How to Rent Your Vacation Home or Condo in Chicago, Illinois

The first thing to consider when renting out a property in Chicago is making sure it’s the right fit. If you don’t want to deal with Airbnb guests or if you require a quieter environment, you may not want to rent out your home on a short-term basis. Similarly, if you want to use your space as an investment property, long-term rentals might be more suitable. More importantly, you should look into local laws and regulations that pertain to short-term rentals. For example, there are restrictions on the number of days a property can be rented out. In addition, there are restrictions on the number of overnight guests allowed and the amount of money that can be charged for stays. These rules vary from city to city and state to state, so make sure to do your research before renting out your Chicago home as a short-term rental.

Current Vacation Rental Trends in Chicago

During the month of September, Chicago and areas including Near North Side, Lakeview, South Loop/Printers Row, River North, Loop, Near West Side, West Town/Noble Square, Logan Square, Lincoln Park, Uptown, Humboldt Park, Bronzeville, Wicker Park, Pilsen, Streeterville, Rogers Park, Bridgeport, Little Italy/UIC, Old Town, Edgewater, Irving Park, Garfield Park, West Loop/Greektown, North Center, Avondale, Ukrainian Village, Hyde Park, River West, South Shore, Woodlawn, Lincoln Square, West Ridge, Wrigleyville, Chinatown, Portage Park, Bucktown, Albany Park, Andersonville, and Roscoe Village are projected to generate over $243/night for a 2 bedroom vacation rental, on average! There were 6,086 vacation active rental properties in Chicago.  4,915 are renting the entire place, and 1,171 are shared rooms.  On average, during the month of September 2022, each vacation rental property in Chicago is booked 81% of the time, and most hosts are projected to generate $4,484 or more during the month of September! See how much you could earn with our free vacation rental income calculator.

$243.00 Per Night*


81% Occupied*


$4,484.00 Per Month*

* Based on the median average of all vacation rentals in the Chicago area.
Get a free estimate for your home or condo.

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Successful short-term vacation rentals in Chicago, Illinois

Positive vacation rental trends in Chicago, Illinois when you considering renting out your Chicago home as a short-term rental include: Many vacation rentals in Chicago are located in historic neighborhoods and offer a unique experience. There are also many new hotels and boutique apartments in the city that rent short term. If you are considering renting out your Chicago home as a short-term rental, it’s important to do your research and consider the positives of renting to guests vs. owning your own home. Rental homes are usually fully furnished, have more space and privacy, and are not subject to mortgage payments.

Positive vacation rental trends in Chicago, Illinois when you considering renting out your Chicago home as a short-term rental include the following: It’s not the most exciting thing to think about - but it’s good business. It’s a great way to supplement your income while you take time off from work. The more people are renting short term, the more demand there will be for vacation rentals. And if you’re a local, it means more money in your pocket every time you rent out your place. And if you’re thinking about taking some well-deserved downtime, why not make it even more relaxing? Rent out part of your space and staycation (even on vacation). Whatever you do, don’t overlook the potential that short-term rentals can have on the local economy.

Revenue Projections for Vacation Rentals in Chicago, Illinois during October, 2022

Based on a 2 bedroom, which is the most common Chicago vacation rental home size, we've come up with an estimated rental amount you could charge per night and how much demand there is for each day in October. Higher bars below can command higher prices, if your Chicago vacation rental is available during these days.

Average Daily Price & Percent Occupied Next Month In Chicago

Note: These averages are based on a 2 bedroom home in Chicago. If you'd like to find out how much revenue your home could make by providing the number of bedrooms and specifics about your vacation rental, please try our  free vacation rental calculator and/or speak with one of our vacation rental experts about your vacation home, condo or unique vacation rental experience.

Interested in learning how you can maximize your vacation rental revenue in Chicago, Illinois?

If you are a speculative home buyer or have another home in Illinois, check out our other Illinois Vacation Rental Management reports in AltonAuroraChampaignEvanstonGalenaOak ParkPontiacRockford,  and Springfield, Illinois or view all of our vacation rental market reports

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