Reserve your Private Jet to
Chicago, Illinois
Reserve your Private Jet to
Chicago, Illinois

Chicago Jet Charters

Make your Chi-Town jet charter reservations

Flex Air Charters provides an exceptional travel experience with Chicago jet charter for residents and visitors alike. Our company foundations are built upon the idea that no client should have to make the choice between comfort, safety or cost. Which is why we offer cost-effective solutions for Chicago jet charter that are operated at the highest safety and service levels in private aviation.

We offer complete travel options aboard the luxury aircraft we charter for our clients including tailored amenities such as customized entertainment, complimentary Wi-Fi, meeting rooms and satellite phones for conferencing on board and customized menu options for catering should you request it. Additionally our concierge agents can assist you in making reservations for accommodation, car services, and activities while you are in the Windy City, providing you with the most options to handle your travel needs with one phone call than any of our competitors.

We are dedicated to making your travel to or out of Chicago as seamless and safe as possible giving you a chance to truly enjoy your flight rather than worry about the next change an airline may impose on you, such as delayed baggage, long airport lines or crowded terminals. Your Chicago jet charter is tailored your way. Meaning you choose the time and place you wish to take off from, your aircraft, amenities, add-ons and more.

Chi-Town Awaits! Charter a Private Jet to Chicago Today!
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Chicago Private Airports and Heliports

One of the most dominant benefits of private travel is the ability to fly into not only commercial airports but also private airports thus increasing your number of landing locations. You have the ability to depart and arrive closer to your final destination when chartering a private jet. This also impacts cost as often commercial aircraft fly out of their way to reach a commercial airport rather than landing closer or departing closer to the travelers actual location. Chicago, with it’s popularity among travelers, has a large amount of airport traffic which means more locations to land and easier access for you once you do.

When you choose to reserve a Chicago jet charter with Flex Air Charters, you will have access to international airports such as Midway (MDW) and O’Hare Intl (ORD) as well as smaller, more personalized airports like (PWK) Chicago Executive and DuPage Airport (DPA). Additional amenities for jet charter clients at private airports include shorter or even nonexistent security check lines, easier baggage claim, the ability to drive up to the terminal itself and less crowded airports in general so you can get to your destination quickly. Additionally, some of these airports include exclusive meeting rooms, the ability to customize the terminal with corporate branding as well as luxury seating areas, restaurants and bars.

Flex Air Charters can also arrange helicopter transport to and from the airport of your choosing. Chicago provides access to three private heliports located throughout the city to make travelling to your hotel much easier without having to wait in traffic. Airports that Flex Air Charters can arrange your flight to depart or land from include but are not limited to:

  • O’Hare International Airport – Chicago, IL


  • DuPage Airport – West Chicago, IL

    (KDPA, DPA)

  • Lansing Municipal – Chicago/Lynwood, IL

    (KIGQ, IGQ)

  • Chicago Executive Airport – Wheeling, IL

    (KPWK, PWK)

  • Waukegan National Airport – Waukegan, IL

    (KUGN, UGN)

  • Schaumburg Regional – Chicago/Schaumburg, IL

    (K06C, 06C)

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Traveling to Chicago

Being the third most populated city in the US (behind NYC and LA), Chicago is considered the gateway to the midwest when it comes to air travel. Positioned along Lake Michigan, many air charter travelers stop in the city for layovers, or just to visit on their way to other destinations making Chicago the second most visited city in the United States. As this is the case, the O'Hare International Airport is one of the busiest airports in the world. With Flex Air Charters, you can arrive at one of the major airports like O’Hare or you can choose to land at one of the smaller private airports the city offers access to. Private air travel gives you this benefit of skipping the overcrowded airports and instead allows you the flexibility to land at a private, non-busy airport instead.

Flex Air Charters has built relationships with operators all around the world, allowing us to offer a varied fleet and access to more locations for you to arrive at your Chicago jet charter. Some of the aircraft included in the fleet include: Cessnas, Cirruses, Gulf streams, Challengers, Hawkers, and even VIP airliners for larger parties, business retreats, sports teams, and more. We are available to discuss your aircraft and amenity options 24 hours a day, 7 days a week and we provide free quotes after discussing your personal travel needs. Whether it be for corporate or business jet charter services, or if you and a group of people are headed to Chicago for vacation, we can arrange a tailored flight experience that suits your budgetary requirements and an itinerary developed to make your trip comfortable and stress-free.

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What to do when you are in The Windy City

Whether you are visiting the city on business or for personal reasons, Chicago has something specifically for you. Most business clients visit this major financial center for the Chicago Stock Exchange, the Chicago Board Options Exchange (CBOE), and the Chicago Mercantile Exchange (the "Merc"). While we see clients visit with their friends and families for the Chicago Symphony, Wrigley Field and for a visit to the Art Institute of Chicago.

If you are staying in Chicago, Flex Air Charters can offer a full concierge service to assist you with accommodations at any one of Chi-Town’s 600+ hotels including:

Top Attractions for Those Visiting Include

  • Million Dollar Quartet

  • Symphony Center – Chicago Symphony Orchestra

  • Jay Pritzker Pavilion

  • Lyric Opera of Chicago

  • Cloud Gate

  • Millennium Park

  • Chicago Shakespeare Theater on Navy Pier

  • Museum of Science and Industry

  • 29 miles of Lakefront Paths


  • Four Seasons Chicago

  • Trump International Chicago

  • The Ritz-Carlton

  • The Peninsula Chicago

  • Fairmont Chicago

  • The Drake

  • Conrad Chicago

  • Museum of Science and Industry

  • The Park Hyatt

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