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New York to Chicago

New York to Chicago

The Cheapest Flights from New York to Chicago

Departure atReturn atAirlineFind tickets
30 December 20235 January 2024Spirit AirlinesTickets from 150
9 January 202410 January 2024Spirit AirlinesTickets from 85
14 February 202414 February 2024Spirit AirlinesTickets from 87
1 March 20243 March 2024Spirit AirlinesTickets from 88
15 April 202419 April 2024American AirlinesTickets from 165
20 May 20244 June 2024American AirlinesTickets from 195
11 June 202416 June 2024Delta Air LinesTickets from 167
20 July 202420 July 2024Delta Air LinesTickets from 167
5 August 20247 August 2024Delta Air LinesTickets from 167
5 September 20245 September 2024JetBlue AirwaysTickets from 167
11 October 202411 October 2024JetBlue AirwaysTickets from 167
7 November 20248 November 2024United AirlinesTickets from 1 425

Cheap Flights from New York

DestinationDeparture atReturn atFind tickets
Miami8 January 202413 January 2024Tickets from 59
Indianapolis8 February 202410 February 2024Tickets from 66
Fort Lauderdale8 January 202413 January 2024Tickets from 71
Orlando8 January 202410 January 2024Tickets from 77
Charlotte13 December 202318 December 2023Tickets from 77
Chicago12 February 202415 February 2024Tickets from 82
West Palm Beach19 December 202324 December 2023Tickets from 84
Boston25 January 202426 January 2024Tickets from 126
Austin21 February 202422 February 2024Tickets from 134
Baltimore15 January 202417 January 2024Tickets from 139

Cheap Flights to Chicago

OriginDeparture atReturn atFind tickets
New York12 February 202415 February 2024Tickets from 82
Atlanta30 December 20233 January 2024Tickets from 84
San Diego11 January 202416 January 2024Tickets from 111
San Francisco11 January 202414 January 2024Tickets from 124
Los Angeles10 January 202411 January 2024Tickets from 134
Oakland22 January 202427 January 2024Tickets from 150
Ontario18 January 202424 January 2024Tickets from 152
Baltimore6 January 20249 January 2024Tickets from 161
Miami29 December 202331 December 2023Tickets from 191
Washington6 January 20249 January 2024Tickets from 199

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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