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$54+ 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 1/23. Fares are subject to change and may not be available on all flights or dates of travel.
JFK — CHI
Jan 1 — Jan 81
Wed 1/1
Wed 1/8
1 adult, Economy
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Cheap flight deals from New York to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from New York (USNY) 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 December 27, 2024.

Round-trip from

$128
(Frontier)

One-way from

$54
(Frontier)
From New York to Chicago (CHI)
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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 December 27, 2024.

This Cheapflightsfares deal was found by Cheapflights users on 12/26. 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 12/319:05 pmLGA - ORD
Nonstop2h 38mSpirit Airlines
Tue 1/711:12 amORD - LGA
Nonstop2h 12mSpirit Airlines
Deal found 12/26$182
This Cheapflightsfares deal was found by Cheapflights users on 12/26. 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 12/315:35 pmEWR - ORD
Nonstop2h 44mSpirit Airlines
Tue 1/71:24 pmORD - EWR
Nonstop2h 16mSpirit Airlines
Deal found 12/26$196
This FlightHub deal was found by Cheapflights users on 12/26. 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.
Fri 12/275:35 pmEWR - ORD
Nonstop2h 44mMultiple Airlines
Wed 1/1512:42 pmORD - EWR
1 stop7h 28mMultiple Airlines
Deal found 12/26$250
This Expedia deal was found by Cheapflights users on 12/27. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/319:05 pmLGA - ORD
Nonstop2h 38mMultiple Airlines
Thu 1/22:19 pmORD - LGA
1 stop8h 25mMultiple Airlines
Deal found 12/27$264
This Mytrip deal was found by Cheapflights users on 12/26. 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.
Tue 12/3111:00 amJFK - ORD
1 stop6h 28mFrontier
Fri 1/3110:59 amORD - JFK
1 stop26h 00mFrontier
Deal found 12/26$271
This American Airlines deal was found by Cheapflights users on 12/26. 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 12/313:54 pmJFK - ORD
Nonstop2h 48mAmerican Airlines
Fri 1/3111:40 amORD - JFK
Nonstop2h 15mAmerican Airlines
Deal found 12/26$292
This American Airlines deal was found by Cheapflights users on 12/26. 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.
Fri 12/276:38 pmROC - ORD
Nonstop2h 11mAmerican Airlines
Thu 1/168:29 amORD - ROC
Nonstop1h 46mAmerican Airlines
Deal found 12/26$304
This Frontier deal was found by Cheapflights users on 12/26. 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.
Mon 12/3012:20 pmLGA - ORD
1 stop10h 52mFrontier
Tue 1/73:00 pmORD - LGA
1 stop6h 00mFrontier
Deal found 12/26$308
This Frontier deal was found by Cheapflights users on 12/26. 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.
Mon 12/3012:20 pmLGA - MDW
1 stop11h 54mFrontier
Thu 1/28:00 amMDW - LGA
1 stop13h 00mFrontier
Deal found 12/26$308
This American Airlines deal was found by Cheapflights users on 12/26. 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.
Fri 12/279:00 pmEWR - ORD
Nonstop2h 40mAmerican Airlines
Wed 1/158:40 amORD - EWR
Nonstop2h 16mAmerican Airlines
Deal found 12/26$320
This Southwest deal was found by Cheapflights users on 12/26. 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.
Fri 12/276:30 amLGA - MDW
Nonstop2h 30mSouthwest
Wed 1/158:05 pmMDW - LGA
Nonstop2h 05mSouthwest
Deal found 12/26$320
This Trip.com deal was found by Cheapflights users on 12/25. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/317:15 amBUF - ORD
1 stop17h 42mFrontier
Wed 1/110:29 amORD - BUF
1 stop22h 03mFrontier
Deal found 12/25$329

Find flights from New York to Chicago within your budget

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 December 27, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Fri 2/7

11:00 am-5:53 pm

1 stop7h 53m

Chicago Midway

Sun 2/9

12:43 pm-6:30 am

1 stop16h 47m

$128

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Sat 2/22

10:59 pm-7:09 am

1 stop9h 10m

Chicago O'Hare Intl

Tue 2/25

2:25 pm-11:00 pm

1 stop7h 35m

$128

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Thu 1/23

10:59 am-6:26 pm

1 stop8h 27m

Chicago Midway

Thu 1/30

7:25 am-5:00 pm

1 stop8h 35m

$128

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Tue 1/28

10:59 am-12:39 pm

Nonstop2h 40m

Chicago O'Hare Intl

Sun 2/2

10:59 am-10:00 am

1 stop22h 01m

$129

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Tue 1/14

11:59 am-11:32 pm

1 stop12h 33m

Chicago O'Hare Intl

Thu 1/16

5:06 pm-8:10 pm

Nonstop2h 04m

$130

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Thu 2/20

11:01 am-10:06 pm

1 stop12h 05m

Chicago O'Hare Intl

Mon 2/24

5:08 am-10:15 am

1 stop28h 07m

$131

NewarkChicago

EWR - ORD

EWRORD

Newark

Fri 1/17

3:49 pm-11:34 pm

1 stop8h 45m

Chicago O'Hare Intl

Mon 1/20

5:50 am-9:06 am

Nonstop2h 16m

$133

NewarkChicago

EWR - ORD

EWRORD

Newark

Sun 2/23

9:29 am-11:16 am

Nonstop2h 47m

Chicago O'Hare Intl

Wed 2/26

8:33 am-9:10 pm

1 stop11h 37m

$136

NewarkChicago

EWR - ORD

EWRORD

Newark

Sat 1/25

6:29 pm-8:13 pm

Nonstop2h 44m

Chicago O'Hare Intl

Wed 1/29

6:20 pm-9:32 pm

Nonstop2h 12m

$139

NewarkChicago

EWR - MDW

EWRMDW

Newark

Fri 1/31

10:00 pm-11:29 pm

1 stop26h 29m

Chicago Midway

Tue 2/4

5:31 pm-9:10 pm

1 stop26h 39m

$141

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/26

Showing 1-10 of 60 results
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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.

Travel insights for flights from New York to Chicago

Get recent, data-driven insights about flights from New York to Chicago including ideal travel times, pricing trends, and more.

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 $317). 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 December 27, 2024.

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.

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 December 27, 2024.

The most flights from USNY to CHI are scheduled on a Thursday (37 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (24 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 December 27, 2024.
Read reviews from past customers who have flown Southwest, American Airlines and JetBlue from New York to Chicago. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,749 reviews

Comfort

8.1

Overall

8.1

Entertainment

7.7

Crew

8.7

Food

7.2

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,749 reviews
Southwest
8.1
Very good
4,749 reviews

Comfort

8.1

Overall

8.1

Entertainment

7.7

Crew

8.7

Food

7.2

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Alaska Airlines
8.0
Very good
9,563 reviews
Southwest
8.1
Very good
4,749 reviews

Comfort

8.1

Overall

8.1

Entertainment

7.7

Crew

8.7

Food

7.2

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,570 reviews
Southwest
8.1
Very good
4,749 reviews

Comfort

8.1

Overall

8.1

Entertainment

7.7

Crew

8.7

Food

7.2

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

JetBlue
7.4
Good
3,240 reviews
Southwest
8.1
Very good
4,749 reviews

Comfort

8.1

Overall

8.1

Entertainment

7.7

Crew

8.7

Food

7.2

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

United Airlines
7.4
Good
9,002 reviews
Southwest
8.1
Very good
4,749 reviews

Comfort

8.1

Overall

8.1

Entertainment

7.7

Crew

8.7

Food

7.2

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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 Frontier, which is currently one of the cheapest options available, starting at $54. American Airlines flights start at $72 while deals on JetBlue 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, 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 China Airlines (97%), Republic Airways (96%) and Kenya Airways (96%).

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

    Looking at all options, your cheapest flight can be booked for $73. While the most popular route (New York John F Kennedy Intl - Chicago O'Hare Intl) can be booked for $124 on average our data indicates $595 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 $317). 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

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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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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 December 27, 2024.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$68Average$145FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$87Average$217FlexibilityNo cancel feeOn-time62%
FrontierCheapest$95Average$260FlexibilityNo cancel feeOn-time62%
DeltaCheapest$105Average$348FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$137Average$328FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$147Average$317FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$148Average$300FlexibilityNo cancel feeOn-time63%
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