Flights from New York to Chicago

Looking for flights from New York to Chicago? CompareWings brings you the latest offers, travel tips, non-stop airline options, and essential information to help you plan a smooth and comfortable journey from the Big Apple to the Windy City.

Route Overview

The New York to Chicago air route is one of the busiest and most vital business corridors in the United States. With immense demand for both corporate travel and leisure trips, airlines operate dozens of daily non-stop flights connecting the East Coast to the Midwest. The average flight duration is approximately 2 hours and 30 minutes, making it an easy trip for weekend getaways or same-day business meetings.

Travelers have extensive options with multiple airport combinations. You can fly from John F. Kennedy (JFK), LaGuardia (LGA), or Newark Liberty (EWR) into Chicago’s major hubs: O'Hare International Airport (ORD) or Midway International Airport (MDW).

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When’s a good time to book a flight New York to Chicago

What’s the cheapest day of the week to fly from New York to Chicago?

If you’re looking for a flight deals from New York to Chicago, it’s recommended to look for departures on Monday. Sunday tends to have higher prices.

What is the cheapest month to fly from New York to Chicago?

Historically, December has been the cheapest month for flights from New York to Chicago. On the other hand, the most expensive months tend to be May.

Airlines & Flight Options

  • Non-stop shuttle services available almost every hour from morning to night
  • Legacy carriers offering premium business class cabins and Wi-Fi
  • Budget airlines providing low-cost fares from secondary airports
  • Multiple airport combinations allowing flexibility based on your location in NYC or NJ
  • Red-eye and early morning options perfect for maximizing your day in Chicago

This highly competitive route ensures that passengers can choose between luxury, convenience, or the lowest possible fare depending on their needs.

Offers, Deals & Best Ways to Save

  • Business route promotions often available on weekends
  • Seasonal airline sales during shoulder seasons (Spring and Fall)
  • Flash deals on budget carriers for light travelers
  • Frequent flyer mile redemptions with high availability
  • Round-trip discounts for booking return legs together
  • Midweek fare drops (Tuesday and Wednesday are often cheapest)

Tips to Get the Best Deals

  • Compare airports: Flights from LGA or EWR might be cheaper than JFK.
  • Check alternative arrival airports: Flying into Midway (MDW) can sometimes save money compared to O'Hare (ORD).
  • Book in advance: Aim for 3 weeks prior for the best “sweet spot” rates.
  • Be flexible with times: Early morning flights (6 AM - 8 AM) are often discounted.
  • Travel light: Avoid checked bag fees by sticking to a carry-on.

Travel Tips for NYC → CHI Flyers

    Airport Access: Allow extra time getting to JFK or LGA due to New York traffic. EWR is often faster to access from Manhattan via NJ Transit.
  • Weather Preparedness: Chicago weather can be unpredictable. Pack layers, especially if traveling in winter or spring.
  • Public Transport: Both O'Hare (Blue Line) and Midway (Orange Line) offer direct, cheap train access into downtown Chicago (The Loop).
  • Security Lines: EWR and JFK can have long security wait times; consider TSA PreCheck or arriving 2 hours early.
  • Wi-Fi Availability: Most flights on this route are equipped with Wi-Fi due to the high volume of business travelers.

Frequently Asked Questions

The average flight time is approximately 2 hours and 30 minutes for non-stop flights, though actual air time is often shorter.

Departures are available from JFK, LaGuardia (LGA), and Newark (EWR). Arrivals land at either O'Hare (ORD) or Midway (MDW) in Chicago.

Yes, this is one of the most connected routes in the U.S., with major airlines operating frequent non-stop service daily.

January and February are typically the cheapest months to fly due to winter weather, while midweek flights (Tuesdays and Wednesdays) generally offer the best fares year-round.

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