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.

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.

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).

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 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.

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 is the cheapest day to fly round-trip from New York to Chicago?

Users have found that flying from New York to Chicago on a Wednesday typically leans towards higher prices. However, this doesn’t mean you still can’t find a deal. Flexibility with other aspects of your flight can still land a great price for your trip.

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

Users have found that booking a flight from New York to Chicago at least 36 days early can save you up to 90% on average compared to booking a flight this week. If booking 36 days before your flight isn’t an option for you, users have found flights from New York to Chicago for as little as £168 when booking for a departure date within the next two weeks. You can also check prices now. Some users have found airline tickets as low as £276 for flights departing within the next 3 days.

What is the cheapest month to fly from New York to Chicago?

Flights from New York to Chicago lean towards being more expensive in December. Prices are generally better when you fly from New York to Chicago in September, with the cheapest ticket starting at £54.

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.

£51+ Flights from New York to Chicago

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

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
5/9-7/9
1 total stop
6h 52m total
New York to Chicago

Search Deals

United Airlines
12/8
Nonstop
2h 42m total
New York to Chicago

Search Deals

Highest demand for flights based on searches. 1% potential increase in price (£1 potential increase over avg. return price).

Search Deals

Cheapest flight prices on average. 2% potential price decrease (£3 potential savings vs. average return price).

Search Deals

Average for round-trip flights in July 2025

Search Deals

Price to beat on a round-trip flight from New York (NYC) to Chicago (CHI).

Search Deals

Price to beat on a one-way flight from New York (NYC) to Chicago (CHI).

Search Deals

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

Best flights from New York to Chicago
Discover carefully curated flight deals from New York to Chicago that have cost, travel time, and stopovers in mind to ensure you get the best travel experience. Data last updated 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

Wed 10/906:00ORD - 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

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

Sat 11/1011:00JFK - ORD

Nonstop2h 40mAmerican Airlines

Wed 15/1010:11ORD - JFK

Nonstop2h 19mAmerican Airlines

Deal found 11/7£127

Tue 5/821:59EWR - ORD

Nonstop2h 42mUnited Airlines

Tue 19/806:00ORD - EWR

Nonstop2h 15mUnited Airlines

Deal found 10/7£106

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

Sat 11/1007:30LGA - ORD

Nonstop2h 41mAmerican Airlines

Wed 15/1018:05ORD - LGA

Nonstop2h 20mAmerican Airlines

Deal found 9/7£132

Thu 11/908:00JFK - ORD

Nonstop2h 56mDelta

Mon 15/907:00ORD - JFK

Nonstop2h 22mDelta

Deal found 11/7£123

Direct flights from New York to Chicago
Explore direct flight options from New York to Chicago based on user searches, and compare prices and availability for your desired travel dates. Data last updated 11 July 2025.

Tue 2/906:00LGA - ORD

Nonstop2h 30mDelta

Wed 10/906:00ORD - LGA

Nonstop2h 10mDelta

Deal found 9/7£104

Thu 21/820:30JFK - ORD

Nonstop2h 58mJetBlue

Fri 22/806:15ORD - 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

Thu 14/807:20LGA - ORD

Nonstop2h 37mUnited Airlines

Fri 15/818:00ORD - LGA

Nonstop2h 20mUnited Airlines

Deal found 10/7£110

Sat 11/1011:00JFK - ORD

Nonstop2h 40mAmerican Airlines

Wed 15/1010:11ORD - JFK

Nonstop2h 19mAmerican Airlines

Deal found 9/7£121

Thu 11/908:00JFK - ORD

Nonstop2h 56mDelta

Mon 15/907:00ORD - JFK

Nonstop2h 22mDelta

Deal found 11/7£123

Sat 11/1019:41EWR - ORD

Nonstop2h 44mAmerican Airlines

Wed 15/1007:04ORD - EWR

Nonstop2h 16mAmerican Airlines

Deal found 9/7£127

Sat 11/1007:30LGA - ORD

Nonstop2h 41mAmerican Airlines

Wed 15/1018:05ORD - LGA

Nonstop2h 20mAmerican Airlines

Deal found 9/7£132

Last-minute flights from New York to Chicago
Discover last-minute flight deals from New York to Chicago. Data last updated 11 July 2025 and is based on user searches.

Wed 16/719:25JFK - ORD

Nonstop3h 18mDelta

Wed 23/707:00ORD - JFK

Nonstop2h 23mDelta

Deal found 9/7£166

Fri 18/720:35LGA - ORD

Nonstop2h 52mDelta

Wed 30/720:10ORD - LGA

Nonstop2h 32mDelta

Deal found 10/7£166

Fri 18/717:59EWR - ORD

1 stop7h 10mDelta

Wed 30/709:00ORD - EWR

1 stop5h 55mDelta

Deal found 9/7£180

Sat 19/715:25LGA - ORD

Nonstop2h 40mUnited Airlines

Wed 3/913:00ORD - LGA

Nonstop2h 17mUnited Airlines

Deal found 10/7£138

Sat 19/706:00EWR - ORD

Nonstop2h 38mUnited Airlines

Wed 3/906:00ORD - EWR

Nonstop2h 15mUnited Airlines

Deal found 10/7£155

Sat 19/706:40LGA - ORD

1 stop7h 05mSouthwest

Wed 3/915:10ORD - LGA

1 stop6h 50mSouthwest

Deal found 10/7£157

Sat 19/718:30LGA - ORD

Nonstop2h 30mSpirit Airlines

Thu 24/708:09ORD - LGA

1 stop8h 21mSpirit Airlines

Deal found 10/7£162

Sat 19/717:00LGA - ORD

1 stop24h 40mFrontier

Thu 24/711:15ORD - LGA

1 stop27h 45mFrontier

Deal found 10/7£205

Sat 19/719:33EWR - ORD

Nonstop2h 52mAmerican Airlines

Tue 22/719:24ORD - EWR

Nonstop2h 16mAmerican Airlines

Deal found 10/7£209

Mon 21/706:20JFK - ORD

1 stop29h 05mFrontier

Tue 22/717:38ORD - JFK

1 stop6h 04mFrontier

Deal found 10/7£156

Mon 21/722:00EWR - ORD

1 stop10h 04mSpirit Airlines

Sat 26/705:05ORD - EWR

1 stop12h 54mSpirit Airlines

Deal found 9/7£170

Mon 21/720:29JFK - ORD

Nonstop2h 58mJetBlue

Fri 1/806:16ORD - JFK

Nonstop2h 13mJetBlue

Deal found 10/7£181

One-way flights from New York to Chicago
Search for one-way flight options from New York to Chicago. Find affordable one-way fares based on user searches. Data last updated 11 July 2025.

Tue 12/821:59EWR - ORD

Nonstop2h 42mUnited Airlines

Deal found 9/7£51

Wed 8/1014:08EWR - ORD

Nonstop2h 41mAmerican Airlines

Deal found 10/7£54

Tue 19/814:00EWR - ORD

1 stop9h 22mSpirit Airlines

Deal found 10/7£56

Sun 31/812:27EWR - ORD

1 stop5h 18mDelta

Deal found 8/7£57

Wed 13/820:30JFK - ORD

Nonstop2h 58mJetBlue

Deal found 11/7£58

Sun 31/820:30LGA - ORD

Nonstop2h 50mDelta

Deal found 10/7£58

Tue 19/806:00LGA - ORD

2 stops16h 30mSouthwest

Deal found 8/7£59

Mon 4/821:30LGA - ORD

Nonstop2h 39mUnited Airlines

Deal found 9/7£60

Sun 24/808:00JFK - ORD

Nonstop2h 55mDelta

Deal found 10/7£62

Thu 4/1215:55JFK - ORD

Nonstop2h 47mAmerican Airlines

Deal found 10/7£64

Tue 26/809:59LGA - ORD

1 stop7h 11mSpirit Airlines

Deal found 8/7£66

Sun 7/911:44EWR - ORD

1 stop7h 18mSun Country Air

Deal found 10/7£88

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

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

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?

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?

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?

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

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

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.

Southwest

8.0

Very Good

4,250 reviews

Check prices

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.

Southwest

8.0

Very Good

4,250 reviews

Southwest

8.0

Very Good

4,250 reviews

Check prices

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.

Delta

8.0

Very Good

7,951 reviews

Southwest

8.0

Very Good

4,250 reviews

Check prices

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.

United Airlines

7.4

Good

8,846 reviews

Southwest

8.0

Very Good

4,250 reviews

Check prices

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.

JetBlue

7.3

Good

2,914 reviews

Southwest

8.0

Very Good

4,250 reviews

Check prices

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.

American Airlines

7.2

Good

10,000 reviews

Southwest

8.0

Very Good

4,250 reviews

Check prices

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

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?
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 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

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

Other flights to Chicago

Heathrow to O'Hare Intl flights

Edinburgh to O'Hare Intl flights

Chicago O'Hare Intl Airport to Houston George Bush Intcntl Airport flights

Chicago O'Hare Intl Airport to Toronto Pearson Intl Airport flights

Chicago O'Hare Intl Airport to Boston flights

Chicago O'Hare Intl Airport to Las Vegas flights

Chicago O'Hare Intl Airport to Miami flights

Chicago O'Hare Intl Airport to Atlanta flights

Chicago O'Hare Intl Airport to Orlando Airport flights

Chicago O'Hare Intl Airport to St. Louis flights

Chicago O'Hare Intl Airport to Los Angeles flights

Chicago O'Hare Intl Airport to Newark Airport flights

Chicago O'Hare Intl Airport to Denver flights

Chicago O'Hare Intl Airport to Minneapolis flights

Chicago O'Hare Intl Airport to New York John F Kennedy Intl Airport flights

Chicago O'Hare Intl Airport to San Diego flights

Chicago O'Hare Intl Airport to New York John F Kennedy Intl Airport flights

Chicago O'Hare Intl Airport to Toronto Pearson Intl Airport flights

Chicago O'Hare Intl Airport to Lisbon flights

Chicago O'Hare Intl Airport to Boston flights

Top 3 airlines flying from New York to Chicago

Airline	Cheapest	Average	Flexibility	On-time
Spirit Airlines	Cheapest£44	Average£92	FlexibilityNo cancel fee	On-time65%	Search Spirit Airlines flights
JetBlue	Cheapest£50	Average£100	FlexibilityNo cancel fee	On-time62%	Search JetBlue flights
American Airlines	Cheapest£93	Average£160	FlexibilityNo cancel fee	On-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.

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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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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.

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

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Good round-trip deal

Good one-way deal

Find flight deals from New York to Chicago

Cheapest flights from New York to ChicagoExplore 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.

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.

Cheapflights Fare Finder

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

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.

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.

What is the cheapest month to book a flight from New York to Chicago?

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.

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.

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.

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

Reviews of airlines servicing Chicago

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.

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?

What are the cheapest airlines to fly from New York to Chicago one-way?

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

What are the most reliable airlines from New York to Chicago?

What are the cheapest flights from New York to Chicago?

Can I find deals for flights from New York to Chicago that include hotel bookings?

How can I find direct flights from New York to Chicago?

Can I find deals for business class flights from New York to Chicago?

What is the cheapest month to book a flight from New York to Chicago?

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Alternative routes for New York to Chicago

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Top 3 airlines flying from New York to Chicago

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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.