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$77+ 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 10/8. Fares are subject to change and may not be available on all flights or dates of travel.
JFK — CHI
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
1 adult, Economy
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Cheapflights Tip: The best prices from New York John F Kennedy Intl to Chicago are usually found in January or September, booked 41 days in advance, depart on a Tuesday or Monday 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 August 14, 2025.

Round-trip from

$147
(Delta)

One-way from

$77
(Cheapflightsfares)

Popular in

June

Cheapest in

January

Average price

$271

Good round-trip deal

$193 or less

Good one-way deal

$149 or less
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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Highest demand for flights based on searches. 15% potential increase in price ($42 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in August 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 August 14, 2025.

This Delta deal was found by Cheapflights users on 8/14. 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 9/37:29 pmJFK - ORD
Nonstop3h 18mDelta
Sat 9/66:20 pmORD - JFK
Nonstop2h 43mDelta
Deal found 8/14$147
This Mytrip deal was found by Cheapflights users on 8/14. 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.
Thu 9/116:15 amJFK - MDW
1 stop10h 43mFrontier
Mon 9/155:15 pmMDW - JFK
1 stop6h 53mFrontier
Deal found 8/14$147
This Gotogate deal was found by Cheapflights users on 8/14. 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.
Sat 9/136:15 amJFK - ORD
1 stop6h 12mFrontier
Mon 9/155:10 amORD - JFK
1 stop5h 49mFrontier
Deal found 8/14$148
This Gotogate deal was found by Cheapflights users on 8/14. 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.
Sat 9/131:01 pmJFK - MDW
1 stop11h 16mFrontier
Mon 9/155:15 pmMDW - JFK
1 stop6h 53mFrontier
Deal found 8/14$148
This Kiwi.com deal was found by Cheapflights users on 8/14. 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.
Sat 9/136:15 amJFK - ORD
1 stop6h 12mFrontier
Sat 9/205:40 pmORD - JFK
1 stop6h 28mFrontier
Deal found 8/14$149
This Flightnetwork deal was found by Cheapflights users on 8/14. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/226:15 amJFK - MDW
1 stop10h 45mFrontier
Fri 9/265:15 pmMDW - JFK
1 stop6h 53mFrontier
Deal found 8/14$149
This lastminute.com deal was found by Cheapflights users on 8/14. 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 lastminute.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/132:30 pmJFK - ORD
Nonstop2h 51mJetBlue
Mon 9/156:45 amORD - JFK
Nonstop2h 14mJetBlue
Deal found 8/14$150
This Bravofly deal was found by Cheapflights users on 8/14. 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 Bravofly is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/64:30 pmJFK - ORD
Nonstop2h 53mJetBlue
Tue 9/161:35 pmORD - JFK
Nonstop2h 24mJetBlue
Deal found 8/14$151
This American Airlines deal was found by Cheapflights users on 8/12. 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.
Sat 9/611:00 amJFK - ORD
Nonstop2h 41mAmerican Airlines
Sat 9/61:59 pmORD - JFK
Nonstop2h 18mAmerican Airlines
Deal found 8/12$152
This Jettzy deal was found by Cheapflights users on 8/12. 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 Jettzy is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/274:30 pmJFK - ORD
Nonstop2h 53mJetBlue
Sat 10/48:34 amORD - JFK
Nonstop2h 30mJetBlue
Deal found 8/12$153
This Kiwi.com deal was found by Cheapflights users on 8/14. 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 9/129:00 amJFK - ORD
1 stop7h 50mFrontier
Thu 9/256:21 pmORD - JFK
1 stop5h 47mFrontier
Deal found 8/14$154
This Delta deal was found by Cheapflights users on 8/12. 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 9/93:29 pmJFK - ORD
Nonstop3h 08mDelta
Tue 9/167:00 amORD - JFK
Nonstop2h 22mDelta
Deal found 8/12$155

Cheapflights Fare Finder

 
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 August 14, 2025.
Use the filters below to find and compare flights from New York John F Kennedy Intl Airport to Chicago that are best for you.

Fly from

John F Kennedy Intl

Fly to

Chicago

Route

Depart

Return

Price

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Wed 10/1

9:00 am-3:58 pm

1 stop7h 58m

Chicago Midway

Fri 10/3

5:15 pm-1:08 am

1 stop6h 53m

$147

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Fri 11/7

10:00 am-6:39 pm

1 stop9h 39m

Chicago Midway

Mon 11/10

1:37 pm-12:33 am

1 stop9h 56m

$148

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Wed 10/22

6:20 am-1:38 pm

1 stop8h 18m

Chicago Midway

Sun 10/26

9:26 pm-7:28 am

1 stop9h 02m

$148

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Sat 9/6

1:01 pm-11:17 pm

1 stop11h 16m

Chicago Midway

Mon 9/8

5:15 pm-1:08 am

1 stop6h 53m

$148

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Wed 9/10

6:15 am-3:58 pm

1 stop10h 43m

Chicago Midway

Thu 9/11

4:56 pm-1:08 am

1 stop7h 12m

$148

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Tue 9/9

9:00 am-3:58 pm

1 stop7h 58m

Chicago Midway

Fri 9/12

5:15 pm-1:08 am

1 stop6h 53m

$148

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Thu 9/18

6:15 am-3:58 pm

1 stop10h 43m

Chicago Midway

Mon 9/22

5:15 pm-1:08 am

1 stop6h 53m

$148

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Tue 11/11

6:25 am-11:38 am

1 stop6h 13m

Chicago Midway

Sat 11/15

1:37 pm-12:33 am

1 stop9h 56m

$148

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Thu 10/2

6:15 am-3:58 pm

1 stop10h 43m

Chicago Midway

Sun 10/5

4:56 pm-1:08 am

1 stop7h 12m

$148

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Fri 10/3

9:00 am-4:00 pm

1 stop8h 00m

Chicago Midway

Sun 10/5

4:56 pm-1:08 am

1 stop7h 12m

$148

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/14

Showing 1-10 of 39 results
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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.

Cheapflights Insights

Everything you need to know about your flight from New York John F Kennedy Intl Airport to Chicago

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 August 8, 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 August 14, 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 at noon tend to be the most expensive. A flight in the evening could potentially save you up to 36% 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 Wednesday evenings when fares are most often at their lowest. Tuesday at noon 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 August 14, 2025.

The most flights from JFK to CHI are scheduled on a Wednesday (53 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (35 on average).

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 August 14, 2025.
Read reviews from past customers who have flown Delta, American Airlines, and JetBlue from New York John F Kennedy Intl Airport to Chicago. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,980 reviews

Overall

8.0

Crew

8.5

Food

7.3

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kymberlee,Oct 2024

JFK - ATL

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.
Delta
8.0
Very good
7,980 reviews
Delta
8.0
Very good
7,980 reviews

Overall

8.0

Crew

8.5

Food

7.3

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kymberlee,Oct 2024

JFK - ATL

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,980 reviews

Overall

8.0

Crew

8.5

Food

7.3

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kymberlee,Oct 2024

JFK - ATL

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.
JetBlue
7.2
Good
2,913 reviews
Delta
8.0
Very good
7,980 reviews

Overall

8.0

Crew

8.5

Food

7.3

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kymberlee,Oct 2024

JFK - ATL

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.
Spirit Airlines
6.3
Okay
8,046 reviews
Delta
8.0
Very good
7,980 reviews

Overall

8.0

Crew

8.5

Food

7.3

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kymberlee,Oct 2024

JFK - ATL

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.
Frontier
5.8
Fair
3,219 reviews
Delta
8.0
Very good
7,980 reviews

Overall

8.0

Crew

8.5

Food

7.3

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kymberlee,Oct 2024

JFK - ATL

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.

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, JetBlue ($83), Frontier ($83), and Spirit Airlines ($96) offers the cheapest pricing from New York John F Kennedy Intl Airport to Chicago. These flights start at 64% 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 ($77), Delta ($78), and American Airlines ($80).

  • 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: Cathay Pacific (100%), China Airlines (87%), Iberia( 87%).

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

    On average you can expect to pay $505 for a flight from New York John F Kennedy Intl Airport to Chicago. The cheapest flight overall is $84 while the most popular route, (New York John F Kennedy Intl - Chicago O'Hare Intl) is currently priced at $73.

  • 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 Chicago?

Book flights to Chicago if you plan to visit one of these locations
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Lansing
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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
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John F Kennedy Intl to Evansville flights
Stewart to Rockford flights
LaGuardia to Bloomington flights
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Newark to Quincy flights
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Newark to Marion flights
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John F Kennedy Intl to Dubuque flights
Newark to Dubuque flights

Top 6 airlines flying from John F Kennedy Intl to Chicago

Discover the top 6 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 August 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$83Average$229FlexibilityNo cancel feeOn-time62%
FrontierCheapest$83Average$200FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$96Average$298FlexibilityNo cancel feeOn-time65%
DeltaCheapest$121Average$350FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$138Average$267FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$217Average$281FlexibilityNo cancel feeOn-time69%

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