Cheap flights from New York to Chicago from £52

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 15/2. Fares are subject to change and may not be available on all flights or dates of travel.
NYC — CHI
14 Nov — 21 Nov1
1 adult
1 adult, Economy

Cheapflights Tip: The best prices from New York to Chicago are usually found in January or February, booked 64 days in advance, depart on a Tuesday or Monday 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 15 October 2025.

Round-trip from

£89

One-way from

£52

Popular in

August

Cheapest in

January

Average price

£180

Good round-trip deal

£134 or less

Good one-way deal

£60 or less
Spirit Airlines
  • Spirit Airlines
  • 13/11-16/11
  • Nonstop
  • 4h 43m total
  • New York to Chicago
American Airlines
  • American Airlines
  • 15/2
  • Nonstop
  • 2h 46m total
  • New York to Chicago
Highest demand for flights based on searches. 7% potential increase in price (£10 potential increase over avg. return price).
Cheapest flight prices on average. 1% potential price decrease (£3 potential savings vs. average return price).
Average for round-trip flights in October 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

Enter your travel dates to find the best prices.

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 15 October 2025.

Tue 28/1011:59LGA - ORD
1 stop14h 04mSpirit Airlines
Thu 30/1011:55ORD - LGA
1 stop10h 30mSpirit Airlines
Deal found 14/10£89
Sat 1/1108:29LGA - ORD
Nonstop2h 44mSpirit Airlines
Sat 1/1111:55ORD - LGA
1 stop10h 30mSpirit Airlines
Deal found 13/10£91
Thu 13/1111:00JFK - ORD
Nonstop2h 45mFrontier
Sun 16/1105:25ORD - JFK
1 stop28h 04mFrontier
Deal found 13/10£92
Wed 29/1011:59LGA - ORD
1 stop14h 04mSpirit Airlines
Thu 30/1005:05ORD - LGA
1 stop9h 54mSpirit Airlines
Deal found 13/10£93
Thu 6/1116:59LGA - ORD
Nonstop2h 35mSpirit Airlines
Mon 10/1115:26ORD - LGA
1 stop17h 34mSpirit Airlines
Deal found 14/10£95
Fri 14/1110:59LGA - ORD
1 stop10h 28mSpirit Airlines
Mon 17/1119:34ORD - LGA
Nonstop2h 08mSpirit Airlines
Deal found 13/10£98
Sat 15/1108:59LGA - ORD
Nonstop2h 31mSpirit Airlines
Sun 16/1119:34ORD - LGA
Nonstop2h 08mSpirit Airlines
Deal found 14/10£99
Sat 1/1111:00JFK - ORD
Nonstop2h 45mFrontier
Sat 1/1117:45ORD - JFK
1 stop5h 48mFrontier
Deal found 12/10£100
Fri 31/1009:59LGA - ORD
1 stop12h 34mSpirit Airlines
Mon 3/1105:10ORD - LGA
1 stop12h 50mSpirit Airlines
Deal found 14/10£101
Wed 22/1015:29LGA - ORD
Nonstop2h 44mSpirit Airlines
Sat 25/1011:12ORD - LGA
Nonstop1h 55mSpirit Airlines
Deal found 13/10£102
Sat 1/1118:45JFK - ORD
Nonstop2h 52mJetBlue
Mon 3/1106:45ORD - JFK
Nonstop2h 14mJetBlue
Deal found 13/10£103
Sat 1/1116:30LGA - ORD
Nonstop2h 42mUnited Airlines
Tue 4/1118:30ORD - LGA
Nonstop2h 16mUnited Airlines
Deal found 14/10£103

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 15 October 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

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Thu 13/11

16:59-18:34

Nonstop2h 35m

Chicago O'Hare Intl

Sun 16/11

19:34-22:42

Nonstop2h 08m

£89

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Sat 1/11

08:29-10:13

Nonstop2h 44m

Chicago O'Hare Intl

Sat 1/11

11:55-23:25

1 stop10h 30m

£91

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Tue 11/11

06:15-07:57

Nonstop2h 42m

Chicago O'Hare Intl

Tue 18/11

14:00-17:07

Nonstop2h 07m

£103

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Fri 21/11

07:15-08:57

Nonstop2h 42m

Chicago O'Hare Intl

Mon 24/11

18:30-21:46

Nonstop2h 16m

£104

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Sat 25/10

08:25-10:02

Nonstop2h 37m

Chicago O'Hare Intl

Tue 28/10

14:00-17:07

Nonstop2h 07m

£104

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Wed 19/11

21:15-22:57

Nonstop2h 42m

Chicago O'Hare Intl

Fri 28/11

20:00-23:16

Nonstop2h 16m

£104

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Thu 11/12

09:15-10:57

Nonstop2h 42m

Chicago O'Hare Intl

Sun 14/12

07:00-10:07

Nonstop2h 07m

£104

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Fri 14/11

21:15-22:57

Nonstop2h 42m

Chicago O'Hare Intl

Sun 16/11

06:00-09:07

Nonstop2h 07m

£104

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Sun 2/11

05:15-06:57

Nonstop2h 42m

Chicago O'Hare Intl

Sun 9/11

06:00-09:07

Nonstop2h 07m

£111

NewarkChicago

EWR - ORD

EWRORD

Newark

Sat 25/10

09:15-10:53

Nonstop2h 38m

Chicago O'Hare Intl

Sun 26/10

06:02-09:09

Nonstop2h 07m

£114

Flights are sorted by cheapest return flights first.

Deals found on 14/10

Showing 1-10 of 59 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 10 October 2025.

To ensure you get the cheapest price possible for a flight from New York to Chicago, you should look to book at least 64 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, May is the cheapest month in which you can book a flight from New York to Chicago (average of £41). Flying from New York to Chicago in July is currently the most expensive (average of £95). 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 15 October 2025.

It’s optimal to fly from New York to Chicago in the evening. By choosing this option you can save up to 34% 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 12 October 2025.

Travellers seeking maximum savings on their New York to Chicago flight should consider departing on Monday at midday when fares are most often at their lowest. Sunday 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 15 October 2025.

The most flights from NYC to CHI are scheduled on a Monday (187 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (86 on average).

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.

Atlanta (ATL) – chosen by Cheapflights users on 67% of one-stop itineraries from New York to Chicago on Cheapflights.

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.

Tampa (TPA) is the most affordable one-stop option, with an average return flight price of £95.

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.

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

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.

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

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 15 October 2025.
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.

Entertainment

7.5

Boarding

8.1

Crew

8.6

Overall

8.0

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Entertainment

7.5

Boarding

8.1

Crew

8.6

Overall

8.0

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
8.0
Very Good

Entertainment

7.5

Boarding

8.1

Crew

8.6

Overall

8.0

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Entertainment

7.5

Boarding

8.1

Crew

8.6

Overall

8.0

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Entertainment

7.5

Boarding

8.1

Crew

8.6

Overall

8.0

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Entertainment

7.5

Boarding

8.1

Crew

8.6

Overall

8.0

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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?

    Departing from New York to Chicago will take you 2h 35m. New York and Chicago are separated by a distance of 731 mi. Generally, flights for this route are direct.

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

    According to our current data, Spirit Airlines (£86), offers the cheapest pricing from New York to Chicago. Spirit Airlines is priced at 52% 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?

    £52 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 £52 and £61, respectively.

  • 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 Hawaiian Airlines (96%), LATAM Airlines (94%) or China Airlines (92%) 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 £59. On average you can expect to pay £151. The most popular route, (New York John F Kennedy Intl - Chicago O'Hare Intl), can usually be booked for £74.

  • 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, May is the cheapest month in which you can book a flight from New York to Chicago (average of £41). Flying from New York to Chicago in July is currently the most expensive (average of £95). 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.

Top airline flying from New York to Chicago

Discover the top airline 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 15 October 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest£86Average£93FlexibilityNo cancel feeOn-time65%
Search Spirit Airlines flights

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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.

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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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