Chicago

$71+ Cheap flights from New York, NY (NYC) 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 1/17. Fares are subject to change and may not be available on all flights or dates of travel.
NYC — CHI
Dec 29 — Jan 51
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Find cheap flights from New York to Chicago with Cheapflights

1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”
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The best prices from New York to Chicago are usually found in September or January, booked 50 days in advance, depart on a Tuesday or Wednesday and return on a Tuesday

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 (NYC) 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 24, 2024.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$129
(Mytrip)

One-way from

$71
(Frontier)

Popular in

December

Cheapest in

September

Average price

$303
Provider with most accurate pricing for New York (NYC)-Chicago (CHI) flight deals.
Provider most trusted by Cheapflights users for New York (NYC)-Chicago (CHI) flights.
From New York (NYC) to Chicago (CHI)
One-way flight from New York (NYC) to Chicago (CHI)
High demand for flights, 6% potential price rise
Best time to find cheap flights, 3% potential price drop
Average for round-trip flights in December 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 December 24, 2024.

This FlightHub deal was found by Cheapflights users on 12/23. 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.
Tue 12/319:05 pmLGA - ORD
Nonstop2h 38mSpirit Airlines
Sat 1/44:45 pmORD - LGA
Nonstop2h 15mSpirit Airlines
Deal found 12/23$129
This FlightHub deal was found by Cheapflights users on 12/23. 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.
Mon 12/305:35 pmEWR - ORD
Nonstop2h 44mSpirit Airlines
Fri 1/31:24 pmORD - EWR
Nonstop2h 16mSpirit Airlines
Deal found 12/23$156
This Booking.com deal was found by Cheapflights users on 12/23. 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.
Sat 12/288:35 amLGA - ORD
Nonstop2h 32mMultiple Airlines
Tue 1/73:00 pmORD - LGA
1 stop6h 00mMultiple Airlines
Deal found 12/23$209
This Southwest deal was found by Cheapflights users on 12/22. 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.
Tue 12/316:55 pmLGA - MDW
Nonstop2h 30mSouthwest
Mon 1/61:10 pmMDW - LGA
Nonstop2h 00mSouthwest
Deal found 12/22$223
This Delta deal was found by Cheapflights users on 12/22. 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 12/315:45 pmJFK - ORD
1 stop6h 07mDelta
Mon 1/66:30 pmORD - JFK
Nonstop2h 36mDelta
Deal found 12/22$259
This American Airlines deal was found by Cheapflights users on 12/24. 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 12/319:57 amEWR - ORD
1 stop6h 54mAmerican Airlines
Sat 1/46:45 pmORD - EWR
Nonstop2h 22mAmerican Airlines
Deal found 12/24$259
This United Airlines deal was found by Cheapflights users on 12/23. 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.
Mon 12/307:05 amEWR - ORD
Nonstop2h 44mUnited Airlines
Fri 1/39:45 pmORD - EWR
Nonstop2h 12mUnited Airlines
Deal found 12/23$266
This American Airlines deal was found by Cheapflights users on 12/22. 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 12/319:00 amJFK - ORD
Nonstop2h 46mAmerican Airlines
Mon 1/63:59 pmORD - JFK
Nonstop2h 17mAmerican Airlines
Deal found 12/22$272
This CheapOair deal was found by Cheapflights users on 12/22. 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.
Tue 12/315:29 pmLGA - MDW
1 stop15h 52mFrontier
Sun 1/58:00 amMDW - LGA
1 stop13h 00mFrontier
Deal found 12/22$283
This Frontier deal was found by Cheapflights users on 12/23. 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.
Thu 12/2612:29 pmLGA - ORD
1 stop9h 21mFrontier
Tue 1/73:00 pmORD - LGA
1 stop6h 00mFrontier
Deal found 12/23$294
This Delta deal was found by Cheapflights users on 12/22. 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 12/3112:00 pmJFK - MDW
1 stop6h 11mDelta
Mon 1/66:28 pmMDW - JFK
1 stop3h 46mDelta
Deal found 12/22$298
This American Airlines deal was found by Cheapflights users on 12/22. 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.
Wed 12/257:30 amLGA - ORD
Nonstop2h 33mAmerican Airlines
Wed 12/2510:05 amORD - LGA
1 stop4h 02mAmerican Airlines
Deal found 12/22$322

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 24, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Tue 1/21

9:15 pm-10:55 pm

Nonstop2h 40m

Chicago O'Hare Intl

Fri 1/24

10:59 am-4:00 pm

1 stop28h 01m

$129

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Mon 2/3

11:04 am-10:16 pm

1 stop12h 12m

Chicago O'Hare Intl

Fri 2/7

10:02 pm-1:59 pm

1 stop14h 57m

$130

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Thu 1/30

11:04 am-12:09 pm

1 stop26h 05m

Chicago Midway

Sun 2/2

8:45 am-10:05 am

1 stop24h 20m

$130

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Sat 1/11

5:00 pm-9:55 am

1 stop17h 55m

Chicago Midway

Mon 1/13

6:15 am-3:10 pm

1 stop7h 55m

$130

NewarkChicago

EWR - ORD

EWRORD

Newark

Mon 1/6

5:35 pm-7:19 pm

Nonstop2h 44m

Chicago O'Hare Intl

Wed 1/8

12:42 pm-9:10 pm

1 stop7h 28m

$134

NewarkChicago

EWR - ORD

EWRORD

Newark

Tue 1/7

5:35 pm-7:19 pm

Nonstop2h 44m

Chicago O'Hare Intl

Sun 1/12

5:50 am-9:06 am

Nonstop2h 16m

$135

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Mon 1/20

10:59 am-12:39 pm

Nonstop2h 40m

Chicago O'Hare Intl

Thu 1/23

7:00 am-10:04 am

Nonstop2h 04m

$136

NewarkChicago

EWR - ORD

EWRORD

Newark

Wed 1/22

3:00 pm-4:40 pm

Nonstop2h 40m

Chicago O'Hare Intl

Wed 1/29

8:40 am-11:56 am

Nonstop2h 16m

$140

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Sun 1/19

10:50 pm-7:43 am

1 stop9h 53m

Chicago O'Hare Intl

Fri 1/24

10:02 pm-4:00 pm

1 stop16h 58m

$140

NewarkChicago

EWR - ORD

EWRORD

Newark

Tue 1/21

1:07 pm-2:48 pm

Nonstop2h 41m

Chicago O'Hare Intl

Fri 1/24

11:51 am-3:09 pm

Nonstop2h 18m

$143

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/23

Showing 1-10 of 60 results
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Compare providers for flights from New York 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 New York to Chicago in December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy3 starsTrust Score*1 star
CheapOairPrice Accuracy2 starsTrust Score*2 stars
PricelinePrice Accuracy2 starsTrust Score*3 stars
FareScanPrice Accuracy3 starsTrust Score*1 star
Kiwi.comPrice Accuracy3 starsTrust Score*3 stars
MytripPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy3 starsTrust 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-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-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from New York-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on New York-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-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

The best insider tips for New York to Chicago flights

Find out what our experts recommend to make the most of your New York to Chicago trip
Airlines
Spirit Airlines

Spirit's self-service bag drop saves time; print your boarding pass to avoid extra fees.


Spirit's Big Front Seats offer 11 inches extra legroom, ideal for short flights.

American Airlines

American's Main Cabin Extra offers more legroom, enhancing comfort on short flights.


American Airlines' Admirals Club Lounges provide a quiet space to relax or work.

United Airlines

United's Economy Plus offers extra legroom, ideal for added comfort.


United's MileagePlus program allows pooling miles, useful for family travel.

Delta

Delta's free Wi-Fi for SkyMiles members enhances productivity on flights.


Delta's Comfort Plus offers extra legroom and early boarding.

Read more about Deltaby Harriet Baskas
Airports
EWR

EWR's security lines can be unpredictable; arrive at least two hours before your flight.

Read more about EWRby Brandon Schultz
LGA

LGA offers free Wi-Fi throughout the airport, ensuring connectivity from check-in through boarding.

Read more about LGAby Brandon Schultz
JFK

For a quick trip to JFK, consider the Long Island Railroad from Penn Station, taking about 20-25 minutes.

Read more about JFKby Chris Dong
ORD

From ORD, the 'L' train is a reliable option to reach downtown Chicago in about 45 minutes.

Read more about ORDby Ramsey Qubein
MDW

The Orange Line connects MDW to downtown Chicago in under 30 minutes, offering a convenient transit option.

Read more about MDWby Ramsey Qubein
Our travel experts
Daniel Scheffler

Daniel Scheffler

Expert on Spirit Airlines

Daniel Scheffler

Daniel Scheffler

Daniel Scheffler is a travel writer, podcaster, and producer. Born in Africa, bred in Europe and now living in America he has traveled to 140 countries (and all 50 U.S. states). Plus he has stayed at over 2500 hotels across the globe. His original shows Everywhere and Without Maps (available on Spotify) showcase his beliefs, travel is about humanity and sharing that beauty. And thus it reminds you that you shouldn’t believe everything you think.

Read more
Marisa Garcia

Marisa Garcia

Expert on American Airlines

Marisa Garcia

Marisa Garcia

Marisa knows planes inside and out, spending 16 years working on aircraft in hangars at airports around the world. She is an aviation industry expert, specialized in airline interiors and regulations. Ten years ago, she pivoted to journalism. She shares her insights in leading aviation, travel, and business publications and on her site FlightChic.

Read more
Harriet Baskas

Harriet Baskas

Expert on United Airlines and Delta

Harriet Baskas

Harriet Baskas

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Read more
Ramsey Qubein

Ramsey Qubein

Expert on ORD and MDW

Ramsey Qubein

Ramsey Qubein

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more
Brandon Schultz

Brandon Schultz

Expert on EWR and LGA

Brandon Schultz

Brandon Schultz

Brandon travels every week and makes friends with stray cats wherever he goes. Dogs, too... he once brought one home to the US from the Amalfi Coast. He’s written 6 books, visited 6 continents (still waiting on Antarctica), and would eat ice cream 6 times a day if he could. He lives in Brooklyn, New York, with his partner and three cats.

Read more
Chris Dong

Chris Dong

Expert on JFK

Chris Dong

Chris Dong

Chris is a consumer travel reporter covering aviation, trending travel news, hotels, and loyalty programs—all for leading global publications like Travel + Leisure, The Washington Post, AFAR, and more. In addition to writing, Chris is a video host for Travel + Leisure, giving consumers an inside look at the latest in air travel.

Read more

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.

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.

How far ahead should I book a flight from New York to Chicago?

Use this chart to determine the optimal time to book a round-trip flight from New York to Chicago. Price data was last updated on December 20, 2024.

To ensure you get the cheapest price possible for a flight from New York to Chicago, you should look to book at least 50 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

What is the cheapest month to book a flight from New York to Chicago?

Currently, August is the cheapest month in which you can book a flight from New York to Chicago (average of $245). Flying from 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 NYC 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 24, 2024.

It’s typically best to fly out from New York to Chicago in the evening. Doing so could potentially save you 19% on the flight price compared to flying at noon, which is usually more expensive.

What is the cheapest day to fly from New York to Chicago?

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

Travelers seeking maximum savings on their New York to Chicago flight should consider departing on Saturday evenings 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 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 24, 2024.

The most flights from NYC to CHI are scheduled on a Monday (128 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (68 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 24, 2024.
Get a feel of what it's like to fly with Frontier, Delta and American Airlines 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.
8.1
Very good
4,765 reviews

Boarding

8.2

Overall

8.1

Comfort

8.1

Crew

8.7

Entertainment

7.7

Food

7.2

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.

8.1
Very good
4,765 reviews
8.1
Very good
4,765 reviews

Boarding

8.2

Overall

8.1

Comfort

8.1

Crew

8.7

Entertainment

7.7

Food

7.2

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.

8.0
Very good
9,555 reviews
8.1
Very good
4,765 reviews

Boarding

8.2

Overall

8.1

Comfort

8.1

Crew

8.7

Entertainment

7.7

Food

7.2

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.

8.0
Very good
8,580 reviews
8.1
Very good
4,765 reviews

Boarding

8.2

Overall

8.1

Comfort

8.1

Crew

8.7

Entertainment

7.7

Food

7.2

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.

7.4
Good
3,258 reviews
8.1
Very good
4,765 reviews

Boarding

8.2

Overall

8.1

Comfort

8.1

Crew

8.7

Entertainment

7.7

Food

7.2

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.

7.4
Good
9,009 reviews
8.1
Very good
4,765 reviews

Boarding

8.2

Overall

8.1

Comfort

8.1

Crew

8.7

Entertainment

7.7

Food

7.2

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.

New York to Chicago Travel Guide

Chicago, with its dramatic location along the shores of Lake Michigan, is the professional, business, educational and cultural hub of the Midwest. When in Chicago, you have a wealth of choices, whether you prefer to tour architectural masterpieces, take in the top comedy improv groups in the country, attend a Chicago Cubs game at Wrigley Field, or just get some business done. Not surprisingly, it's easy to find flights between the first and third-largest cities in the United States: New York City and Chicago.

Whether you're traveling for business or vacation, Chicago is a friendly, welcoming town that combines high-end urban style with Midwestern hospitality. Take a cruise down the Chicago River to marvel at the architecture of this city's startling skyscrapers, or head to the suburbs to explore some of Frank Lloyd Wright's greatest designs. The Art Institute of Chicago is home to some of the greatest Impressionist paintings in the world, and the Magnificent Mile along Michigan Avenue satisfies even the most demanding shopper. Finish a day in Chicago with uproarious laughter at one of the many improv performances around town.

Your visit to Chicago can combine business and fun seamlessly. Just remember to bundle up against the wind that sweeps off Lake Michigan during all seasons. To find a cheap flight to Chicago from NYC at the perfect time of day, use our smart search engine.

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.
  • How long is the flight from New York City to Chicago?

    The flight from New York City to Chicago, just over 700 miles, will take you slightly less than two hours. Add to that the time spent getting to and from your gate, which may vary depending on the airport you choose.

  • Which airlines operate flights from New York City to Chicago?

    With two airports to choose from in Chicago and three in the area of New York City, you have a wide variety of airlines to choose from when booking your flight. Check out flights from American, Delta, jetBlue, Spirit, United and Southwest to find the right combination of time and price.

  • How frequent are flights between New York City and Chicago?

    With almost 100 flights running from New York's three airports to Chicago each day, you should be able to find a flight that meets your schedule. Flights begin at 6 a.m. each day, with the last flight departing shortly before midnight.

  • Which airports serve New York City to Chicago?

    You can reach Chicago departing from any of New York's three major airports - JFK International, LaGuardia, and Newark Liberty International Airport. Most Chicago-bound flights head to O'Hare, the second-busiest airport in the country, though a few land at Midway.

  • Which direct flight route between New York City and Chicago is cheapest?

    You'll typically find cheaper flights when departing from LaGuardia than from JFK, though prices do fluctuate seasonally and even daily. Landing at O'Hare in Chicago is typically a cheaper choice than looking for a flight to Midway.

  • How busy are the airports in New York and Chicago?

    Because New York and Chicago are two very large cities in the United States there are several airport options in each city that allow you to make the trip between these cities. Some of the choices when you are leaving from the New York City area include John F. Kennedy International Airport (JFK), Newark International Airport (EWR), and New York La Guardia Airport (LGA) and the choice of which airport to use often comes down to which one is most convenient for you depending on your departure point within the New York City area. In terms of airports that are available to you in Chicago, they include both Chicago O' Hare International Airport (ORD) and Chicago Midway (MDW) both of which offer excellent public transportation options to get from the airport to downtown Chicago after your flight to Chicago from New York.

  • Which airlines offer direct flights from New York to Chicago?

    If the airport you will be using in New York City is New York La Guardia Airport, some of your direct flight options include those aboard United Airlines and American Airlines that both offer nonstop service to the Chicago O' Hare International Airport. If instead, you will be departing from John F. Kennedy International Airport there are nonstop flights available aboard American Airlines, Delta Airlines, and JetBlue to Chicago O' Hare International Airport. When departing from Newark International Airport you can fly directly to Chicago O' Hare International Airport from John F. Kennedy International Airport aboard both United Airlines and American Airlines.

  • What are some of the layover options between New York to Chicago?

    There are also one-stop flights that offer a better value than some of these nonstop flights. Spirit Airlines offers one-stop service that departs from both Newark International Airport (EWR) and New York La Guardia Airport that has a layover at Orlando (MCO) that will add about five hours to your travel time. You can also travel on a one-stop flight that has a layover in Orlando or Frontier Airlines and this trip will add about four hours to your travel time. If you would like to travel to Chicago Midway, you can do so from both Newark International Airport and John F. Kennedy International Airport aboard Delta Airlines with a layover at Detroit Metropolitan Wayne County (DTW).

  • When I am flying from New York to Chicago will I require a visa or a passport?

    Since the cities of both Chicago and New York lie within the United States citizens of the United States do not need a passport or visa to travel to these two cities. Something important to remember on this flight route is that in the very near future airlines will require a REAL ID to make this trip.

  • What are the cheapest airlines flying from New York to Chicago round-trip?

    According to our current data, Frontier ($130), Spirit Airlines ($134), and American Airlines ($140) offers the cheapest pricing from New York to Chicago. Frontier is priced at 43% lower than the current average price of a flight leaving 3 months from now.

  • What are the cheapest airlines to fly from 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 $71. Delta flights start at $73 while deals on JetBlue start at $74 one-way.

  • What are the most popular routes from New York to Chicago?

  • What are the most reliable airlines from New York to Chicago?

    No one likes to see their flight delayed. When booking a flight from New York to Chicago consider choosing China Airlines (97%), Republic Airways (96%) or Kenya Airways (96%) as they are the most reliable in getting you off to your destination on time.

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

    On average you can expect to pay $595 for a flight from New York to Chicago. The cheapest flight overall is $73 while the most popular route, (New York John F Kennedy Intl - Chicago O'Hare Intl) is currently priced at $132.

  • 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 New York to Chicago?

    Currently, August is the cheapest month in which you can book a flight from New York to Chicago (average of $245). Flying from 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 are the most eco-friendly airlines from New York to Chicago?

    When you are traveling to Chicago from New York and you are looking for the most eco-friendly airlines to make the trip, some choices include American Airlines, Delta Air Lines, JetBlue Airlines, and United Airlines. Since 2013 American Airlines has retired and replaced over 600 aircraft with newer generation technologies that on average offer 10 to 15% improvements in their fuel efficiency. JetBlue offers a program to its passengers to allow them to offset the carbon footprint of their flight for about the price of a cup of coffee. Delta Air Lines has set a goal of replacing 10% of its jet fuel with sustainable aviation fuel by the end of 2030.

  • How can I fly more sustainably from New York to Chicago?

    In an effort to utilize sustainable travel methods, travelers have plenty of things they can do on trips to Chicago from New York. Start out at home by packing as little as possible to reduce the weight needed to carry you to your destination to save fuel. When booking your flight look for routes that employ newer advanced aircraft that are more fuel-efficient. As you are considering your ground transportation choices to get you to the airports in New York, think about one of the many light rail services offered by the Metropolitan Transit Authority of New York as this is one of the most fuel-efficient ways to get to the airport. Do the same thing when you arrive in Chicago by taking either the CTA Blue Line or the CTA Orange Line depending on which airport you arrive at in Chicago. During your time in Chicago do your best to shop locally so that the products that you consume during your stay have traveled the shortest distance to get to you, thus reducing their carbon footprint on the environment.

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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.

Top 6 airlines flying from New York to Chicago

Discover the top 6 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 24, 2024.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$68Average$145FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$87Average$244FlexibilityNo cancel feeOn-time62%
DeltaCheapest$105Average$307FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$137Average$271FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$147Average$280FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$148Average$255FlexibilityNo cancel feeOn-time63%
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