Investment Property Loans in Chicago, IL

A Chicago unit rented through a platform for 31 days or fewer needs a shared housing registration number, renewed yearly at $250, and stays owe the 4.5% hotel accommodation tax plus a 6% surcharge.

For investors: Licensed platforms remit the city's combined 10.5% for you, but bookings taken directly require your own city tax account. Renewal opens two months before expiration, so calendar it; once a registration lapses the unit can no longer be rented short term.

Source: City of Chicago BACP, Shared Housing Registrations and 2026 Registration Guide, Oct 2026

Under Chicago's shared housing rules, a short-term rental in a single-family home or two- to four-unit building must be the host's primary residence, and only one unit may be active.

For investors: That ends the plan of buying a two-flat or three-flat to run nightly rentals from afar, short of a Commissioner's Adjustment from BACP. Also check for a Restricted Residential Zone precinct, the Prohibited Buildings List and any lease or HOA ban, since each blocks registration.

Source: City of Chicago BACP, Shared Housing Registration Common Eligibility Criteria, Oct 2026

In Chicago buildings of five or more units, short-term rentals need not be the host's home but are capped at one quarter of the units or six, whichever is less.

For investors: A 12-unit building could run at most three nightly units. A host approved for more than one registration also needs a Shared Housing Unit Operator License, while each unit still carries its own registration and $250 fee.

Source: City of Chicago BACP, Shared Housing Registration Common Eligibility Criteria, Oct 2026

Chicago's real property transfer tax is $5.25 per $500 of price: the buyer generally pays the $3.75 city portion and the seller the $1.50 transit (CTA) portion.

For investors: On a $400,000 two-flat the buyer's city share is $3,000 and the seller's transit share $1,200, before state and Cook County stamps. Put the buyer share in the cash-to-close budget alongside the down payment and reserves.

Source: City of Chicago Department of Finance, Real Property Transfer Tax (Municipal Code 3-33), Oct 2026

Cook County adds its own real property transfer tax of $0.25 per $500 of price on Chicago sales, on top of the city's $5.25 and the state's $0.50 per $500.

For investors: On a $400,000 Chicago purchase the county share is $200, and the three layers together reach $4,800, or 1.2% of price. The city splits only its own portion by custom, so settle in the contract who pays the county and state stamps.

Source: Cook County Clerk's Office, Transfer Fees, Oct 2026

The Cook County Assessor reassesses Chicago every three years; the city's townships were reassessed in 2024 and are next scheduled for 2027, while the suburban triads follow other years.

For investors: A Chicago purchase underwritten on the 2024 assessment may see a new value mailed in 2027. Build a property tax cushion into DSCR coverage and watch for your township's appeal window when those reassessment notices arrive.

Source: Cook County Assessor's Office, The Cook County Property Tax System, Oct 2026

Chicago's Residential Landlord and Tenant Ordinance governs deposits, access, notices and repairs for most city rentals, but exempts units in owner-occupied buildings with six or fewer units.

For investors: A two-flat or six-flat where the owner lives on site sits outside most RLTO rules, but a non-owner-occupied investor building of any size is covered, including the duty to attach the city's RLTO summary to every lease and renewal.

Source: City of Chicago Department of Housing, Residential Landlord and Tenant Ordinance, Oct 2026

For RLTO-covered Chicago units, landlords must keep deposits in a federally insured, interest-bearing Illinois account, name the institution in writing within 14 days, and pay yearly interest after six months; the 2026 rate is 0.01%.

For investors: The interest owed is tiny, but mistakes are not: a landlord who breaks the deposit rules can owe the tenant twice the deposit plus interest. On a purchase, review every inherited deposit, receipt and account before closing.

Source: City of Chicago Department of Housing, Security Deposit Interest Rates; RLTO Summary (Mun. Code 5-12-080, 5-12-081), Jan 2026

Chicago's Fair Notice rules require 30 days' notice of a non-renewal or rent increase for tenants under six months, 60 days up to three years, and 120 days beyond three years, even in RLTO-exempt units.

For investors: When you buy an occupied Chicago building, long-tenured tenants may need four months' notice before a rent increase takes effect, so pro forma rents should lag closing. Covered tenants facing eviction for nonpayment also get a one-time right to pay and stay.

Source: City of Chicago Department of Housing, RLTO Summary (Fair Notice Ordinance, 2020), Oct 2026

Under the Keep Chicago Renting Ordinance, a qualified tenant in a foreclosed rental can take $10,600 in relocation aid or a renewal of at least 12 months, and may refuse the renewal for the payment.

For investors: The duty falls on whoever buys at a confirmed foreclosure auction or during a pending foreclosure, not on a later arm's-length buyer from the bank. Auction bidders should count occupied units and budget $10,600 for each qualified tenant who may choose to leave.

Source: City of Chicago Department of Housing, Municipal Code Chapter 5-14 (Keep Chicago Renting Ordinance), Oct 2026

Chicago's heat ordinance runs September 15 to June 1 and, in buildings with shared heating, requires 68 degrees from 8:30 a.m. to 10:30 p.m. and 66 overnight, with fines of $500 to $1,000 daily.

For investors: Where one boiler serves every unit, the owner supplies the heat and carries the fuel bill and the fine risk all winter. Units with their own furnaces let the owner shift the gas bill to tenants, as the ordinance allows, which changes expense projections.

Source: City of Chicago Department of Buildings, Chicago Heat Ordinance (Mun. Code 14X-8-803), Oct 2026

Under Chicago's 2025 ADU expansion, a lot with one to four units in a multifamily or mixed-use district may add one conversion unit in a building at least 20 years old, plus one coach house.

For investors: Pre-certification from the Department of Housing comes before Buildings Department permits. No added parking is required, but conversion units and post-2021 coach houses cannot be short-term rentals, and coach house contractors must take part in registered apprenticeship programs.

Source: City of Chicago Department of Housing, ADU Ordinance home page and Program Requirements, Oct 2026