Chicago

$61+ 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 8/24. Fares are subject to change and may not be available on all flights or dates of travel.
NYC — CHI
jun. 17 — jun. 241
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Cheapflights Tip: The best prices from New York to Chicago are usually found in September or January, booked 35 days in advance, depart on a Wednesday or Thursday and return on a Thursday

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 junio 12, 2025.

Round-trip from

$117
(Kiwi.com)

One-way from

$61
(CheapOair)

Popular in

December

Cheapest in

September

Average price

$268

Good round-trip deal

$203 or less

Good one-way deal

$120 or less
From New York (NYC) to Chicago (CHI)
One-way flight from New York (NYC) to Chicago (CHI)
Highest demand for flights based on searches. 2% potential increase in price ($4 potential increase over avg. RT price).
Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
Average for round-trip flights in June 2025
Price to beat on a round-trip flight from New York (NYC) to Chicago (CHI).
Price to beat on a one-way flight from New York (NYC) to Chicago (CHI).

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 junio 12, 2025.

This Kiwi.com deal was found by Cheapflights users on 6/10. 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.
mar. 7/15:00 amEWR - ORD
Nonstop2h 37mSpirit Airlines
sáb. 7/59:28 pmORD - EWR
Nonstop2h 18mSpirit Airlines
Deal found 6/10$117
This Cheapflightsfares deal was found by Cheapflights users on 6/12. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 10/185:35 pmLGA - ORD
Nonstop2h 42mSpirit Airlines
mar. 10/218:12 pmORD - LGA
Nonstop2h 19mSpirit Airlines
Deal found 6/12$135
This JetBlue deal was found by Cheapflights users on 6/10. 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.
mar. 7/158:30 pmJFK - ORD
Nonstop2h 58mJetBlue
sáb. 7/196:16 amORD - JFK
Nonstop2h 13mJetBlue
Deal found 6/10$137
This United Airlines deal was found by Cheapflights users on 6/10. 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.
mar. 7/87:54 pmEWR - ORD
Nonstop2h 42mUnited Airlines
mar. 7/156:00 amORD - EWR
Nonstop2h 13mUnited Airlines
Deal found 6/10$137
This United Airlines deal was found by Cheapflights users on 6/10. 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.
mar. 7/81:17 pmLGA - ORD
Nonstop2h 38mUnited Airlines
jue. 7/108:00 pmORD - LGA
Nonstop2h 22mUnited Airlines
Deal found 6/10$137
This Southwest deal was found by Cheapflights users on 6/10. 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.
jue. 7/109:05 amLGA - MDW
Nonstop2h 25mSouthwest
sáb. 7/127:00 pmMDW - LGA
Nonstop2h 10mSouthwest
Deal found 6/10$137
This Delta deal was found by Cheapflights users on 6/11. 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.
mar. 7/296:00 amLGA - ORD
Nonstop2h 32mDelta
jue. 8/76:00 amORD - LGA
Nonstop2h 12mDelta
Deal found 6/11$140
This American Airlines deal was found by Cheapflights users on 6/12. 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.
vie. 10/317:39 pmLGA - ORD
Nonstop2h 46mAmerican Airlines
dom. 11/25:00 amORD - LGA
Nonstop2h 00mAmerican Airlines
Deal found 6/12$143
This Kiwi.com deal was found by Cheapflights users on 6/10. 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.
mié. 9/106:30 amLGA - ORD
1 stop7h 55mMultiple Airlines
sáb. 9/138:12 pmORD - LGA
Nonstop2h 19mMultiple Airlines
Deal found 6/10$154
This Delta deal was found by Cheapflights users on 6/11. 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.
mié. 8/133:29 pmJFK - ORD
Nonstop3h 08mDelta
sáb. 8/167:00 amORD - JFK
Nonstop2h 23mDelta
Deal found 6/11$157
This Delta deal was found by Cheapflights users on 6/11. 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.
sáb. 9/1312:00 pmEWR - MDW
1 stop7h 07mDelta
mar. 9/165:25 pmMDW - EWR
1 stop6h 30mDelta
Deal found 6/11$157
This American Airlines deal was found by Cheapflights users on 6/12. 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.
vie. 11/77:20 amEWR - ORD
Nonstop2h 45mAmerican Airlines
lun. 11/106:35 pmORD - EWR
Nonstop2h 16mAmerican Airlines
Deal found 6/12$160

Cheapflights Fare Finder

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 junio 12, 2025.
Use the filters below to find and compare flights from New York to Chicago that are best for you.

Fly from

New York

Fly to

Chicago

Route

Depart

Return

Price

NewarkChicago

EWR - ORD

EWRORD

Newark

mar. 7/1

5:00 am-6:37 am

Nonstop2h 37m

Chicago O'Hare Intl

sáb. 7/5

9:28 pm-12:46 am

Nonstop2h 18m

$117

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

sáb. 10/18

5:35 pm-7:17 pm

Nonstop2h 42m

Chicago O'Hare Intl

mar. 10/21

8:12 pm-11:31 pm

Nonstop2h 19m

$135

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

mar. 7/15

8:30 pm-10:28 pm

Nonstop2h 58m

Chicago O'Hare Intl

mié. 7/23

6:16 am-9:29 am

Nonstop2h 13m

$137

NewarkChicago

EWR - ORD

EWRORD

Newark

mar. 7/8

7:54 pm-9:36 pm

Nonstop2h 42m

Chicago O'Hare Intl

mar. 7/15

6:00 am-9:13 am

Nonstop2h 13m

$137

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

mar. 7/8

8:35 pm-10:27 pm

Nonstop2h 52m

Chicago O'Hare Intl

mar. 7/15

6:59 pm-10:30 pm

Nonstop2h 31m

$137

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

jue. 7/10

9:05 am-10:30 am

Nonstop2h 25m

Chicago Midway

sáb. 7/12

7:00 pm-10:10 pm

Nonstop2h 10m

$137

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

vie. 10/31

7:39 pm-9:25 pm

Nonstop2h 46m

Chicago O'Hare Intl

lun. 11/3

6:00 am-9:00 am

Nonstop2h 00m

$143

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

sáb. 7/12

6:05 am-7:44 am

Nonstop2h 39m

Chicago O'Hare Intl

sáb. 7/19

5:56 pm-11:39 pm

1 stop4h 43m

$152

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

mié. 9/10

6:30 am-1:25 pm

1 stop7h 55m

Chicago O'Hare Intl

sáb. 9/13

8:12 pm-11:31 pm

Nonstop2h 19m

$154

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

mié. 8/13

3:29 pm-5:37 pm

Nonstop3h 08m

Chicago O'Hare Intl

sáb. 8/16

7:00 am-10:23 am

Nonstop2h 23m

$157

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

Showing 1-10 of 60 results
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The best insider tips for New York to Chicago flights

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.
Cheapflights partnered with top experts to bring you the best recommendations for your New York to Chicago trip
Airlines
Spirit Airlines

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


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

United Airlines

United's Economy Plus offers extra legroom and priority boarding, ideal for business travelers.


United's Polaris Lounges in Chicago offer showers and dining, perfect for premium travelers.

Southwest

Southwest's free checked bags policy includes two bags, great for budget-conscious travelers.


Southwest offers free in-flight entertainment streamed to your device, perfect for leisure travelers.

Airports
EWR

EWR's security lines vary greatly; check live wait times and arrive at least two hours early to avoid delays.

Read more about EWRby Brandon Schultz
LGA

LGA's security lines are efficient, rarely exceeding 15 minutes. Terminal A may have longer waits, but 15 minutes is typically the max.

Read more about LGAby Brandon Schultz
ORD

ORD's 'L' train offers a reliable way to reach downtown Chicago, avoiding traffic delays common with taxis or rideshares.

Read more about ORDby Ramsey Qubein
MDW

The Orange Line train is the easiest and cheapest way to reach downtown Chicago from MDW, taking less than 30 minutes.

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
Harriet Baskas

Harriet Baskas

Expert on United Airlines

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
Marisa Garcia

Marisa Garcia

Expert on Southwest

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
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 Schultz is an award-winning food and travel writer based in New York City. His work has appeared in Forbes, AAA, Thrillist, Travel + Leisure, and The Daily Meal, among many others, and he is the author of 6 books, including 3 cookbooks.

Read more

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.

Cheapflights Insights

Everything you need to know about your flight from New York to Chicago

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 June 9, 2025.

To ensure you get the cheapest price possible for a flight from New York to Chicago, you should look to book at least 35 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 $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 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 junio 12, 2025.

It’s typically best to fly out from New York to Chicago in the evening. Doing so could potentially save you 30% 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 Tuesday evenings when fares are most often at their lowest. Sunday at noon 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 junio 12, 2025.

The most flights from NYC to CHI are scheduled on a Thursday (188 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (74 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 junio 12, 2025.
Get a feel of what it's like to fly with Alaska Airlines, Southwest and Delta 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.

Food

7.1

Entertainment

7.1

Boarding

8.1

Overall

8.0

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

Food

7.1

Entertainment

7.1

Boarding

8.1

Overall

8.0

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

Food

7.1

Entertainment

7.1

Boarding

8.1

Overall

8.0

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
8.0
Very good

Food

7.1

Entertainment

7.1

Boarding

8.1

Overall

8.0

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

Food

7.1

Entertainment

7.1

Boarding

8.1

Overall

8.0

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

Food

7.1

Entertainment

7.1

Boarding

8.1

Overall

8.0

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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, Spirit Airlines ($117), JetBlue ($137), and United Airlines ($137) offers the cheapest pricing from New York to Chicago. Spirit Airlines is priced at 48% 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 Spirit Airlines, which is currently one of the cheapest options available, starting at $61. United Airlines flights start at $69 while deals on American Airlines start at $73 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 Qatar Airways (85%), Etihad Airways (85%) or China Airlines (84%) 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 $606 for a flight from New York to Chicago. The cheapest flight overall is $69 while the most popular route, (New York John F Kennedy Intl - Chicago O'Hare Intl) is currently priced at $97.

  • 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 $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 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

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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 junio 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$66Average$154FlexibilityNo cancel feeOn-time65%
DeltaCheapest$68Average$328FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$84Average$227FlexibilityNo cancel feeOn-time62%
FrontierCheapest$98Average$280FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$137Average$264FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$147Average$277FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$152Average$252FlexibilityNo cancel feeOn-time63%

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