Planning a quick getaway from New York to Chicago? FareRadius helps you find the best deals for a weekend trip. You'll typically fly from Newark Liberty International Airport (EWR) to O'Hare International Airport (ORD). While direct flights are available, sometimes a flight with one transfer can save you money, especially if you have a bit more time.
The cheapest time to fly from New York to Chicago is often in December, with prices as low as $86. If you can be flexible with your travel dates, our calendar below will show you the best fares. Direct flights are offered by American Airlines, Southwest Airlines, and United Airlines, with the fastest trip taking just 2 hours and 25 minutes.
FAQ
How much is a flight from New York to Chicago?
The cheapest one-way ticket is $86 right now (Dec 9, Frontier Airlines, 1 stop).
Are there nonstop flights from New York to Chicago?
Yes — American Airlines, Southwest Airlines, United Airlines fly nonstop; the flight takes about 2h 25m.
When is it cheapest to fly from New York to Chicago?
in December from $86; priciest in April (from $176).
Which New York airport should I fly from to Chicago?
For flights to Chicago, you will typically depart from Newark Liberty International Airport (EWR).
What is the best way to find the lowest price for a New York to Chicago flight?
To catch the lowest price, consider being flexible with your travel dates. December 2026 currently offers the cheapest fares at $86. Our calendar below can help you spot the best deals.