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Wingman Jobs in Chicago, IL (NOW HIRING)

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$10

$18

$25

How much do wingman jobs pay per hour?

As of Sep 1, 2026, the average hourly pay for wingman in Chicago, IL is $18.73, according to ZipRecruiter salary data. Most workers in this role earn between $16.59 and $20.05 per hour, depending on experience, location, and employer.

What is a wingman?

A Wingman job typically involves providing support, guidance, or assistance to an individual or team in various contexts, such as social settings, sales, or aviation. In social or dating environments, a Wingman helps a friend with introductions and conversation. In professional settings, a Wingman may act as a supportive partner, ensuring success in tasks or interactions. The role depends on the industry but generally focuses on enhancing confidence, communication, and outcomes.

What are the key skills and qualifications needed to thrive as a wingman, and why are they important?

To thrive as a Wingman, you need excellent interpersonal and communication skills, strong situational awareness, and the ability to support and collaborate with partners or team members, often in dynamic environments. Familiarity with communication radios, GPS navigation, and relevant safety certifications such as CPR or first aid may be required depending on the industry. Adaptability, teamwork, reliability, and quick decision-making are standout soft skills for this role. These competencies ensure efficient support, enhanced team performance, and safety during high-pressure or changing situations.

What are some common challenges faced by a wingman, and how can they be addressed?

Common challenges for a Wingman include managing rapidly changing situations, maintaining clear communication, and reacting quickly to support the primary lead or team. It is important to stay calm under pressure and remain constantly aware of both the environment and team dynamics. Proactively seeking feedback, participating in regular training sessions, and cultivating strong partnerships help in overcoming these challenges. Many Wingmen find that experience and preparation are key to responding effectively and confidently in unpredictable scenarios.

What are the most commonly searched types of Wingman jobs in Chicago, IL?

The most popular types of Wingman jobs in Chicago, IL are:

What are popular job titles related to Wingman jobs in Chicago, IL?

For Wingman jobs in Chicago, IL, the most frequently searched job titles are:

What job categories do people searching Wingman jobs in Chicago, IL look for?

The top searched job categories for Wingman jobs in Chicago, IL are:

Wingman jobs near you
Infographic showing various Wingman job openings in Chicago, IL as of August 2026, with employment types broken down into 90% Full Time, and 10% Part Time. Highlights an 95% Physical, 1% Hybrid, and 4% Remote job distribution, with an average salary of $38,968 per year, or $18.7 per hour.

CDL A OTR Tanker Driver in the Midwest Region

Chicago, IL

Flowtrans (search conducted by Drive My Way)
Trucking • 201 - 500 employees
Learn more about Flowtrans (search conducted by Drive My Way)external

$1.8K/wk

Full-time

Medical, Dental, Vision, Life, Retirement, PTO

Re-posted 21 days ago

Job description

FlowTrans is a specialty hauler of liquid food grade products across North America. The company is one of the largest haulers of liquid ingredients to food manufacturers and is a vital part of the supply chain keeping America fed.

No Hazmat endorsement or TWIC Card? NO PROBLEM! FlowTrans LLC is hiring OTR and long haul drivers for food-grade freight.

No hoses, pumps or hazmat!

Compensation

  • Average Weekly Gross Pay: $1,800
    • $1,400 Weekly Earnings guarantee! (Must be available for dispatch)
    • 61 CPM loaded and empty + 2 CPM Monthly Safety/Performance Bonus
  • Sign On bonus - $3,000: $500 1stpaycheck - $1,000 after 90 days, $1,500 after 6 months of employment
  • Referral bonus program - $3,000: $300 Per week for first 10 weeks (while referred driver is employed)
  • Detention pay - Layover pay - Breakdown pay
  • Paid via direct deposit weekly 

Benefits & Perks

  • Great company benefits starting the first of the month after 30 days of employment:
    • Medical, Dental, and Vision Insurance 
    • Basic Life/Voluntary Life
    • Short Term and Long Term Disability
    • 401K with Company Match
  • No pumps, hoses, or hazmat
  • Paid Vacations
  • 4 paid Holidays - $100 each (Thanksgiving - Christmas - 4th of July - New Year's)
  • Paid orientation: $150 each day
  • $150 paid per crossing into Canada (plus mileage)
  • Pet and Rider Policy

Home Time, Route, & Schedule

  • OTR: Out 2 1/2  Weeks, Home 3 full days
  • Run all 48 states (exclude NYC)
  • Level of Touch: No Touch

Equipment

  • Volvo and Peterbilt’s
  • Automatics
  • Bunk heater, refrigerator, inverter, APU
  • Bendix Wingman Fusion outward facing camera
  • Governed speed: 65 mph on pedal, 70 mph on cruise

Qualifications

  • Must be at least 23 years of age  
  • Must have CDL A license 
  • 1 Year OTR experience within the Last 3 Years
  • Tanker Endorsement or willing to obtain
  • No DWI/DUI in last 5 years.
  • No more than 3 moving violations in the last 3 years.
  • No more than 6 points on your MVR in the last 3 years.
  • No more than 3 preventable accidents in the last 3 years.
  • Must be able to pass a DOT physical examination, Drug Test, and be in physical condition to perform all essential functions required by the driver’s job description, with or without reasonable accommodations
  • Hiring Radius: Drivers must live in the below states or be willing to relocate for this position 
    • OH, IN, IL, MI, WI, IA, MN, WV,VA
.

This job search is being conducted by Drive My Way ([www.drivemyway.com](https://www.drivemyway.com)) on behalf of Company.