Private Jets from Chicago, Illinois to Placida, Florida to Chicago, Illinois

Round Trip Private Jets From Chicago, Illinois to Placida, Florida to Chicago, Illinois

Ideal Position Price™

Ideal Position Prices Available

Book your multi-leg itinerary as separate one way trips to take advantage of the following aircraft ideally positioned for part of your itinerary. Click a button below to update your search and view one way pricing for the ideally positioned aircraft.


Leg 2: to PWK One Way Ideal Position Prices:

  • Midsize Cabin Jet - One way, 1 day, 4 hours earlier - Save $$$

    Change to a one way departing 1 day, 4 hours earlier on Saturday, November 20th at 9:00am.

  • Midsize Cabin Jet - One way, 3 days earlier - Save $

    Change to a one way departing 3 days earlier on Thursday, November 18th at 1:05pm.


After booking a one way Ideal Position Price trip, you can book your remaining itinerary legs as separate one way bookings.

    Suggested Aircraft

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

  • Light Cabin Jet

    Embraer Phenom 300, Cessna Citation CJ4, Beechcraft Beechjet 400A or similar

    6
    Thursday, November 18th
    9:05am PWK
    2h 28m Nonstop
    12:33pm FA54
    Sunday, November 21st
    1:05pm FA54
    2h 45m Nonstop
    2:50pm PWK
    $34,643 Plus $2,615.43 tax
    Book Have more questions? (332) 241-5100
    Real-Time Eligible Aircraft

    Out of 1144 Light Cabin Jets, only 30 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 Embraer Phenom 300, Cessna Citation CJ4, 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

  • Small Cabins

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

  • Light Cabin Jet

    Embraer Phenom 300, Cessna Citation CJ4, Beechcraft Beechjet 400A or similar

    6
    Thursday, November 18th
    9:05am PWK
    2h 28m Nonstop
    12:33pm FA54
    Sunday, November 21st
    1:05pm FA54
    2h 45m Nonstop
    2:50pm PWK
    $34,643 Plus $2,615.43 tax
    Book Have more questions? (332) 241-5100
    Real-Time Eligible Aircraft

    Out of 1144 Light Cabin Jets, only 30 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 Embraer Phenom 300, Cessna Citation CJ4, 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

  • Midsize Cabin Jet

    Bombardier Lear 40, Cessna Citation XLS, Bombardier Lear 45 or similar

    6
    Thursday, November 18th
    9:05am PWK
    2h 14m Nonstop
    12:19pm FA54
    Sunday, November 21st
    1:05pm FA54
    2h 29m Nonstop
    2:34pm PWK
    $41,105 Plus $3,100.08 tax
    Book Have more questions? (332) 241-5100
    Real-Time Eligible Aircraft

    Out of 1268 Midsize Cabin Jets, only 34 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 40, Cessna Citation XLS, Bombardier Lear 45 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, Bombardier Challenger 300 or similar

    8
    Thursday, November 18th
    9:05am PWK
    1h 57m Nonstop
    12:02pm FA54
    Sunday, November 21st
    1:05pm FA54
    2h 8m Nonstop
    2:13pm PWK
    $51,606 Plus $3,887.65 tax
    Book Have more questions? (332) 241-5100
    Real-Time Eligible Aircraft

    Out of 525 Super-Midsize Cabin Jets, only 18 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, Bombardier Challenger 300 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.

  • Gulfstream®

    Gulfstream G550, Gulfstream G450, Gulfstream GV or similar

    10
    Required Changes
    • PWK is too short, use ORD instead
      • ORD (Chicago O'Hare International) is 10 mi away
    • PWK is too short, use ORD instead
      • ORD (Chicago O'Hare International) is 10 mi away
    Estimated Price $75k Plus $5,621.50 tax
    View more
  • Large Cabin Jet

    Bombardier Challenger 604, Dassault Falcon 2000, Bombardier Challenger 605 or similar

    8
    Required Changes
    • PWK is too short, use ORD instead
      • ORD (Chicago O'Hare International) is 10 mi away
    • PWK is too short, use ORD instead
      • ORD (Chicago O'Hare International) is 10 mi away
    Estimated Price $56k Plus $4,221.17 tax
    View more
  • Super-Midsize Cabin Jet

    Gulfstream G200, Gulfstream G280, Cessna Citation X or similar

    8
    Required Changes
    • PWK is too short, use ORD instead
      • ORD (Chicago O'Hare International) is 10 mi away
    • FA54 is too short, use PGD instead
      • PGD (Punta Gorda) is 17 mi away
    • FA54 is too short, use PGD instead
      • PGD (Punta Gorda) is 17 mi away
    • PWK is too short, use ORD instead
      • ORD (Chicago O'Hare International) is 10 mi away
    Estimated Price $59k Plus $4,430.88 tax
    View more
  • Midsize Cabin Jet

    Bombardier Lear 45XR, Bombardier Lear 75, Bombardier Lear 60 or similar

    6
    Required Changes
    • PWK is too short, use ORD instead
      • ORD (Chicago O'Hare International) is 10 mi away
    • PWK is too short, use ORD instead
      • ORD (Chicago O'Hare International) is 10 mi away
    Estimated Price $38k Plus $2,845.30 tax
    View more
  • Light Cabin Jet

    Cessna Citation Encore, Bombardier Lear 70 or similar

    6
    Required Changes
    • PWK is too short, use ORD instead
      • ORD (Chicago O'Hare International) is 10 mi away
    • PWK is too short, use ORD instead
      • ORD (Chicago O'Hare International) is 10 mi away
    Estimated Price $37k Plus $2,760.63 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.