Top 35 Commercial pilot Jobs in Illinois

Transportation Manager
Blue Peak Tents Inc. —Batavia, IL
- $110,000 - $115,000 a year
- Urgently hiring
- CDL B
- Dedicated
- Military
- Paid holidays
- Dental insurance
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2d
SIC- Gulfstream G200
Jet Linx Aviation —Wheeling, IL
- $124,000 - $160,000 a year
- Weekends as needed
- Pass drug screening
- Bachelor's degree
- Travel
- Disability insurance
- Health insurance
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23h
Citation CJ3/CJ2/CJ1+ – PIC/SIC
Aviation Advisor —Chicago, IL
- Full-time
- Microsoft Outlook
- High school diploma or GED
- Driver's License
- Health insurance
- Dental insurance
Chief Pilot - US
Nutrien US LLC —Chicago, IL
- $169,100 - $314,000 a year
- Full-time
- Background check
- 5 years
- Bachelor's degree
- Paid holidays
- Disability insurance
NTT Faculty (Flight Instructor) (Multiple Vacancies)
Southern Illinois University Carbondale —Carbondale, IL
- $3,863 - $3,875 a month
- Full-time
- Classroom
- Residential
- Master's degree
- AD&D insurance
- Disability insurance
Captain - Challenger 350
Jet Aviation —Chicago, IL
- $230,000 - $240,000 a year
- Clean driving record
- Customer service
- High school diploma or GED
- Disability insurance
- Dental insurance
Lear 45XR PIC
Aviation Advisor —Chicago, IL
- Weekends as needed
- Microsoft Outlook
- High school diploma or GED
- Driver's License
- Health insurance
- Dental insurance
Certified Flight Instructor - CFI, CFII
SPARTA AERO SERVICES INC —Sparta, IL
- $36 - $39 an hour
- Part-time
- Classroom
- Mid-level
- Accounting
- Paid time off
- Employee discount
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1d
CITATION XLS+ PIC
Aviation Advisor —Aurora, IL
- Weekends as needed
- Microsoft Outlook
- High school diploma or GED
- Driver's License
- Health insurance
- Dental insurance
Line Pilot - AEL 035 Marion, IL
Air Evac Lifeteam —Marion, IL
- $106,511 - $117,162 a year
- Full-time
- High school diploma or GED
- Senior level
- Commercial
Challenger 300 Captain - Chicago, IL
Solairus Aviation —Wheeling, IL
- $50,000 - $500,000 a year
- Full-time
- Residential
- Senior level
- Health insurance
- 401(k) matching
Falcon 900EX EASy Captain - Chicago Area
Solairus Aviation —Chicago, IL
- $50,000 - $500,000 a year
- Full-time
- Residential
- Senior level
- Health insurance
- 401(k) matching
Shoreside Tank Barge PIC (MMC Required)
psc-tankbargepic —Joliet, IL
- $35.05 - $42.75 an hour
- Full-time
- Background check
- 18 years or older
- Military
- Disability insurance
- Health insurance
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Certified Flight Instructor
Lewis University —Romeoville, IL
- $30 an hour
- Part-time
- Bachelor of Science
- University
- Bachelor's degree
Pilot & Training Specialist | Defense & Autonomous Systems
WingXpand —Schaumburg, IL
- Part-time
- Classroom
- Mid-level
- Travel
- Paid time off
Quick Apply
9d
Senior Captain
AbbVie —North Chicago, IL
- $141,500 - $268,500 a year
- Full-time
- Hybrid work
- Bachelor's degree
- Mentoring
- Cleaning
- Paid holidays
- Health insurance
Flight Coordinator - Overnight
Superior Air-Ground Ambulance —Elmhurst, IL
- Weekends as needed
- Word processing
- Computer literacy
- Mid-level
Captain - PC-24 -DuPage, Illinois
Jet Aviation —West Chicago, IL
- $160,000 - $200,000 a year
- Clean driving record
- Customer service
- High school diploma or GED
- Disability insurance
- Dental insurance
Global 6000 Captain - Wheeling, IL
Solairus Aviation —Wheeling, IL
- $50,000 - $500,000 a year
- Full-time
- Residential
- Senior level
- Health insurance
- 401(k) matching
AEL Helicopter Pilot - HAA
Air Evac Lifeteam —Jacksonville, IL
- $106,511 - $117,162 a year
- Full-time
- High school diploma or GED
- Senior level
- Commercial

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commercial pilot jobs near illinois

Transportation Manager

Blue Peak Tents Inc. -
Batavia, IL

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Job Details

Full-time
$110,000 - $115,000 a year
2 days ago

Benefits

Paid holidays
Dental insurance
Paid time off
Vision insurance
401(k) matching

Qualifications

Vendor relationship building
Team leadership
Metrics Reporting
Team development
Leading team collaboration initiatives
Management reporting
Straight truck
Project leadership

Full Job Description

ABOUT BLUE PEAK

Blue Peak Tents is a rapidly growing event infrastructure company based in Batavia, Illinois. We provide tenting, structures, flooring, restroom trailers, generators, and related event services for corporate galas, estate weddings, festivals, and large-scale productions across the Chicagoland area and select national markets. Our fleet is the backbone of our field operations, and we are building a transportation function that can scale with the business and stand as a model for the broader organization.

THE OPPORTUNITY

We are hiring a Transportation Manager to take full ownership of the readiness, compliance, lifecycle, and people leadership of Blue Peak's transportation function. The mission is straightforward: when an asset and a driver are assigned to an event, the asset is road-ready and legally compliant, and the driver is qualified, safe, and accountable. Today this work is distributed across several people. Going forward it sits with one leader.

This is an aspirational hire. The right candidate carries the Transportation Manager title and compensation from day one, with scope expanding over a structured 24-month development track as defined milestones are met. We are hiring above the immediate need on purpose. We want a leader who can stabilize and run transportation now, and who has the ceiling to grow into a senior operations partner as the business scales.

If you are a proven leader who learns fast, builds systems where none exist, and holds a high standard, this role is built for you. We are particularly interested in junior military officers and others with strong leadership development backgrounds who are looking for a real ownership opportunity in a growing company.

WHAT YOU WILL DO

At full scope, the Transportation Manager owns the following. Scope phases in over the first 24 months against the milestones below.

Fleet Operations and Readiness

Own preventative maintenance, repair coordination, and field readiness for the entire fleet of vehicles, trailers, generators, and restroom trailers
Manage third-party maintenance providers and hold them to PM cadence, turnaround, and cost standards; continuously evaluate whether the right partners and the right buy-versus-lease mix are in place
Own pre-trip and post-trip inspection processes and the data that comes out of them
Own cost-per-mile, total cost of ownership, and repair-versus-replace recommendations to leadership

Compliance and Safety

Own DOT and FMCSA compliance across the fleet, including inspection records, registration, insurance, IFTA, and IRP where applicable
Carry indirect accountability for every CDL holder in the company; anyone who operates a regulated vehicle for Blue Peak operates inside the Transportation Manager's compliance program
Lead monthly safety meetings with the driver pool, reinforce standards, and drive down preventable fleet damage

People Leadership

Lead the Fleet Equipment Technician and fleet technicians as the team comes online
Lead the dedicated driver group as drivers transition into the transportation function
Set the standard, cadence, and accountability culture for the team, removing the daily tactical load that currently sits on Field Operations leadership

Vendor, Lease, and Capital Management

Serve as Blue Peak's single point of contact for fleet vendors and leasing partners
Manage active vehicle leases including mileage allowances, terms, expirations, excess mileage exposure, and buyout options
Support capital planning by identifying replacement timing and fleet expansion needs tied to growth

Strategic Partnership (Upside)

Partner with the Director on strategic initiatives, including a planned off-season transportation capacity pilot designed to stabilize the driver base year-round and turn seasonal capacity into a revenue line
Demonstrate the judgment and ceiling to take on broader operations scope as the organization grows

WHERE THIS GOES

A structured 24-month development track with clear milestones. The title and compensation are held from day one. Scope and team expand as each gate is met. Milestones are assessment points, not promotions. The end state is full, independent ownership of transportation and a confirmed mutual fit for broader scope as the company grows.

MONTHS 0 to 6 Fleet Stabilization

Complete a full fleet inventory and condition assessment. Establish vendor relationships and remediate any compliance gaps. By month 6, the PM schedule is running with no overdue units, DOT and registration are current, vehicle binders are complete and in every truck, and cost-per-mile data is flowing for road-worthy assets.

MONTHS 6 to 12 Team and Standards

Drivers begin transitioning into the function. The Fleet Equipment Technician onboards. Monthly driver safety meetings are established. The indirect CDL compliance program is stood up across all company CDL holders. Fleet technicians report into the role. Performance metrics are defined and baselined, and reporting cadence to the Director is dialed in.

MONTHS 12 to 24 Full Scope

Drivers and technicians run as a functional unit under the Transportation Manager. Performance tracks against baselined metrics and improves on them. The role operates with minimal day-to-day support from the Director. By month 24, full Transportation Manager scope is live and owned independently across fleet, drivers, technicians, compliance, vendors, and capital, with a clear view of whether the role should expand or evolve next.

WHAT YOU BRING

Required

Proven leadership experience with direct responsibility for people, standards, and accountability
Demonstrated ability to learn a new operating environment quickly and build systems and process where none exist
Strong organizational discipline across multiple priorities, vendors, and deadlines
Comfort with data, tracking tools, and clear reporting
Valid driver's license with the ability to operate pickup and box trucks as needed for fleet positioning

Preferred

Junior military officer background or other strong leadership development pipeline. We value the discipline, ownership mindset, and ability to master regulated environments that this background builds
Military experience in transportation, logistics, or motor pool operations
Working knowledge of DOT regulations and commercial fleet compliance, or a clear track record of mastering regulated environments
CDL Class A or B, or willingness to obtain
Experience with leased fleet management or vendor and service contract management
Experience in event, construction, or rental equipment industries

COMPENSATION AND BENEFITS

Salary: $110,000 to $115,000 annually, held from day one. Full-time, exempt, year-round
Health, dental, and vision insurance
401(k) with company match (per plan eligibility)
Paid time off and paid holidays per the Blue Peak handbook
Real growth opportunity tied to clearly defined milestones and the chance to take on broader operations scope as the company scales
As the function matures, this role joins a weekend on-call rotation supporting field operations escalation

Compensation details: 110000-115000 Yearly Salary

PI6d0c184dc23c-25404-40956914

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Refine Your Search

commercial pilot jobs in illinois

Transportation Manager

SIC- Gulfstream G200

Citation CJ3/CJ2/CJ1+ – PIC/SIC

Chief Pilot - US

NTT Faculty (Flight Instructor) (Multiple Vacancies)

Captain - Challenger 350

Lear 45XR PIC

Certified Flight Instructor - CFI, CFII

CITATION XLS+ PIC

Line Pilot - AEL 035 Marion, IL

Challenger 300 Captain - Chicago, IL

Falcon 900EX EASy Captain - Chicago Area

Shoreside Tank Barge PIC (MMC Required)

Certified Flight Instructor

Pilot & Training Specialist | Defense & Autonomous Systems

Senior Captain

Flight Coordinator - Overnight

Captain - PC-24 -DuPage, Illinois

Global 6000 Captain - Wheeling, IL

AEL Helicopter Pilot - HAA

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