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From coast to coast and beyond, Chicago-based flyers are choosing private jets to unlock premium summer destinations in 2025.

Whether heading to the mountains, beaches, or international resorts, discover where Chicago’s elite are
flying this summer by private jet.

Chicago Business Leisure Charter Trends

Summer Private Jet Destinations from Chicago – 2025 Travel Trends

In 2025, Chicago’s private jet travelers are embracing bespoke luxury and seamless access to the country’s most exclusive summer getaways. From Lake Michigan views to international escapes, private charter activity is booming from the Windy City this summer season.

Top Private Jet Destinations from Chicago

  • Newport, Rhode Island – A favorite for yachting, coastal charm, and Northeast summer culture.
  • Aspen & Vail, Colorado – While known for winter sports, these mountain towns are thriving summer hotspots for hiking and luxury lodging.
  • The Hamptons, New York – East Coast glamour and private beach retreats

20 Years Industry Leading Service. The Most-Accredited Charter Brokerage Worldwide:

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  • 12 Separate Accreditations
  • Perfect Safety Record
  • Multi-Award Winning, A+ Rated
  • Charter's Most Experienced Team

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    “I have used New Flight Charters over the last 4-5 years and have been very pleased with the quality of service, follow up and competitive prices I have received. I will fly 6-7 times a year for both personal and business and always know I will be flying safely with high quality jets, qualified and personable pilots, at a fair price. Safety is never compromised and New Flight Charters is always accessible, and on short notice. It has been my pleasure to refer them to several of my friends and business associates.”
    - Bob H.Chicago WY
    “I submitted an online request for a quote to which Michelle responded directly, shepherded me through the process beautifully and managed all of my questions with terrific patience, kindness and professionalism.”
    - N. ChoudruhuriFacebook Inc.
    “The President’s trips are not simple and you’ve again handled it well. Thank you for your help this week.”
    - Travel Aid to Former-U.S. President
    “Please use FlightSafety as a reference. Every aspect of the trip was handled with professionalism. The pilot did an outstanding job and displayed to us that he was an expert at what he was doing.”
    - FlightSafety International
    “Another thing we really like about New Flight Charters is the excellent service provided by their personnel, who are always very prompt in responding to requests, courteous and a pleasure to deal with in every way …”
    - CKMRSanta Barbara CA
    “The flight went well as always, and the helicopter transfer was perfect for her flight schedule.”
    - Office of Sarah FergusonDutchess of York
    “When a friend recommended New Flight Charters, we were very impressed with the professional and helpful information we received. They have made planning our trips a breeze, and have the best pricing we have seen. …”
    - Ken StoweIdyllwild CA
    “Mr. Brokaw conveys his thanks for LA to Dulles. You are absolutely terrific to work with. We will continue to call you for future travel needs.”
    - Tom Brokaw's assistant
    “Once again your quotes were the most reasonable and the service was excellent as always.”
    - Lexington Financial Management
    “The trip yesterday was a success. Thank you very much. I will definitely recommend your services and be sure to contact you next time.”
    - Goldman Sachs Group
    “Thank you, everything went well. We would like to reserve a plane each Monday for the next two months.”
    - McKinsey & Company
    “You are at the top of our list. You’ve really proven yourselves as the best charter company to work with.”
    - Tahoe Mountain Resorts
    “The flight went well and was handled smoothly. He enjoyed the crew. We will call you next time.”
    - Office of Mexico President, Vicente Fox
    “I just wanted you to know everything went smoothly and we were happy with the service, transport etc. Thanks for all your help and I look forward to next time!”
    - Trinity Capital, LLC
    “Thank you for your quick response. I’ve called about 10 places and you’ve bee the best thus far. I called you last and you responded first. I really appreciate that!”
    FAA jet operator
    “The pilots were great and the flight worked out wonderful. We will contact you in the future.”
    - Empry Riddle Aeronautical University