Cheap flights from New York to Chicago from £54
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 6/9. 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
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 4 July 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 4 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 4 July 2025.
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 4 July 2025.
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
JFK - ORD
JFKORD
New York John F Kennedy Intl
Sat 30/8
19:29-21:47
Nonstop3h 18m
Chicago O'Hare Intl
Wed 3/9
07:00-10:23
Nonstop2h 23m
New YorkChicago
JFK - ORD
JFKORD
New York John F Kennedy Intl
Sat 30/8
20:30-22:28
Nonstop2h 58m
Chicago O'Hare Intl
Sat 6/9
08:34-12:00
Nonstop2h 26m
NewarkChicago
EWR - ORD
EWRORD
Newark
Wed 3/9
20:15-21:56
Nonstop2h 41m
Chicago O'Hare Intl
Sat 6/9
10:35-13:52
Nonstop2h 17m
New YorkChicago
LGA - ORD
LGAORD
New York LaGuardia
Tue 26/8
18:55-20:47
Nonstop2h 52m
Chicago O'Hare Intl
Wed 3/9
09:25-12:40
Nonstop2h 15m
New YorkChicago
LGA - ORD
LGAORD
New York LaGuardia
Thu 2/10
15:13-16:51
Nonstop2h 38m
Chicago O'Hare Intl
Mon 6/10
11:13-14:18
Nonstop2h 05m
New YorkChicago
LGA - ORD
LGAORD
New York LaGuardia
Sun 24/8
07:28-09:05
Nonstop2h 37m
Chicago O'Hare Intl
Tue 26/8
20:00-23:24
Nonstop2h 24m
NewarkChicago
EWR - ORD
EWRORD
Newark
Fri 24/10
13:23-22:28
1 stop10h 05m
Chicago O'Hare Intl
Sun 26/10
17:10-20:28
Nonstop2h 18m
New YorkChicago
JFK - ORD
JFKORD
New York John F Kennedy Intl
Tue 26/8
06:00-13:33
1 stop8h 33m
Chicago O'Hare Intl
Mon 1/9
19:46-10:28
1 stop13h 42m
NewarkChicago
EWR - ORD
EWRORD
Newark
Sat 30/8
13:00-16:13
1 stop4h 13m
Chicago O'Hare Intl
Wed 3/9
07:15-12:03
1 stop3h 48m
New YorkChicago
LGA - ORD
LGAORD
New York LaGuardia
Sat 23/8
14:30-22:00
1 stop8h 30m
Chicago O'Hare Intl
Mon 25/8
07:00-15:55
1 stop7h 55m
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.
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 4 July 2025.
It’s optimal to fly from New York to Chicago in the evening. By choosing this option you can save up to 60% 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 29 June 2025.
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
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 4 July 2025.
The most flights from NYC to CHI are scheduled on a Friday (169 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (51 on average).
How much does it cost for a return flight from New York to Chicago?
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 4 July 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
Overall
Comfort
Crew
Boarding
Food
Reviews
John,May 2025
PVD - BNA
Entertainment
Overall
Comfort
Crew
Boarding
Food
Reviews
John,May 2025
PVD - BNA
Entertainment
Overall
Comfort
Crew
Boarding
Food
Reviews
John,May 2025
PVD - BNA
Entertainment
Overall
Comfort
Crew
Boarding
Food
Reviews
John,May 2025
PVD - BNA
Entertainment
Overall
Comfort
Crew
Boarding
Food
Reviews
John,May 2025
PVD - BNA
Entertainment
Overall
Comfort
Crew
Boarding
Food
Reviews
John,May 2025
PVD - BNA
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 3 airlines flying from New York to Chicago
Discover the top 3 airlines 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 4 July 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.