Transportation Staff Jobs, Employment in Chicago,IL Now Hiring October 2026

Featured Opportunity

Tucker Freight Lines - Calumet City, IL

CDL-A Truck Driver - Home Weekly - Earn Up to $2,400/Week

$250/day

~ 35 min Onsite

Recommended

CDL-A Truck Driver - Earn $1,300-$1,600/Week + 100% No-Touch Freight

West Side Transport

Oak Lawn, IL 60453

$1,300-$1,600/wk

Requires TravelUrgently HiringHealth InsuranceRetirement Benefit

Earn $1,300-$1,600/Week

$1,300 - $1,600 Per Week

Monthly and quarterly bonuses

A $1,100 weekly pay commitment

Fuel and safety bonuses

Health insurance, plus dental, vision, and life insurance

401(k) with company match

Home All Weekend

On the road Monday, home by Friday

CDL-A

Valid Class A CDL

6+ months Of class A experience

No SAP drivers

53' Dry Van trailer experience

CDL-A Truck Driver - Most Weekends Off - Earn Up to $111,917.87/Year

System Transport

Cicero, IL 60804

$1,018.63-$2,152.27/wk

~ 16 min OnsiteUrgently HiringHealth InsurancePaid Time OffRetirement Benefit

$52,968.74 - $111,917.87 per Year

$1,800 transition package including $1,000 orientation pay

$0.65 to $0.69 per mile

$1,018.63 - $2,152.27 per week

Tarp pay, stop pay, detention pay, border crossing pay, safety bonuses, and over-dimensional pay

$1,800 transition package

Airfare, single-occupancy room, breakfast, and lunch are all on us!

Medical, dental, vision, & life insurance

Long and short-term disability

Health savings account

401(k) with match

Employee assistance program

Life insurance

Accrue 1 hour of sick time per 30 hours worked, then 1-9 years get 80 hours PTO, 10+ years get 120 hours PTO

System Transport allows riders aged 7 and up after 90 days of safe driving

We will train you

Off most weekends for 34-hour reset

Must have a valid Class A driver's license (CDL-A)

A safe driving record on the road

Must be 21 years of age or older

No more than 6 jobs in the last 3 years

Background check required

A clean drug test required

Clean clearinghouse results required

For all flatbed driver opportunities, the driver must be physically able to lift a 90-pound tarp onto a 5-foot high platform twice.

Minimum of 6+ months of driving experience preferred (if you are a RECENT CDL-A Grad, we will train you)

Prefer 1-year truck driving experience, but not necessary

Recommended

Poached Jobs

Sous Chef

ROOP Chicago Innovative Indian Restaurant & Cocktail Bar

Chicago, IL 60661

Recommended

CDL-A Truck Driver - Average $1,863/Week + $2,000 Hiring Bonus

Koch Trucking

Berwyn, IL 60402

$1,863/wk

$2,000 bonus

~ 20 min OnsiteUrgently HiringHealth InsurancePaid Time OffRetirement Benefit

Average $1,863/Week

$2,000 Hiring Bonus

Average $1,863 weekly - top performers average $2,161 weekly

Starting pay: 67 CPM based on experience

$2,000 hiring bonus (paid monthly)

$1,000 orientation pay (first dispatch)

$75-$200 based on miles

$400 for any load over 64K

Stop pay: $30 per stop

Securement pay: $25 per stop

Tarp pay: $50 per stop

$100 for each loaded border crossing for drivers who choose to go to Canada

$3,000 referral bonus

PTO package - Start accruing PTO on the first day in addition to three floating holidays each year

Health, Dental, Vision, Life, and Disability Insurance

401(k) with company match

No flatbed experience? No problem, we provide additional training during orientation to ensure you are capable and confident before hitting the road.

All expenses paid orientation including hotel stay in Roseville, MN

All trucks are 3 years old or newer - average age of truck fleet is 16 months

Volvo 860 and Freightliner Cascadia come equipped with: refrigerators, leather interior, double curtain wrap, double bunks, built-in inverters, and other driver-friendly features

Free iPad with data package to ensure you stay connected with family and friends

Pet policy and rider policy

24/7/365 road service assistance

Rolling Strong driver app

Free drivers' lounge benefits: soap, shampoo, towels, toothbrush, toothpaste, laundry soap, pizza, and sandwiches

Home time every 14-21 days based on location

Paid weekly

CDL-A

All candidates must have a valid CDL-A license and one year of driving experience.

Valid Class A CDL

Minimum 1 year of driving experience is required

New, Posted 1 day ago

careersingear.com

12 Days Out CDL A Driver Job w/ 1 Year Experience

Crete Carrier Corporation

Cicero, IL 60804

$1,945/wk

~ 16 min OnsiteUrgently HiringHealth InsuranceRetirement Benefit

Top 50% average $96,483 per year

Starting pay $.64 to $.67 cpm

More than $101,176 annually

Over $1,945 weekly; $.64 to $.67 CPM

$93,347 annually ($1,795 per week), with starting pay ranging from $0.65 to $0.68 per mile

Profit-sharing plan that contributed $11.5 million in 2025 and more than $103 million to employee retirement accounts since 2018

Comprehensive and affordable health insurance

Matching 401k

Health insurance from BCBS of Nebraska, dental, vision, life, 401K, and a profit-sharing program

12 Days Out. 1 Day Home for Every 6 Days

One-year verifiable tractor trailer experience with a class A CDL

12 Days Out. 1 Day Home for Every 6 Days

New, Posted 1 day ago

CDL-A Truck Driver - Home Weekly

APL CARGO

Berwyn, IL 60402

$25/hr

~ 20 min OnsiteUrgently HiringHealth Insurance

Earn $72,800 - $98,800+ Annually

Earn $1,400 - $1,900 per week + bonus incentives for MPG and safety

Start at 65 CPM - Earn $72,800 - $98,800+ per year including bonuses

Up to 2 CPM performance bump after 90 days

Up to 2 CPM increase at 1-year milestone

1 CPM annual increase

A $100.00 per week bonus is now available for drivers in their first 52 weeks of employment

Breakdown pay

Detention pay: $25 per hour after 3 hours

Layover pay: $150 per day

Clean DOT inspection & on-time delivery bonuses

7 MPG fuel efficiency bonus

Clear path to higher-paying routes & regular performance reviews with actual pay increases

Comprehensive health coverage after 90 days

24/7 Driver support team

Late-model reefer fleet

Driver recognition program

Store Director, MaxMara Chicago

Max Mara Fashion Group

Chicago, IL 60290

New, Posted 6 hours ago

CDL-A Truck Driver - Home Weekly

Roehl Transport

Mount Prospect, IL 60056

$1,482-$2,484/wk

OnsiteUrgently HiringHealth InsurancePaid Time OffRetirement Benefit

$1,482 - $2,484 Weekly

$1,675+ weekly

Dynamic Pay Plans that better reward drivers for their time & performance

Dynamic Mileage Pay

Referral bonuses

New, expertly maintained equipment

Comprehensive benefits package

Health, dental, vision, & life insurance

Paid vacation

401(k) plan & profit sharing

Passenger/rider policy

Our smartphone app helps you do your job more efficiently

24/7 maintenance support

Career path opportunities

Long-Term Disability (LTD)

Life Insurance: Basic & Supplemental

Short-Term Income Protection

Flexible Spending Accounts (FSAs)

At least 4 months of recent driving experience

Recommended

Apply Directly

Administrative Assistant

Tekwissen

Chicago, IL 60637

$25/hr

89% of jobs ask for a resume

Don't let the perfect job slip away—upload your resume and we'll personalize your results instantly.

89% of jobs ask for a resume

Don't let the perfect job slip away—upload your resume and we'll personalize your results instantly.

Recommended

Apply Directly

Carrier Sales Representative

Transportation One LLC

Chicago, IL 60290

2157 Transportation Staff jobs in Chicago,IL

$250/day

CDL-A Truck Driver - Earn $1,300-$1,600/Week + 100% No-Touch Freight

$1,300-$1,600/wk

CDL-A Truck Driver - Most Weekends Off - Earn Up to $111,917.87/Year

$1,018.63-$2,152.27/wk

Pay$52,968.74 - $111,917.87 per YearPay$1,800 transition package including $1,000 orientation payPay$0.65 to $0.69 per mile

Sous Chef

CDL-A Truck Driver - Average $1,863/Week + $2,000 Hiring Bonus

$1,863/wk

$2,000 bonus

PayAverage $1,863/WeekPay$2,000 Hiring BonusPayAverage $1,863 weekly - top performers average $2,161 weekly

12 Days Out CDL A Driver Job w/ 1 Year Experience

$1,945/wk

PayTop 50% average $96,483 per yearPayStarting pay $.64 to $.67 cpmPayMore than $101,176 annually

CDL-A Truck Driver - Home Weekly

$25/hr

PayEarn $72,800 - $98,800+ AnnuallyPayUp to 2 CPM performance bump after 90 daysPayUp to 2 CPM increase at 1-year milestone

Store Director, MaxMara Chicago

CDL-A Truck Driver - Home Weekly

$1,482-$2,484/wk

Pay$1,482 - $2,484 WeeklyPay$1,675+ weeklyPayDynamic Mileage Pay

Administrative Assistant

$25/hr

89% of jobs ask for a resume

89% of jobs ask for a resume

Carrier Sales Representative

2157 Transportation Staff jobs in Chicago,IL

$250/day

CDL-A Truck Driver - Earn $1,300-$1,600/Week + 100% No-Touch Freight

$1,300-$1,600/wk

CDL-A Truck Driver - Most Weekends Off - Earn Up to $111,917.87/Year

$1,018.63-$2,152.27/wk

Pay$52,968.74 - $111,917.87 per YearPay$1,800 transition package including $1,000 orientation payPay$0.65 to $0.69 per mile

Sous Chef

CDL-A Truck Driver - Average $1,863/Week + $2,000 Hiring Bonus

$1,863/wk

$2,000 bonus

PayAverage $1,863/WeekPay$2,000 Hiring BonusPayAverage $1,863 weekly - top performers average $2,161 weekly

12 Days Out CDL A Driver Job w/ 1 Year Experience

$1,945/wk

PayTop 50% average $96,483 per yearPayStarting pay $.64 to $.67 cpmPayMore than $101,176 annually

CDL-A Truck Driver - Home Weekly

$25/hr

PayEarn $72,800 - $98,800+ AnnuallyPayUp to 2 CPM performance bump after 90 daysPayUp to 2 CPM increase at 1-year milestone

Store Director, MaxMara Chicago

CDL-A Truck Driver - Home Weekly

$1,482-$2,484/wk

Pay$1,482 - $2,484 WeeklyPay$1,675+ weeklyPayDynamic Mileage Pay

Administrative Assistant

$25/hr

89% of jobs ask for a resume

89% of jobs ask for a resume

Carrier Sales Representative