Can you do rental arbitrage in Chicago?
Mostly in buildings of 5 or more units. We have 5 Chicago homes where the landlord already said yes to Airbnb. The city is the hard part: our guide rates Chicago a red light, because a short-term rental must be your primary residence unless it's in a building of 5 or more units, and the host must be a person, so an LLC can't register.
From our Chicago guide, where every rule links to its source.
Chicago homes you're allowed to Airbnb
5 homes where the landlord already said yes. Members see the address, real photos and rent.
IllustrationChicago, IL
Est. $7,750/mo profitEst. $15,000 to $16,000/mo on Airbnb
IllustrationChicago, IL
Est. $7,500/mo profitEst. $14,000 to $15,000/mo on Airbnb
IllustrationChicago, IL
Est. $3,250/mo profitEst. $8,000 to $9,000/mo on Airbnb
IllustrationChicago, IL
Est. $2,250/mo profitEst. $9,000 to $10,000/mo on AirbnbPictures are illustrations, not the real homes. Profit and revenue are estimates from BNBCalc and AirDNA data.
Chicago's rules for rental arbitrage
Skip Chicago unless you can hold a unit in a building of 5 or more units and the building owner has already said yes.
- Tenants can register as shared housing hosts, and buildings of 5 or more units need no primary residence
- Licensed platforms remit the city taxes for you
- Primary residence required in single-family homes and buildings of 2 to 4 units
- A building owner can ban rentals or join the Prohibited Buildings List
- 1Get the landlord's written OK first, and check the building isn't on the Prohibited Buildings List.
- 2Ask the City Clerk whether the precinct is a Restricted Residential Zone.
How it works with STR Exchange
- 1Pick an approved home. Every home on our list has the landlord's OK to Airbnb. We find them by calling landlords every day.
- 2Sign the lease. Usually through your LLC. We help with the tour, the application and the deal.
- 3List it on Airbnb. Guests cover the rent and bills.
Questions
Do I need a license in Chicago?
Yes. Each unit needs a shared housing registration at $125 a year, or a vacation rental license at $250 for 2 years.
What taxes do guests pay in Chicago?
10.5% in city taxes, and the state hotel tax is separate.
Whose name goes on the lease?
Usually your LLC. We recommend it for your protection. If a landlord will only sign a personal lease, it's your call. The city registers a person as the host, not an LLC.
What does STR Exchange cost?
Free to create an account. Membership is $149 a month after you're approved. The acquisition fee, our finder's fee, is $2,500 unfurnished or $3,500 furnished per home, due the day you sign the lease. Never before.
More cities with homes
San Diego 24 homesNashville 10 homesWest Palm Beach 9 homesScottsdale 9 homesMiami 7 homesKissimmee 6 homesSavannah 6 homesAnaheim 5 homesPhiladelphia 5 homes
Tell us your market. Our team calls landlords and sends you properties already approved for Airbnb.
- Landlord-approved listings
- New deals weekly
- Search any US market
Rules tell you where. We find the landlord who says yes.
STR Exchange members get landlord-approved rentals, new deals every week and a team that searches their market.
- Landlord-approved listings
- New deals weekly
- Many markets