1099 CDL Driver Jobs in Maryland April 2026

Xcalibur Logistics

CDL Pick-up Company Driver - Hotshot Car Hauling

Hiring in Maryland and 46 other locations
Flexible
$2,000 - 2,500 Per week

Experienced Dispatch: Our dispatchers are former drivers, so they understand your needs
24-Hour Road Support & In-House Repair Shop
Top-Notch Equipment: Most of our trucks and equipment are brand new

Legal Miles

Only 3-4 Car Hauling

Small Owner Operated Fleet

C1 Transportation Inc

CDL A Flatbed OTR Driver

Hiring in Maryland and 45 other locations
Flexible
30% Of gross

Two day fast PAID orientation
Direct Deposit weekly, payments should be received by Friday each week.
8 driver maximum per one dispatcher, which allows our dispatchers to pre-plan loads for you.

Steady Weekly Paycheck

Paid Orientation

Pre-planned Trips

A&V Cargo Inc

Small Fleet Is Hiring A Company Driver

Hiring in Maryland and 46 other locations
2 weeks out
30% Of gross
/
$0.60 Per mile

Small fleet is hiring. Flatbed trailer - we will haul everything that will fit on a 53ft flatbed.
Running all over Midwest, South and South East
Forwarding all rate confirmations. We offer a respectful and fair treatment, on-time salary and all around support!

Owner Operated Small Company

Full Transparency

Industrial Cargo Logistics Inc

Owners-Operators - Flatbed/Step Deck/Conestoga

Hiring in Maryland and 46 other locations
Flexible
88% Of gross

A+ Insurance with $250k of coverage
Main load and partials, we don't let the truck travel half empty, any available space on the trailer is used.
Best rates negotiation. Reputable brokers. Trip planning.

A+ Insurance with $250k coverage

USA Based Dispatchers

Direct Freight

Hugo Hunter Inc

CDL-A Owner Operator | 90% of Load Gross

Hiring in Maryland and 46 other locations
Flexible
90% Of gross

90 Percent of Gross Pay! 24/7/365 Dispatch and Road Service. Weekly Pay Via Direct Deposit.
100% Fuel Advance with Competitive Fuel Discounts. Premium Health Benefits Package.
Reefer, Open-Deck, And Dry van Trailer Rental for as low as $250 per week. Full Service.

Thompson Transportation Inc

Company CDL-A OTR Driver | Home Every Weekend

Hiring in Maryland and 46 other locations
Weekly
$0.50 Per mile

Minimum CDL driver pay starts at $.50 but could be higher based on CDL driving experience.
Quarterly truck driver safety bonus of $.02 added to all miles driven within the quarter.
Truck Driver averages 2,500 miles per week. 401k plan with employer match. Holiday pay.

Keep Trucking LLC

OTR Flatbed/Stepdeck CDL-A Company Driver | 1099 Position

Hiring in Maryland and 46 other locations
Flexible
$0.70 Per mile
/
25% Of gross

Drivers Average $1,750 - $2,450 Weekly Gross. CPM $0.70 or 25% for the Load for Flatbed. Cash Advance.
All miles are paid Empty & Loaded. Extra Stops($50). 2022 and Newer Volvos, and Peterbuilts. Rider and Pet friendly
Get Paid Every week via Direct Deposit. Drivers can Switch beetween divisions and get paid either by % or CMP.

Just Trucking Services

CDL A - Lease to purchase with $0 Down

Hiring in Maryland and 45 other locations
Flexible
$90,000 - 120,000 Per year

OTR drivers wanted willing to start their own business.
Low weekly payments. Weekly gross 6k-8k. No hidden fees
Start and grow your trucking business with us!

No Credit Check

Get One or Multiple Trucks

$0 Down for Truck and Trailer

U.S. Xpress, Inc.

CDL Class A Team Drivers

Hiring in Maryland and 46 other locations
Weekly
$200,000 Per year

Your team can average $200,000 or more!
Average 5,000 miles per week or more.
Extra cash for every doubles lead.

Kora Freight, Inc.

Owner Operator CDL A | $5500 per week

Hiring in Maryland and 46 other locations
3 weeks out
$2,500 - 5,500 Per week

Pay: $2,500.00 - $5,500.00 per week.
Trucking driver type: Solo driver, Team driver
Trucking home time: Home every 3 weeks

Hittman Transport Services, Inc.

Owner Operators CDL A Team Truck Drivers

Hiring in Maryland and 46 other locations
Daily, Flexible
$10,000 Per week

Hittman Transport Services, Inc. is contracting owner operators.
Teams make up to $10,000 weekly. Quarterly Fuel Discount, plus Discounts at the pump.
Hittman Transport pays for the yearly expenses: tolls, fuel tax, tractor washes...

TPA Cargo Solutions LLC

CDL A Owner Operator | $4,000-5,000 take-home

Hiring in Maryland and 46 other locations
Flexible
85% Of gross

Drop & hook, live load & live unload loads
No touch freight. 24/7 support. Consistent back to back loads
Average owner operator gets a paycheck of $4,000-$5,000 per week after all expenses

Consistent Back To Back Loads

$4,000-$5,000 Weekly Take-home

Professional No Forced Dispatch

CDL DNA

CDL A Team Drivers for Amazon Loads - Flat Rate

Hiring in Maryland and 46 other locations
4 weeks out
$1,900 Per week
/
$0.75 Per mile

Drivers that are willing to run make $2,500 - $3,200 per week
We have a great variety of trucks from 2022 to 2024 year models
We can give you north of 6,000 mi per week

$1,900 Weekly Flat Rate

Drop & Hook Loads

Team Matching Available

CDL DNA

CDL A Reefer Truck Driver - Up to 31%

Hiring in Maryland and 45 other locations
3 weeks out
27 - 31% Of gross

We have one of the most experienced dispatchers in the industry
As a Company Driver, you can expect exceptional service , support and communication
We have a CPM option if you feel more comfortable being paid per mile

$2,000 - $2,500 Weekly Take-home

Company With Great Reputation

Professional and Friendly Environment

Transurfing Inc

CDL A Reefer & Dry van Company Driver OTR

Hiring in Maryland and 46 other locations
3 weeks out
$0.63 - 0.65 Per mile
/
28 - 30% Of gross

2021 - 2023 Kenworth T680 with automatic transmission
We have a lot of customer freight and need professional, responsible and safe drivers to help us move it
Operating in Midwest and West Coast

Only For Safe and Responsible Drivers

Great New Trucks & Equipment

Consistent Direct Freight

1099 CDL driver jobs in Maryland