New York to Chicago

Are you planning a trip from NY to Chicago?

If so, you could opt to drive the 790 miles inland, or take a commercial flight, arriving at your destination frazzled and exhausted. Or, you could board a private jet, travel in style and land refreshed and ready for action.

When you take a private plane, there are no layovers, missed connections, or traffic jams to contend with. You’ll arrive ready to enjoy all the best that the Windy City has to offer. Whether you’re traveling for business or pleasure, you’ll find there are plenty of options for recreation and entertainment within your reach in this bustling metropolis.

Today, we’re letting you in on the reasons why more people are choosing to fly private with XO than ever before and how we can make your journey as convenient and comfortable as possible.

Ready to find out more? Let’s get started!

What does a Private Jet Charter from NY to Chicago Cost?

When you take all the benefits of chartering a jet into consideration, it will amaze you how affordable they can be. These are our current rates for flying from New York to Chicago:


Low - $9,900

High - $12,160


Low - $13,976

High - $18,926


Low - $23,623

High - $42,178

Please note that all prices are subject to fluctuation and change.

Getting Started on Your Journey: Choosing Your Private Flight

When you need to book a last-minute trip, you need private aviation options that are available at a moment’s notice. That’s why XO offers a centralized platform that allows you to choose between three different flight options, according to your needs. Flyers traveling from New York to Chicago have access to all three of these options. Here’s what you can expect from each one:

XO Private Charter Flights

XO Private Charter

Are you interested in booking a private charter?

When you’re ready, you can take advantage of on-demand charter access to our remarkable fleet of 160 private aircraft, all owned by our group companies. If you need something a little different, we offer an additional partner network of over 2,100 jets worldwide.

Our jets feature cabin classes ranging from light to long-range, suitable for a variety of scenarios. You can quickly learn more about each jet, along with its main amenities and features when you book online or via our state-of-the-art XO app.

If you need further assistance, your dedicated Aviation Advisor will guide you through each step to guarantee a seamless trip from the outset.

XO Shared Charter

XO Shared Charter

Are you interested in flying on a private charter, but not excited about the idea of reserving every seat on the plane? Our Shared Charter option is the answer, allowing you to offset your investment. If anyone books the extra seats after you set up your charter, you’ll gain flight credits to use on future flights, upgrades or extra seats!

Fly By The Seat

Fly By The Seat

Are you traveling with a small group from New York to Chicago?

If so, you can choose to fly by the seat and offset the costs even more. How does this work? Search for flights that are already traveling to your destination during your timeframe by logging onto our app. Next, reserve a seat on an existing flight. You’ll get to enjoy all the perks of flying privately at the most affordable rate!

What Makes XO Special?

Why should you take the time and spend the money to book a private jet with XO? After all, there are so many flights departing from New York to Chicago every day. The simple answer is that our user-friendly platform makes it so easy to curate the perfect flight for your mission.

Flexible Booking Options

Whether you’re planning an extravagant, weeklong vacation with a dozen or more friends or you’re traveling alone for a quick and easy work trip, we can help you make the most of your time in the sky.

Message Center

When you use our XO app or online scheduling tool, a dedicated Aviation Advisor works with you from the start. With their expert help, you can easily find the ideal flight that suits your budget, timeline, and expectations.

Message Center

After that, you’ll move on to our experienced Client Service professionals, who are at hand 24/7 to answer any questions and coordinate every aspect of in-air services, from the concierge to the catering.

Thanks to our easy-to-use platform and friendly, efficient team, it’s easy to find your perfect flight and even cancel a reservation if your needs change.

The XO App

By definition, frequent fliers are always on the go. That’s why we’ve made it simpler than ever before to book private flights when you need them. With the XO App, you can book your next private flight anytime from anywhere in the world.

Once you’ve downloaded the app, you become part of our seamless XO Experience. We don’t frustrate you with complicated choices, industry jargon, and confusing processes. Our live support crew is available at your fingertips to help you get where you need to go quickly and efficiently. All it takes is a few clicks.

Membership Plans

There’s one more thing that sets XO apart from the competition.

Our scalable membership plans offer customers several perks according to their travel needs and preferences. These include:

Pay as you go

Find out more about each plan here, and see a summary of what each one entails. We offer a convenient range of options for every traveler, whether you’re booking seats on an existing flight, selling seats on your flight or creating a new charter flight.

You’ll always have maximum flexibility and more options with an XO membership, whether you’re selling seats on your flight, booking seats on an existing flight, or creating a new flight. You’ll also have access to some of the best prices on charters!

Flying Out of New York

New York is home to several excellent airports, but only a select few can accommodate private flights.

The leading airports for private charter flights and business jets include:

Teterboro Airport


Long Island MacArthur Airport


Republic Airport (Farmington)


Westchester County Airport (White Plains)


Flying Into Chicago

Likewise, when you’re flying into Chicago from New York, there are several airports capable of receiving executive and leisure private aircraft. The most popular ones are:

These include:

Chicago Executive Airport


DuPage Airport


Midway International Airport


O’Hare International Airport


Waukegan National Airport


Where to Eat in Chicago

Chicago is a foodie’s paradise and was recently hailed as the food and drink capital of the world. During your visit, you’re sure to find out why. Here are some don’t miss restaurants to help you choose from the wide array of options available:

Band of Bohemia


Cellar Door Provisions

Lula Café

Fat Rice

Mi Tocaya Antojería



Honey Butter Fried Chicken

Smoque BBQ

Where to Stay in Chicago

While overnighting in Chicago, you want accommodations that match your plush in-flight experiences. These top-rated hotels offer a restful, relaxing, and luxurious stay:

The Peninsula Chicago

The Ritz-Carlton, Chicago

Four Seasons Hotel Chicago

Park Hyatt Chicago

The Langham, Chicago

Thompson Chicago

Waldorf Astoria Chicago

The Blackstone, Autograph Collection

Trump International Hotel & Tower Chicago

The Talbott Hotel

What to Do in Chicago

With the sixth-largest freshwater lake in the world on your doorstep, you’d be missing out if you didn’t head out onto the water during your trip to Chicago.

All along the city’s imposing shoreline, you’ll find opportunities to enjoy water sports, cruises, and scenic trips. Don’t miss the chance to lap up the luxury with one of the following:

Chicago Yachting

Odyssey Lake Michigan

Elite Private Charters


Invert Sports

Shoreline Sightseeing

Jet Ski Chicago

Spirit of Chicago

Mystic Blue

Tall Ship Windy

Chicago is well-known for its excellent museums, but there are plenty of other opportunities for amusement in town. These are the top ten:

Buckingham Fountain

Millennium Park

Cloud Gate

Navy Pier

Garfield Park Conservatory

Symphony Center

Grant Park

Willis Tower Sky Deck

Magnificent Mile

The Riverwalk

The Weather in Chicago

Are you wondering what to pack for your trip to Chicago? The city may have experienced some chilly temperatures of late, but you may want to check the forecast before you pack your bags.


The average temperature in Chicago varies wildly during the year. In summer, the city is hot and humid, while the winter months are snowy and cold. The warmest month of the year is July, while January sees the mercury plunge to annual lows.

Travel From New York to Chicago in Style

Whenever you travel from NY to Chicago, you’re assured of maximum comfort and convenience when you charter one of our planes.

We deliver a world-class flight experience, no matter which one of our jets you choose. Our fleet of aircraft is one of the world’s most elite and varied offerings while our packages offer the widest variety in the industry today.

We’re based across the United States as well as in Europe and the Middle East, so we’re always on hand to assist you with our range of exceptional private jets.

Get in touch today to find out more about how you can take your travels to the next level and fly in style wherever you go.

Happy flying!