New York to Chicago

The Cheapest Flights from New York to Chicago

Departure at	Return at	Airline	Find tickets
28 May 2025	31 May 2025		Tickets from 127
10 June 2025	12 June 2025		Tickets from 83
19 July 2025	20 July 2025		Tickets from 121
20 August 2025	22 August 2025		Tickets from 132
4 September 2025	7 September 2025		Tickets from 107
25 October 2025	27 October 2025		Tickets from 115

Cheap Flights From New York (JFK) to Chicago (CHI)

The Windy City is a popular travel destination for both business and leisure travelers. You’ll find a thriving art scene, lots of social attractions, and an impressive array of shopping locations in this vibrant metropolis.

Luckily, there are many cheap ways to get from New York to Chicago. The average flight time is two hours and ten minutes, making it a quick and convenient journey. If you’re able to avoid peak travel times, such as during holidays and school breaks, you can often snag an even better deal on flights from NYC to ORD.

One of the best ways to find cheap flights from New York to Chicago is to keep an eye on airfare trends. Fares fluctuate constantly, so it’s important to monitor price fluctuations and be ready to jump on a great deal when it appears. It’s also a good idea to sign up for a flight alert. This way, you’ll be notified when prices are low and can easily book your ticket.

It’s a common myth that you can only find cheap flights on Tuesdays or big travel days like Black Friday and Travel Tuesday, but this isn’t always the case. In reality, it’s more about timing than anything else. Flights to Chicago tend to be cheaper on Tuesdays and Wednesdays than they are during weekends or major holidays, so if you’re flexible with your dates, it’s a good idea to search on these non-peak days.

The cheapest flights from New York to Chicago are found on Southwest Airlines. This airline offers competitive prices throughout the year and frequent sales on this route. If you have flexible dates, plug them into the Southwest Low Fare Calendar to see which days offer the lowest fares. You can also browse Southwest Vacations to find special deals on flights, hotels, rental cars, and more.

Another way to save on New York to Chicago flights is to search for multi-stop flights. These routes allow you to explore a few different destinations on your trip and often cost less than direct flights. Plus, you can get to know a bit of the culture of a new city along the way.

Flair Airlines is bringing a new low-cost option to Toronto, launching flights from Toronto to both New York and Chicago this spring. Expect fares to start around $84 one-way, which is significantly less than what you’ll pay for an Air Canada or United flight. The only drawback is that it takes a little longer to reach your final destination. Still, if saving money is your top priority, it’s definitely worth considering this option.