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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 8/5. Fares are subject to change and may not be available on all flights or dates of travel.
NYC — CHI
3 feb — 10 feb1
1 adult

The best prices from New York to Chicago are usually found in September or February, booked 30 days in advance, depart on a Saturday or Tuesday 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 29 gennaio 2025.

Round-trip from

£105

One-way from

£51

Popular in

December

Cheapest in

September

Average price

£158

Good round-trip deal

£119 or less

Good one-way deal

£59 or less
Frontier
  • Frontier
  • 27/2-2/3
  • 2 total stops
  • 36h 30m total
  • New York to Chicago
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Frontier
  • Frontier
  • 8/5
  • 1 total stop
  • 17h 33m total
  • New York to Chicago
Search Deals
Highest demand for flights based on searches. 5% potential increase in price (£8 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 January 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 gennaio 2025.

mar 4/210:59LGA - ORD
Nonstop2h 40mMultiple Airlines
mar 11/214:59ORD - LGA
1 stop6h 01mMultiple Airlines
Deal found 28/1£86
gio 27/211:15JFK - ORD
1 stop25h 55mFrontier
dom 2/322:26ORD - JFK
1 stop10h 35mFrontier
Deal found 28/1£105
ven 7/317:54EWR - ORD
1 stop7h 02mMultiple Airlines
sab 8/314:25ORD - EWR
1 stop5h 44mMultiple Airlines
Deal found 28/1£106
lun 3/208:00JFK - ORD
Nonstop2h 55mDelta
gio 13/212:45ORD - JFK
Nonstop2h 19mDelta
Deal found 29/1£117
lun 3/214:20LGA - ORD
Nonstop2h 49mDelta
mar 4/212:35ORD - LGA
Nonstop2h 16mDelta
Deal found 28/1£117
gio 20/214:55JFK - ORD
Nonstop2h 50mJetBlue
lun 24/217:40ORD - JFK
Nonstop2h 29mJetBlue
Deal found 29/1£117
lun 3/214:50LGA - ORD
1 stop5h 05mUnited Airlines
sab 8/211:00ORD - LGA
Nonstop2h 12mUnited Airlines
Deal found 28/1£126
mar 11/312:43EWR - ORD
1 stop5h 45mDelta
mar 18/306:45ORD - EWR
1 stop4h 22mDelta
Deal found 28/1£128
mar 4/205:45LGA - ORD
2 stops18h 47mSpirit Airlines
mar 11/208:00ORD - LGA
1 stop13h 25mSpirit Airlines
Deal found 28/1£137
mar 15/407:00EWR - ORD
Nonstop2h 40mUnited Airlines
sab 19/406:00ORD - EWR
Nonstop2h 14mUnited Airlines
Deal found 28/1£145
lun 10/218:29EWR - ORD
Nonstop2h 44mAmerican Airlines
mar 11/214:50ORD - EWR
Nonstop2h 08mAmerican Airlines
Deal found 28/1£156
gio 27/307:30LGA - ORD
1 stop8h 30mSouthwest
mar 1/406:15ORD - LGA
1 stop10h 55mSouthwest
Deal found 27/1£158

Find flights from New York to Chicago within your budget

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 gennaio 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

gio 27/2

11:15-12:10

1 stop25h 55m

Chicago O'Hare Intl

dom 2/3

22:26-10:01

1 stop10h 35m

£105

NewarkChicago

EWR - ORD

EWRORD

Newark

ven 7/3

17:54-23:56

1 stop7h 02m

Chicago O'Hare Intl

sab 8/3

14:25-21:09

1 stop5h 44m

£106

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

mar 18/2

07:30-09:18

Nonstop2h 48m

Chicago O'Hare Intl

gio 20/2

06:00-09:25

Nonstop2h 25m

£117

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

gio 20/2

14:55-16:45

Nonstop2h 50m

Chicago O'Hare Intl

lun 24/2

17:40-21:09

Nonstop2h 29m

£117

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

gio 20/2

15:55-17:47

Nonstop2h 52m

Chicago O'Hare Intl

lun 24/2

18:30-22:02

Nonstop2h 32m

£118

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

lun 10/2

19:29-23:15

1 stop4h 46m

Chicago O'Hare Intl

mar 11/2

06:00-09:10

Nonstop2h 10m

£126

NewarkChicago

EWR - ORD

EWRORD

Newark

mar 11/3

12:43-17:28

1 stop5h 45m

Chicago O'Hare Intl

mar 18/3

06:45-12:07

1 stop4h 22m

£128

NewarkChicago

EWR - ORD

EWRORD

Newark

mar 15/4

07:00-08:40

Nonstop2h 40m

Chicago O'Hare Intl

sab 19/4

06:00-09:14

Nonstop2h 14m

£145

NewarkChicago

EWR - ORD

EWRORD

Newark

lun 10/2

18:29-20:13

Nonstop2h 44m

Chicago O'Hare Intl

mar 11/2

14:50-17:58

Nonstop2h 08m

£156

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

gio 27/3

07:30-15:00

1 stop8h 30m

Chicago O'Hare Intl

mar 1/4

06:15-18:10

1 stop10h 55m

£158

Flights are sorted by cheapest return flights first.

Deals found on 28/1

Showing 1-10 of 40 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.

Travel insights for flights from New York to Chicago

Get recent, data-driven insights about flights from New York to Chicago including ideal travel times, pricing trends, and more.

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 24 January 2025.

To ensure you get the cheapest price possible for a flight from New York to Chicago, you should look to book at least 30 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 gennaio 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 26 January 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. Friday evenings 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 gennaio 2025.

The most flights from NYC to CHI are scheduled on a Monday (171 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (39 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 gennaio 2025.
Read through reviews of airlines operating flights from New York to Chicago, such as Southwest, Alaska Airlines and Delta. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very Good
4,592 reviews
Check prices

Food

7.1

Boarding

8.2

Entertainment

7.7

Comfort

8.1

Crew

8.7

Overall

8.1

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very Good
4,592 reviews
Southwest
8.1
Very Good
4,592 reviews
Check prices

Food

7.1

Boarding

8.2

Entertainment

7.7

Comfort

8.1

Crew

8.7

Overall

8.1

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Alaska Airlines
8.0
Very Good
9,690 reviews
Southwest
8.1
Very Good
4,592 reviews
Check prices

Food

7.1

Boarding

8.2

Entertainment

7.7

Comfort

8.1

Crew

8.7

Overall

8.1

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very Good
8,458 reviews
Southwest
8.1
Very Good
4,592 reviews
Check prices

Food

7.1

Boarding

8.2

Entertainment

7.7

Comfort

8.1

Crew

8.7

Overall

8.1

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

JetBlue
7.4
Good
3,163 reviews
Southwest
8.1
Very Good
4,592 reviews
Check prices

Food

7.1

Boarding

8.2

Entertainment

7.7

Comfort

8.1

Crew

8.7

Overall

8.1

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

United Airlines
7.4
Good
8,934 reviews
Southwest
8.1
Very Good
4,592 reviews
Check prices

Food

7.1

Boarding

8.2

Entertainment

7.7

Comfort

8.1

Crew

8.7

Overall

8.1

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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, Frontier (£105), Delta (£117), and JetBlue (£117) offers the cheapest pricing from New York to Chicago. Frontier is priced at 41% 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 Frontier. You may also be able to find cheap deals on Delta and Spirit Airlines, with prices starting from £59 and £64, respectively.

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

    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.

  • 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 Royal Air Maroc (100%), Etihad Airways (100%) or Royal Jordanian (100%) 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 £363. The most popular route, (New York John F Kennedy Intl - Chicago O'Hare Intl), can usually be booked for £116.

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

Top 2 airlines flying from New York to Chicago

Discover the top 2 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 gennaio 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest£55Average£109FlexibilityNo cancel feeOn-time62%
Search JetBlue flights
American AirlinesCheapest£102Average£204FlexibilityNo cancel feeOn-time71%
Search American Airlines flights

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travellers can enjoy low prices and a wide availability of flights to their desired destinations.

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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