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Cheap flights from New York to Chicago from £53

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 28/5. Fares are subject to change and may not be available on all flights or dates of travel.
NYC — CHI
29 May — 5 Jun1
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 38 days in advance, depart on a Tuesday or Friday and return on a Wednesday

Cheap flight deals from New York to Chicago

Enter your travel dates to find the best prices.

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 April 2026.

Fri 29/522:00
LGA
-
ORD
1 stop10h 55m
Multiple Airlines
Tue 9/613:49
ORD
-
LGA
Nonstop2h 11m
Multiple Airlines
Deal found 26/4£107
Mon 1/620:42
LGA
-
ORD
Nonstop2h 38m
Spirit Airlines
Fri 5/613:49
ORD
-
LGA
Nonstop2h 11m
Spirit Airlines
Deal found 26/4£107
Tue 2/620:42
LGA
-
ORD
Nonstop2h 38m
Spirit Airlines
Fri 5/613:49
ORD
-
LGA
Nonstop2h 11m
Spirit Airlines
Deal found 26/4£112
Mon 8/620:42
LGA
-
ORD
Nonstop2h 38m
Spirit Airlines
Mon 15/613:49
ORD
-
LGA
Nonstop2h 11m
Spirit Airlines
Deal found 24/4£116
Thu 4/616:59
LGA
-
ORD
1 stop7h 16m
Spirit Airlines
Tue 9/613:49
ORD
-
LGA
Nonstop2h 11m
Spirit Airlines
Deal found 26/4£118
Fri 29/517:01
EWR
-
ORD
Nonstop2h 37m
Spirit Airlines
Thu 4/612:59
ORD
-
EWR
Nonstop2h 07m
Spirit Airlines
Deal found 26/4£120
Tue 18/814:45
EWR
-
ORD
Nonstop2h 26m
Spirit Airlines
Thu 20/817:06
ORD
-
EWR
Nonstop2h 22m
Spirit Airlines
Deal found 28/4£121
Mon 1/620:42
LGA
-
ORD
Nonstop2h 38m
Multiple Airlines
Sat 6/613:50
ORD
-
LGA
1 stop8h 24m
Multiple Airlines
Deal found 26/4£124
Sat 24/1006:30
LGA
-
ORD
Nonstop2h 31m
Spirit Airlines
Tue 27/1016:30
ORD
-
LGA
Nonstop2h 11m
Spirit Airlines
Deal found 25/4£125
Mon 1/622:29
EWR
-
ORD
1 stop10h 26m
Multiple Airlines
Fri 5/612:59
ORD
-
EWR
Nonstop2h 07m
Multiple Airlines
Deal found 26/4£126
Tue 2/620:42
LGA
-
ORD
Nonstop2h 38m
Multiple Airlines
Sat 6/613:50
ORD
-
LGA
1 stop8h 24m
Multiple Airlines
Deal found 26/4£129
Wed 27/510:59
LGA
-
ORD
1 stop13h 16m
Multiple Airlines
Wed 3/613:50
ORD
-
LGA
1 stop8h 24m
Multiple Airlines
Deal found 27/4£130

Find 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 April 2026.

Round-trip from

£107

One-way from

£53

Popular in

June

Cheapest in

January

Average price

£206

Good round-trip deal

£212 or less

Good one-way deal

£99 or less
Spirit Airlines
  • Spirit Airlines
  • 29/5-9/6
  • 1 total stop
  • 13h 06m total
  • New York to Chicago
Search Deals
Frontier
  • Frontier
  • 28/5
  • 1 total stop
  • 10h 26m total
  • New York to Chicago
Search Deals
Highest demand for flights based on searches. 10% potential increase in price (£16 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease (£3 potential savings vs. average return price).
Search Deals
Average for round-trip flights in April 2026
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

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 29 April 2026.
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

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Wed 17/6

20:42-22:20

Nonstop2h 38m

Chicago O'Hare Intl

Sat 20/6

05:10-15:38

1 stop9h 28m

£116

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Thu 2/7

07:10-08:49

Nonstop2h 39m

Chicago O'Hare Intl

Tue 7/7

17:00-20:22

Nonstop2h 22m

£138

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Wed 27/5

19:35-21:36

Nonstop3h 01m

Chicago O'Hare Intl

Wed 3/6

18:31-22:00

Nonstop2h 29m

£142

NewarkChicago

EWR - ORD

EWRORD

Newark

Tue 28/7

06:00-10:37

1 stop5h 37m

Chicago O'Hare Intl

Tue 11/8

13:35-19:27

1 stop4h 52m

£146

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Sat 30/5

17:10-19:09

Nonstop2h 59m

Chicago O'Hare Intl

Fri 5/6

17:50-21:02

Nonstop2h 12m

£146

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Wed 20/5

14:45-16:34

Nonstop2h 49m

Chicago O'Hare Intl

Sun 24/5

07:05-10:21

Nonstop2h 16m

£146

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Wed 3/6

08:50-10:39

Nonstop2h 49m

Chicago O'Hare Intl

Fri 5/6

17:50-21:02

Nonstop2h 12m

£146

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Mon 14/9

06:00-07:36

Nonstop2h 36m

Chicago O'Hare Intl

Fri 18/9

20:20-23:44

Nonstop2h 24m

£146

NewarkChicago

EWR - ORD

EWRORD

Newark

Fri 10/7

21:40-23:30

Nonstop2h 50m

Chicago O'Hare Intl

Mon 13/7

21:30-00:53

Nonstop2h 23m

£149

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Wed 10/6

12:59-14:44

Nonstop2h 45m

Chicago O'Hare Intl

Wed 17/6

18:27-22:13

Nonstop2h 46m

£149

Flights are sorted by cheapest return flights first.

Deals found on 24/4

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
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 37 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 £147). Flying from New York to Chicago in June is currently the most expensive (average of £224). 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 April 2026.

It’s optimal to fly from New York to Chicago in the morning. By choosing this option you can save up to 28% on the cost of your flight, compared to a flight at midday.

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 25 April 2026.

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.

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 April 2026.

The most flights from NYC to CHI are scheduled on a Tuesday (177 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (37 on average).

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

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 158 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?

Saturday 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 14% of flights being delayed.

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 April 2026.
Read through reviews of airlines operating flights from New York to Chicago, such as Southwest,Delta, andAmerican Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very Good
4,315 reviews
Check prices

Overall

8.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
8.0
Very Good
4,315 reviews
Southwest
8.0
Very Good
4,315 reviews
Check prices

Overall

8.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Delta
7.9
Good
8,467 reviews
Southwest
8.0
Very Good
4,315 reviews
Check prices

Overall

8.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
American Airlines
7.1
Good
11,680 reviews
Southwest
8.0
Very Good
4,315 reviews
Check prices

Overall

8.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Spirit Airlines
6.3
Okay
8,631 reviews
Southwest
8.0
Very Good
4,315 reviews
Check prices

Overall

8.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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.

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

    Departing from New York to Chicago will take you 2h 38m. New York and Chicago are separated by a distance of 731 mi. Generally, flights for this route are direct.

  • What is the cheapest airline to fly from New York to Chicago round-trip?

    According to our current data, Spirit Airlines (£114), offers the cheapest pricing from New York to Chicago. Spirit Airlines is priced at 36% lower than the current average price of a flight leaving 3 months from now.

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

    Most travelers choose New York LaGuardia - Chicago O'Hare Intl, Newark - 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 (100%), Gulf Air (80%) or Hawaiian Airlines (76%) 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 £91. On average you can expect to pay £187. The most popular route, (New York LaGuardia - Chicago O'Hare Intl), can usually be booked for £169.

  • 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 £147). Flying from New York to Chicago in June is currently the most expensive (average of £224). 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.
LaGuardia to O'Hare Intl flights
Newark to O'Hare Intl flights
John F Kennedy Intl to O'Hare Intl flights

Top airline flying from New York to Chicago

Discover the top airline 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 April 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest£114Average£137FlexibilityNo cancel feeOn-time65%
Search Spirit 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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