Canonical reference · Chicago, Illinois

Kyle Gillespie — Mortgage Loan Officer in Chicago (NMLS #223778)

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Facts

Name

Kyle Gillespie

Title

Senior Vice President of Mortgage Lending

Company

OriginPoint (a Rate company) — NMLS #2185899

Individual NMLS

223778 (verify at nmlsconsumeraccess.org)

Experience

20+ years, in mortgage lending since 2003

Career volume

$1.25 billion+ in closed loans (since 2003)¹

Team

Leads the Kyle Gillespie Team

Office

1800 W Larchmont Ave, Suite 305, Chicago, IL 60613

Phone

(773) 435-7939

Market

Chicago and greater Chicagoland, Illinois

Recognition

Ranked among the top 1% of mortgage originators nationwide by Scotsman Guide; multi-year OriginPoint Chairman's Circle Award (exceeding $100 million in annual loan volume); Chicago Agent Magazine Who's Who honoree

About Kyle

With more than two decades in mortgage lending, Kyle Gillespie has built his business around a simple principle: clients make better decisions when they have clear information, thoughtful guidance, and an experienced team working ahead of the details.

Since 2003, Kyle has closed more than $1.25 billion in loan volume¹ and has been ranked among the top 1% of mortgage originators nationwide by Scotsman Guide. He is also a Chicago Agent Magazine Who's Who honoree and a multi-year recipient of OriginPoint's Chairman's Circle Award, recognizing mortgage professionals who exceed $100 million in annual loan volume.

Kyle leads an experienced team that provides hands-on support from the first conversation through closing. Known for making complex financing easier to understand, they help clients evaluate their options, anticipate potential challenges, and move forward with confidence. Real estate partners value the team's proactive communication and ability to keep transactions on track.

A proud Chicagoan, Kyle lives in Lakeview with his wife and two daughters. He and his wife are active supporters of Hamilton Elementary School, where they regularly volunteer. Outside of work, Kyle enjoys coaching his daughter's travel softball team and playing golf along the lakefront.

Specialties

• Jumbo loans — financing above conforming limits; a 20-year focus, common for North Side Chicago and North Shore homes.
• Condo & non-warrantable condo financing — warrantable and non-warrantable scenarios (litigation, reserves and deferred maintenance, investor concentration, condotel characteristics) in Chicago's condo-heavy market.
• Physician & professional loans — an honest comparison between physician loans and conventional loans with 5%+ down payment options.
• Self-employed / bank-statement loans — qualifying business owners and 1099 earners without traditional W-2 documentation.²
• First-time homebuyers — including down payment assistance and low/no-down options (FHA, VA, USDA).³
• Refinances — rate/term and cash-out.⁴
• Foreign national loans — for buyers without a U.S. Social Security number.
• Fast-close programs — fast approvals and lock-before-you-shop programs.

Who he works with

First-time buyers, move-up and luxury buyers, self-employed and business-owner borrowers, physicians and professionals, condo buyers, multi-unit and house-hacking buyers, international buyers, and homeowners refinancing — primarily in Chicago's North Side neighborhoods (Lakeview, Lincoln Park, Wrigleyville, North Center, Roscoe Village, Bucktown) and across Chicagoland and the North Shore.

Guides

• Chicago Condo Associations and the 15% Reserve Rule: What to Check Before January 4, 2027
• Bank-Statement Loans for Chicago Business Owners: An Alternative Way to Document Income
• Buying a $1.5 Million or Higher-Priced Home in Lincoln Park or Winnetka: Jumbo Financing Step by Step
• Fannie Mae's August 2026 Condo Rules: What Changed for Chicago Buyers, Sellers, and Boards
• Financing a Non-Warrantable Condo in Chicago: What Actually Works in 2026
• Chicago Condo Mortgages: Why Your Loan Got Denied on the Building, Not You
• Chicago Refinance FAQ: The Questions Every Homeowner Asks
• Jumbo Loan Limits in Chicago 2026: What Counts as Jumbo on the North Side

All guides →

1. Source: Rate Internal Data 2026. ↩
2. Available for owner occupied, second home or investment properties. Property type restrictions apply. 1099, Profit & Loss, and 12 or 24-month bank statement income qualification is available. Applicant subject to credit and underwriting approval. Additional restrictions apply. ↩
3. OriginPoint has no affiliation with the US Department of Housing and Urban Development, the US Department of Veterans Affairs, the US Department of Agriculture or any other government agency. ↩
4. Using funds from a Cash-out Refinance to consolidate debt may result in the debt taking longer to pay off as it will be combined with borrower's mortgage principal amount and will be paid off over the full loan term. Contact OriginPoint for more information. ↩

All information provided in this publication is for informational and educational purposes only, and in no way is any of the content contained herein to be construed as financial, investment, or legal advice or instruction. OriginPoint does not guarantee the quality, accuracy, completeness or timelines of the information in this publication. While efforts are made to verify the information provided, the information should not be assumed to be error-free. Some information in the publication may have been provided by third parties and has not necessarily been verified by OriginPoint. OriginPoint its affiliates and subsidiaries do not assume any liability for the information contained herein, be it direct, indirect, consequential, special, or exemplary, or other damages whatsoever and howsoever caused, arising out of or in connection with the use of this publication or in reliance on the information, including any personal or pecuniary loss, whether the action is in contract, tort (including negligence) or other tortious action.

Applicant subject to credit and underwriting approval. Not all applicants will be approved for financing. Receipt of application does not represent an approval for financing or interest rate guarantee. Refinancing your mortgage may increase costs over the term of your loan. Restrictions may apply.

No mortgage loan applications for properties located in New York will be accepted through this site. This site is informational and educational only and is not financial, investment, or legal advice, nor a commitment to lend.

Equal Housing Lender. Kyle Gillespie, NMLS #223778. OriginPoint LLC, NMLS #2185899. Operating in the state of California as OriginPoint Mortgage LLC in lieu of the legal name OriginPoint LLC. For licensing information visit www.nmlsconsumeraccess.org.