Private Jets from Chicago, Illinois to Cancun, Quintana Roo to Chicago, Illinois

Round Trip Private Jets From Chicago, Illinois to Cancun, Quintana Roo to Chicago, Illinois

    Suggested Aircraft

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

    International Trip: Our concierge team has more options available for this international itinerary. Call us at (332) 241-5100

  • Midsize Cabin Jet

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

    6
    Friday, March 4th
    1:55am PWK
    3h 3m Nonstop
    5:58am CUN
    Saturday, March 12th
    1:10pm CUN
    3h 18m Nonstop
    3:28pm PWK
    $56,140 Includes all taxes and fees
    Book Have more questions? (332) 241-5100
    Real-Time Eligible Aircraft

    Out of 1268 Midsize Cabin Jets, only 22 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 Cessna Citation XLS, Cessna Citation Excel, 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

  • Small Cabins

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

    International Trip: Our concierge team has more options available for this international itinerary. Call us at (332) 241-5100

  • Light Cabin Jet

    Cessna Citation CJ4, Embraer Phenom 300, Cessna Citation CJ2 or similar

    6
    Friday, March 4th
    1:55am PWK
    3h 18m Nonstop
    6:13am CUN
    Saturday, March 12th
    1:10pm CUN
    3h 33m Nonstop
    3:43pm PWK
    $48,919 Includes all taxes and fees
    Book Have more questions? (332) 241-5100
    Real-Time Eligible Aircraft

    Out of 1144 Light Cabin Jets, only 15 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 CJ4, Embraer Phenom 300, Cessna Citation CJ2 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

    International Trip: Our concierge team has more options available for this international itinerary. Call us at (332) 241-5100

  • Midsize Cabin Jet

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

    6
    Friday, March 4th
    1:55am PWK
    3h 3m Nonstop
    5:58am CUN
    Saturday, March 12th
    1:10pm CUN
    3h 18m Nonstop
    3:28pm PWK
    $56,140 Includes all taxes and fees
    Book Have more questions? (332) 241-5100
    Real-Time Eligible Aircraft

    Out of 1268 Midsize Cabin Jets, only 22 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 Cessna Citation XLS, Cessna Citation Excel, 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
    Friday, March 4th
    1:55am PWK
    2h 31m Nonstop
    5:26am CUN
    Saturday, March 12th
    1:10pm CUN
    2h 41m Nonstop
    2:51pm PWK
    $75,477 Includes all taxes and fees
    Book Have more questions? (332) 241-5100
    Real-Time Eligible Aircraft

    Out of 525 Super-Midsize Cabin Jets, only 11 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

    14
    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 $113k Includes all taxes and fees
    View more
  • Large Cabin Jet

    Dassault Falcon 2000, Gulfstream GV, Dassault Falcon 2000S or similar

    9
    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 Includes all taxes and fees
    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
    • PWK is too short, use ORD instead
      • ORD (Chicago O'Hare International) is 10 mi away
    Estimated Price $78k Includes all taxes and fees
    View more
  • Midsize Cabin Jet

    Bombardier Lear 45XR, Bombardier Lear 75, Beechcraft Hawker 800XP or similar

    7
    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 $51k Includes all taxes and fees
    View more
  • Light Cabin Jet

    Cessna Citation Encore, Bombardier Lear 75, 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 $52k Includes all taxes and fees
    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 28 times. These dates have normal availability.