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$52+ Cheap flights from John F Kennedy Intl, NY (JFK) 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 3/17. Fares are subject to change and may not be available on all flights or dates of travel.
JFK — CHI
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
1 adult, Economy
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The best prices from New York John F Kennedy Intl to Chicago are usually found in January or February, booked 41 days in advance, depart on a Tuesday or Saturday and return on a Friday

Cheap flight deals from John F Kennedy Intl to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from John F Kennedy Intl (JFK) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$98
(Cheapflightsfares)

One-way from

$52
(Mytrip)

Popular in

December

Cheapest in

January

Average price

$189

Good round-trip deal

$182 or less

Good one-way deal

$95 or less
Provider with most accurate pricing for New York John F Kennedy Intl-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for New York John F Kennedy Intl-Chicago (CHI) flights.
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From New York John F Kennedy Intl to Chicago (CHI)
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One-way flight from New York John F Kennedy Intl to Chicago (CHI)
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High demand for flights, 1% potential price rise
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Cheapest flight prices on average. 3% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in February 2025
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Price to beat on a round-trip flight from New York John F Kennedy Intl to Chicago (CHI).
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Price to beat on a one-way flight from New York John F Kennedy Intl to Chicago (CHI).
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Find flight deals from John F Kennedy Intl to Chicago

Cheapest flights from John F Kennedy Intl to Chicago
Explore the most affordable flight options available from John F Kennedy Intl to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 20, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 2/19. 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 3/2511:01 amJFK - MDW
1 stop5h 52mFrontier
Tue 4/14:40 pmMDW - JFK
1 stop7h 03mFrontier
Deal found 2/19$98
This Frontier deal was found by Cheapflights users on 2/19. 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 5/69:00 amJFK - ORD
1 stop8h 43mFrontier
Wed 5/711:10 amORD - JFK
1 stop12h 25mFrontier
Deal found 2/19$100
This JetBlue deal was found by Cheapflights users on 2/19. 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.
Thu 5/18:29 pmJFK - ORD
Nonstop2h 51mJetBlue
Wed 5/71:12 pmORD - JFK
Nonstop2h 18mJetBlue
Deal found 2/19$147
This KAYAK deal was found by Cheapflights users on 2/19. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/268:00 amJFK - ORD
Nonstop2h 55mDelta
Thu 2/2710:05 amORD - JFK
Nonstop2h 24mDelta
Deal found 2/19$155
This American Airlines deal was found by Cheapflights users on 2/20. 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 4/19:00 amJFK - ORD
Nonstop2h 51mAmerican Airlines
Tue 4/85:10 pmORD - JFK
Nonstop2h 20mAmerican Airlines
Deal found 2/20$158
This Gotogate deal was found by Cheapflights users on 2/19. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/1011:21 amJFK - ORD
1 stop7h 45mMultiple Airlines
Sat 4/127:20 amORD - JFK
1 stop16h 23mMultiple Airlines
Deal found 2/19$213
This Delta deal was found by Cheapflights users on 2/20. 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 3/257:15 amJFK - MDW
1 stop11h 47mDelta
Thu 3/279:25 amMDW - JFK
1 stop8h 15mDelta
Deal found 2/20$233
This Sun Country Air deal was found by Cheapflights users on 2/20. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/1911:21 amJFK - ORD
1 stop10h 33mSun Country Air
Sun 4/278:15 amORD - JFK
1 stop25h 08mSun Country Air
Deal found 2/20$265

Find flights from John F Kennedy Intl to Chicago within your budget

Customize your flight search to find flights from John F Kennedy Intl 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 February 20, 2025.

Fly from

John F Kennedy Intl

Fly to

Chicago

Route

Depart

Return

Price

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Tue 3/25

11:01 am-3:53 pm

1 stop5h 52m

Chicago Midway

Tue 4/1

4:40 pm-12:43 am

1 stop7h 03m

$98

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Tue 5/6

9:00 am-4:43 pm

1 stop8h 43m

Chicago O'Hare Intl

Wed 5/7

11:10 am-12:35 am

1 stop12h 25m

$100

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Thu 5/1

10:35 am-12:17 pm

Nonstop2h 42m

Chicago O'Hare Intl

Sun 5/4

6:20 am-9:33 am

Nonstop2h 13m

$147

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Mon 3/3

8:00 am-9:55 am

Nonstop2h 55m

Chicago O'Hare Intl

Thu 3/6

10:05 am-1:30 pm

Nonstop2h 25m

$155

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Tue 4/1

9:00 am-10:51 am

Nonstop2h 51m

Chicago O'Hare Intl

Tue 4/8

5:10 pm-8:30 pm

Nonstop2h 20m

$158

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Thu 4/10

11:21 am-6:06 pm

1 stop7h 45m

Chicago O'Hare Intl

Sat 4/12

7:20 am-12:43 am

1 stop16h 23m

$213

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Tue 3/25

7:15 am-6:02 pm

1 stop11h 47m

Chicago Midway

Wed 3/26

2:55 pm-9:00 am

1 stop17h 05m

$223

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Sat 4/19

11:21 am-8:54 pm

1 stop10h 33m

Chicago O'Hare Intl

Sun 4/27

8:15 am-10:23 am

1 stop25h 08m

$265

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Mon 3/17

1:01 pm-7:35 pm

1 stop7h 34m

$52

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Sat 5/10

6:59 am-11:32 pm

1 stop17h 33m

$53

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

Showing 1-10 of 18 results
1
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Compare providers for flights from John F Kennedy Intl to Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from John F Kennedy Intl to Chicago in February.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars
CheapOairPrice Accuracy1 starTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on New York John F Kennedy Intl Airport-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on New York John F Kennedy Intl Airport-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from New York John F Kennedy Intl Airport-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on New York John F Kennedy Intl Airport-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for New York John F Kennedy Intl Airport-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from John F Kennedy Intl to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from John F Kennedy Intl 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.

Travel insights for flights from John F Kennedy Intl to Chicago

Get recent, data-driven insights about flights from John F Kennedy Intl to Chicago including ideal travel times, pricing trends, and more.

How far ahead should I book a flight from New York John F Kennedy Intl Airport to Chicago?

Use this chart to determine the optimal time to book a round-trip flight from John F Kennedy Intl to Chicago. Price data was last updated on February 14, 2025.

Booking 41 days in advance of your planned departure date is, on average, the best time to get cheap flights from New York John F Kennedy Intl Airport to Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

What is the cheapest month to book a flight from New York John F Kennedy Intl Airport to Chicago?

Currently, August is the cheapest month in which you can book a flight from New York John F Kennedy Intl Airport to Chicago (average of $245). Flying from New York John F Kennedy Intl Airport 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 JFK to CHI?

Find hourly flight availability from John F Kennedy Intl 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 February 20, 2025.

One of the essential ways to save on airfare from New York John F Kennedy Intl Airport to Chicago is to remain as flexible as possible. Flights that are in the afternoon tend to be the most expensive. A flight at noon could potentially save you up to 28% on airfare.

What is the cheapest day to fly from New York John F Kennedy Intl Airport to Chicago?

Use this chart to determine the cheapest time to fly round-trip from John F Kennedy Intl to Chicago. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their New York John F Kennedy Intl Airport to Chicago flight should consider departing on Tuesday at noon when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from New York John F Kennedy Intl Airport to Chicago

Explore weekly flight availability from John F Kennedy Intl 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 February 20, 2025.

The most flights from JFK to CHI are scheduled on a Thursday (46 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (15 on average).

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 February 20, 2025.
Get a feel of what it's like to fly with Alaska Airlines, Delta and JetBlue from New York to Chicago by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
9,692 reviews

Crew

8.5

Food

7.1

Comfort

7.9

Overall

8.0

Boarding

8.2

Entertainment

7.1

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Alaska Airlines
8.0
Very good
9,692 reviews
Alaska Airlines
8.0
Very good
9,692 reviews

Crew

8.5

Food

7.1

Comfort

7.9

Overall

8.0

Boarding

8.2

Entertainment

7.1

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Delta
8.0
Very good
8,220 reviews
Alaska Airlines
8.0
Very good
9,692 reviews

Crew

8.5

Food

7.1

Comfort

7.9

Overall

8.0

Boarding

8.2

Entertainment

7.1

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

JetBlue
7.4
Good
3,070 reviews
Alaska Airlines
8.0
Very good
9,692 reviews

Crew

8.5

Food

7.1

Comfort

7.9

Overall

8.0

Boarding

8.2

Entertainment

7.1

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
9,692 reviews

Crew

8.5

Food

7.1

Comfort

7.9

Overall

8.0

Boarding

8.2

Entertainment

7.1

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Sun Country Air
7.0
Good
374 reviews
Alaska Airlines
8.0
Very good
9,692 reviews

Crew

8.5

Food

7.1

Comfort

7.9

Overall

8.0

Boarding

8.2

Entertainment

7.1

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Related info for your journey

Find useful and relevant information for your journey from John F Kennedy Intl 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 flying from New York John F Kennedy Intl Airport to Chicago round-trip?

    According to our current data, Frontier ($98), JetBlue ($147), and Delta ($155) offers the cheapest pricing from New York John F Kennedy Intl Airport to Chicago. These flights start at 58% lower than the current average price 3 months from now.

  • What are the cheapest airlines to fly from New York John F Kennedy Intl Airport to Chicago one-way?

    The cheapest airlines for a one-way flight from New York John F Kennedy Intl Airport to Chicago are Frontier ($52), JetBlue ($74), and Delta ($78).

  • What are the most reliable airlines from New York John F Kennedy Intl Airport to Chicago?

    Before booking your flight to Chicago from New York John F Kennedy Intl Airport, check out the most reliable airlines to get you to your destination on time: Royal Air Maroc (100%), Royal Jordanian (100%), Air Europa( 93%).

  • What are the cheapest flights from New York John F Kennedy Intl Airport to Chicago?

    On average you can expect to pay $563 for a flight from New York John F Kennedy Intl Airport to Chicago. The cheapest flight overall is $58 while the most popular route, (New York John F Kennedy Intl - Chicago O'Hare Intl) is currently priced at $95.

  • Can I find deals for flights from John F Kennedy Intl to Chicago that include hotel bookings?

    Yes. In addition to deals on John F Kennedy Intl to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from John F Kennedy Intl to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from John F Kennedy Intl to Chicago.

  • Can I find deals for business class flights from John F Kennedy Intl to Chicago?

    Yes. Cheapflights offers flight deals from John F Kennedy Intl 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 New York John F Kennedy Intl Airport to Chicago?

    Currently, August is the cheapest month in which you can book a flight from New York John F Kennedy Intl Airport to Chicago (average of $245). Flying from New York John F Kennedy Intl Airport 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 John F Kennedy Intl Airport?

Book flights to New York John F Kennedy Intl Airport if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for John F Kennedy Intl 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
Newark to O'Hare Intl flights
LaGuardia to O'Hare Intl flights
Newark to Midway flights
John F Kennedy Intl to Midway flights
LaGuardia to Midway flights
Newark to St. Louis flights
LaGuardia to St. Louis flights
John F Kennedy Intl to St. Louis flights
LaGuardia to Moline flights
John F Kennedy Intl to Moline flights
Newark to Moline flights
Newark to Peoria flights
Newark to Rockford flights
LaGuardia to Peoria flights
Newark to Bloomington flights
John F Kennedy Intl to Bloomington flights
John F Kennedy Intl to Peoria flights
Stewart to O'Hare Intl flights
LaGuardia to Bloomington flights
LaGuardia to Evansville flights
Newark to Springfield flights
Newark to Evansville flights
Newark to Dubuque flights
John F Kennedy Intl to Evansville flights
Stewart to St. Louis flights
Stewart to Rockford flights
LaGuardia to Dubuque flights
John F Kennedy Intl to Dubuque flights
John F Kennedy Intl to Champaign flights
LaGuardia to Springfield flights
John F Kennedy Intl to Springfield flights
Newark to Champaign flights
Stewart to Peoria flights
Stewart to Midway flights
LaGuardia to Champaign flights
Newark to Quincy flights
Stewart to Evansville flights
LaGuardia to Paducah flights
Newark to Paducah flights
Stewart to Moline flights
LaGuardia to Marion flights
Newark to Marion flights
LaGuardia to Decatur flights

Top 5 airlines flying from John F Kennedy Intl to Chicago

Discover the top 5 airlines that operate flights from John F Kennedy Intl 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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$83Average$144FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$84Average$245FlexibilityNo cancel feeOn-time62%
DeltaCheapest$106Average$384FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$137Average$272FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$168Average$227FlexibilityNo cancel feeOn-time69%
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