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.

When partnering with RedAwning for your property management needs, we can make sure your Chicago rental is set up correctly and ready to generate the most amount of revenue possible per stay.

Current Vacation Rental Trends in Chicago

During the month of November, Chicago and areas including Near North Side, Lakeview, Loop, Near West Side, South Loop/Printers Row, River North, West Town/Noble Square, Lincoln Park, Logan Square, Streeterville, Uptown, West Loop/Greektown, Wicker Park, Humboldt Park, Pilsen, Edgewater, Old Town, Little Italy/UIC, Bronzeville, Rogers Park, Hyde Park, Avondale, Ukrainian Village, Bridgeport, Irving Park, North Center, Gold Coast, Lincoln Square, Bucktown, Wrigleyville, Woodlawn, Andersonville, Garfield Park, West Ridge, Albany Park, Kenwood, South Shore, Boystown, and Portage Park are projected to generate over $206/night for a 2 bedroom vacation rental, on average! There were 8,101 vacation active rental properties in Chicago.  6,532 are renting the entire place, and 1,569 are shared rooms.  On average, during the month of November 2023, each vacation rental property in Chicago is booked 67% of the time, and most hosts are projected to generate $3,052 or more during the month of November! See how much you could earn with our free vacation rental income calculator.

$206.00 Per Night*


67% Occupied*


$3,052.00 Per Month*

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

Featured Chicago Vacation Rental Generating Record Profits With RedAwning

Lincoln Park Mega Space 2 Parking Spaces Sleeps 20 Starting at $508 to $2,804 per night!

Stylish and spacious space nestled in the heart of Lincoln Park. This gorgeous historic Lincoln Park townhouse can accommodate up to 20 guest with 8 bedrooms, two living areas, two dining areas, two fully sticked kitchens, 4 full bathrooms and two parking spaces!! Early Check-Ins and Late Check-Outs are difficult to accommodate. If you need additional time, please consider booking an extra day. Guests between the ages of 18-24 are permitted to book on an exception basis only. In... Read More

This Chicago vacation home is presented on every travel website, where travelers are looking to book accommodations (Airbnb, VRBO, Expedia, Google Travel, and hundreds more). And, with RedAwning's dynamic pricing, daily rates are adjusted based on seasonality and demand in Chicago.

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.

RedAwning takes the guess-work out of Chicago property management, and we work with you to ensure your Chicago short-term rental is set up perfectly to attract guests and maximize your rental revenue, from day-one.

See how much your Chicago vacation rental could earn:

Revenue Projections for Vacation Rentals in Chicago, Illinois during December, 2023

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 December. 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 ParkPontiacRockfordSpringfieldJerusalemBellevilleLincolnNorth AuroraHoliday HillsO'FallonBull ValleyPark ForestPlainfieldMelrose ParkBentonBolingbrookSavoyCarlinvilleDes PlainesPeoria,  and Swansea, Illinois or view all of our vacation rental market reports

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