President Joe Biden's campaign is assembling top donors in Chicago this week with questions looming about how the campaign's high dollar and grassroots donor operations will fare as a key fundraising deadline approaches at month's end.

The multi-day confab, which is set to begin Wednesday, will give donors a chance to hear from Democratic officials and Biden advisers about the campaign's strategy and goals as the president's reelection operation nears the five-month mark. Vice President Kamala Harris is expected to speak to the gathering on Wednesday evening and attendees are also expected to hear more about plans for the Democratic National Convention in Chicago next summer.

It also puts top campaign officials in front of deep-pocketed donors one day after House Speaker Kevin McCarthy called on relevant committees to open a formal impeachment inquiry into Biden, even as they have yet to prove allegations that he directly profited off his son's foreign business dealings.

The Biden team has blasted McCarthy, who reversed course after previously saying a vote would be needed to start such an inquiry. A White House spokesperson described it as "extreme politics at its worst," and the Biden campaign called the House speaker "the Trump campaign's super surrogate."

But fresh off the announcement, it was unclear if the campaign would choose to start raising money off McCarthy's moves or if an impeachment inquiry could hurt or help Democrats' fundraising efforts.

The Democratic Congressional Campaign Committee, however, moved to fundraise off an impeachment inquiry quickly, sending out an email Tuesday evening about McCarthy's decision and saying, "This MAGA Majority needs to be DEFEATED."

The Biden campaign is also grappling with polls showing widespread concern about the president's age and decreased confidence among Democratic-aligned voters.

"Age is a bummer for everyone," said one donor who requested anonymity to describe private conversations with peers. "The big money will be there, but they're not jumping up and down."

Biden officials expected to participate in the talks include campaign manager Julie Chavez Rodriguez, deputy campaign managers Quentin Fulks and Rob Flaherty, Biden campaign finance chair Rufus Gifford, Biden Victory Fund chair Chris Korge and Harris' campaign chief of staff Sheila Nix, a source familiar with the plans said.

A similar meeting to court high-dollar fundraisers was held in late April in Washington, DC, days after the president's campaign announcement, kicking off a flurry of fundraising efforts that netted Biden and the Democratic Party $72 million in his first quarter in the 2024 race.

That figure eclipsed the fundraising hauls of the current crop of Republican presidential candidates but fell short of the $86 million raised by former President Barack Obama and the Democratic National Committee when he launched his reelection bid during the same fundraising period in 2011.

Now, Biden faces a fresh challenge ahead of the deadline for the end of the third fundraising quarter, a July-to-September period that is traditionally sluggish for raising money with one longtime Democratic bundler describing the summer months as a "slog."

While officials are optimistic about the campaign's cash -- and ability to compete against a Republican nominee -- there's an acknowledgment that the third-quarter numbers may come in lighter than expected.

"Summer is very hard. It's just hard to get people to events," one DNC official told CNN.

Biden prepares to hit the fundraising circuit

This week's high-dollar donor retreat comes as Biden is preparing to hit the fundraising circuit himself with less than three weeks to go before the end of the third quarter. The president has only attended three in-person fundraisers since the quarter's start in July but is prepared to expand that list in the coming week.

He'll attend an event in McLean, Virginia, on Wednesday, and several donor events are scheduled in New York City around the president's attendance at the UN General Assembly meeting, according to Democratic donors familiar with the plans.

The New York fundraisers include a glitzy "Broadway for Biden" concert, hosted in part by Jeffrey Seller and Thomas Kail, the producer and director of the hit Broadway show "Hamilton," respectively. Online tickets for the Monday evening event, which will feature performances from Broadway stars, range from $250 to $7,500.

At least two other fundraising events, including one for lawyers supporting the president, are in the works for New York City next Wednesday and the president is expected to add other campaign fundraisers before the end of the month.

The campaign also has plans to again lean on Harris and first lady Dr. Jill Biden to hit up donors for money over the next few weeks.

Key test on grassroots fundraising looms

But the Biden campaign is also focusing its attention on boosting grassroots fundraising efforts as they face persistent questions about their ability to bring in small-dollar donors, which are often used as a metric of enthusiasm. Those types of donors helped fuel Biden's record-shattering $1 billion haul in 2020 with $700 million coming from online donations.

Initial fundraising reports showed some signs of a slow start on the small-dollar fundraising front. The president's reelection campaign and Biden Victory Fund brought in more than $10 million from donors giving $200 or less, according to quarterly FEC reports filed in July. By comparison, Obama's reelection campaign, which launched earlier in the month of April than Biden, brought in double that figure in the same period of 2011.

But small-dollar fundraising across both parties is down, compared to 2019, and some argue the lack of a less competitive Democratic primary has lessened the urgency for some donors to give.

"It's pretty obvious [the Biden campaign] is trying to offset that with big dollar donations," a source familiar with campaign dynamics told CNN. "Voters aren't tuned in. So their thing is --'Let's hold a bunch of massive events, in the biggest places in the country.'"

A Democratic source close to the campaign and its fundraising strategy contends the campaign's small dollar fundraising has been "going very well" and is "exceeding their goals" even during the slow summer months. The source said they anticipate small-dollar donations to become the "primary fundraising engine for the campaign once the general election kicks into high gear."

Ahead of the September 30 deadline, the campaign has sent out fundraising pleas to small-dollar donors on social media and via e-mail, including launching a contest for one online to donor to meet Obama and Biden.

One donor told CNN the campaign is actively ramping up it's small-dollar donation operation, driven in large part by Gifford.

"People are feeling more bullish" the donor said, referring to the campaign's fundraising ability. "But you know, they've still got to get the rust kicked off a bit."

Campaign staff begins to expand.

The Biden campaign has kept its operation lean, boasting $77 million cash on hand at the end of the last fundraising quarter. It has started to make its case on the television airwaves with a 16-week, $25 million ad blitz that kicked off in August, marking an early foray into advertising by an incumbent president.

During these summer months, the campaign has hired more staff, many now working out of offices in Wilmington, Delaware. That has included building out its finance team after the DNC ran much of the fundraising apparatus for the opening weeks of the campaign.

That has included building out its finance team after the DNC ran much of the fundraising apparatus for the opening weeks of the campaign. In addition to naming Giffords and Korge as finance chairs, the Biden campaign has also brought on two finance leads from the DNC to serve as the campaign's finance co-directors -- Colleen Coffey and Michael Pratt -- as well as naming Jessica Porter, who ran the DNC's online fundraising operation and served as the SMS fundraising manager for Biden in the 2020 general election, the grassroots fundraising director.

Flaherty, who led Biden's digital team at the White House and on the 2020 campaign, also joined the reelection effort as a deputy campaign manager with an eye in part on utilizing digital tactics to boost small dollar donations.

One tool the campaign hopes to leverage early on in their efforts is a joint fundraising agreement between the campaign, DNC and state Democratic parties, consolidating efforts to raise money early in the race and allow individual donors to contribute up to $929,600 to the Biden Victory Fund.

Donors anticipate this week's donor retreat to including informational and "rally the troops" type of programming, including from Harris.

"What has been impressed upon her is, she needs to energize donors," one of the sources said. "And get them to buy into the campaign."

Harris has increased her time with donors and bundlers, in part, at the urging of the campaign, a source familiar with her plans said. Harris' fundraising push in Milwaukee in early August brought in around $400,000, a DNC official said, describing it as a strong haul for an ancillary city.

The vice president's allies have said they anticipate Harris being a big part of the campaign's fundraising and messaging calculus going forward with some donors telling CNN they've been impressed with her ability to work fundraising circles.

"I remember thinking to myself, 'If I wasn't aware of [Harris'] negative narrative, I wouldn't know it existed," said Orin Kramer, an influential Democratic fundraiser and hedge fund founder who saw Harris at a New York fundraiser. Kramer added he was impressed with her ability to charm donors individually and address the entire room: "That's real."