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$53+ 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 1/11. Fares are subject to change and may not be available on all flights or dates of travel.
JFK — CHI
Nov 25 — Dec 21
Mon 11/25
Mon 12/2
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 November 20, 2024.

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 November 20, 2024.

This Kiwi.com deal was found by Cheapflights users on 11/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/38:29 pmLGA - ORD
Nonstop2h 37mSpirit Airlines
Wed 12/114:19 pmORD - LGA
Nonstop2h 05mSpirit Airlines
Deal found 11/20$113
This Flightnetwork deal was found by Cheapflights users on 11/20. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/511:19 amJFK - MDW
1 stop25h 22mFrontier
Mon 12/95:01 amMDW - JFK
1 stop28h 15mFrontier
Deal found 11/20$115
This CheapOair deal was found by Cheapflights users on 11/19. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/45:59 pmLGA - ORD
1 stop15h 25mMultiple Airlines
Tue 12/108:02 pmORD - LGA
1 stop13h 58mMultiple Airlines
Deal found 11/19$115
This Mytrip deal was found by Cheapflights users on 11/19. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/55:59 pmLGA - ORD
1 stop16h 55mFrontier
Mon 12/910:59 amORD - LGA
1 stop29h 01mFrontier
Deal found 11/19$116
This Kiwi.com deal was found by Cheapflights users on 11/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/610:55 pmEWR - ORD
Nonstop2h 39mSpirit Airlines
Mon 12/96:42 pmORD - EWR
Nonstop2h 18mSpirit Airlines
Deal found 11/19$117
This Booking.com deal was found by Cheapflights users on 11/19. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/43:00 pmJFK - ORD
1 stop18h 24mFrontier
Mon 12/166:07 pmORD - JFK
1 stop18h 52mFrontier
Deal found 11/19$118
This eDestinos deal was found by Cheapflights users on 11/19. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/510:55 pmEWR - ORD
Nonstop2h 39mMultiple Airlines
Mon 12/93:25 pmORD - EWR
1 stop20h 35mMultiple Airlines
Deal found 11/19$124
This Flightnetwork deal was found by Cheapflights users on 11/19. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/510:59 amLGA - MDW
1 stop7h 19mFrontier
Mon 12/911:33 amMDW - LGA
1 stop28h 27mFrontier
Deal found 11/19$132
This JetBlue deal was found by Cheapflights users on 11/20. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/47:29 amJFK - ORD
Nonstop2h 55mJetBlue
Fri 1/105:05 pmORD - JFK
Nonstop2h 26mJetBlue
Deal found 11/20$147
This United Airlines deal was found by Cheapflights users on 11/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/134:29 pmLGA - ORD
Nonstop2h 39mUnited Airlines
Sat 12/148:00 pmORD - LGA
Nonstop2h 12mUnited Airlines
Deal found 11/20$147
This American Airlines deal was found by Cheapflights users on 11/19. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/79:00 amJFK - ORD
Nonstop2h 58mAmerican Airlines
Tue 12/1011:45 amORD - JFK
Nonstop2h 15mAmerican Airlines
Deal found 11/19$148
This American Airlines deal was found by Cheapflights users on 11/19. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/77:00 amLGA - ORD
Nonstop2h 48mAmerican Airlines
Mon 12/98:25 pmORD - LGA
Nonstop2h 08mAmerican Airlines
Deal found 11/19$148

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 2,629,791 searches. Data last updated November 20, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Tue 12/31

9:05 pm-10:43 pm

Nonstop2h 38m

Chicago O'Hare Intl

Thu 1/2

4:45 pm-8:00 pm

Nonstop2h 15m

$113

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Wed 1/8

3:00 pm-9:29 am

1 stop19h 29m

Chicago O'Hare Intl

Mon 1/13

3:25 pm-10:03 am

1 stop17h 38m

$114

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Sat 1/18

11:04 am-3:21 pm

1 stop29h 17m

Chicago Midway

Mon 1/20

7:15 am-10:05 am

1 stop25h 50m

$114

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Wed 12/4

5:59 pm-8:24 am

1 stop15h 25m

Chicago O'Hare Intl

Tue 1/7

3:00 pm-10:00 pm

1 stop6h 00m

$114

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Tue 1/7

5:30 am-2:36 pm

1 stop10h 06m

Chicago O'Hare Intl

Tue 1/14

3:00 pm-10:00 pm

1 stop6h 00m

$115

NewarkChicago

EWR - ORD

EWRORD

Newark

Mon 1/6

5:35 pm-7:19 pm

Nonstop2h 44m

Chicago O'Hare Intl

Sat 1/11

5:05 am-9:03 am

Nonstop2h 58m

$117

NewarkChicago

EWR - ORD

EWRORD

Newark

Sun 1/12

10:00 pm-7:40 am

1 stop10h 40m

Chicago O'Hare Intl

Wed 1/15

12:42 pm-9:10 pm

1 stop7h 28m

$118

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Tue 2/4

10:59 am-4:16 pm

1 stop6h 17m

Chicago Midway

Fri 2/7

6:40 am-3:10 pm

1 stop7h 30m

$123

NewarkChicago

EWR - ORD

EWRORD

Newark

Wed 2/12

9:15 pm-10:52 pm

Nonstop2h 37m

Chicago O'Hare Intl

Wed 2/19

8:33 am-9:10 pm

1 stop11h 37m

$124

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Tue 1/7

8:55 am-4:14 pm

1 stop8h 19m

Chicago Midway

Thu 1/9

7:30 am-5:00 pm

1 stop8h 30m

$144

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/19

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, September is the cheapest month in which you can book a flight from State of New York to Chicago (average of $232). Flying from State of New York to Chicago in June is currently the most expensive (average of $308). 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 November 20, 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 November 20, 2024.

The most flights from USNY to CHI are scheduled on a Wednesday (40 on average). You will have fewer flight options on Friday, which is when the least amount of flights are scheduled (29 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 November 20, 2024.
Read reviews from past customers who have flown Spirit Airlines, American Airlines and Frontier 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
5,014 reviews

Comfort

8.1

Crew

8.7

Boarding

8.2

Overall

8.1

Food

7.2

Entertainment

7.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Southwest
8.1
Very good
5,014 reviews
Southwest
8.1
Very good
5,014 reviews

Comfort

8.1

Crew

8.7

Boarding

8.2

Overall

8.1

Food

7.2

Entertainment

7.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Delta
8.0
Very good
8,756 reviews
Southwest
8.1
Very good
5,014 reviews

Comfort

8.1

Crew

8.7

Boarding

8.2

Overall

8.1

Food

7.2

Entertainment

7.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Alaska Airlines
8.0
Very good
9,461 reviews
Southwest
8.1
Very good
5,014 reviews

Comfort

8.1

Crew

8.7

Boarding

8.2

Overall

8.1

Food

7.2

Entertainment

7.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Porter Airlines
7.8
Good
288 reviews
Southwest
8.1
Very good
5,014 reviews

Comfort

8.1

Crew

8.7

Boarding

8.2

Overall

8.1

Food

7.2

Entertainment

7.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Air Transat
7.8
Good
389 reviews
Southwest
8.1
Very good
5,014 reviews

Comfort

8.1

Crew

8.7

Boarding

8.2

Overall

8.1

Food

7.2

Entertainment

7.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

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 $53. Frontier flights start at $54 while deals on JetBlue start at $73 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 Malaysia Airlines (96%), China Airlines (95%) and SkyWest 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 $73. While the most popular route (New York John F Kennedy Intl - Chicago O'Hare Intl) can be booked for $128 on average our data indicates $395 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, September is the cheapest month in which you can book a flight from State of New York to Chicago (average of $232). Flying from State of New York to Chicago in June is currently the most expensive (average of $308). 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.

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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 2,629,791 searches. Data last updated November 20, 2024.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$68Average$144FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$87Average$216FlexibilityNo cancel feeOn-time62%
FrontierCheapest$95Average$260FlexibilityNo cancel feeOn-time62%
DeltaCheapest$105Average$350FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$137Average$328FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$142Average$314FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$147Average$294FlexibilityNo cancel feeOn-time63%
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