The Ultimate First-Time Homebuyer Checklist for Chicago (2025 Edition)

Are you ready to swap your landlord for a mortgage lender, or finally stop Googling “how much rent is TOO much in Chicago”? Welcome to the first-time buyer’s club! This is your step-by-step roadmap to navigating the Chicago real estate jungle—without losing your mind or your savings account. (Bonus: I’ll even help you avoid buying next door to that guy who practices his tuba at midnight.)

1. Get Your Money Ducks in a Row

• Check your credit score. You don’t need a 900 (it doesn’t even go that high), but higher scores = better mortgage rates.

• Count your cash. Down payment time! Illinois has programs for as little as 3% down. Don’t forget closing costs, moving expenses, and, let’s be real, at least three deep-dish pizzas to celebrate.

• Set your budget. Include property taxes (hello, Illinois!), HOA fees, insurance, and a “rainy day” fund for those unexpected repairs. Because if it can break, it will—usually right after you move in.

• Get pre-approved. A pre-approval letter from a local lender makes you look serious to sellers—even if you still feel like you have no idea what you’re doing.

2. Define Your Must-Haves (and Your “Nice-to-Haves”)

• Location, location, location. Want a lake view, a short commute to the Loop, or space for your dog to actually run?

• Type of home. High-rise condo with a doorman? Classic Chicago bungalow? Or maybe a trendy loft?

• Essentials. Parking (trust me, you’ll thank me in February), in-unit laundry, work-from-home space, pet policies, and storage for all those winter coats.

• Schools. Even if you don’t have kids, good schools = better resale value.

3. Start the (Fun) Search

• Find an agent who “gets” you. (Hi, I’m Jason! Realtor, Chicago enthusiast, and sworn enemy of shady deals.)

• Set up MLS alerts. Get new listings sent right to your inbox, so you don’t miss “the one.”

• Tour homes. Bring a notepad (or just your phone) and snap pics—after five showings, they all blur together like a bad Zoom call.

• Scope out the neighborhood. Visit at different times of day to see what parking, traffic, and the local coffee scene are really like.

4. Do Your Homework on Each Home

• Property taxes. In Chicago, they can vary wildly—even from block to block.

• HOA rules and fees. Not all buildings allow pets or short-term rentals, and some charge a lot for amenities.

• Check the bones. Has the home had recent updates? How old are the roof, furnace, and windows? (You want a home, not a money pit.)

• Walk scores & transit. Can you walk to the L or will you be shoveling out your car all winter?

5. Make an Offer (Without Breaking a Sweat)

• Check the “comps.” What are similar homes selling for nearby? This isn’t The Price is Right, but it’s close.

• Contingencies. Inspection, financing, and appraisal—yes, you want all three.

• Negotiation time! Sometimes you need to sweeten the deal—maybe a flexible closing date, or even a heartfelt “pick me!” letter to the seller.

6. Inspections, Appraisals, and “Paperwork Olympics”

• Hire a licensed inspector. They’ll find stuff you’d never spot (like the “mystery smell” in the basement).

• Negotiate repairs or credits. No home is perfect, but some fixes are deal-breakers.

• Get your lender all their docs ASAP. It’s a paperwork marathon, but don’t worry—I’ll coach you through it!

7. Closing Time (Cue the Music!)

• Final walk-through. Make sure everything’s as agreed (and that questionable chandelier is finally gone).

• Review your closing disclosure. No surprises allowed!

• Sign a small forest of paperwork. Stretch your signing hand!

• Get your keys and celebrate. Pizza, Instagram post, happy dance in your new living room—you earned it.

Chicago Buyer Pro Tips

• Shop in winter for less competition! Bundle up, you might score a deal.

• Ask about first-time buyer grants. Illinois and Chicago offer great programs.

• No silly questions here! I love explaining the process—and I know all the best pizza places.

Ready to Make Your Chicago Dream Happen?

Whether you’re just starting or already obsessed with Zillow, let’s make your first home purchase a breeze.Contact Jason Rosenberg for expert help, a good laugh, and maybe even a pizza recommendation! Get in touch here! or call/text 312.882.9797.