Private Jets from Chicago, Illinois to San Diego, California to Chicago, Illinois

Round Trip Private Jets From Chicago, Illinois to San Diego, California to Chicago, Illinois

    Suggested Aircraft

    The ideal option for your trip based on your preference for:

    Short Notice: Due to high demand our team has to confirm crew availability. Call us at (332) 241-5100

  • Super-Midsize Cabin Jet

    Bombardier Challenger 350, Gulfstream G200, Cessna Citation X or similar

    8
    Thursday, October 22nd
    5:00am ORD
    3h 23m Nonstop
    6:23am SAN
    Friday, October 23rd
    5:00am SAN
    2h 56m Nonstop
    9:56am ORD
    $75,794 Plus $5,753.35 tax
    Hello, Time Traveller (332) 241-5100 Flights in the past aren't available for instant booking... yet. Call now to book your flight.
    Real-Time Eligible Aircraft

    Out of 525 Super-Midsize Cabin Jets, only 25 aircraft are eligible for your trip based on scheduled position, real-time availability, and price.

    If you book this Super-Midsize Cabin Jet now, you'll be flying on a Bombardier Challenger 350, Gulfstream G200, Cessna Citation X or similar with recovery guaranteed.

    Every aircraft is hand-vetted to ensure a quality, consistent experience.

    • ARGUS, WYVERN, or ISBAO audited
    • $50m+ Liability Coverage Limits
    • Manufactured or Refurbished within 5 years on average
    • Approved and verified models only

  • Small Cabins

    Our small cabins are ideal for shorter trips with up to 4-6 passengers

    Short Notice: Due to high demand our team has to confirm crew availability. Call us at (332) 241-5100

  • Light Cabin Jet

    Cessna Citation Encore, Beechcraft Hawker 400XP, Beechcraft Beechjet 400A or similar

    8
    Thursday, October 22nd
    5:00am ORD
    4h 17m 1 Stop
    7:17am SAN
    Friday, October 23rd
    5:00am SAN
    3h 39m Possible Stop
    10:39am ORD
    $53,103 Plus $4,051.53 tax
    Hello, Time Traveller (332) 241-5100 Flights in the past aren't available for instant booking... yet. Call now to book your flight.
    Real-Time Eligible Aircraft

    Out of 1144 Light Cabin Jets, only 20 aircraft are eligible for your trip based on scheduled position, real-time availability, and price.

    If you book this Light Cabin Jet now, you'll be flying on a Cessna Citation Encore, Beechcraft Hawker 400XP, Beechcraft Beechjet 400A or similar with recovery guaranteed.

    Every aircraft is hand-vetted to ensure a quality, consistent experience.

    • ARGUS, WYVERN, or ISBAO audited
    • $50m+ Liability Coverage Limits
    • Manufactured or Refurbished within 5 years on average
    • Approved and verified models only

  • Medium Cabins

    Our medium cabins offer longer range with more cabin space for groups of 6-9 passengers

    Short Notice: Due to high demand our team has to confirm crew availability. Call us at (332) 241-5100

  • Midsize Cabin Jet

    Bombardier Lear 45XR, Bombardier Lear 75, Cessna Citation XLS or similar

    8
    Thursday, October 22nd
    5:00am ORD
    4h 2m 1 Stop
    7:02am SAN
    Friday, October 23rd
    5:00am SAN
    3h 25m Nonstop
    10:25am ORD
    $55,135 Plus $4,203.92 tax
    Hello, Time Traveller (332) 241-5100 Flights in the past aren't available for instant booking... yet. Call now to book your flight.
    Real-Time Eligible Aircraft

    Out of 1268 Midsize Cabin Jets, only 35 aircraft are eligible for your trip based on scheduled position, real-time availability, and price.

    If you book this Midsize Cabin Jet now, you'll be flying on a Bombardier Lear 45XR, Bombardier Lear 75, Cessna Citation XLS or similar with recovery guaranteed.

    Every aircraft is hand-vetted to ensure a quality, consistent experience.

    • ARGUS, WYVERN, or ISBAO audited
    • $50m+ Liability Coverage Limits
    • Manufactured or Refurbished within 5 years on average
    • Approved and verified models only

  • Super-Midsize Cabin Jet

    Bombardier Challenger 350, Gulfstream G200, Cessna Citation X or similar

    8
    Thursday, October 22nd
    5:00am ORD
    3h 23m Nonstop
    6:23am SAN
    Friday, October 23rd
    5:00am SAN
    2h 56m Nonstop
    9:56am ORD
    $75,794 Plus $5,753.35 tax
    Hello, Time Traveller (332) 241-5100 Flights in the past aren't available for instant booking... yet. Call now to book your flight.
    Real-Time Eligible Aircraft

    Out of 525 Super-Midsize Cabin Jets, only 25 aircraft are eligible for your trip based on scheduled position, real-time availability, and price.

    If you book this Super-Midsize Cabin Jet now, you'll be flying on a Bombardier Challenger 350, Gulfstream G200, Cessna Citation X or similar with recovery guaranteed.

    Every aircraft is hand-vetted to ensure a quality, consistent experience.

    • ARGUS, WYVERN, or ISBAO audited
    • $50m+ Liability Coverage Limits
    • Manufactured or Refurbished within 5 years on average
    • Approved and verified models only

  • Large Cabins

    Our large cabins offer all amenities with complementary flight attendant for up to 14 passengers

    Short Notice: Due to high demand our team has to confirm crew availability. Call us at (332) 241-5100

  • Large Cabin Jet

    Gulfstream GV, Bombardier Challenger 605, Gulfstream GIV-SP or similar

    8
    Thursday, October 22nd
    5:00am ORD
    3h 41m Nonstop
    6:41am SAN
    Friday, October 23rd
    5:00am SAN
    3h 9m Nonstop
    10:09am ORD
    $89,920 Plus $6,812.81 tax
    Hello, Time Traveller (332) 241-5100 Flights in the past aren't available for instant booking... yet. Call now to book your flight.
    Real-Time Eligible Aircraft

    Out of 724 Large Cabin Jets, only 36 aircraft are eligible for your trip based on scheduled position, real-time availability, and price.

    If you book this Large Cabin Jet now, you'll be flying on a Gulfstream GV, Bombardier Challenger 605, Gulfstream GIV-SP or similar with recovery guaranteed.

    Every aircraft is hand-vetted to ensure a quality, consistent experience.

    • ARGUS, WYVERN, or ISBAO audited
    • $50m+ Liability Coverage Limits
    • Manufactured or Refurbished within 5 years on average
    • Approved and verified models only

  • Gulfstream®

    Gulfstream G550, Gulfstream G450, Gulfstream GV or similar

    12
    Thursday, October 22nd
    5:00am ORD
    3h 41m Nonstop
    6:41am SAN
    Friday, October 23rd
    5:00am SAN
    3h 9m Nonstop
    10:09am ORD
    $109,957 Plus $8,315.58 tax
    Hello, Time Traveller (332) 241-5100 Flights in the past aren't available for instant booking... yet. Call now to book your flight.
    Real-Time Eligible Aircraft

    Out of 523 Gulfstream®s, only 14 aircraft are eligible for your trip based on scheduled position, real-time availability, and price.

    If you book this Gulfstream® now, you'll be flying on a Gulfstream G550, Gulfstream G450, Gulfstream GV or similar with recovery guaranteed.

    Every aircraft is hand-vetted to ensure a quality, consistent experience.

    • ARGUS, WYVERN, or ISBAO audited
    • $50m+ Liability Coverage Limits
    • Manufactured or Refurbished within 5 years on average
    • Approved and verified models only

  • There's more:

    Based on your criteria, we have made adjustments to make your trip possible. This may be due to aircraft size or runway length.
    These results are still the closest to your desired locations with your choice of aircraft.

  • Midsize Cabin Jet

    Bombardier Lear 40XR, Cessna Citation Excel, Bombardier Lear 45 or similar

    6
    Required Changes
    • Limit to 6 passengers
    Estimated Price $65k Plus $4,920.03 tax
    View more
  • Light Cabin Jet

    Cessna Citation CJ3, Cessna Citation CJ2, Embraer Phenom 300 or similar

    5
    Required Changes
    • Limit to 5 passengers
    Estimated Price $54k Plus $4,102.30 tax
    View more
  • Find a better price? We'll beat it

    Our pricing is based on real-time positioning of aircraft and their actual operating costs, and will not be beat. If you find a better quote for your itinerary, it’s either an aircraft we do not have in our system or has not met our quality standards.

    Send us the better quote and if it meets our quality standards we’ll add the aircraft to our system and beat the price by $500 or more.

    Share the quote

    Need Something Specific?

    Our instant booking ensures a consistent experience but we want to make sure you get exactly what you need. If you would like to book a specific model or have special requirements, our flight advisors are standing by to assist.


    Personally Confirmed

    Charles Denault, Founder & CEO SimpleCharters We know that technology isn't always enough. Our team of flight advisors will personally ensure the accuracy of all trip details, safety, and special requests. Have a question? Call us at (332) 241-5100

    Our flight advisors pay special attention to all of the following:

    • Your itinerary and special requirements
    • Pilot experience and background
    • Aircraft quality, history, and safety
    • Weather impacts & potential delays
    • All regulatory requirements, TFRs/NOTAMs, etc.

    How It Works

    We make booking private jets simple. Here's what to expect when instant booking your trip:

    • Book & Instant Confirmation

      Securely book online to receive instant confirmation and your preliminary trip sheet. Update your passenger and luggage information at your convenience

    • Flight Advisor Review

      Your flight advisor will review all details, make FBO arrangements, and personally review your trip

    • Final Flight & Weather Review

      Within 24 hours of departure, your captain will conduct a final review of the flight plan, weather, and safety

    • Final Tail Number

      Within 12-24 hours before departure you'll receive your assigned tail number, flight tracking, and the names of your flight crew

    • Time To Fly!

      Arrive at the FBO 30 minutes before departure, meet your crew, board the aircraft, and take off!


    Demand Outlook

    Over the last 7 days, customers have looked at pricing for similar itineraries 29 times. These dates have normal availability.