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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 12/8. Fares are subject to change and may not be available on all flights or dates of travel.
NYC — CHI
16 Jul — 23 Jul1
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 Sunday 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 11 July 2025.

Round-trip from

£104

One-way from

£51

Popular in

December

Cheapest in

September

Average price

£174

Good round-trip deal

£145 or less

Good one-way deal

£41 or less
United Airlines
  • United Airlines
  • 5/9-7/9
  • 1 total stop
  • 6h 52m total
  • New York to Chicago
United Airlines
  • United Airlines
  • 12/8
  • Nonstop
  • 2h 42m total
  • New York to Chicago
Highest demand for flights based on searches. 1% potential increase in price (£1 potential increase over avg. return price).
Cheapest flight prices on average. 2% potential price decrease (£3 potential savings vs. average return price).
Average for round-trip flights in July 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 11 July 2025.

Fri 5/906:00LGA - ORD
1 stop4h 36mUnited Airlines
Sun 7/906:00ORD - LGA
Nonstop2h 16mUnited Airlines
Deal found 10/7£104
Tue 2/906:00LGA - ORD
Nonstop2h 30mDelta
Tue 9/906:00ORD - LGA
Nonstop2h 10mDelta
Deal found 9/7£104
Thu 23/1006:40LGA - ORD
1 stop8h 20mSouthwest
Sat 25/1013:50ORD - LGA
1 stop8h 25mSouthwest
Deal found 11/7£105
Thu 21/820:30JFK - ORD
Nonstop2h 58mJetBlue
Mon 25/806:15ORD - JFK
Nonstop2h 12mJetBlue
Deal found 10/7£106
Tue 5/821:59EWR - ORD
Nonstop2h 42mUnited Airlines
Tue 19/806:00ORD - EWR
Nonstop2h 15mUnited Airlines
Deal found 10/7£106
Sat 9/819:59EWR - ORD
1 stop12h 05mSpirit Airlines
Sat 16/820:12ORD - EWR
1 stop12h 14mSpirit Airlines
Deal found 10/7£112
Sat 11/1013:01JFK - ORD
1 stop11h 20mFrontier
Wed 15/1018:16ORD - JFK
1 stop12h 12mFrontier
Deal found 11/7£113
Mon 4/819:55LGA - ORD
1 stop14h 00mSpirit Airlines
Wed 20/805:05ORD - LGA
1 stop9h 53mSpirit Airlines
Deal found 11/7£113
Sat 6/916:59EWR - ORD
1 stop4h 24mDelta
Tue 9/907:15ORD - EWR
1 stop3h 48mDelta
Deal found 9/7£116
Thu 11/908:00JFK - ORD
Nonstop2h 56mDelta
Mon 15/907:00ORD - JFK
Nonstop2h 22mDelta
Deal found 11/7£123
Sat 11/1011:00JFK - ORD
Nonstop2h 40mAmerican Airlines
Wed 15/1010:11ORD - JFK
Nonstop2h 19mAmerican Airlines
Deal found 11/7£127
Sat 11/1019:41EWR - ORD
Nonstop2h 44mAmerican Airlines
Wed 15/1007:04ORD - EWR
Nonstop2h 16mAmerican Airlines
Deal found 9/7£127

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 11 July 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

Fri 5/9

06:00-09:36

1 stop4h 36m

Chicago O'Hare Intl

Sun 7/9

06:00-09:16

Nonstop2h 16m

£104

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Tue 2/9

06:00-07:30

Nonstop2h 30m

Chicago O'Hare Intl

Wed 10/9

06:00-09:10

Nonstop2h 10m

£104

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Thu 23/10

06:40-14:00

1 stop8h 20m

Chicago O'Hare Intl

Sat 25/10

13:50-23:15

1 stop8h 25m

£105

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Thu 21/8

20:30-22:28

Nonstop2h 58m

Chicago O'Hare Intl

Mon 25/8

06:15-09:27

Nonstop2h 12m

£106

NewarkChicago

EWR - ORD

EWRORD

Newark

Tue 5/8

21:59-23:41

Nonstop2h 42m

Chicago O'Hare Intl

Tue 19/8

06:00-09:15

Nonstop2h 15m

£106

NewarkChicago

EWR - ORD

EWRORD

Newark

Sat 9/8

19:59-07:04

1 stop12h 05m

Chicago O'Hare Intl

Sat 16/8

20:12-09:26

1 stop12h 14m

£112

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Sat 11/10

13:01-23:21

1 stop11h 20m

Chicago O'Hare Intl

Wed 15/10

18:16-07:28

1 stop12h 12m

£113

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Mon 4/8

19:55-08:55

1 stop14h 00m

Chicago O'Hare Intl

Wed 20/8

05:05-15:58

1 stop9h 53m

£113

NewarkChicago

EWR - ORD

EWRORD

Newark

Sat 6/9

06:00-10:20

1 stop5h 20m

Chicago O'Hare Intl

Sat 6/9

17:45-23:30

1 stop4h 45m

£116

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Thu 11/9

08:00-09:56

Nonstop2h 56m

Chicago O'Hare Intl

Mon 15/9

07:00-10:22

Nonstop2h 22m

£123

Flights are sorted by cheapest return flights first.

Deals found on 9/7

Showing 1-10 of 27 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 27 June 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 11 July 2025.

It’s optimal to fly from New York to Chicago in the evening. By choosing this option you can save up to 48% 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 6 July 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. Saturday 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 11 July 2025.

The most flights from NYC to CHI are scheduled on a Friday (188 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (78 on average).

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

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 11 July 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.

Food

7.0

Comfort

8.0

Overall

8.0

Boarding

8.1

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

Food

7.0

Comfort

8.0

Overall

8.0

Boarding

8.1

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
8.0
Very Good

Food

7.0

Comfort

8.0

Overall

8.0

Boarding

8.1

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

Food

7.0

Comfort

8.0

Overall

8.0

Boarding

8.1

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

Food

7.0

Comfort

8.0

Overall

8.0

Boarding

8.1

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

Food

7.0

Comfort

8.0

Overall

8.0

Boarding

8.1

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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, United Airlines (£104), Delta (£104), and Southwest (£105) offers the cheapest pricing from New York to Chicago. United Airlines is priced at 38% 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 United Airlines. You may also be able to find cheap deals on American Airlines and Spirit Airlines, with prices starting from £54 and £56, 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 Cathay Pacific (100%), China Airlines (84%) or American Airlines (80%) 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 £118. On average you can expect to pay £194. The most popular route, (Newark - Chicago O'Hare Intl), can usually be booked for £132.

  • 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.

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 11 July 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest£44Average£92FlexibilityNo cancel feeOn-time65%
Search Spirit Airlines flights
JetBlueCheapest£50Average£100FlexibilityNo cancel feeOn-time62%
Search JetBlue flights
American AirlinesCheapest£93Average£160FlexibilityNo cancel feeOn-time71%
Search American Airlines flights

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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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