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$64+ 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 10/23. Fares are subject to change and may not be available on all flights or dates of travel.
JFK — CHI
Jul 8 — Jul 151
Tue 7/8
Tue 7/15
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 July 3, 2025.

Round-trip from

$132
(Priceline)

One-way from

$64
(FlightHub)

Popular in

December

Cheapest in

September

Average price

$236

Good round-trip deal

$226 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. 1% potential increase in price ($3 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 July 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 July 3, 2025.

This FlightHub deal was found by Cheapflights users on 7/3. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/169:33 pmEWR - ORD
Nonstop2h 37mSpirit Airlines
Sun 10/195:10 pmORD - EWR
Nonstop2h 18mSpirit Airlines
Deal found 7/3$130
This Priceline deal was found by Cheapflights users on 7/2. 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.
Tue 7/2911:04 amEWR - ORD
1 stop6h 34mMultiple Airlines
Mon 8/44:37 pmORD - EWR
1 stop6h 35mMultiple Airlines
Deal found 7/2$132
This Priceline deal was found by Cheapflights users on 7/2. 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.
Tue 10/1412:59 pmJFK - ORD
1 stop8h 10mFrontier
Sun 10/195:10 amORD - JFK
1 stop5h 49mFrontier
Deal found 7/2$136
This JetBlue deal was found by Cheapflights users on 7/1. 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.
Sat 8/309:29 amJFK - ORD
Nonstop2h 49mJetBlue
Tue 9/211:35 amORD - JFK
Nonstop2h 23mJetBlue
Deal found 7/1$137
This Kiwi.com deal was found by Cheapflights users on 7/1. 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 9/153:13 pmLGA - ORD
Nonstop2h 38mSpirit Airlines
Fri 9/2611:13 amORD - LGA
Nonstop2h 05mSpirit Airlines
Deal found 7/1$137
This Southwest deal was found by Cheapflights users on 7/2. 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.
Sat 8/307:30 amLGA - MDW
Nonstop2h 20mSouthwest
Wed 9/35:55 pmMDW - LGA
Nonstop2h 15mSouthwest
Deal found 7/2$137
This Priceline deal was found by Cheapflights users on 7/2. 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.
Sat 8/235:55 amEWR - ORD
1 stop6h 41mFrontier
Wed 8/272:40 pmORD - EWR
1 stop8h 33mFrontier
Deal found 7/2$139
This Priceline deal was found by Cheapflights users on 7/1. 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 7/236:30 amLGA - ORD
1 stop10h 34mMultiple Airlines
Tue 7/298:09 amORD - LGA
1 stop8h 21mMultiple Airlines
Deal found 7/1$139
This Priceline deal was found by Cheapflights users on 7/3. 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 9/1911:15 amEWR - MDW
1 stop5h 43mFrontier
Mon 9/225:04 pmMDW - EWR
1 stop6h 30mFrontier
Deal found 7/3$141
This Priceline deal was found by Cheapflights users on 6/30. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/96:30 amLGA - MDW
1 stop10h 28mFrontier
Sat 9/1311:23 amMDW - LGA
1 stop7h 39mFrontier
Deal found 6/30$144
This Priceline deal was found by Cheapflights users on 7/2. 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 10/249:00 amJFK - MDW
1 stop10h 18mFrontier
Sun 10/2610:03 pmMDW - JFK
1 stop11h 22mFrontier
Deal found 7/2$146
This United Airlines deal was found by Cheapflights users on 7/2. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/38:15 pmEWR - ORD
Nonstop2h 41mUnited Airlines
Sat 9/610:35 amORD - EWR
Nonstop2h 17mUnited Airlines
Deal found 7/2$147

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 3, 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

Thu 10/16

9:33 pm-11:10 pm

Nonstop2h 37m

Chicago O'Hare Intl

Sun 10/19

5:10 pm-8:28 pm

Nonstop2h 18m

$130

NewarkChicago

EWR - ORD

EWRORD

Newark

Tue 7/29

11:04 am-4:38 pm

1 stop6h 34m

Chicago O'Hare Intl

Mon 8/4

4:37 pm-12:12 am

1 stop6h 35m

$132

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Sat 8/30

9:29 am-11:18 am

Nonstop2h 49m

Chicago O'Hare Intl

Tue 9/2

11:35 am-2:58 pm

Nonstop2h 23m

$137

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Sat 8/30

7:30 am-8:50 am

Nonstop2h 20m

Chicago Midway

Tue 9/2

6:00 am-9:00 am

Nonstop2h 00m

$137

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Mon 9/15

3:13 pm-4:51 pm

Nonstop2h 38m

Chicago O'Hare Intl

Fri 9/26

11:13 am-2:18 pm

Nonstop2h 05m

$137

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Thu 7/31

6:59 am-3:27 pm

1 stop9h 28m

Chicago O'Hare Intl

Sat 8/2

5:07 pm-12:42 am

1 stop6h 35m

$138

NewarkChicago

EWR - ORD

EWRORD

Newark

Sat 8/23

5:55 am-11:36 am

1 stop6h 41m

Chicago O'Hare Intl

Wed 8/27

2:40 pm-12:13 am

1 stop8h 33m

$139

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Wed 7/23

6:30 am-4:04 pm

1 stop10h 34m

Chicago O'Hare Intl

Tue 7/29

8:09 am-5:30 pm

1 stop8h 21m

$139

NewarkChicago

EWR - MDW

EWRMDW

Newark

Fri 9/19

11:15 am-3:58 pm

1 stop5h 43m

Chicago Midway

Mon 9/22

5:04 pm-12:34 am

1 stop6h 30m

$141

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Tue 9/9

6:30 am-3:58 pm

1 stop10h 28m

Chicago Midway

Sat 9/13

11:23 am-8:02 pm

1 stop7h 39m

$144

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/1

Showing 1-10 of 60 results
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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, 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 July 3, 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.

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated July 3, 2025.
Read through reviews of airlines operating flights from New York State to Chicago, such as Southwest, Delta, and United Airlines. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,266 reviews

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,266 reviews
Southwest
8.0
Very good
4,266 reviews

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,982 reviews
Southwest
8.0
Very good
4,266 reviews

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
United Airlines
7.4
Good
8,861 reviews
Southwest
8.0
Very good
4,266 reviews

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
JetBlue
7.3
Good
2,916 reviews
Southwest
8.0
Very good
4,266 reviews

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,266 reviews

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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.

  • 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 Spirit Airlines, which is currently one of the cheapest options available, starting at $64. Frontier flights start at $66 while deals on United Airlines 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 Cathay Pacific (100%), China Airlines (84%) and American Airlines (80%).

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

    Looking at all options, your cheapest flight can be booked for $88. While the most popular route (New York John F Kennedy Intl - Chicago O'Hare Intl) can be booked for $137 on average our data indicates $724 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 New York State?

Book flights to New York State if you plan to visit one of these locations
Merrillville
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
Chesterton

Browse thousands of different options on Cheapflights for your next trip

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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 July 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$58Average$256FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$66Average$158FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$84Average$230FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$96Average$344FlexibilityNo cancel feeOn-time69%
DeltaCheapest$118Average$361FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$137Average$325FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$151Average$415FlexibilityNo cancel feeOn-time63%

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