h 31mSpirit Airlines
Sat 11/227:21 pmORD - LGA
Nonstop2h 08mSpirit Airlines
Deal found 10/30$103
This Frontier deal was found by Cheapflights users on 10/28. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1311:00 amJFK - ORD
Nonstop2h 45mFrontier
Thu 11/206:45 pmORD - JFK
1 stop10h 16mFrontier
Deal found 10/28$104
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/612:59 pmLGA - ORD
Nonstop2h 32mSpirit Airlines
Mon 11/107:34 pmORD - LGA
Nonstop2h 08mSpirit Airlines
Deal found 10/29$104
This Priceline deal was found by Cheapflights users on 10/28. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/121:00 pmJFK - ORD
Nonstop2h 57mFrontier
Sat 12/138:36 amORD - JFK
Nonstop2h 24mFrontier
Deal found 10/28$105
This Cheapflightsfares deal was found by Cheapflights users on 10/28. 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 11/2212:59 pmLGA - ORD
Nonstop2h 32mSpirit Airlines
Sat 12/612:09 pmORD - LGA
1 stop6h 51mSpirit Airlines
Deal found 10/28$105
This Mytrip deal was found by Cheapflights users on 10/28. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/711:00 amJFK - ORD
Nonstop2h 45mFrontier
Mon 11/106:40 amORD - JFK
Nonstop2h 23mFrontier
Deal found 10/28$106
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/2112:59 pmLGA - ORD
Nonstop2h 32mSpirit Airlines
Thu 11/273:53 pmORD - LGA
Nonstop2h 07mSpirit Airlines
Deal found 10/28$106

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 October 30, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$100
(Cheapflightsfares)

One-way from

$55
(Frontier)

Popular in

August

Cheapest in

January

Average price

$242

Good round-trip deal

$138 or less

Good one-way deal

$82 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. 7% potential increase in price ($19 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 October 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 October 30, 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 - MDW

JFKMDW

New York John F Kennedy Intl

Thu 11/20

1:00 pm-12:13 am

1 stop12h 13m

Chicago Midway

Thu 12/4

2:16 pm-12:07 am

1 stop8h 51m

$110

NewarkChicago

EWR - MDW

EWRMDW

Newark

Thu 12/4

10:30 pm-10:12 pm

1 stop24h 42m

Chicago Midway

Sun 12/7

7:44 am-10:45 am

Nonstop2h 01m

$135

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Wed 11/19

10:50 am-12:39 pm

Nonstop2h 49m

Chicago O'Hare Intl

Wed 11/19

6:33 pm-10:05 pm

Nonstop2h 32m

$137

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Sat 11/15

8:35 am-10:00 am

Nonstop2h 25m

Chicago Midway

Mon 11/17

7:15 pm-10:20 pm

Nonstop2h 05m

$137

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Sat 11/15

11:30 am-1:17 pm

Nonstop2h 47m

Chicago O'Hare Intl

Mon 11/17

9:30 am-12:41 pm

Nonstop2h 11m

$137

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Thu 11/13

6:15 am-7:55 am

Nonstop2h 40m

Chicago O'Hare Intl

Wed 11/19

7:00 am-10:15 am

Nonstop2h 15m

$137

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Tue 11/11

10:59 am-12:27 am

1 stop14h 28m

Chicago O'Hare Intl

Wed 11/12

10:52 am-11:21 pm

1 stop11h 29m

$138

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Thu 1/15

7:30 am-9:27 am

Nonstop2h 57m

Chicago O'Hare Intl

Sun 1/18

10:45 am-1:58 pm

Nonstop2h 13m

$138

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Sat 2/7

7:00 pm-8:53 pm

Nonstop2h 53m

Chicago O'Hare Intl

Sat 2/14

7:30 am-10:56 am

Nonstop2h 26m

$139

NewarkChicago

EWR - MDW

EWRMDW

Newark

Sun 11/23

10:13 am-11:42 am

Nonstop2h 29m

Chicago Midway

Tue 12/2

2:49 pm-1:10 am

1 stop9h 21m

$141

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/30

Showing 1-10 of 60 results
1
2
3
...
6

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, November is the cheapest month in which you can book a flight from State of New York to Chicago (average of $54). 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 October 30, 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 October 26, 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. Monday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

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. Frontier provides one of the quickest options available for as low as $137. State of New York and Chicago are separated by a distance of 722 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 $65. United Airlines flights start at $69 while deals on Southwest 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 Atlas Air (100%), Finnair (100%) and Hawaiian Airlines (95%).

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

    Looking at all options, your cheapest flight can be booked for $30. While the most popular route (New York John F Kennedy Intl - Chicago O'Hare Intl) can be booked for $71 on average, our data indicates $614 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, November is the cheapest month in which you can book a flight from State of New York to Chicago (average of $54). 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
Merrillville
Lansing
Hammond
Porter
Benton Harbor

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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
Dallas/Fort Worth to O'Hare Intl flights
LaGuardia to O'Hare Intl flights
Newark to O'Hare Intl flights
Los Angeles to O'Hare Intl flights
San Francisco to O'Hare Intl flights
Reagan-National to O'Hare Intl flights
Baltimore to O'Hare Intl flights
Dulles Intl to O'Hare Intl flights
Seattle to O'Hare Intl flights
Denver to O'Hare Intl flights
Philadelphia to O'Hare Intl flights
Boston to O'Hare Intl flights
Atlanta to O'Hare Intl flights
John F Kennedy Intl to Midway flights
Baltimore to Midway flights
Dallas/Fort Worth to Midway flights
Ontario to O'Hare Intl flights
Minneapolis to O'Hare Intl flights
Los Angeles to Midway flights
Hobby to Midway flights
Atlanta to Midway flights
LaGuardia to Midway flights
Newark to Midway flights
Sky Harbor Intl to O'Hare Intl flights
Newark to St. Louis flights
Denver to Midway flights
Philadelphia to Midway flights
Charlotte to O'Hare Intl flights
Fort Lauderdale to O'Hare Intl flights
San Francisco to Midway flights
George Bush Intcntl to O'Hare Intl flights
Dulles Intl to Midway flights
Hobby to O'Hare Intl flights
Tampa to O'Hare Intl flights
Miami to O'Hare Intl flights
Minneapolis to Midway flights
Raleigh to O'Hare Intl flights
Santa Ana to O'Hare Intl flights
John F Kennedy Intl to St. Louis flights
Reagan-National to Midway flights
Austin to O'Hare Intl flights
Cleveland to O'Hare Intl flights
Love Field to O'Hare Intl flights
Hartford to O'Hare Intl flights
Orlando to O'Hare Intl flights
San Diego to O'Hare Intl flights
Portland to O'Hare Intl flights
LaGuardia to St. Louis flights
Boston to Midway 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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$55Average$205FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$66Average$198FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$87Average$229FlexibilityNo cancel feeOn-time62%
DeltaCheapest$101Average$370FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$147Average$338FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$147Average$337FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$156Average$429FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.