Cheap flights from New York to Chicago (CHI)

JFK — CHI
Aug 13 — Aug 201

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

To save on the cost of your flight from State of New York to Chicago, book at least 26 days before your planned departure. Booking around this time can save you about 21% on the cost of this flight compared to booking a flight leaving this week. We have found prices from $256 if you need a flight within two weeks. For flights within the next 72 hours, you can find tickets from as low as $300.

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

Flights from State of New York to Chicago lean towards being more expensive in August. Prices are generally better when you fly from State of New York to Chicago in January, with the cheapest ticket starting at $117.

When is the cheapest time to fly from State of New York to Chicago (NY - CHI)?

When flying from State of New York to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Cheap flights from New York to Chicago in August, September 2022

The best prices found for New York to CHI flights for August, September
Sep 20 - Sep 27
EWR

Newark

ORD

Chicago O'Hare Intl

1 stop

9h 11m
ORD

Chicago O'Hare Intl

EWR

Newark

1 stop

9h 55m
$95

Spirit Airlines

Pick Dates

Deal found 7/8/22

Sep 21 - Sep 27
EWR

Newark

MDW

Chicago Midway

1 stop

5h 34m
MDW

Chicago Midway

EWR

Newark

1 stop

13h 48m
$108

Multiple Airlines

Pick Dates

Deal found 6/8/22

Aug 24 - Sep 7
EWR

Newark

MDW

Chicago Midway

1 stop

7h 02m
MDW

Chicago Midway

EWR

Newark

1 stop

7h 18m
$109

Multiple Airlines

Pick Dates

Deal found 8/8/22

New York to Chicago 2022 flight deals

Cheap flights to Chicago from New York found for this year
Sep 20 - Sep 27
EWR

Newark

ORD

Chicago O'Hare Intl

1 stop

9h 11m
ORD

Chicago O'Hare Intl

EWR

Newark

1 stop

9h 55m
$95

Spirit Airlines

Pick Dates

Deal found 7/8/22

Oct 12 - Oct 17
EWR

Newark

MDW

Chicago Midway

1 stop

5h 38m
MDW

Chicago Midway

EWR

Newark

1 stop

7h 28m
$107

Multiple Airlines

Pick Dates

Deal found 7/8/22

Sep 21 - Sep 27
EWR

Newark

MDW

Chicago Midway

1 stop

5h 34m
MDW

Chicago Midway

EWR

Newark

1 stop

13h 48m
$108

Multiple Airlines

Pick Dates

Deal found 6/8/22

Cheap United Airlines flights from New York to Chicago

Sep 3 - Sep 4
ROC

Rochester Greater Rochester Intl

ORD

Chicago O'Hare Intl

Nonstop

1h 56m
ORD

Chicago O'Hare Intl

ROC

Rochester Greater Rochester Intl

Nonstop

1h 43m
$186

United Airlines

Pick Dates

Deal found 6/8/22

Sep 3 - Sep 4
HPN

White Plains Westchester County

ORD

Chicago O'Hare Intl

Nonstop

2h 37m
ORD

Chicago O'Hare Intl

HPN

White Plains Westchester County

Nonstop

2h 11m
$196

United Airlines

Pick Dates

Deal found 8/8/22

Sep 3 - Sep 12
HPN

White Plains Westchester County

ORD

Chicago O'Hare Intl

Nonstop

2h 37m
ORD

Chicago O'Hare Intl

HPN

White Plains Westchester County

Nonstop

2h 06m
$202

United Airlines

Pick Dates

Deal found 7/8/22

Cheap Spirit Airlines flights from New York to Chicago

Sep 14 - Sep 17
EWR

Newark

ORD

Chicago O'Hare Intl

1 stop

9h 11m
ORD

Chicago O'Hare Intl

EWR

Newark

1 stop

9h 55m
$95

Spirit Airlines

Pick Dates

Deal found 8/8/22

Sep 6 - Sep 10
EWR

Newark

ORD

Chicago O'Hare Intl

1 stop

19h 00m
ORD

Chicago O'Hare Intl

EWR

Newark

1 stop

9h 55m
$112

Spirit Airlines

Pick Dates

Deal found 7/8/22

Sep 3 - Sep 10
EWR

Newark

ORD

Chicago O'Hare Intl

2 stops

18h 58m
ORD

Chicago O'Hare Intl

EWR

Newark

1 stop

9h 55m
$114

Spirit Airlines

Pick Dates

Deal found 5/8/22

Non-stop flights to Chicago from New York

Save time with New York to Chicago direct flight deals
Sep 7 - Sep 14
LGA

New York LaGuardia

ORD

Chicago O'Hare Intl

Nonstop

2h 35m
ORD

Chicago O'Hare Intl

LGA

New York LaGuardia

Nonstop

2h 25m
$169

United Airlines

Pick Dates

Deal found 8/8/22

Aug 30 - Aug 30
EWR

Newark

ORD

Chicago O'Hare Intl

Nonstop

2h 33m
ORD

Chicago O'Hare Intl

EWR

Newark

Nonstop

2h 02m
$172

American Airlines

Pick Dates

Deal found 5/8/22

Aug 30 - Aug 30
LGA

New York LaGuardia

ORD

Chicago O'Hare Intl

Nonstop

2h 45m
ORD

Chicago O'Hare Intl

LGA

New York LaGuardia

Nonstop

2h 02m
$172

JetBlue

Pick Dates

Deal found 5/8/22

Last minute flights from New York to Chicago

Late deals on return flights to Chicago from New York, departing today and this week
Aug 17 - Aug 24
LGA

New York LaGuardia

MDW

Chicago Midway

1 stop

8h 53m
MDW

Chicago Midway

LGA

New York LaGuardia

1 stop

6h 19m
$165

Frontier

Pick Dates

Deal found 5/8/22

Aug 18 - Aug 18
LGA

New York LaGuardia

ORD

Chicago O'Hare Intl

Nonstop

2h 46m
ORD

Chicago O'Hare Intl

LGA

New York LaGuardia

1 stop

18h 23m
$167

American Airlines

Pick Dates

Deal found 5/8/22

Aug 16 - Sep 17
EWR

Newark

ORD

Chicago O'Hare Intl

1 stop

23h 35m
ORD

Chicago O'Hare Intl

EWR

Newark

1 stop

9h 55m
$173

Spirit Airlines

Pick Dates

Deal found 8/8/22

One-way flights to Chicago from New York

The cheapest one-way flights from New York to Chicago
Aug 30
SWF

New Windsor Stewart

ORD

Chicago O'Hare Intl

1 stop

17h 32m
$52

Multiple Airlines

Pick Dates

Deal found 7/8/22

Sep 3
EWR

Newark

ORD

Chicago O'Hare Intl

2 stops

18h 58m
$56

Spirit Airlines

Pick Dates

Deal found 5/8/22

Sep 17
EWR

Newark

ORD

Chicago O'Hare Intl

1 stop

9h 11m
$57

Spirit Airlines

Pick Dates

Deal found 5/8/22

Related info for your journey

Useful info, stats and facts about New York to Chicago flights.

Which airlines flying from New York to Chicago have flexible cancellations due to COVID-19?

Some of our airline partners flying from New York to Chicago have new flexible policies in place due to COVID-19. American Airlines, United Airlines, and JetBlue are some of the carriers where you may find flexible cancellation policies. You can use our site to filter for airlines like American Airlines with this kind of flexibility.

Can I find flights from State of New York to Chicago for under $100 on Cheapflights?

Yes, there are multiple flights from State of New York to Chicago for under $100. The cheapest flight booked recently is on Spirit Airlines for just $95, but on average you can expect to pay $114.

Are there nonstop flights from State of New York to Chicago for under $200 on Cheapflights?

Cheapflights has at least 20 direct flights from State of New York to Chicago under $200. A good price for a nonstop flight from State of New York to Chicago is less than $178.

Are there last-minute flights available from State of New York to Chicago for under $200?

There are currently 20+ open flights from State of New York to Chicago within the next 7 days for less than $200.

What days are nonstop flights available from State of New York to Chicago?

Nonstop flights are available for this route on the following days: Tuesday, Saturday.

How many flights depart from State of New York to Chicago on average per day?

On average, you can expect to see 4 flights from State of New York to Chicago a day.
Morning (6am - Noon) - 50% of flight departures
Afternoon (Noon - 6pm) - 50% of flight departures

How long is the flight from State of New York to Chicago?

A quick flight from State of New York to Chicago can take about 9h 11m. Spirit Airlines provides one of the quickest options available for as low as $95. State of New York and Chicago are separated by a distance of 742 mi. This flight may include one or multiple stops.

What are the most popular routes from State of 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 State of New York to Chicago.

What are the most popular airlines that fly from State of New York to Chicago?

American Airlines, Alaska Airlines and JetBlue are the most popular airlines when flying from State of New York to Chicago.

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

The top 3 most reliable airlines when flying from State of New York to Chicago are LATAM Airlines (81%), Gulf Air (79%) and China Airlines (79%).

What are the cheapest flights from State of New York to Chicago?

Looking at all options, your cheapest flight can be booked for $18. While the most popular route (Newark - Chicago O'Hare Intl) can be booked for $95 on average our data indicates $342 when flying from State of New York to Chicago.

Departure points for flights from New York to Chicago

Select to see more specific information for flights to Chicago from all departure points in New York

Top 8 airlines flying from New York to Chicago

The chart below displays the airlines Cheapflights users traveling from New York to Chicago choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
AirlineCheapestAverageFlexibilityOn-timeCOVID-19 safety
Juneyao AirlinesCheapest$13Average$23FlexibilityNo cancel feeOn-time66%COVID-19 safety
Search Juneyao Airlines flights
FrontierCheapest$28Average$85FlexibilityNo cancel feeOn-time62%COVID-19 safety
Search Frontier flights
Spirit AirlinesCheapest$48Average$126FlexibilityNo cancel feeOn-time65%COVID-19 safety
Search Spirit Airlines flights
JetBlueCheapest$75Average$231FlexibilityNo cancel feeOn-time62%COVID-19 safety
Search JetBlue flights
DeltaCheapest$86Average$357FlexibilityNo cancel feeOn-timeN/ACOVID-19 safety
Search Delta flights
United AirlinesCheapest$97Average$268FlexibilityNo cancel feeOn-time69%COVID-19 safety
Search United Airlines flights
American AirlinesCheapest$103Average$308FlexibilityNo cancel feeOn-time71%COVID-19 safety
Search American Airlines flights
Alaska AirlinesCheapest$144Average$363FlexibilityNo cancel feeOn-time75%COVID-19 safety
Search Alaska Airlines flights

Hourly flight availability from New York to Chicago

See what time of day planes typically take off from New York to Chicago
15%of flight departuresEarly morningMidnight to 6 am
34%of flight departuresMorning6 am to noon
41%of flight departuresAfternoonNoon to 6 pm
10%of flight departuresEvening6 pm to midnight
Midnight
6 AM
Noon
6 PM