CAD 29 : Cheap Flights from Chicago to New York

Flight FAQs

• Which airlines offer the cheapest flights from Chicago (CHI) to New York (NYC)?

  Based on Trip.com data, Frontier Airlines offers one-way fares as low as CAD 29 on Cheapest nonstop routes (e.g. MDW to EWR on Tue, Jan 13), while Frontier Airlines offers Cheapest nonstop round-trips from CAD 70 departing on Thu, Jan 15 and returning on Thu, Jan 22.

• Which airlines offer direct flights from Chicago to New York?

  At the moment, you can catch a direct flight from Chicago to New York with the following airlines, including: Frontier Airlines Selected airlines are based on historical data collected from flight bookings users made on Trip.com within the last 90 days.

• How long is the flight from Chicago (CHI) to New York (NYC)?

  It takes about 2 hours 20 minutes to fly from Chicago (CHI) to New York (NYC).

• When is the best time to book flights from Chicago to New York?

  By analyzing data from all airlines on the Trip.com flight calendar, it looks like the best time to book a flight from Chicago to New York is around 40 days (6 weeks) in advance, and the best time to fly is usually on Tuesday, Wednesday, and Saturday. Tuesday typically offers the cheapest flights for departure, while Saturday offers the best return deals.

• How many flights are there per week from Chicago to New York?

  Based on Trip.com data in the past 4 weeks, there is 126 flight per week flying from Chicago to New York. You can check the weekly schedule for popular airlines on this route below: Delta Air Lines: S/M/T/W/T/F/S -- DL5680 (07:17)

• How can I find the best deals on flights from Chicago to New York?

  To find best deals on flights from Chicago to New York, you can use various tools on Trip.com:
  · Be flexible with your travel dates to get the cheapest flight deal. Now the cheapest flight deal is on Tue, Jan 13, with one-way flights priced at just CAD 29.
  · Compare airlines strategically. Budget carriers often provide the lowest base fares, while we found the most affordable airline currently operating on this route is Frontier Airlines.
  · Set up price alerts to easily monitor ticket prices without having to check every day.
  · Check Trip.com flight deals and promo codes frequently.
  · Avoid peak season unless you book very early. It seems the peak season for New York travel is around July.
  · Get exclusive promo codes for Trip.com app users.

• When is the best time to book a flight from Chicago to New York to get the best price?

  The cheapest months to fly from Chicago to New York is October, when demand for travel is lower.

• Which upcoming date is the cheapest for flights from Chicago to New York?

  After crunching the numbers on our December flight calendar, it's currently cheapest to fly from Chicago to New York on December 18, 2025 with Frontier Airlines, with prices starting at CAD 34.

• Which airports can I fly through when travelling to New York from Chicago?

  You can land at any one of the following hubs in New York, with Midway International Airport to Newark Liberty International Airport (MDW-EWR) is by far the most common option on this route: Newark Liberty International Airport (EWR) John F. Kennedy International Airport (JFK) LaGuardia Airport (LGA) New York Skyports Seaplane Base (NYS) Stewart International Airport (SWF).

• What is the time difference between Chicago and New York?

  The time difference between New York and Chicago is 1h.

• How can I change or cancel my flight ticket from Chicago to New York?

  Tickets can only be changed or cancelled if permitted by airline policy. To submit a change or cancellation request, go to the flight bookings page, select the option to change or cancel your booking, choose the relevant passengers and segment, and submit a request. Please note that additional charges may apply according to the airline ticket policy. However, if the flight has been rescheduled and you would like to change or cancel your ticket, you can submit an involuntary cancellation request. For more details about change and cancellation policies, please check the customer support pages.