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This Weekend's Flight Deals to Chicago

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Fares from $48 One Way, $95 Round Trip from New York to Chicago

Prices starting at $95 for return flights and $48 for one-way flights to Chicago were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Chicago economy flight packages

Chicago first class flight packages

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More About Flying To Chicago from New York

Route Information for Flights from New York to Chicago

Origin Airport IATA CodeNYC
Destination Airport IATA CodeCHI
Distance737 mi
Direct Flight AirlinesAmerican Airlines, Qatar Airways, KLM, Air Europa, Air France, Emirates, China Airlines, Delta Air Lines, El Al, Aerolineas Argentinas, Alaska Airlines, JetBlue Airways, LATAM Airlines, Hawaiian Airlines, Alitalia, Korean Air, Malaysia Airlines, Virgin Atlantic, Singapore Airlines, Gulf Air, British Airways
Earliest Flight Arrival1:29PM UTC
Latest Flight Arrival1:39AM UTC

Flights Review

Mar 1, 2020

Service was excellent. The flight was smooth

Feb 20, 2020

Always a pleasure flying with Delta. Staff is family-friendly too

Feb 19, 2020

Not that pleased with check in, had to check carry ons even though we had room in 1st class. The service was mediocre at best...I feel we would have had the same service on Business...

Feb 18, 2020

Love the free carryon

Feb 13, 2020

I'm still waiting for my luggage to make it, but I'm home safe and sound!

Feb 12, 2020

I’m not one who enjoys flying; it’s a necessary evil, but my 2 American Airlines flights were a breeze. I managed to sleep during the duration of the flight. The free internet was a plus, but it was especially slow so I didn’t use while I was awake and able b

Feb 5, 2020

I am a tall person. (6'0" )This flight had tight quarters and was tolerable for a 2 hr flight. I could see how others might have trouble.

Jan 31, 2020

Keep up the good work.

Jan 30, 2020

Friendly staff

Jan 25, 2020

Nothing else for a short flight

Millions of people fly between New York and Chicago each year, making it one of the world’s busiest air routes. If you want to join them, then Orbitz offers you all the cheapest flights to Chicago.


Popular Routes from New York to Chicago

New York has three major airports, John F. Kennedy International, LaGuardia and Newark Liberty in New Jersey, and you catch a direct flight to Chicago from any of them. Flights from JFK head to O’Hare International and from LaGuardia and Newark you can fly to both O’Hare and Chicago’s other main hub, Chicago Midway International.

More than four million people fly between the cities each year and there are scores of flights every day, taking off every few minutes from early in the morning to late at night.

Among the airlines with services between the cities are America, Delta, JetBlue, Southwest and United.


The Flight from New York to Chicago

The 730-mile journey from west from New York to Chicago usually takes around two and a half hours, although you will only spend around two hours in the air. During the trip your plane will reach speeds of 500mph and altitudes of 35,000 feet.

The exact flight path depends on weather conditions and other air traffic, but the usual route takes your aircraft up towards the Great Lakes, over Lake Erie across Michigan and into Chicago over Lake Michigan. If you are lucky, and have a seat on the right of the plane, you may even catch a glimpse of Niagara Falls on the way.

The five main airports in New York and Chicago are among the biggest in the US. All of them feature in the top 30 busiest airports in the country, and both Midway and O’Hare once held the title of the world’s busiest airport. Today the most popular route between the cities is from LaGuardia to O’Hare, with 1.6 million passengers each year. Around 700,000 people fly from Newark to O’Hare each year.

Although the flight is domestic, with quicker check in times than for international journeys, it is still a good idea to get to the airport well before takeoff. If you want to check in bags then remember to check if your ticket includes a luggage allowance – some airlines charge extra to put bags in the hold.

US citizens will need some form of photo ID to board the plane, non-US citizens should bring their passport.

Getting to LaGuardia is easy, you can get a taxi, shuttle or bus from Manhattan or Queens, and there are connections to the subway system. There are also long-stay parking lots near the airport if you plan to drive.

Whether you are flying from LaGuardia, JFK or Newark there is plenty to do once you have checked in, with bars, shops, restaurants and even spas where you can relax before you board your flight.

O’Hare is the third largest airport in the US with almost 80 million passengers a year, and more than 50 airlines flying to hundreds of destinations around the world, and you can get into the city center by rail, bus, shuttle or cab. If you book with Orbitz, you can reserve a rental car to collect at the airport.


Other Flight Destinations near the Great Lakes

If you want to explore the Great Lakes, or are looking for cheap flights to alternative destinations in the region, why not consider the following.

Flights from New York to Detroit

Flights from New York to Milwaukee

Flights from New York to Chicago - Frequently Asked Questions

Are there non-stop flights from New York to Chicago?

Yes, there are 13 airlines that fly nonstop from LaGuardia Airport (LGA) to O'Hare Airport. Find exactly what you need with one of these leading carriers:

  • Delta
  • American Airlines
  • American Airlines
  • Delta
  • United Airlines
What is the shortest flight from New York to Chicago?

It can zip by in as little as 2 hours and 24 minutes. If you think your vacation hours should be spent 'vacationing' instead of flying, you'll enjoy the ride from New York to Chicago.

What airlines fly from New York to Chicago most frequently?

We've pulled together a list of the airlines that have the most flights from LaGuardia Airport to O'Hare Airport. You're sure to find one that suits your travel plans: United Airlines - (UA) with 417 flights every month Delta - (DL) with 417 flights every month American Airlines - (AA) with 417 flights every month Delta - (DL) with 417 flights every month American Airlines - (AA) with 417 flights every month United Airlines - (UA) with 417 flights every month

If I am not able to travel due to COVID-19, can I cancel my flight to Chicago?

We get that traveling right now has its challenges, so it's good to know that many reservations booked through us are able to be cancelled or changed. If your travel plans to Chicago have been affected by COVID-19, a lot of airlines are making things easier by offering credits to use at a later date. Just sign in to your account and you'll quickly see what options are available. Our Customer Service Portal is the place to go for more information.

Are there flights to Chicago with flexible change policies?

In most cases you'll have the option to reschedule your flight to Chicago without a change fee. All you have to do then is pay the difference between the old flight and the new one. Look for the "no change fees" filter and book with confidence.

What is the cheapest day of the week to fly?

Consider flying out early in the week to save on your airfare. Orbitz data from 2020 shows that Monday is the cheapest day to depart, followed by Tuesday. Saturday showed the highest average ticket prices likely because many travelers prefer to start their vacation on a weekend.

What is the cheapest month to fly?

We won't keep you guessing, according to Orbitz data the cheapest month to fly is August. Perfect for those who need a weekend getaway, or just a break from it all before the weather changes. Be aware that the most expensive time to fly is the height of summer, with ticket prices peaking in the month of June.

How can I save money on flights?

To really save big on your next vacation, think outside the box. Select two different airlines or fare types for your return trip and you'll generally get a much better deal. Those who tried this on Orbitz in 2020 saved up to 45% on their airfares. Get mixing and matching today!

*According to flight demand on Orbitz.com from January to December 2020. Savings are subject to change based on departure location, date and destination.

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.