OTR & Long Haul Jobs in Chicago, IL — Now Hiring

As of October 2026, there are 178 otr & long haul openings in Chicago, IL. Local pay ranges from $61,200 to $418,600/year. Listings are updated daily — many roles offer flexible hours and employee discounts.

Foremost Transport

Mobile Home Transport Driver - CDL A Oversize Load

Chicago, IL

$90,000 - $120,000

Matheson Postal Services

USPS Mail Haul Truck Driver - CDL A Contractor

Chicago, IL

$61,600 - $79,200

Jack Cooper Transport

Chicago CDL A Truck Driver-Auto Hauler Car Transport with

Chicago, IL

$86,450 - $122,850

Shaffer Trucking

Immediate Opening in Chicago for a CDL A Truck Driver-OTR Refrigerated

Chicago, IL

$92,000 - $109,249

Quantix

CDL A Truck Driver-Regional Liquid Tanker Hazmat•Chicago,IL•Quantix

Chicago, IL

$90,000 - $110,000

Black Eagle Express

Chicago Job:CDL A Truck Driver-OTR Flatbed Conestoga(Full-time)

Chicago, IL

$104,000 - $130,000

Hora Express

Hora Express Needs CDL A Owner Operator Truck Driver-91% Pay in

Chicago, IL

$236,600 - $331,240

CRST The Transportation Solution

Chicago Career:CDL A Truck Driver-OTR Team Driver at CRST The

Chicago, IL

$99,474 - $126,499

Crete Carrier

CDL A Truck Driver-Regional Dry Van Home

Chicago, IL

$65,520 - $83,720

Schneider National

Chicago,IL:CDL A Truck Driver-OTR Dry Van at Schneider National

Chicago, IL

$75,000 - $96,000

Jack Cooper Transport

Chicago CDL A Truck Driver-Auto Hauler Car Transport(Full-time)-Jack

Chicago, IL

$95,000 - $135,000

Shaffer Trucking

Chicago:CDL A Truck Driver-OTR Refrigerated Reefer

Chicago, IL

$92,000 - $109,249

OTR & Long Haul Jobs in Chicago — FAQ

How many otr & long haul jobs are open in Chicago, IL?
There are currently 178+ otr & long haul in Chicago, IL. New otr & long haul roles are added regularly — check this page for the latest openings.
How much do otr & long haul jobs pay in Chicago?
Pay for otr & long haul in Chicago varies by employer, equipment and how much time you spend away. Many positions offer flexible scheduling and employee discounts, and some include shift differentials for nights and weekends. Browse the listings above to see pay details for each opening.
Do these otr & long haul positions require experience in Chicago?
Many otr & long haul positions in Chicago require no prior experience, and most employers provide paid on-the-job training. Check individual listings for specific requirements.
How do I apply for otr & long haul jobs in Chicago?
Browse the 178+ otr & long haul listings above, click on any position for full details including pay and shift times, then follow the application link to the employer. Most driver applications take about 10–20 minutes online.

OTR & Long Haul Jobs in Other Cities

OTR & Long Haul Jobs in New York

112 open positions

OTR & Long Haul Jobs in Los Angeles

114 open positions

OTR & Long Haul Jobs in Houston

101 open positions

OTR & Long Haul Jobs in Phoenix

167 open positions

OTR & Long Haul Jobs in Philadelphia

134 open positions

OTR & Long Haul Jobs in San Antonio

101 open positions

OTR & Long Haul Jobs in San Diego

145 open positions

OTR & Long Haul Jobs in Dallas

134 open positions

OTR & Long Haul Jobs in Fort Worth

79 open positions

OTR & Long Haul Jobs in Jacksonville

136 open positions

Other Driving Careers in Chicago

Full-Time Driving Jobs in Chicago

477 open positions

CDL-A Truck Driving Jobs in Chicago

360 open positions

Part-Time Driving Jobs in Chicago

187 open positions

Delivery Driver Jobs in Chicago

157 open positions

Local Driving Jobs (Home Daily) in Chicago

149 open positions

CDL-B Driving Jobs in Chicago

109 open positions

Regional Driving Jobs in Chicago

87 open positions

Weekend Driving Jobs in Chicago

57 open positions

Last updated: October 29, 2026