Uber Technologies Inc. is digging deeper into the freight business, ramping up hiring at a planned new hub in Chicago and rolling out logistics services even as its core ride-hailing business continues to post steep losses.

The company’s Uber Freight said Tuesday it is expanding a service aimed at making it easier for truckers to pick up already-loaded trailers ready for transport. It is the latest in a stream of upgrades at the business as it looks to grab business from traditional freight transport companies and compete with a growing field of like-minded digital brokerages.

Uber Freight also said carriers using its mobile app can now book multiple loads at one time, a service it says will help truckers plan better and reduce the number of miles spent hauling empty trailers. Rival freight-booking startup Convoy rolled out a similar service earlier this year.

The actions mark the latest steps to extend Uber Technologies’ reach beyond its ride-hailing app.

Uber’s overall revenue reached $3.17 billion in the second quarter, but the company still expects to lose $3 billion to $3.2 billion this year.

Uber, which logged $11.3 billion in full-year revenue for 2018, doesn’t break out financial results for Uber Freight, which it launched in 2017, but said in its IPO filing that the division had $359 million in gross freight bookings in 2018. The company’s Other Bets segment, which primarily consists of Uber Freight and its mobility business focused on electric bikes and scooters, generated $373 million in revenue in 2018.

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That is a small sliver of the U.S. domestic freight transportation management business estimated at $86.5 billion, according to research group Armstrong & Associates.

Uber Freight “is to a point now where they have hit scale,” said Armstrong & Associates President Evan Armstrong. “Really the next target for them is to get to $1 billion.”

Uber said last week it is opening an office in Chicago that will serve as its Freight headquarters and will be the division’s first engineering hub outside of San Francisco. Uber says it plans to invest over $200 million annually in the region and hire 2,000 employees in the next three years.

Chicago is a major transit point for North American shipping and home to several big operators. Freight brokers Echo Global Logistics Inc., Hub Group Inc. and United Parcel Service Inc.’s Coyote Logistics brokerage division are based in the region, along with a number of tech-focused logistics ventures.

To scale up faster, Uber Freight and rival digital freight platforms are also adding services intended to help truckers potentially make more money and boost efficiency for the customers whose freight they are hauling. They include ratings features for cargo pickup and drop-off facilities that help carriers decide which loads they want to accept.

Uber Freight is expanding a trucking service known in the industry as “drop-and-hook” to California after an initial rollout in Texas. With the service, truckers can hitch their vehicles to already-loaded trailers instead of having to wait for goods to be loaded and unloaded. The aim is to speed up cargo transfers for shippers and for drivers. Such services can help smaller truckers gain business that is typically the province of big trucking companies with large fleets of trailers.

Write to Jennifer Smith at jennifer.smith@wsj.com