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Cheap flights from New York to Chicago from £52
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 22/1. Fares are subject to change and may not be available on all flights or dates of travel.
NYC — CHI
12 Oct — 19 Oct1
Cheapflights Tip: The best prices from New York to Chicago are usually found in January or September, booked 35 days in advance, depart on a Tuesday or Monday 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 12 September 2025.
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 12 September 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 12 September 2025.
Tue 30/910:30JFK - ORD
Nonstop2h 40mJetBlue
Wed 1/1013:35ORD - JFK
Nonstop2h 24mJetBlue
Deal found 11/9£98
Tue 30/918:30LGA - ORD
Nonstop2h 37mUnited Airlines
Wed 1/1008:00ORD - LGA
Nonstop2h 16mUnited Airlines
Deal found 11/9£98
Tue 21/1010:30JFK - ORD
Nonstop2h 52mJetBlue
Wed 29/1006:45ORD - JFK
Nonstop2h 14mJetBlue
Deal found 12/9£99
Tue 14/1010:29JFK - ORD
Nonstop2h 49mDelta
Sat 25/1018:20ORD - JFK
Nonstop2h 40mDelta
Deal found 10/9£101
Tue 28/1007:44LGA - ORD
1 stop11h 54mSpirit Airlines
Thu 30/1011:08ORD - LGA
Nonstop1h 55mSpirit Airlines
Deal found 10/9£102
Tue 21/1007:20LGA - ORD
1 stop9h 00mSouthwest
Wed 22/1012:40ORD - LGA
1 stop9h 40mSouthwest
Deal found 11/9£103
Wed 8/1016:28LGA - ORD
Nonstop2h 37mUnited Airlines
Fri 17/1018:30ORD - LGA
Nonstop2h 24mUnited Airlines
Deal found 11/9£104
Tue 30/908:25LGA - ORD
Nonstop2h 37mUnited Airlines
Sun 5/1006:00ORD - LGA
Nonstop2h 16mUnited Airlines
Deal found 11/9£106
Sun 26/1008:29LGA - ORD
Nonstop2h 44mMultiple Airlines
Sun 2/1105:11ORD - LGA
1 stop5h 18mMultiple Airlines
Deal found 11/9£107
Sat 4/1006:25LGA - ORD
Nonstop2h 37mUnited Airlines
Fri 10/1018:00ORD - LGA
Nonstop2h 17mUnited Airlines
Deal found 10/9£108
Wed 1/1008:00JFK - ORD
Nonstop2h 56mDelta
Wed 1/1018:28ORD - JFK
Nonstop2h 40mDelta
Deal found 10/9£109
Sun 21/922:56LGA - ORD
1 stop11h 41mFrontier
Tue 23/911:45ORD - LGA
1 stop11h 12mFrontier
Deal found 10/9£109
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 12 September 2025.
Use the filters below to find and compare flights from New York to Chicago that are best for you.
Fly from
New York
Fly to
Chicago
Route
Depart
Return
Price
New YorkChicago
JFK - ORD
JFKORD
New York John F Kennedy Intl
Wed 10/12
20:00-21:48
Nonstop2h 48m
Chicago O'Hare Intl
Tue 16/12
07:00-10:13
Nonstop2h 13m
£98
New YorkChicago
JFK - ORD
JFKORD
New York John F Kennedy Intl
Tue 7/10
10:30-12:10
Nonstop2h 40m
Chicago O'Hare Intl
Wed 8/10
13:20-16:44
Nonstop2h 24m
£98
New YorkChicago
LGA - ORD
LGAORD
New York LaGuardia
Wed 28/1
08:30-10:22
Nonstop2h 52m
Chicago O'Hare Intl
Mon 2/2
06:00-09:23
Nonstop2h 23m
£102
New YorkChicago
LGA - ORD
LGAORD
New York LaGuardia
Sun 19/10
21:30-23:07
Nonstop2h 37m
Chicago O'Hare Intl
Wed 22/10
17:00-20:17
Nonstop2h 17m
£104
New YorkChicago
LGA - ORD
LGAORD
New York LaGuardia
Mon 26/1
05:45-07:13
Nonstop2h 28m
Chicago O'Hare Intl
Fri 30/1
19:05-22:14
Nonstop2h 09m
£108
New YorkChicago
JFK - ORD
JFKORD
New York John F Kennedy Intl
Mon 15/12
20:00-21:48
Nonstop2h 48m
Chicago O'Hare Intl
Wed 17/12
07:00-10:13
Nonstop2h 13m
£110
New YorkChicago
JFK - ORD
JFKORD
New York John F Kennedy Intl
Mon 29/9
19:00-20:49
Nonstop2h 49m
Chicago O'Hare Intl
Tue 30/9
06:45-09:59
Nonstop2h 14m
£111
New YorkChicago
JFK - ORD
JFKORD
New York John F Kennedy Intl
Mon 29/9
19:00-20:49
Nonstop2h 49m
Chicago O'Hare Intl
Wed 1/10
13:35-16:59
Nonstop2h 24m
£111
New YorkChicago
LGA - ORD
LGAORD
New York LaGuardia
Wed 10/12
06:00-09:36
1 stop4h 36m
Chicago O'Hare Intl
Wed 17/12
12:00-15:11
Nonstop2h 11m
£111
New YorkChicago
JFK - ORD
JFKORD
New York John F Kennedy Intl
Fri 30/1
15:40-17:37
Nonstop2h 57m
Chicago O'Hare Intl
Mon 2/2
18:10-21:46
Nonstop2h 36m
£112
Showing 1-10 of 60 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?
Use this chart to determine the optimal time to book a return flight from New York to Chicago. Price data was last updated on 29 August 2025.
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?
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 12 September 2025.
It’s optimal to fly from New York to Chicago in the evening. By choosing this option you can save up to 31% 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 7 September 2025.
Travellers seeking maximum savings on their New York to Chicago flight should consider departing on Tuesday 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
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 12 September 2025.
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 (83 on average).
What’s the top stopover airport for flights from New York to Chicago?
Share of one-stop return flights from New York to Chicago chosen by Cheapflights users in the past 12 months, using the same stopover each way.
Atlanta (ATL) – chosen by Cheapflights users on 67% of one-stop itineraries from New York to Chicago on Cheapflights.
What’s the cheapest stopover airport for flights from New York to Chicago?
Average return fare for one-stop flights from New York to Chicago, chosen by Cheapflights users in the past 12 months, with the same stopover each way.
Tampa (TPA) is the most affordable one-stop option, with an average return flight price of £93.
What’s the fastest stopover option from New York to Chicago?
Shortest average travel time for one-stop one-way flights from New York to Chicago, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by stopover airport.
Flights via Atlanta (ATL) have the shortest average one-way travel time for one-stop routes: 5h 49m.
Which airport typically offers the quickest stopover for flights from New York to Chicago?
Average stopover duration for one-stop one-way flights from New York to Chicago, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.
Flights via Atlanta (ATL) offer the fastest connection on this route, with an average stopover time of 2h 40m.
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 12 September 2025.
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.
Entertainment
7.5
Crew
8.6
Boarding
8.1
Comfort
8.0
Overall
8.0
Food
7.0
Reviews
1 / 20
2.0
MediocreMike,Aug 2025
OKC - AUS
Entertainment
7.5
Crew
8.6
Boarding
8.1
Comfort
8.0
Overall
8.0
Food
7.0
Reviews
1 / 20
2.0
MediocreMike,Aug 2025
OKC - AUS
Entertainment
7.5
Crew
8.6
Boarding
8.1
Comfort
8.0
Overall
8.0
Food
7.0
Reviews
1 / 20
2.0
MediocreMike,Aug 2025
OKC - AUS
Entertainment
7.5
Crew
8.6
Boarding
8.1
Comfort
8.0
Overall
8.0
Food
7.0
Reviews
1 / 20
2.0
MediocreMike,Aug 2025
OKC - AUS
Entertainment
7.5
Crew
8.6
Boarding
8.1
Comfort
8.0
Overall
8.0
Food
7.0
Reviews
1 / 20
2.0
MediocreMike,Aug 2025
OKC - AUS
Entertainment
7.5
Crew
8.6
Boarding
8.1
Comfort
8.0
Overall
8.0
Food
7.0
Reviews
1 / 20
2.0
MediocreMike,Aug 2025
OKC - AUS
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.
Browse thousands of different options on Cheapflights for your next trip
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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.
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 12 September 2025.
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.