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New York to Chicago

New York to Chicago

The Cheapest Flights from New York to Chicago

Departure atReturn atAirlineFind tickets
31 May 20232 June 2023Frontier AirlinesTickets from 296
14 June 202315 June 2023Spirit AirlinesTickets from 169
7 July 202311 July 2023United AirlinesTickets from 175
13 August 202316 August 2023United AirlinesTickets from 122
27 September 202327 September 2023United AirlinesTickets from 101
30 October 20233 November 2023United AirlinesTickets from 101

Cheap Flights from New York

DestinationDeparture atReturn atFind tickets
Orlando7 June 202310 June 2023Tickets from 91
Fort Lauderdale20 June 202324 June 2023Tickets from 98
Atlanta15 September 202320 September 2023Tickets from 100
Miami20 June 202324 June 2023Tickets from 112
Chicago5 September 20238 September 2023Tickets from 116
Tampa9 June 202313 June 2023Tickets from 132
Jacksonville19 July 202325 July 2023Tickets from 132
Detroit24 August 202327 August 2023Tickets from 134
Nashville14 July 202318 July 2023Tickets from 144
Washington21 December 202323 December 2023Tickets from 156

Cheap Flights to Chicago

OriginDeparture atReturn atFind tickets
Denver15 September 202317 September 2023Tickets from 110
New York5 September 20238 September 2023Tickets from 116
Miami6 June 20237 June 2023Tickets from 122
Dallas7 October 20239 October 2023Tickets from 145
Atlanta9 June 202312 June 2023Tickets from 145
Fort Lauderdale6 June 20237 June 2023Tickets from 167
Phoenix11 July 202315 July 2023Tickets from 220
Sioux Falls1 July 20234 July 2023Tickets from 223
Kansas City25 July 202326 July 2023Tickets from 225
Los Angeles3 June 20239 June 2023Tickets from 228

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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