Q: How much does it cost for a return flight from New York to Chicago?

Airfare is below average for this route at the moment. New York to Chicago flights typically cost between £142 and £267 in September. The cheapest return flight price found within the last 3 days was £105 on JetBlue (4 Sept-16 Sept).

Question 1

What’s the fastest stopover option from New York to Chicago?

Accepted Answer

Flights via Atlanta (ATL) have the shortest average one-way travel time for one-stop routes: 5h 49m.

Question 2

How much does it cost for a return flight from New York to Chicago?

Accepted Answer

Airfare is below average for this route at the moment.New York to Chicago flights typically cost between £142 and £267 in September.
The cheapest return flight price found within the last 3 days was £105 on JetBlue (4 Sept-16 Sept).

Question 3

What’s the cheapest stopover airport for flights from New York to Chicago?

Accepted Answer

Tampa (TPA) is the most affordable one-stop option, with an average return flight price of £93.

Question 4

Which airport typically offers the quickest stopover for flights from New York to Chicago?

Accepted Answer

Flights via Atlanta (ATL) offer the fastest connection on this route, with an average stopover time of 2h 40m.

Question 5

What’s the top stopover airport for flights from New York to Chicago?

Accepted Answer

Tampa (TPA) – chosen by Cheapflights users on 50% of one-stop itineraries from New York to Chicago on Cheapflights.

Question 6

How long is the flight from New York to Chicago?

Accepted Answer

Departing from New York to Chicago will take you 2h 40m. New York and Chicago are separated by a distance of 738 mi. Both multi-stop and direct flights can be found to your destination and back.

Question 7

What is the cheapest airline to fly from New York to Chicago round-trip?

Accepted Answer

According to our current data, Spirit Airlines (£84), offers the cheapest pricing from New York to Chicago. Spirit Airlines is priced at 51% lower than the current average price of a flight leaving 3 months from now.

Question 8

What are the cheapest airlines to fly from New York to Chicago one-way?

Accepted Answer

£58 is the cheapest one-way deal found within the past few days, from Frontier. You may also be able to find cheap deals on JetBlue and Delta, with prices starting from £58 and £58, respectively.

Question 9

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

Accepted Answer

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.

Question 10

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

Accepted Answer

Currently, January is the cheapest month in which you can book a flight from New York to Chicago (average of £595). Flying from New York to Chicago in July is currently the most expensive (average of £843). 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.

Question 11

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

Accepted Answer

Travellers seeking maximum savings on their New York to Chicago flight should consider departing on Wednesday evenings when fares are most often at their lowest. Saturday at midday flights should be avoided if possible as fares are typically the most expensive at this time.

Question 12

Weekly flight availability from New York to Chicago

Accepted Answer

The most flights from NYC to CHI are scheduled on a Monday (195 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (91 on average).

Question 13

E

Accepted Answer

In terms of precipitation, rainfall in Chicago ranges from 43.0 - 125.0 inches per month. August is typically the wettest month, when rainfall can reach 125.0 mm. January is typically the driest time to visit Chicago when rainfall is around 43.0 mm.

Question 14

E

Accepted Answer

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 23.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around -5.0 C).

Question 15

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

Accepted Answer

Most travelers choose New York John F Kennedy Intl - Chicago O'Hare Intl, Newark - Chicago O'Hare Intl or New York LaGuardia - Chicago O'Hare Intl when deciding on the best route from New York to Chicago.

Question 16

What are the cheapest flights from New York to Chicago?

Accepted Answer

The cheapest flight price from New York to Chicago is £51. On average you can expect to pay £177. The most popular route, (New York John F Kennedy Intl - Chicago O'Hare Intl), can usually be booked for £94.

Question 17

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

Accepted Answer

No one likes to see their flight delayed. When booking a flight from New York to Chicago consider choosing China Airlines (90%), LATAM Airlines (79%) or Iberia (75%) as they are the most reliable in getting you off to your destination on time.

Question 18

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

Accepted Answer

Users have found that flying from New York to Chicago on a Wednesday typically leans towards higher prices. However, this doesn’t mean you still can’t find a deal. Flexibility with other aspects of your flight can still land a great price for your trip.

Question 19

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

Accepted Answer

Users have found that booking a flight from New York to Chicago at least 36 days early can save you up to 97% on average compared to booking a flight this week. If booking 36 days before your flight isn’t an option for you, users have found flights from New York to Chicago for as little as £182 when booking for a departure date within the next two weeks. You can also check prices now. Some users have found airline tickets as low as £290 for flights departing within the next 3 days.

Question 20

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

Accepted Answer

Flights from New York to Chicago lean towards being more expensive in June. Prices are generally better when you fly from New York to Chicago in September, with the cheapest ticket starting at £56.

Question 21

What is the cheapest time of day to fly from NYC to CHI?

Accepted Answer

It’s optimal to fly from New York to Chicago in the evening. By choosing this option you can save up to 39% on the cost of your flight, compared to a flight in the afternoon.

Question 22

Can I find deals for flights from New York to Chicago that include hotel bookings?

Accepted Answer

Yes. In addition to deals on New York to Chicago flights, Cheapflights offers holiday packages that include both flights and hotel.

Question 23

How can I find direct flights from New York to Chicago?

Accepted Answer

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.

Question 24

Can I find deals for business class flights from New York to Chicago?

Accepted Answer

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.

Question 25

How does Cheapflights help users find flights from New York to Chicago?

Accepted Answer

Cheapflights makes it easy to find New York to Chicago flights by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.

Question 26

Why should you use Cheapflights to find cheap flight tickets from New York to Chicago?

Accepted Answer

It’s simple! Cheapflights, which is free to use for everyone, saves millions of users time and money every year by helping them find the cheapest and most suitable flights from New York to Chicago.

Question 27

Can Cheapflights find flights from New York to Chicago with no change fees?

Accepted Answer

Certainly. Search results for flights to Chicago from New York shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.

Question 28

Can Cheapflights notify me if prices for flights from New York to Chicago become cheaper?

Accepted Answer

Of course! You can now track prices for flights from New York to Chicago and get an alert from Cheapflights when they change. Have a valid email address ready and click the bell icon next to the flight deals above to set up your price alerts.

Round-trip from	£105
One-way from	£58
Popular in	June
Cheapest in	September
Average price	£199
Good round-trip deal	£51 or less
Good one-way deal	£51 or less

Cheap flights from New York to Chicago from £58

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 12/9. Fares are subject to change and may not be available on all flights or dates of travel.

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 Tuesday or Saturday and return on a Tuesday

Cheap flight deals from New York to Chicago

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Find flight deals from New York to Chicago

Cheapest flights from New York to ChicagoExplore 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 19 August 2025.

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 19 August 2025.

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

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.

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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 return flight from New York to Chicago. Price data was last updated on 8 August 2025.

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

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 19 August 2025.

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

Use this chart to determine the cheapest time to fly return from New York to Chicago. Price data was last updated on 17 August 2025.

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 19 August 2025.

How much does it cost for a return flight from New York to Chicago?

What’s the top stopover airport for flights from New York to Chicago?

Share of one-stop return flights from New York to Chicago chosen by Cheapflights users in the past 12 months, using the same stopover each way.

What’s the cheapest stopover airport for flights from New York to Chicago?

Average return fare for one-stop flights from New York to Chicago, chosen by Cheapflights users in the past 12 months, with the same stopover each way.

What’s the fastest stopover option from New York to Chicago?

Shortest average travel time for one-stop one-way flights from New York to Chicago, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by stopover airport.

Which airport typically offers the quickest stopover for flights from New York to Chicago?

Average stopover duration for one-stop one-way flights from New York to Chicago, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.

Reviews of airlines servicing Chicago

Read through reviews of airlines operating flights from New York to Chicago, such as Southwest, Delta, andUnited Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.

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 to Chicago?

What is the cheapest airline to fly from New York to Chicago round-trip?

What are the cheapest airlines to fly from New York to Chicago one-way?

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

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

What are the cheapest flights from New York to Chicago?

Can I find deals for flights from New York to Chicago that include hotel bookings?

How can I find direct flights from New York to Chicago?

Can I find deals for business class flights from New York to Chicago?

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

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Alternative routes for New York to Chicago

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Top airline flying from New York to Chicago

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How does Cheapflights help users find flights from New York to Chicago?

Why should you use Cheapflights to find cheap flight tickets from New York to Chicago?

Can Cheapflights find flights from New York to Chicago with no change fees?

Can Cheapflights notify me if prices for flights from New York to Chicago become cheaper?

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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 19 August 2025.