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Cheap flights from New York to Chicago from £51

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 24/5. Fares are subject to change and may not be available on all flights or dates of travel.
NYC — CHI
4 May — 11 May1
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 29 April 2025.

Round-trip from

£92

One-way from

£51

Popular in

December

Cheapest in

September

Average price

£177

Good round-trip deal

£53 or less

Good one-way deal

£70 or less
Spirit Airlines
  • Spirit Airlines
  • 4/6-6/6
  • 1 total stop
  • 8h 13m total
  • New York to Chicago
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JetBlue
  • JetBlue
  • 24/5
  • Nonstop
  • 2h 54m total
  • New York to Chicago
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Highest demand for flights based on searches. 2% potential increase in price (£2 potential increase over avg. return price).
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Cheapest flight prices on average. 2% potential price decrease (£4 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 29 April 2025.

Wed 4/605:00EWR - ORD
Nonstop2h 32mSpirit Airlines
Fri 6/614:19ORD - EWR
1 stop5h 41mSpirit Airlines
Deal found 28/4£92
Tue 13/511:00JFK - ORD
Nonstop2h 48mDelta
Wed 21/510:31ORD - JFK
Nonstop2h 19mDelta
Deal found 28/4£110
Sat 24/520:30EWR - ORD
Nonstop2h 42mUnited Airlines
Sun 25/506:00ORD - EWR
Nonstop2h 13mUnited Airlines
Deal found 28/4£110
Mon 19/520:00JFK - ORD
Nonstop2h 54mJetBlue
Tue 27/506:15ORD - JFK
Nonstop2h 15mJetBlue
Deal found 28/4£114
Tue 10/611:55LGA - ORD
1 stop9h 08mSpirit Airlines
Mon 16/605:51ORD - LGA
Nonstop2h 09mSpirit Airlines
Deal found 29/4£115
Tue 20/511:25LGA - ORD
Nonstop2h 41mUnited Airlines
Tue 20/518:30ORD - LGA
Nonstop2h 18mUnited Airlines
Deal found 28/4£117
Wed 18/607:00EWR - ORD
Nonstop2h 53mAmerican Airlines
Wed 23/720:29ORD - EWR
Nonstop2h 30mAmerican Airlines
Deal found 28/4£119
Tue 20/514:45LGA - ORD
Nonstop2h 43mDelta
Wed 21/507:00ORD - LGA
Nonstop2h 12mDelta
Deal found 28/4£126
Wed 16/713:16EWR - ORD
1 stop6h 33mDelta
Sat 19/707:10ORD - EWR
1 stop4h 20mDelta
Deal found 28/4£133
Tue 13/509:00JFK - ORD
1 stop8h 41mFrontier
Wed 14/511:10ORD - JFK
1 stop12h 25mFrontier
Deal found 29/4£148
Wed 18/608:11LGA - ORD
1 stop4h 12mAmerican Airlines
Wed 23/711:35ORD - LGA
Nonstop2h 10mAmerican Airlines
Deal found 28/4£162
Thu 10/707:35LGA - ORD
1 stop8h 25mSouthwest
Sat 12/716:20ORD - LGA
1 stop5h 50mSouthwest
Deal found 29/4£166

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 29 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

Wed 4/6

05:00-06:32

Nonstop2h 32m

Chicago O'Hare Intl

Fri 6/6

14:19-21:00

1 stop5h 41m

£92

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Tue 13/5

11:00-12:48

Nonstop2h 48m

Chicago O'Hare Intl

Wed 21/5

10:31-13:50

Nonstop2h 19m

£110

NewarkChicago

EWR - ORD

EWRORD

Newark

Sat 24/5

20:30-22:12

Nonstop2h 42m

Chicago O'Hare Intl

Sun 25/5

06:00-09:13

Nonstop2h 13m

£110

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Mon 19/5

20:00-21:54

Nonstop2h 54m

Chicago O'Hare Intl

Tue 27/5

06:15-09:30

Nonstop2h 15m

£114

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Tue 10/6

11:55-20:03

1 stop9h 08m

Chicago O'Hare Intl

Mon 16/6

05:51-09:00

Nonstop2h 09m

£115

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Tue 20/5

11:25-13:06

Nonstop2h 41m

Chicago O'Hare Intl

Tue 20/5

18:30-21:48

Nonstop2h 18m

£117

NewarkChicago

EWR - ORD

EWRORD

Newark

Wed 18/6

07:00-08:53

Nonstop2h 53m

Chicago O'Hare Intl

Wed 23/7

20:29-23:59

Nonstop2h 30m

£119

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Tue 20/5

14:45-16:28

Nonstop2h 43m

Chicago O'Hare Intl

Wed 21/5

07:00-10:12

Nonstop2h 12m

£126

NewarkChicago

EWR - ORD

EWRORD

Newark

Wed 16/7

13:16-18:49

1 stop6h 33m

Chicago O'Hare Intl

Sat 19/7

07:10-12:30

1 stop4h 20m

£133

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

£148

Flights are sorted by cheapest return flights first.

Deals found on 28/4

Showing 1-10 of 34 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 25 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 29 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 29 April 2025.

The most flights from NYC to CHI are scheduled on a Tuesday (184 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (48 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 29 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
9,961 reviews
Check prices

Food

7.1

Boarding

8.2

Crew

8.5

Overall

8.0

Entertainment

7.1

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very Good
9,961 reviews
Alaska Airlines
8.0
Very Good
9,961 reviews
Check prices

Food

7.1

Boarding

8.2

Crew

8.5

Overall

8.0

Entertainment

7.1

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Southwest
8.0
Very Good
4,295 reviews
Alaska Airlines
8.0
Very Good
9,961 reviews
Check prices

Food

7.1

Boarding

8.2

Crew

8.5

Overall

8.0

Entertainment

7.1

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very Good
7,929 reviews
Alaska Airlines
8.0
Very Good
9,961 reviews
Check prices

Food

7.1

Boarding

8.2

Crew

8.5

Overall

8.0

Entertainment

7.1

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,696 reviews
Alaska Airlines
8.0
Very Good
9,961 reviews
Check prices

Food

7.1

Boarding

8.2

Crew

8.5

Overall

8.0

Entertainment

7.1

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
JetBlue
7.3
Good
2,922 reviews
Alaska Airlines
8.0
Very Good
9,961 reviews
Check prices

Food

7.1

Boarding

8.2

Crew

8.5

Overall

8.0

Entertainment

7.1

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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 (£92), United Airlines (£110), and JetBlue (£117) offers the cheapest pricing from New York to Chicago. Spirit Airlines is priced at 45% 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?

    £51 is the cheapest one-way deal found within the past few days, from JetBlue. You may also be able to find cheap deals on United Airlines and Spirit Airlines, with prices starting from £51 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 £63. On average you can expect to pay £151. The most popular route, (Newark - Chicago O'Hare Intl), can usually be booked for £67.

  • 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

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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 29 April 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest£44Average£92FlexibilityNo cancel feeOn-time65%
Search Spirit Airlines flights
JetBlueCheapest£51Average£102FlexibilityNo cancel feeOn-time62%
Search JetBlue flights
American AirlinesCheapest£95Average£189FlexibilityNo 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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