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Cheap Flights From Nyc To Chicago

How Long In Chicago Or New York City

Flight costs expected to drop

Both Chicago and New York City have a number of activities to choose from. With generally more activities and things to do, visitors tend to spend more time in New York City than Chicago.

The ideal length of time for a trip to Chicago is 3-5 days, and the ideal length of time for a trip to New York City is 3-7 days.

  • How many days in Chicago or New York City?Ideal Length of StayChicago3-5 New York City 3-7

One day in Chicago or New York City?

Chicago is a bustling city that offers something for everyone. Your budget might influence how long you stay. Since there is so much to do in the area, one day is probably not enough for all of it.

In New York City, youll find food and shopping. This city offers something for everyone. One day is usually not enough time for a trip here as there is plenty to do.

A weekend in Chicago or New York City?

Its hard to know how much time to spend in Chicago. It has many unique tourist attractions and fascinating things to do. A weekend is usually not enough time for a trip here as there is plenty to do.

In New York City, youll find shopping and museums. The length of your trip often depends on your style of travel. Since there is so much to do in the area, a weekend is probably not enough for all of it.

Five days in Chicago or New York City?

A week in Chicago or New York City?

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 OHare International and from LaGuardia and Newark you can fly to both OHare and Chicagos 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.

Related Info For Your Journey

Useful info, stats and facts about New York to Chicago flights.

Chicago, with its dramatic location along the shores of Lake Michigan, is the professional, business, educational and cultural hub of the Midwest. When in Chicago, you have a wealth of choices, whether you prefer to tour architectural masterpieces, take in the top comedy improv groups in the country, attend a Chicago Cubs game at Wrigley Field, or just get some business done. Not surprisingly, it’s easy to find flights between the first and third-largest cities in the United States: New York City and Chicago.

How long is the flight from New York City to Chicago?

The flight from New York City to Chicago, just over 700 miles, will take you slightly less than two hours. Add to that the time spent getting to and from your gate, which may vary depending on the airport you choose.

Which airlines operate flights from New York City to Chicago?

With two airports to choose from in Chicago and three in the area of New York City, you have a wide variety of airlines to choose from when booking your flight. Check out flights from American, Delta, jetBlue, Spirit, United and Southwest to find the right combination of time and price.

How frequent are flights between New York City and Chicago?

With almost 100 flights running from New York’s three airports to Chicago each day, you should be able to find a flight that meets your schedule. Flights begin at 6 a.m. each day, with the last flight departing shortly before midnight.

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Where Does The Bus Arrive In New York

Image credit: Rob Young

Main arrival station: Port Authority Bus Station

Port Authority Bus Terminal is the largest bus station in New York City. First opened in 1950, it is the main Manhattan bus stop for various regional and nationwide bus carriers that provide intercity transportation to and from NYC such as Greyhound, NY Trailways, Peter Pan Bus Lines, and Ourbus, among many others. Port Authoritys central location just steps away from Times Square provides easy connections to various other forms of transportation, including 13 lines of the NYC Subway, 11 lines of the NYC Bus, over 60 lines of the NJ Transit Bus, and shuttle services to each of the three airports in New Yorks metropolitan area. At the terminal, you will find a variety of fast food restaurants and convenience stores, as well as a USPS branch and a bowling alley.

All bus stations in New York:

  • Port Authority Bus Station

The Flight From New York To Chicago

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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 OHare once held the title of the worlds busiest airport. Today the most popular route between the cities is from LaGuardia to OHare, with 1.6 million passengers each year. Around 700,000 people fly from Newark to OHare 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.

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How Far Is It The Other Way

The distance is the same either way if youre flying a straight line . But for a real trip, there can be plenty of differencesso go ahead and check the reverse directions to get thedistance from New York City to Chicago, or go to the main pageto calculate the distance between cities.

If you happen to know Chicago, dont forget to help othertravelers and answer some questions about Chicago!

Chicago To New York City Route

service waypoints


This route can be ridden from mid-spring to mid-fall. Expect high temperatures and humid conditions during the summer. In Indiana, prevailing winds are from the southwest during most of the year. Watch for tornadoes in the spring. Due to changing local conditions, it is difficult to predict any major wind patterns along the remainder of the route.

Services are generally plentiful, though there will be occasional exceptions. Multiple bike shops are located in the larger metropolitan areas. To camp every night, you will need to plan your overnights carefully and ride off the route. Very few campgrounds are located on route.

Some cyclists may want to ride this route during the colors of autumn. If you do, call ahead to verify campground availability because many close after Labor Day. If staying indoors, make advance reservations.

Some campgrounds will charge a cyclist traveling alone less if they have hiker/biker sites, but often they will charge the price of a regular tent site, and that can easily be $10-$20/night. If youre friendly and ask around, you can often get yourself invited to camp in a yard. Many small town city parks are free to camp in.

You may also wish to sign up with Warmshowers, a reciprocal hospitality site for bicycle travelers, for other overnight options.

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Tips For Your Stay In Chicago

  • Chicago is a big and busy city, and youll want to stay aware of your surroundings to keep yourself and your family and friends safe. Keep purses and valuables close to your person, or better yet, leave them in an in-room safe before you head out for the day.
  • Security at Chicagos attraction is generally a given, and your bags and belongings will be searched, making this another good reason to travel lightly as you tour the citys treasures.
  • Traffic throughout the Chicago area is heavy, with rush hour lasting basically throughout the day. Consider budgeting a taxi into your visit or use the subway to get around town.
  • Theres a lot to see when you visit Chicago, and youll want to plan your days accordingly. Consider investing in a Go Chicago pass, which lets you add the attractions to one convenient card that saves you money on admissions.

What Is The Cheapest Month To Fly To Chicago

The cheapest ticket to Chicago found for each month in 2023 based on historical flight searches by Cheapflights users.


Currently, the cheapest month for flights to Chicago is . The most expensive month for flights is . The cheapest prices are shown above but prices will vary according to departure times, airlines, class and how early you book.

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Best Places To Stop Between Chicago And New York City

So, while you could technically make the journey in one day, particularly if you use the direct route, its not going to be much fun for anyone involved.

The most common strategy likely to be taken will be to split the journey into 2 days, with a stop around the halfway point.

Were road trippers though, so making the most of our journey is much higher up the agenda than a speedy arrival, so splitting it into 3 days would ensure we can do just that.

In fact, for some, even 3 days might not be enough. Instead, lets say well be staying at 3 locations as opposed to stating how many days it will take.

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Which City Is Cheaper New York City Or Chicago

These are the overall average travel costs for the two destinations.

Hired Cars and Shuttles in New York City

Also for New York City, here are a few examples of actual transportation services:

  • Airport Limousine Transfer one-way John F Kennedy Airport Lincoln MKT:$239
  • Airport Limousine Transfer one-way LaGuardia Airport Lincoln MKT:$194
  • Airport Limousine Transfer one-way Newark Liberty International Airport MKT:$256
  • JFK Executive Class Airport Sedan/SUV/Van Transfer:$119
  • Manhattan Private Luxury Transfer to NYC Airports:$98
  • New York Airport Luxury Departure Transfer via Stretch Limousine, SUV, Sedan:$100
  • New York Airport Luxury Transfer : New York City to Newark Airport:$181
  • New York Airport Private Luxury Departure transfer via Sedan, Limousine or SUV:$159
  • New York Airport Transfers: New York to J.F. Kennedy Airport JFK in Business Car:$124
  • New York City Shared Shuttle Departure Transfer: Hotel to NYC Airports:$30
  • New York JFK Airport Departure Transfer :$216
  • Private Airport Transfer in New York:$180
Is it cheaper to fly into Chicago or New York City?

Prices for flights to both New York City and Chicago change regularly based on dates and travel demand. We suggest you find the best prices for your next trip on Kayak, because you can compare the cost of flights across multiple airlines for your prefered dates.

Food Tours and Cooking Classes in Chicago

Also, here are some specific examples of food and dining related activities in Chicago.

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The Southwest Travel Experience

Chicago Midway International Airport is a quick 30-minute ‘L’ ride from downtown Chicago. Get goingadventure awaits.

At Southwest, we know it takes more than great deals on Chicago airfares and convenient scheduling options to make your trip memorable. So from booking to boarding, we offer services and features designed to make your travel from New York to Chicago the best it can be. Learn more about the Southwest® travel experience before you book your flight from LaGuardia Airport to Chicago Midway International Airport.

Flying with Southwest is simple and fun, no matter which of our dozens of exciting destinations you choose. When you search for your next flight to Chicago , know that you wont be surprised at checkout. Low fares and no hidden fees. That’s Transfarency®. And as always, two bags fly free®1. Want the latest news, information, and promotional offers from Southwest? from us. Book your flight today and know that you’ll earn Rapid Rewards® points when you fly.

1First and second checked bags. Weight and size limits apply.

2Fare difference may apply.

3Failure to cancel a reservation at least 10 minutes prior to departure may result in forfeited Travel Funds.

4Flight credits unexpired on or created on or after July 28, 2022, do not expire and will show an expiration date until our systems are updated. See full details here.

5Available only on WiFi-enabled aircraft. Limited-time offer. Where available.

Cheap Flights From New York To Chicago In December January 2022

Are you planning to visit New York John F Kennedy (JFK) from Chicago ...
The best prices found for NYC to CHI flights for December, January

Deal found 12/11

  • One of the most popular airlines traveling from New York to Chicago is Frontier. Flights from Frontier traveling this route typically cost $286.37 RT. This price is typically 40% cheaper than other airlines that offer New York to Chicago flights. When booking this route, the cheapest RT price found was $95. New York John F Kennedy Intl Airport is the most common New York airport to take off from when flying to Chicago. Chicago O’Hare Intl Airport is the most popular arrival airport in Chicago. When flying from New York to Chicago, Frontier flights are 20% more popular than any other airline flying that same route.

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New York To Chicago Flight Schedule

Scan through flights from LaGuardia Airport to O’Hare International Airport for the upcoming week. Sort the list by any column, and click on a dollar sign to see the latest prices available for each flight.

Flights.com only offers pricing for airlines that display a check fare on the days of the week each flight is available. A dot indicates a flight is scheduled, but online booking is not currently available.

Can I Get A Direct Flight From New York To Chicago

Yes the average flight time is 2 hours and 43 minutes.

This information is correct as of February 2016

Airlines that fly from New York to Chicago

Theres a good selection of airlines providing direct flights from New York to Chicago. There are Delta, United, American Airlines and Spirit Airlines flights from LaGuardia Airport. United and American Airlines also offer flights from New York Newark Airport and both Delta and American Airlines also fly from New York John F. Kennedy Airport. All of these flights arrive to Chicago OHare International Airport.

Terminal Information

New York LaGuardia Airport

LaGuardia is located north of Queens, 12 miles from New York city centre. There are four terminals at the airport, all connected by walkways and buses. Delta flights to Chicago depart from Terminal A whilst all other flights to Chicago depart from Terminal B.

In Terminal A there are convenience stores, WorldBean and Yankee Clipper food outlets, device charging stations and cash machines. Terminal B is much bigger and has a greater selection of food, drink and shopping venues. Theres Auntie Annes, Figs Café, Metro Burger Bar and MexiJoes for a bite to eat, and Lacoste, Desigual, Hudson and a duty free store for a little retail therapy. Complimentary Wi-Fi for up to 30 minutes is available throughout both terminals.

New York John F. Kennedy Airport

New York Newark Airport

Chicago OHare International Airport

Practical Information

What to Expect in Chicago

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Cheap United Airlines Flights From New York To Chicago

Deal found 12/8

  • One of the most popular airlines traveling from New York to Chicago is United Airlines. Flights on this route from United Airlines typically cost $279.60 RT, a price that is 56% more expensive than the average New York to Chicago flight. The cheapest flight found was $94 RT. When traveling from New York to Chicago on United Airlines, the most popular airport to depart from is New York John F Kennedy Intl Airport and the most popular airport to arrive at is Chicago O’Hare Intl Airport. When flying from New York to Chicago, United Airlines flights are -100% more popular than any other airline flying that same route.

How To Get The Cheapest Flight Ticket From New York To Chicago

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Look no further. We’ve gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

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

What is the cheapest day to depart New York for Chicago?

Tuesday. The cheapest day of the week is typically Tuesday. The most expensive is typically Friday

When is the cheapest time to fly from New York to Chicago?

in the morning. New York to Chicago flights are approximately 5% more expensive in the afternoon than in the morning

What is the cheapest airline that flies to Chicago from New York?

What is the cheapest New York to Chicago flight route?

New York LaGuardia – Chicago O’Hare Intl. Fly from New York LaGuardia to Chicago O’Hare Intl for the best New York – Chicago flight prices

How far in advance should you book New York to Chicago flights?

27 days before. The cheapest time to buy a flight from New York to Chicago is approximately 27 days to departure
Newark Airport to Chicago O’Hare Intl Airport $150
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