CHICAGO — On Monday, members of the so-called gig economy were finally able to file for unemployment benefits.

From Uber drivers to musicians, these are not typically workers who are eligible for unemployment.

CBS 2’s Chris Tye had a look Monday afternoon at how the first day went.

Illinois Gov. JB Pritzker said 44,000 gig and 1099 workers filed on Monday alone. It has been a grueling wait.

But until the money shows up in their account, for gig workers, resting easy will be a tricky task.

Kevin McGourty gave the first day of the Pandemic Unemployment Assistance program a grade of D.

A new website has been set up for the program. Kathleen Budwitis got through, but the weekly benefit of $198 was far lower than she was owed.

Meanwhile, the website’s helper assistance, we’re told, lacked any humans to help troubleshoot.

“When I ask for assistance, the chatbox is telling me to file an appeal, which doesn’t make sense because I’m not being considered,” said Amy Falk.

And for those trying by phone?

“We had some glitches, again, with phone calls today. The entire phone system for the State of Illinois, actually, had some interruption today, and so that went down,” Pritzker said. “I believe it’s back up again.”

Gig workers or 1099 workers who made it through receive up to 39 weeks of benefits. They must file for “regular” unemployment first.

The money arrives through direct deposit or debit cards.

The state said it is adding hundreds of staff to help with the onslaught of filings.

McGourty did file and got rejected for regular unemployment, which is a qualification for Pandemic Unemployment Insurance, or PUA.

“The system says you need to be denied to file for the PUA, and when you go in and do that? It won’t allow me to file for PUA because it says I have an active claim previous to that,” McGourty said.

It’s a day that’s been circled on the calendar for clarity, but instead has been putting new worries into focus.

“It’s scary. It’s frightening,” McGourty said. “Every day, you live with it.”

And was no cheap endeavor. The state hired consulting firm Deloitte to manage it, and it cost nearly $22 million for the state to put the PUA program together on deadline.

CBS 2 is committing to Working For Chicago, connecting you every day with the information you or a loved one might need about the jobs market, and helping you remove roadblocks to getting back to work.

We’ll keep uncovering information every day to help this community get back to work, until the job crisis passes. CBS 2 has several helpful items right here on our website, including a look at specific companies that are hiring, and information from the state about the best way to get through to file for unemployment benefits in the meantime.