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Cheap flights from New York to Chicago from £95

NYC — CHI
5 Nov — 12 Nov1
1 adult
1 adult, Economy, 0 bags
Cheapflights Tip: The best prices from New York to Chicago are usually found in January or February, booked 83 days in advance, depart on a Tuesday or Friday and return on a Sunday

Cheap flight deals from New York to Chicago

Enter your travel dates to find the best prices.

Cheapest flights from New York to Chicago

Thu 19/1110:00 -
Nonstop2h 40m
Mon 23/1105:00 -
Nonstop2h 05m
Deal found 4/10£187
Wed 11/1106:40 -
1 stop6h 20m
Sat 14/1113:00 -
1 stop7h 29m
Deal found 5/10£188
Sat 7/1106:40 -
1 stop6h 20m
Tue 10/1113:00 -
1 stop7h 29m
Deal found 5/10£188
Fri 6/1116:25 -
1 stop7h 20m
Tue 10/1108:10 -
2 stops7h 45m
Deal found 5/10£188
Fri 13/1106:40 -
1 stop6h 20m
Sat 14/1113:00 -
1 stop5h 59m
Deal found 5/10£189
Fri 6/1116:25 -
1 stop7h 20m
Mon 9/1108:45 -
1 stop8h 10m
Deal found 5/10£189
Sat 31/1015:24 -
Nonstop2h 56m
Mon 2/1106:10 -
Nonstop2h 17m
Deal found 5/10£190
Thu 5/1106:05 -
Nonstop2h 46m
Sun 8/1108:00 -
Nonstop2h 12m
Deal found 5/10£190
Sat 31/1010:05 -
Nonstop2h 20m
Sun 1/1119:15 -
Nonstop2h 05m
Deal found 5/10£190
Thu 29/1006:40 -
1 stop6h 20m
Sat 31/1013:00 -
1 stop5h 59m
Deal found 5/10£191
Thu 29/1008:55 -
Nonstop2h 30m
Fri 30/1019:35 -
Nonstop2h 10m
Deal found 5/10£191
Fri 30/1013:26 -
1 stop7h 03m
Fri 6/1113:00 -
1 stop7h 29m
Deal found 6/10£191

Find flight deals from New York to Chicago

Round-trip from

£187

One-way from

£95

Popular in

July

Cheapest in

January

Average price

£234

Good round-trip deal

£165 or less

Good one-way deal

£116 or less
Southwest
  • Southwest
  • 19/11-23/11
  • Nonstop
  • 4h 45m total
  • New York to Chicago
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Frontier
  • Frontier
  • 12/12-31/12
  • 1 total stop
  • 13h 32m total
  • New York to Chicago
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Highest demand for flights based on searches. 14% potential increase in price (£26 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 October 2026
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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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Cheapflights Fare Finder

 
Use the filters below to find and compare flights from New York to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest return flight

NewarkChicago

EWR Newark - ORD Chicago O'Hare Intl

EWRORD

Newark

Mon 23/11

15:30-17:17

Nonstop2h 47m

Chicago O'Hare Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

£105

New YorkChicago

LGA New York LaGuardia - ORD Chicago O'Hare Intl

LGAORD

New York LaGuardia

Tue 17/11

20:30-22:18

Nonstop2h 48m

Chicago O'Hare Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

£105
Fastest return journey

New YorkChicago

LGA New York LaGuardia - MDW Chicago Midway

LGAMDW

New York LaGuardia

Thu 29/10

15:35-16:55

Nonstop2h 20m

Chicago Midway

Wed 31/12

00:00-01:00

Nonstop0h 00m

£105

New YorkChicago

LGA New York LaGuardia - ORD Chicago O'Hare Intl

LGAORD

New York LaGuardia

Thu 12/11

13:05-14:55

Nonstop2h 50m

Chicago O'Hare Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

£105

New YorkChicago

LGA New York LaGuardia - MDW Chicago Midway

LGAMDW

New York LaGuardia

Tue 17/11

18:35-20:15

Nonstop2h 40m

Chicago Midway

Wed 31/12

00:00-01:00

Nonstop0h 00m

£105

NewarkChicago

EWR Newark - ORD Chicago O'Hare Intl

EWRORD

Newark

Thu 3/12

08:00-09:45

Nonstop2h 45m

Chicago O'Hare Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

£112

New YorkChicago

JFK New York John F Kennedy Intl - ORD Chicago O'Hare Intl

JFKORD

New York John F Kennedy Intl

Wed 2/12

19:36-21:36

Nonstop3h 00m

Chicago O'Hare Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

£113

New YorkChicago

JFK New York John F Kennedy Intl - ORD Chicago O'Hare Intl

JFKORD

New York John F Kennedy Intl

Fri 13/11

07:30-09:27

Nonstop2h 57m

Chicago O'Hare Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

£113

New YorkChicago

LGA New York LaGuardia - MDW Chicago Midway

LGAMDW

New York LaGuardia

Fri 23/10

07:15-08:35

Nonstop2h 20m

Chicago Midway

Wed 31/12

00:00-01:00

Nonstop0h 00m

£113

New YorkChicago

JFK New York John F Kennedy Intl - ORD Chicago O'Hare Intl

JFKORD

New York John F Kennedy Intl

Sun 22/11

07:30-09:27

Nonstop2h 57m

Chicago O'Hare Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

£113

Flights are sorted by cheapest return flights first.

Deals found on 1/10

Showing 1-10 of 60 resultsSorted by cheapest first
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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

Cheapflights Insights

Everything you need to know about your flight from New York to Chicago

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 £144). Flying from New York to Chicago in July is currently the most expensive (average of £261). 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?

It’s optimal to fly from New York to Chicago in the morning. By choosing this option you can save up to 27% on the cost of your flight, compared to a flight in the afternoon.

Weekly flight availability from New York to Chicago

The most flights from NYC to CHI are scheduled on a Sunday (192 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (60 on average).

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

Airfare is typical for this route at the moment.
New York to Chicago flights typically cost between £166 and £302 in November.
The cheapest return price found within the last 5 days was £187 on Southwest (19 Nov–23 Nov).

How often are flights from New York to Chicago delayed?

About 19% of weekly flights between New York and Chicago have experienced delays in the past year, with the average delay time being 150 minutes.

What is the most punctual flight time for New York to Chicago flights?

Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving at night tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Tuesday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on New York to Chicago flights?

Over the past year, United Airlines have had the lowest number of delays on this route, with just 13% of flights being delayed.

How far ahead should I book a flight from New York to Chicago?

To ensure you get the cheapest price possible for a flight from New York to Chicago, you should look to book at least 82 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 day to fly from New York to Chicago?

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.

Reviews of airlines servicing Chicago

Read through reviews of airlines operating flights from New York to Chicago, such as Southwest and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
7.9
Good
4,214 reviews
Check prices

Crew

8.6

Boarding

8.1

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

7.9

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
Southwest
7.9
Good
4,214 reviews
Southwest
7.9
Good
4,214 reviews
Check prices

Crew

8.6

Boarding

8.1

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

7.9

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
American Airlines
7.0
Good
12,129 reviews
Southwest
7.9
Good
4,214 reviews
Check prices

Crew

8.6

Boarding

8.1

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

7.9

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers

Related info for your journey

  • How long is the flight from New York to Chicago?

    Departing from New York to Chicago will take you 2h 32m. New York and Chicago are separated by a distance of 731 mi. Generally, flights for this route are direct.

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

    Most travelers choose Newark - Chicago O'Hare Intl, New York LaGuardia - Chicago O'Hare Intl or New York John F Kennedy Intl - 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 Malaysia Airlines (76%), American Airlines (75%) or Air Europa (75%) 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 £69. On average you can expect to pay £183. The most popular route, (Newark - Chicago O'Hare Intl), can usually be booked for £228.

  • 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 £144). Flying from New York to Chicago in July is currently the most expensive (average of £261). 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

Alternative routes for New York to Chicago

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

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