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Cheap flights from New York to Chicago from £42

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 4/10. Fares are subject to change and may not be available on all flights or dates of travel.
NYC — CHI
23 Apr — 30 Apr1
1 adult

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 Wednesday and return on a Friday

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 18 April 2025.

Round-trip from

£95

One-way from

£42

Popular in

December

Cheapest in

September

Average price

£174

Good round-trip deal

£90 or less

Good one-way deal

£67 or less
Spirit Airlines
  • Spirit Airlines
  • 30/5-4/6
  • Nonstop
  • 4h 53m total
  • New York to Chicago
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Spirit Airlines
  • Spirit Airlines
  • 4/10
  • Nonstop
  • 2h 37m total
  • New York to Chicago
Search Deals
Highest demand for flights based on searches. 2% potential increase in price (£4 potential increase over avg. return price).
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Cheapest flight prices on average. 2% potential price decrease (£3 potential savings vs. average return price).
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Average for round-trip flights in April 2025
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Price to beat on a round-trip flight from New York (NYC) to Chicago (CHI).
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Price to beat on a one-way flight from New York (NYC) to Chicago (CHI).
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Find flight deals from New York to Chicago

Cheapest flights from New York to Chicago
Explore the most affordable flight options available from New York to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 18 April 2025.

Fri 30/505:55EWR - ORD
Nonstop2h 32mSpirit Airlines
Wed 4/621:08ORD - EWR
Nonstop2h 21mSpirit Airlines
Deal found 17/4£95
Sun 25/513:20JFK - ORD
Nonstop2h 44mJetBlue
Wed 28/516:03ORD - JFK
Nonstop2h 26mJetBlue
Deal found 17/4£103
Mon 26/506:05LGA - ORD
Nonstop2h 37mDelta
Wed 28/518:55ORD - LGA
Nonstop2h 22mDelta
Deal found 17/4£103
Fri 30/518:30LGA - ORD
Nonstop2h 37mSpirit Airlines
Wed 4/605:51ORD - LGA
Nonstop2h 09mSpirit Airlines
Deal found 17/4£106
Sat 24/518:30EWR - ORD
1 stop5h 47mDelta
Wed 28/515:33ORD - EWR
1 stop6h 55mDelta
Deal found 17/4£119
Wed 28/506:00LGA - ORD
1 stop4h 38mUnited Airlines
Wed 28/518:30ORD - LGA
Nonstop2h 24mUnited Airlines
Deal found 16/4£126
Tue 6/515:48JFK - ORD
Nonstop3h 07mDelta
Tue 20/507:00ORD - JFK
Nonstop2h 25mDelta
Deal found 17/4£131
Wed 30/706:00EWR - ORD
Nonstop2h 38mUnited Airlines
Wed 30/721:24ORD - EWR
Nonstop2h 21mUnited Airlines
Deal found 17/4£134
Tue 13/509:00JFK - ORD
1 stop8h 41mFrontier
Wed 14/511:10ORD - JFK
1 stop12h 25mFrontier
Deal found 17/4£134
Sat 3/507:10EWR - ORD
Nonstop2h 48mAmerican Airlines
Tue 6/519:11ORD - EWR
Nonstop2h 19mAmerican Airlines
Deal found 17/4£134
Tue 13/509:00JFK - ORD
Nonstop3h 09mAmerican Airlines
Wed 14/509:42ORD - JFK
1 stop6h 17mAmerican Airlines
Deal found 17/4£159
Fri 9/507:25LGA - ORD
1 stop10h 20mSouthwest
Sun 11/507:00ORD - LGA
1 stop7h 55mSouthwest
Deal found 17/4£168

Cheapflights Fare Finder

Customise 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 858,174 searches. Data last updated 18 April 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

Fri 30/5

05:55-07:27

Nonstop2h 32m

Chicago O'Hare Intl

Wed 4/6

21:08-00:29

Nonstop2h 21m

£95

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Sun 25/5

13:20-15:04

Nonstop2h 44m

Chicago O'Hare Intl

Wed 28/5

16:03-19:29

Nonstop2h 26m

£103

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Mon 26/5

06:05-07:42

Nonstop2h 37m

Chicago O'Hare Intl

Wed 28/5

18:55-22:17

Nonstop2h 22m

£103

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Fri 30/5

18:30-20:07

Nonstop2h 37m

Chicago O'Hare Intl

Wed 4/6

05:51-09:00

Nonstop2h 09m

£106

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Wed 21/5

06:25-08:00

Nonstop2h 35m

Chicago O'Hare Intl

Tue 27/5

18:30-21:54

Nonstop2h 24m

£116

NewarkChicago

EWR - ORD

EWRORD

Newark

Sat 24/5

18:30-23:17

1 stop5h 47m

Chicago O'Hare Intl

Wed 28/5

15:33-23:28

1 stop6h 55m

£119

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Tue 6/5

15:48-17:55

Nonstop3h 07m

Chicago O'Hare Intl

Tue 20/5

07:00-10:25

Nonstop2h 25m

£131

NewarkChicago

EWR - ORD

EWRORD

Newark

Wed 30/7

06:00-07:38

Nonstop2h 38m

Chicago O'Hare Intl

Wed 30/7

21:24-00:45

Nonstop2h 21m

£134

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Tue 13/5

09:00-16:41

1 stop8h 41m

Chicago O'Hare Intl

Wed 14/5

11:10-00:35

1 stop12h 25m

£134

NewarkChicago

EWR - ORD

EWRORD

Newark

Sat 3/5

07:10-08:58

Nonstop2h 48m

Chicago O'Hare Intl

Tue 6/5

19:11-22:30

Nonstop2h 19m

£134

Flights are sorted by cheapest return flights first.

Deals found on 17/4

Showing 1-10 of 35 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 return 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 return flight from New York to Chicago. Price data was last updated on 11 April 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, 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.

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 18 April 2025.

It’s optimal to fly from New York to Chicago in the evening. By choosing this option you can save up to 45% on the cost of your flight, compared to a flight in the afternoon.

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 30 March 2025.

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. Thursday at midday 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 18 April 2025.

The most flights from NYC to CHI are scheduled on a Thursday (185 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (81 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 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.

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 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).

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 18 April 2025.
Read through reviews of airlines operating flights from New York to Chicago, such as Alaska Airlines, Southwest and Delta. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very Good
9,887 reviews
Check prices

Boarding

8.1

Comfort

7.9

Overall

8.0

Food

7.1

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Alaska Airlines
8.0
Very Good
9,887 reviews
Alaska Airlines
8.0
Very Good
9,887 reviews
Check prices

Boarding

8.1

Comfort

7.9

Overall

8.0

Food

7.1

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Southwest
8.0
Very Good
4,280 reviews
Alaska Airlines
8.0
Very Good
9,887 reviews
Check prices

Boarding

8.1

Comfort

7.9

Overall

8.0

Food

7.1

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Delta
8.0
Very Good
7,917 reviews
Alaska Airlines
8.0
Very Good
9,887 reviews
Check prices

Boarding

8.1

Comfort

7.9

Overall

8.0

Food

7.1

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
United Airlines
7.4
Good
8,667 reviews
Alaska Airlines
8.0
Very Good
9,887 reviews
Check prices

Boarding

8.1

Comfort

7.9

Overall

8.0

Food

7.1

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
JetBlue
7.3
Good
2,928 reviews
Alaska Airlines
8.0
Very Good
9,887 reviews
Check prices

Boarding

8.1

Comfort

7.9

Overall

8.0

Food

7.1

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >

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 flying from New York to Chicago round-trip?

    According to our current data, Spirit Airlines (£95), JetBlue (£103), and Delta (£103) offers the cheapest pricing from New York to Chicago. Spirit Airlines is priced at 44% 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?

    £42 is the cheapest one-way deal found within the past few days, from Spirit Airlines. You may also be able to find cheap deals on JetBlue and United Airlines, with prices starting from £52 and £52, respectively.

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

    Most travelers choose Newark - Chicago O'Hare Intl, New York John F Kennedy Intl - Chicago O'Hare Intl or New York LaGuardia - Chicago O'Hare Intl when deciding on the best route 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 GOL (88%), Kenya Airways (85%) or Republic Airways (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?

    The cheapest flight price from New York to Chicago is £51. On average you can expect to pay £151. The most popular route, (Newark - Chicago O'Hare Intl), can usually be booked for £127.

  • 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 holiday 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, 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.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

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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.
Newark to O'Hare Intl flights
John F Kennedy Intl to O'Hare Intl flights
LaGuardia to O'Hare Intl flights

Top 3 airlines flying from New York to Chicago

Discover the top 3 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 858,174 searches. Data last updated 18 April 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest£45Average£94FlexibilityNo cancel feeOn-time65%
Search Spirit Airlines flights
JetBlueCheapest£47Average£103FlexibilityNo cancel feeOn-time62%
Search JetBlue flights
American AirlinesCheapest£96Average£191FlexibilityNo cancel feeOn-time71%
Search American Airlines flights

Fly with Cheapflights

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

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.

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

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.

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

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.

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

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.

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