Private Jets from Houston, Texas to Chicago, Illinois

One Way Private Jets From Houston, Texas to Chicago, Illinois

    Suggested Aircraft

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

    Short Notice: Flights within 48 hours require our concierge team to confirm crew availability. Call now to book your flight (929) 339-1710

  • Turboprop

    6
    Tuesday, February 2nd
    9:00am IAH
    3h 11m Nonstop
    12:11pm DPA
    Instant Book Price $12,447 Plus $933.53 tax
    Hello, Time Traveller (929) 339-1710 Call Flights in the past aren't available for instant booking... yet. Call now to book your flight.
    Actual Photos

    Our team has hand verified every aircraft to ensure a quality, consistent experience. View the actual aircraft eligible for your trip below. Exact tail-number assigned after confirmation of crew availability.

    Personally Confirmed

    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. Take comfort in knowing every detail is addressed with expertise.

    Safety Factors

    • Pilot training and proficiency
    • Aircraft maintenance history
    • Operator history and safety ratings
    • Performance and weather impacts
    • COVID-19 Protocols and sanitizing

    Aircraft Quality

    • $50m+ Liability Coverage
    • Manufactured in 2008 on average
    • Refurbished within 5 years on average
    • Approved Models Only

    Aircraft Intelligence

    Out of 1830 Turboprops, only 73 aircraft are eligibile for your trip based on position, safety, and quality.

    We've selected the top 3 options with backups guaranteed.
    (Completed in 2.0430 seconds)

    Demand Outlook

    We analyze how many other SimpleCharters customers are exploring flights similar to your itinerary. These dates have normal availability.

  • Large Cabins

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

    Short Notice: Flights within 48 hours require our concierge team to confirm crew availability. Call now to book your flight (929) 339-1710

  • Ultra Large Cabin Jet

    11
    Tuesday, February 2nd
    9:00am IAH
    2h 12m Nonstop
    11:12am DPA
    Instant Book Price $34,241 Plus $2,568.04 tax
    Hello, Time Traveller (929) 339-1710 Call Flights in the past aren't available for instant booking... yet. Call now to book your flight.
    Actual Photos

    Our team has hand verified every aircraft to ensure a quality, consistent experience. View the actual aircraft eligible for your trip below. Exact tail-number assigned after confirmation of crew availability.

    Personally Confirmed

    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. Take comfort in knowing every detail is addressed with expertise.

    Safety Factors

    • Pilot training and proficiency
    • Aircraft maintenance history
    • Operator history and safety ratings
    • Performance and weather impacts
    • COVID-19 Protocols and sanitizing

    Aircraft Quality

    • $50m+ Liability Coverage
    • Manufactured in 2008 on average
    • Refurbished within 5 years on average
    • Approved Models Only

    Aircraft Intelligence

    Out of 523 Ultra Large Cabin Jets, only 25 aircraft are eligibile for your trip based on position, safety, and quality.

    We've selected the top 3 options with backups guaranteed.
    (Completed in 2.0430 seconds)

    Demand Outlook

    We analyze how many other SimpleCharters customers are exploring flights similar to your itinerary. These dates have normal availability.

  • Large Cabin Jet

    8
    Tuesday, February 2nd
    9:00am IAH
    2h 11m Nonstop
    11:11am DPA
    Instant Book Price $24,452 Plus $1,833.94 tax
    Hello, Time Traveller (929) 339-1710 Call Flights in the past aren't available for instant booking... yet. Call now to book your flight.
    Actual Photos

    Our team has hand verified every aircraft to ensure a quality, consistent experience. View the actual aircraft eligible for your trip below. Exact tail-number assigned after confirmation of crew availability.

    Personally Confirmed

    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. Take comfort in knowing every detail is addressed with expertise.

    Safety Factors

    • Pilot training and proficiency
    • Aircraft maintenance history
    • Operator history and safety ratings
    • Performance and weather impacts
    • COVID-19 Protocols and sanitizing

    Aircraft Quality

    • $50m+ Liability Coverage
    • Manufactured in 2008 on average
    • Refurbished within 5 years on average
    • Approved Models Only

    Aircraft Intelligence

    Out of 724 Large Cabin Jets, only 64 aircraft are eligibile for your trip based on position, safety, and quality.

    We've selected the top 3 options with backups guaranteed.
    (Completed in 2.0430 seconds)

    Demand Outlook

    We analyze how many other SimpleCharters customers are exploring flights similar to your itinerary. These dates have normal availability.

  • Medium Cabins

    Our medium cabins offer longer range with more cabin space for groups of 8-9 passengers

    Short Notice: Flights within 48 hours require our concierge team to confirm crew availability. Call now to book your flight (929) 339-1710

  • Super-Midsize Cabin Jet

    7
    Tuesday, February 2nd
    9:00am IAH
    2h 19m Nonstop
    11:19am DPA
    Instant Book Price $19,899 Plus $1,492.44 tax
    Hello, Time Traveller (929) 339-1710 Call Flights in the past aren't available for instant booking... yet. Call now to book your flight.
    Actual Photos

    Our team has hand verified every aircraft to ensure a quality, consistent experience. View the actual aircraft eligible for your trip below. Exact tail-number assigned after confirmation of crew availability.

    Personally Confirmed

    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. Take comfort in knowing every detail is addressed with expertise.

    Safety Factors

    • Pilot training and proficiency
    • Aircraft maintenance history
    • Operator history and safety ratings
    • Performance and weather impacts
    • COVID-19 Protocols and sanitizing

    Aircraft Quality

    • $50m+ Liability Coverage
    • Manufactured in 2008 on average
    • Refurbished within 5 years on average
    • Approved Models Only

    Aircraft Intelligence

    Out of 525 Super-Midsize Cabin Jets, only 59 aircraft are eligibile for your trip based on position, safety, and quality.

    We've selected the top 3 options with backups guaranteed.
    (Completed in 2.0430 seconds)

    Demand Outlook

    We analyze how many other SimpleCharters customers are exploring flights similar to your itinerary. These dates have normal availability.

  • Midsize Cabin Jet

    4
    Tuesday, February 2nd
    9:00am IAH
    2h 17m Nonstop
    11:17am DPA
    Instant Book Price $17,153 Plus $1,286.45 tax
    Hello, Time Traveller (929) 339-1710 Call Flights in the past aren't available for instant booking... yet. Call now to book your flight.
    Actual Photos

    Our team has hand verified every aircraft to ensure a quality, consistent experience. View the actual aircraft eligible for your trip below. Exact tail-number assigned after confirmation of crew availability.

    Personally Confirmed

    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. Take comfort in knowing every detail is addressed with expertise.

    Safety Factors

    • Pilot training and proficiency
    • Aircraft maintenance history
    • Operator history and safety ratings
    • Performance and weather impacts
    • COVID-19 Protocols and sanitizing

    Aircraft Quality

    • $50m+ Liability Coverage
    • Manufactured in 2008 on average
    • Refurbished within 5 years on average
    • Approved Models Only

    Aircraft Intelligence

    Out of 1268 Midsize Cabin Jets, only 98 aircraft are eligibile for your trip based on position, safety, and quality.

    We've selected the top 3 options with backups guaranteed.
    (Completed in 2.0430 seconds)

    Demand Outlook

    We analyze how many other SimpleCharters customers are exploring flights similar to your itinerary. These dates have normal availability.

  • Small Cabins

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

    Short Notice: Flights within 48 hours require our concierge team to confirm crew availability. Call now to book your flight (929) 339-1710

  • Light Cabin Jet

    4
    Tuesday, February 2nd
    9:00am IAH
    2h 32m Nonstop
    11:32am DPA
    Instant Book Price $14,737 Plus $1,105.25 tax
    Hello, Time Traveller (929) 339-1710 Call Flights in the past aren't available for instant booking... yet. Call now to book your flight.
    Actual Photos

    Our team has hand verified every aircraft to ensure a quality, consistent experience. View the actual aircraft eligible for your trip below. Exact tail-number assigned after confirmation of crew availability.

    Personally Confirmed

    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. Take comfort in knowing every detail is addressed with expertise.

    Safety Factors

    • Pilot training and proficiency
    • Aircraft maintenance history
    • Operator history and safety ratings
    • Performance and weather impacts
    • COVID-19 Protocols and sanitizing

    Aircraft Quality

    • $50m+ Liability Coverage
    • Manufactured in 2008 on average
    • Refurbished within 5 years on average
    • Approved Models Only

    Aircraft Intelligence

    Out of 1144 Light Cabin Jets, only 66 aircraft are eligibile for your trip based on position, safety, and quality.

    We've selected the top 3 options with backups guaranteed.
    (Completed in 2.0430 seconds)

    Demand Outlook

    We analyze how many other SimpleCharters customers are exploring flights similar to your itinerary. These dates have normal availability.

  • Turboprop

    6
    Tuesday, February 2nd
    9:00am IAH
    3h 11m Nonstop
    12:11pm DPA
    Instant Book Price $12,447 Plus $933.53 tax
    Hello, Time Traveller (929) 339-1710 Call Flights in the past aren't available for instant booking... yet. Call now to book your flight.
    Actual Photos

    Our team has hand verified every aircraft to ensure a quality, consistent experience. View the actual aircraft eligible for your trip below. Exact tail-number assigned after confirmation of crew availability.

    Personally Confirmed

    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. Take comfort in knowing every detail is addressed with expertise.

    Safety Factors

    • Pilot training and proficiency
    • Aircraft maintenance history
    • Operator history and safety ratings
    • Performance and weather impacts
    • COVID-19 Protocols and sanitizing

    Aircraft Quality

    • $50m+ Liability Coverage
    • Manufactured in 2008 on average
    • Refurbished within 5 years on average
    • Approved Models Only

    Aircraft Intelligence

    Out of 1830 Turboprops, only 73 aircraft are eligibile for your trip based on position, safety, and quality.

    We've selected the top 3 options with backups guaranteed.
    (Completed in 2.0430 seconds)

    Demand Outlook

    We analyze how many other SimpleCharters customers are exploring flights similar to your itinerary. These dates have normal availability.

  • Specialized Requests

    Do you have specialized requirements for your trip? Our flight advisors can customize your booking to exactly what you need— whether it's a particular model of aircraft, unique luggage, or even specific itinerary changes. Enter your preferences to get started:

    Update Your Preferences