How do Chicago buyers navigate financing and commuting when buying a second home here?

How do Chicago buyers navigate financing and commuting when buying a second home here?

They win by treating it like a project, not a weekend impulse: lock financing early, build reserves, and pick a location that matches their commute tolerance.

Financing playbook (what works)

• Second-home underwriting is stricter: expect higher down payments and reserve requirements than a primary.

• If STR income matters: you need a lender who can underwrite the strategy (and you need local rules to allow it).

• Get insurance quotes upfront (lakefront can surprise people).

Commuting options that buyers actually use

• Amtrak Wolverine has a stop in New Buffalo (nice for Chicago buyers who want train optionality).

• South Shore Line is the workhorse option for Northwest Indiana commuting into Chicago.

• Driving: Chicago ↔ New Buffalo is roughly ~70 miles / ~75 minutes in normal traffic, but weekend patterns can be brutal—plan accordingly.