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New York to Chicago

New York to Chicago

The Cheapest Flights from New York to Chicago

Departure atReturn atAirlineFind tickets
28 May 202531 May 2025Spirit AirlinesTickets from 127
10 June 202512 June 2025Spirit AirlinesTickets from 83
19 July 202520 July 2025Spirit AirlinesTickets from 121
20 August 202522 August 2025Spirit AirlinesTickets from 132
4 September 20257 September 2025Spirit AirlinesTickets from 107
25 October 202527 October 2025Spirit AirlinesTickets from 115

Cheap Flights from New York

DestinationDeparture atReturn atFind tickets
Fort Lauderdale14 June 202517 June 2025Tickets from 81
Miami14 June 202517 June 2025Tickets from 81
Chicago10 June 202512 June 2025Tickets from 82
Atlanta18 September 202522 September 2025Tickets from 101
Detroit23 September 202526 September 2025Tickets from 104
Charlotte10 June 202516 June 2025Tickets from 104
Raleigh/Durham28 June 20253 July 2025Tickets from 105
Houston18 July 202523 July 2025Tickets from 108
New Orleans5 June 20258 June 2025Tickets from 116
Nashville9 June 202513 June 2025Tickets from 116

Cheap Flights to Chicago

OriginDeparture atReturn atFind tickets
New York10 June 202512 June 2025Tickets from 83
Miami14 June 202518 June 2025Tickets from 115
Los Angeles23 August 202526 August 2025Tickets from 115
Fort Lauderdale14 June 202518 June 2025Tickets from 125
Boston23 August 202526 August 2025Tickets from 130
Atlanta5 June 20257 June 2025Tickets from 133
Denver9 October 202513 October 2025Tickets from 159
Ontario30 May 20253 June 2025Tickets from 177
Baltimore29 May 202531 May 2025Tickets from 178
Fort Myers3 October 20256 October 2025Tickets from 192

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.

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